<?xml version='1.0' encoding='utf-8'?>
<response><drugs><drug><applicants><value>Alembic Pharmaceuticals Ltd</value><value>Novitium Pharma Llc</value><value>Lannett Co Inc</value><value>Msn Laboratories Private Ltd</value><value>Granules Pharmaceuticals Inc</value><value>Mylan Pharmaceuticals Inc</value><value>Appco Pharma Llc</value><value>Ani Pharmaceuticals Inc</value><value>Watson Laboratories Inc</value><value>Teva Pharmaceuticals Usa</value></applicants><atc_classification><drug><code>C02CA01</code><description>CARDIOVASCULAR SYSTEM: ANTIHYPERTENSIVES: ANTIADRENERGIC AGENTS, PERIPHERALLY ACTING: Alpha-adrenoreceptor antagonists</description></drug></atc_classification><availability_type>1</availability_type><biotherapeutic/><black_box/><black_box_warning>0</black_box_warning><chirality>2</chirality><drug_type>1</drug_type><first_approval>1976</first_approval><first_in_class/><helm_notation/><max_phase>4.0</max_phase><molecule_chembl_id>CHEMBL2</molecule_chembl_id><molecule_properties><alogp>1.78</alogp><aromatic_rings>3</aromatic_rings><full_molformula>C19H21N5O4</full_molformula><full_mwt>383.41</full_mwt><hba>8</hba><hbd>1</hbd><heavy_atoms>28</heavy_atoms><mw_freebase>383.41</mw_freebase><np_likeness_score>-1.29</np_likeness_score><num_ro5_violations/><psa>106.95</psa><qed_weighted>0.73</qed_weighted><ro3_pass>N</ro3_pass><rtb>4</rtb></molecule_properties><molecule_structures><canonical_smiles>COc1cc2nc(N3CCN(C(=O)c4ccco4)CC3)nc(N)c2cc1OC</canonical_smiles><molfile>
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    0.9375   -1.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9292   -2.6917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3208   -2.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2875   -3.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3042   -1.6167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3208   -1.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3917   -0.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5542   -1.6417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7792   -0.9542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9500   -3.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0125   -0.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9250   -1.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5833   -2.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708   -1.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2417   -1.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5417   -0.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1667   -2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1667   -0.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7792   -1.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4042    0.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5792   -0.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9417   -1.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1542   -0.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2667   -3.7542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2000   -2.9917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1833   -1.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7958   -1.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7958   -2.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  6  1  0
  4  2  1  0
  5  1  1  0
  6  5  2  0
  7  9  1  0
  8  1  1  0
  9 19  1  0
 10  3  1  0
 11  7  1  0
 12  6  1  0
 13 14  1  0
 14 12  2  0
 15 11  1  0
 16  8  1  0
 17  8  1  0
 18 16  1  0
 19 17  1  0
 20  7  2  0
 21 11  2  0
 22 15  1  0
 23 21  1  0
 24  4  1  0
 25 13  1  0
 26 14  1  0
 27 26  1  0
 28 25  1  0
  3  4  2  0
  9 18  1  0
 10 13  2  0
 22 23  2  0
M  END
</molfile><standard_inchi>InChI=1S/C19H21N5O4/c1-26-15-10-12-13(11-16(15)27-2)21-19(22-17(12)20)24-7-5-23(6-8-24)18(25)14-4-3-9-28-14/h3-4,9-11H,5-8H2,1-2H3,(H2,20,21,22)</standard_inchi><standard_inchi_key>IENZQIKPVFGBNW-UHFFFAOYSA-N</standard_inchi_key></molecule_structures><molecule_synonyms><drug><molecule_synonym>CP-122991</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>CP-122991</synonyms></drug><drug><molecule_synonym>Prazosin</molecule_synonym><syn_type>ATC</syn_type><synonyms>PRAZOSIN</synonyms></drug><drug><molecule_synonym>Prazosin</molecule_synonym><syn_type>BAN</syn_type><synonyms>PRAZOSIN</synonyms></drug><drug><molecule_synonym>Prazosin</molecule_synonym><syn_type>INN</syn_type><synonyms>PRAZOSIN</synonyms></drug><drug><molecule_synonym>Prazosin</molecule_synonym><syn_type>MERCK_INDEX</syn_type><synonyms>PRAZOSIN</synonyms></drug><drug><molecule_synonym>Prazosin</molecule_synonym><syn_type>OTHER</syn_type><synonyms>PRAZOSIN</synonyms></drug><drug><molecule_synonym>Prazosina</molecule_synonym><syn_type>INN_SPANISH</syn_type><synonyms>PRAZOSINA</synonyms></drug><drug><molecule_synonym>Prazosine</molecule_synonym><syn_type>INN_FRENCH</syn_type><synonyms>PRAZOSINE</synonyms></drug></molecule_synonyms><ob_patent/><oral>1</oral><parenteral/><prodrug/><research_codes><value>NSC-292810</value><value>CP-12299-1</value><value>CP-12,299-1</value><value>CP-122991</value></research_codes><rule_of_five>1</rule_of_five><sc_patent/><synonyms><value>Prazosin hydrochloride (JAN, MI, USAN, USP)</value><value>Prazosin (BAN, INN, MI)</value><value/></synonyms><topical/><usan_stem>-azosin</usan_stem><usan_stem_definition>antihypertensives (prazosin type)</usan_stem_definition><usan_stem_substem>-azosin(-azosin)</usan_stem_substem><usan_year>1968</usan_year><withdrawn_flag>0</withdrawn_flag></drug><drug><applicants><value>Pld Acquisitions Llc Dba Avema Pharma Solutions</value><value>Aveva Drug Delivery Systems Inc</value><value>Ivax Pharmaceuticals Inc Sub Teva Pharmaceuticals Usa</value><value>P And L Development Llc</value><value>Difgen Pharmaceuticals Llc</value><value>Perrigo R And D Co</value><value>Perrigo Pharma International Dac</value><value>Chattem Inc Dba Sanofi Consumer Healthcare</value><value>Mcneil Consumer Healthcare</value><value>Dr Reddys Laboratories Sa</value></applicants><atc_classification><drug><code>N07BA01</code><description>NERVOUS SYSTEM: OTHER NERVOUS SYSTEM DRUGS: DRUGS USED IN ADDICTIVE DISORDERS: Drugs used in nicotine dependence</description></drug></atc_classification><availability_type>2</availability_type><biotherapeutic/><black_box/><black_box_warning>0</black_box_warning><chirality>1</chirality><drug_type>1</drug_type><first_approval>1984</first_approval><first_in_class/><helm_notation/><max_phase>4.0</max_phase><molecule_chembl_id>CHEMBL3</molecule_chembl_id><molecule_properties><alogp>1.85</alogp><aromatic_rings>1</aromatic_rings><full_molformula>C10H14N2</full_molformula><full_mwt>162.24</full_mwt><hba>2</hba><hbd/><heavy_atoms>12</heavy_atoms><mw_freebase>162.24</mw_freebase><np_likeness_score>-0.41</np_likeness_score><num_ro5_violations/><psa>16.13</psa><qed_weighted>0.63</qed_weighted><ro3_pass>Y</ro3_pass><rtb>1</rtb></molecule_properties><molecule_structures><canonical_smiles>CN1CCC[C@H]1c1cccnc1</canonical_smiles><molfile>
     RDKit          2D

 12 13  0  0  1  0  0  0  0  0999 V2000
    3.3250   -3.3500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7500   -3.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1417   -3.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9042   -3.3792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5167   -3.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9042   -3.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3375   -2.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9542   -4.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6667   -4.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1417   -2.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9125   -2.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5292   -2.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  1
  4  5  2  0
  5  3  1  0
  6  1  1  0
  7  1  1  0
  8  2  1  0
  9  6  1  0
 10  3  2  0
 11 12  2  0
 12 10  1  0
  9  8  1  0
 11  4  1  0
M  END
</molfile><standard_inchi>InChI=1S/C10H14N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3/t10-/m0/s1</standard_inchi><standard_inchi_key>SNICXCGAKADSCV-JTQLQIEISA-N</standard_inchi_key></molecule_structures><molecule_synonyms><drug><molecule_synonym>Habitrol</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>HABITROL</synonyms></drug><drug><molecule_synonym>Nicabate</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>NICABATE</synonyms></drug><drug><molecule_synonym>Nicoderm cq</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>NICODERM CQ</synonyms></drug><drug><molecule_synonym>Nicopass</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>NICOPASS</synonyms></drug><drug><molecule_synonym>Nicopatch</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>NICOPATCH</synonyms></drug><drug><molecule_synonym>Nicorette invisi</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>NICORETTE INVISI</synonyms></drug><drug><molecule_synonym>Nicotine</molecule_synonym><syn_type>ATC</syn_type><synonyms>NICOTINE</synonyms></drug><drug><molecule_synonym>Nicotine</molecule_synonym><syn_type>BNF</syn_type><synonyms>NICOTINE</synonyms></drug><drug><molecule_synonym>Nicotine</molecule_synonym><syn_type>FDA</syn_type><synonyms>NICOTINE</synonyms></drug><drug><molecule_synonym>Nicotine</molecule_synonym><syn_type>MERCK_INDEX</syn_type><synonyms>NICOTINE</synonyms></drug><drug><molecule_synonym>Nicotine</molecule_synonym><syn_type>OTHER</syn_type><synonyms>NICOTINE</synonyms></drug><drug><molecule_synonym>Nicotine</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>NICOTINE</synonyms></drug><drug><molecule_synonym>Nicotine</molecule_synonym><syn_type>USP</syn_type><synonyms>NICOTINE</synonyms></drug><drug><molecule_synonym>Nicotinell classic</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>NICOTINELL CLASSIC</synonyms></drug><drug><molecule_synonym>Nicotinell support</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>NICOTINELL SUPPORT</synonyms></drug><drug><molecule_synonym>Nicotinell tts 10</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>NICOTINELL TTS 10</synonyms></drug><drug><molecule_synonym>Nicotinell tts 20</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>NICOTINELL TTS 20</synonyms></drug><drug><molecule_synonym>Nicotinell tts 30</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>NICOTINELL TTS 30</synonyms></drug><drug><molecule_synonym>Nicotrol</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>NICOTROL</synonyms></drug><drug><molecule_synonym>Nicotrol inhaler</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>Nicotrol Inhaler</synonyms></drug><drug><molecule_synonym>Nicotrol ns</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>Nicotrol NS</synonyms></drug><drug><molecule_synonym>Niquitin</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>NIQUITIN</synonyms></drug><drug><molecule_synonym>Niquitin clr</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>NIQUITIN CLR</synonyms></drug><drug><molecule_synonym>Niquitin minis cherry</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>NIQUITIN MINIS CHERRY</synonyms></drug><drug><molecule_synonym>Niquitin minis mint</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>NIQUITIN MINIS MINT</synonyms></drug><drug><molecule_synonym>Niquitin minis orange</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>NIQUITIN MINIS ORANGE</synonyms></drug><drug><molecule_synonym>Niquitin mint</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>NIQUITIN MINT</synonyms></drug><drug><molecule_synonym>Niquitin pre-quit</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>NIQUITIN PRE-QUIT</synonyms></drug><drug><molecule_synonym>Niquitin strips mint</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>NIQUITIN STRIPS MINT</synonyms></drug><drug><molecule_synonym>Prostep</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>PROSTEP</synonyms></drug><drug><molecule_synonym>Stoppers</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>STOPPERS</synonyms></drug><drug><molecule_synonym>Stubit</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>STUBIT</synonyms></drug></molecule_synonyms><ob_patent>8323683</ob_patent><oral>1</oral><parenteral/><prodrug/><research_codes><value>NSC-97238</value></research_codes><rule_of_five>1</rule_of_five><sc_patent>US-8323683-B2</sc_patent><synonyms><value>Nicotine bitartrate (MI, USAN)</value><value>Nicotine bitartrate dihydrate (USP)</value><value>Nicotine (MI, USP)</value><value>Nicotine polacrilex (USAN, USP)</value><value/></synonyms><topical>1</topical><usan_stem/><usan_stem_definition/><usan_stem_substem/><usan_year>1985</usan_year><withdrawn_flag>0</withdrawn_flag></drug><drug><applicants/><atc_code_description/><availability_type/><biotherapeutic/><black_box/><black_box_warning>0</black_box_warning><chirality>1</chirality><drug_type>1</drug_type><first_approval/><first_in_class/><helm_notation/><max_phase>1.0</max_phase><molecule_chembl_id>CHEMBL6200</molecule_chembl_id><molecule_properties><alogp>1.51</alogp><aromatic_rings>1</aromatic_rings><full_molformula>C9H12N2</full_molformula><full_mwt>148.21</full_mwt><hba>2</hba><hbd>1</hbd><heavy_atoms>11</heavy_atoms><mw_freebase>148.21</mw_freebase><np_likeness_score>-0.09</np_likeness_score><num_ro5_violations/><psa>24.92</psa><qed_weighted>0.65</qed_weighted><ro3_pass>Y</ro3_pass><rtb>1</rtb></molecule_properties><molecule_structures><canonical_smiles>c1cncc([C@@H]2CCCN2)c1</canonical_smiles><molfile>
     RDKit          2D

 11 12  0  0  0  0  0  0  0  0999 V2000
    6.8984   -4.7940    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4277   -4.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1426   -4.4669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7185   -6.1312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4277   -5.7194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4482   -4.1720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7185   -4.4783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0036   -5.7194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2200   -3.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0036   -4.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0249   -3.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  6
  3  1  1  0
  4  5  2  0
  5  2  1  0
  6  1  1  0
  7  2  2  0
  8 10  2  0
  9  3  1  0
 10  7  1  0
 11  6  1  0
  9 11  1  0
  4  8  1  0
M  END</molfile><standard_inchi>InChI=1S/C9H12N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7,9,11H,2,4,6H2/t9-/m0/s1</standard_inchi><standard_inchi_key>MYKUKUCHPMASKF-VIFPVBQESA-N</standard_inchi_key></molecule_structures><molecule_synonyms><drug><molecule_synonym>1'-demethylnicotine</molecule_synonym><syn_type>OTHER</syn_type><synonyms>1'-DEMETHYLNICOTINE</synonyms></drug><drug><molecule_synonym>3-(2-pyrrolidinyl)-(s)-pyridine</molecule_synonym><syn_type>OTHER</syn_type><synonyms>3-(2-PYRROLIDINYL)-(S)-PYRIDINE</synonyms></drug><drug><molecule_synonym>Nicotine related compound f</molecule_synonym><syn_type>OTHER</syn_type><synonyms>NICOTINE RELATED COMPOUND F</synonyms></drug><drug><molecule_synonym>Nornicotine</molecule_synonym><syn_type>MERCK_INDEX</syn_type><synonyms>NORNICOTINE</synonyms></drug><drug><molecule_synonym>Nornicotine</molecule_synonym><syn_type>OTHER</syn_type><synonyms>NORNICOTINE</synonyms></drug></molecule_synonyms><ob_patent/><oral/><parenteral/><prodrug/><research_codes/><rule_of_five>1</rule_of_five><sc_patent/><synonyms><value>Nornicotine (MI)</value><value/></synonyms><topical/><usan_stem/><usan_stem_definition/><usan_stem_substem/><usan_year/><withdrawn_flag>0</withdrawn_flag></drug><drug><applicants><value>Somerset Therapeutics Llc</value><value>Ranbaxy Laboratories Ltd</value><value>Janssen Pharmaceuticals Inc</value><value>Teva Pharmaceuticals Usa Inc</value><value>Sandoz Inc</value><value>Daiichi Pharmaceutical Corp</value><value>Ortho Mcneil Pharmaceutical Inc</value><value>Allergan Inc</value><value>Bedford Laboratories Div Ben Venue Laboratories Inc</value><value>Dr Reddys Laboratories Ltd</value></applicants><atc_classification><drug><code>S01AE01</code><description>SENSORY ORGANS: OPHTHALMOLOGICALS: ANTIINFECTIVES: Fluoroquinolone</description></drug><drug><code>J01MA01</code><description>ANTIINFECTIVES FOR SYSTEMIC USE: ANTIBACTERIALS FOR SYSTEMIC USE: QUINOLONE ANTIBACTERIALS: Fluoroquinolone</description></drug><drug><code>S02AA16</code><description>SENSORY ORGANS: OTOLOGICALS: ANTIINFECTIVES: Antiinfectives</description></drug></atc_classification><availability_type>1</availability_type><biotherapeutic/><black_box>1</black_box><black_box_warning>1</black_box_warning><chirality/><drug_type>1</drug_type><first_approval>1990</first_approval><first_in_class/><helm_notation/><max_phase>4.0</max_phase><molecule_chembl_id>CHEMBL4</molecule_chembl_id><molecule_properties><alogp>1.54</alogp><aromatic_rings>2</aromatic_rings><full_molformula>C18H20FN3O4</full_molformula><full_mwt>361.37</full_mwt><hba>6</hba><hbd>1</hbd><heavy_atoms>26</heavy_atoms><mw_freebase>361.37</mw_freebase><np_likeness_score>-0.21</np_likeness_score><num_ro5_violations/><psa>75.01</psa><qed_weighted>0.87</qed_weighted><ro3_pass>N</ro3_pass><rtb>2</rtb></molecule_properties><molecule_structures><canonical_smiles>CC1COc2c(N3CCN(C)CC3)c(F)cc3c(=O)c(C(=O)O)cn1c23</canonical_smiles><molfile>
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    3.0250   -1.8625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6417   -2.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4042   -2.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7875   -1.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1792   -2.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7875   -1.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1792   -2.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8042   -3.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5542   -1.8792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2583   -3.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0167   -1.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6833   -1.1792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0375   -3.9917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3917   -0.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0583   -2.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5500   -1.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2625   -3.9875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5667   -3.3042    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6750   -1.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0708   -0.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8708   -2.9208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3000   -0.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6292   -0.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  2  0
  3  1  1  0
  4  3  1  0
  5  3  2  0
  6  1  1  0
  7  2  1  0
  8  4  2  0
  9 17  1  0
 10  8  1  0
 11  5  1  0
 12  8  1  0
 13  2  1  0
 14  1  1  0
 15 23  1  0
 16  7  2  0
 17 14  1  0
 18 12  1  0
 19 12  1  0
 20 13  2  0
 21 10  1  0
 22 18  1  0
 23 19  1  0
 24 13  1  0
 25 15  1  0
 26 14  1  0
  5  7  1  0
  4  9  1  0
 11 10  2  0
 15 22  1  0
M  END
</molfile><standard_inchi>InChI=1S/C18H20FN3O4/c1-10-9-26-17-14-11(16(23)12(18(24)25)8-22(10)14)7-13(19)15(17)21-5-3-20(2)4-6-21/h7-8,10H,3-6,9H2,1-2H3,(H,24,25)</standard_inchi><standard_inchi_key>GSDSWSVVBLHKDQ-UHFFFAOYSA-N</standard_inchi_key></molecule_structures><molecule_synonyms><drug><molecule_synonym>DL-8280</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>DL-8280</synonyms></drug><drug><molecule_synonym>Exocin</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>EXOCIN</synonyms></drug><drug><molecule_synonym>Floxin</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>FLOXIN</synonyms></drug><drug><molecule_synonym>Floxin otic</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>FLOXIN OTIC</synonyms></drug><drug><molecule_synonym>HOE 280</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>HOE 280</synonyms></drug><drug><molecule_synonym>HOE-280</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>HOE-280</synonyms></drug><drug><molecule_synonym>J01MA01</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>J01MA01</synonyms></drug><drug><molecule_synonym>NSC-727071</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>NSC-727071</synonyms></drug><drug><molecule_synonym>NSC-758178</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>NSC-758178</synonyms></drug><drug><molecule_synonym>Ocuflox</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>OCUFLOX</synonyms></drug><drug><molecule_synonym>Ofloxacin</molecule_synonym><syn_type>ATC</syn_type><synonyms>OFLOXACIN</synonyms></drug><drug><molecule_synonym>Ofloxacin</molecule_synonym><syn_type>BAN</syn_type><synonyms>OFLOXACIN</synonyms></drug><drug><molecule_synonym>Ofloxacin</molecule_synonym><syn_type>BNF</syn_type><synonyms>OFLOXACIN</synonyms></drug><drug><molecule_synonym>Ofloxacin</molecule_synonym><syn_type>FDA</syn_type><synonyms>OFLOXACIN</synonyms></drug><drug><molecule_synonym>Ofloxacin</molecule_synonym><syn_type>INN</syn_type><synonyms>OFLOXACIN</synonyms></drug><drug><molecule_synonym>Ofloxacin</molecule_synonym><syn_type>JAN</syn_type><synonyms>OFLOXACIN</synonyms></drug><drug><molecule_synonym>Ofloxacin</molecule_synonym><syn_type>MERCK_INDEX</syn_type><synonyms>OFLOXACIN</synonyms></drug><drug><molecule_synonym>Ofloxacin</molecule_synonym><syn_type>OTHER</syn_type><synonyms>OFLOXACIN</synonyms></drug><drug><molecule_synonym>Ofloxacin</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>OFLOXACIN</synonyms></drug><drug><molecule_synonym>Ofloxacin</molecule_synonym><syn_type>USAN</syn_type><synonyms>OFLOXACIN</synonyms></drug><drug><molecule_synonym>Ofloxacin</molecule_synonym><syn_type>USP</syn_type><synonyms>OFLOXACIN</synonyms></drug><drug><molecule_synonym>Ofloxacine</molecule_synonym><syn_type>INN_FRENCH</syn_type><synonyms>OFLOXACINE</synonyms></drug><drug><molecule_synonym>Ofloxacino</molecule_synonym><syn_type>INN_SPANISH</syn_type><synonyms>OFLOXACINO</synonyms></drug><drug><molecule_synonym>Tarivid</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>TARIVID</synonyms></drug><drug><molecule_synonym>Tarivid 400</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>TARIVID 400</synonyms></drug><drug><molecule_synonym>Tarivid i.v.</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>TARIVID I.V.</synonyms></drug><drug><molecule_synonym>Visiren</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>Visiren</synonyms></drug></molecule_synonyms><ob_patent/><oral>1</oral><parenteral>1</parenteral><prodrug/><research_codes><value>DL-8280</value><value>J01MA01</value><value>NSC-727071</value><value>HOE 280</value><value>HOE-280</value><value>NSC-758178</value></research_codes><rule_of_five>1</rule_of_five><sc_patent/><synonyms><value>Ofloxacin (BAN, INN, JAN, MI, USAN, USP)</value><value/></synonyms><topical>1</topical><usan_stem>-oxacin</usan_stem><usan_stem_definition>antibacterials (quinolone derivatives)</usan_stem_definition><usan_stem_substem>-oxacin(-oxacin)</usan_stem_substem><usan_year>1984</usan_year><withdrawn_flag>0</withdrawn_flag></drug><drug><applicants><value>Sanofi Aventis Us Llc</value><value>Watson Laboratories Inc</value><value>Sun Pharmaceutical Industries Inc</value></applicants><atc_classification><drug><code>J01MB02</code><description>ANTIINFECTIVES FOR SYSTEMIC USE: ANTIBACTERIALS FOR SYSTEMIC USE: QUINOLONE ANTIBACTERIALS: Other quinolones</description></drug></atc_classification><availability_type/><biotherapeutic/><black_box/><black_box_warning>0</black_box_warning><chirality>2</chirality><drug_type>1</drug_type><first_approval>1964</first_approval><first_in_class/><helm_notation/><max_phase>4.0</max_phase><molecule_chembl_id>CHEMBL5</molecule_chembl_id><molecule_properties><alogp>1.42</alogp><aromatic_rings>2</aromatic_rings><full_molformula>C12H12N2O3</full_molformula><full_mwt>232.24</full_mwt><hba>4</hba><hbd>1</hbd><heavy_atoms>17</heavy_atoms><mw_freebase>232.24</mw_freebase><np_likeness_score>-0.98</np_likeness_score><num_ro5_violations/><psa>72.19</psa><qed_weighted>0.85</qed_weighted><ro3_pass>N</ro3_pass><rtb>2</rtb></molecule_properties><molecule_structures><canonical_smiles>CCn1cc(C(=O)O)c(=O)c2ccc(C)nc21</canonical_smiles><molfile>
     RDKit          2D

 17 18  0  0  0  0  0  0  0  0999 V2000
    4.2125   -4.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4375   -4.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4417   -4.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8250   -3.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8292   -5.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2167   -4.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0625   -5.1792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5917   -3.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0542   -3.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8250   -3.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6042   -3.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6750   -4.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9625   -4.1042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667   -4.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8250   -5.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2917   -5.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2167   -6.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  5  1  0
  4  1  1  0
  5  6  1  0
  6  1  2  0
  7  3  1  0
  8  1  1  0
  9  2  1  0
 10  4  2  0
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 12  7  2  0
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 15  5  1  0
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 17 15  1  0
  2  3  2  0
 14 12  1  0
M  END
</molfile><standard_inchi>InChI=1S/C12H12N2O3/c1-3-14-6-9(12(16)17)10(15)8-5-4-7(2)13-11(8)14/h4-6H,3H2,1-2H3,(H,16,17)</standard_inchi><standard_inchi_key>MHWLWQUZZRMNGJ-UHFFFAOYSA-N</standard_inchi_key></molecule_structures><molecule_synonyms><drug><molecule_synonym>Acide nalidixique</molecule_synonym><syn_type>INN_FRENCH</syn_type><synonyms>ACIDE NALIDIXIQUE</synonyms></drug><drug><molecule_synonym>Acido nalidixico</molecule_synonym><syn_type>INN_SPANISH</syn_type><synonyms>ACIDO NALIDIXICO</synonyms></drug><drug><molecule_synonym>Mictral</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>MICTRAL</synonyms></drug><drug><molecule_synonym>Nalidixane</molecule_synonym><syn_type>OTHER</syn_type><synonyms>NALIDIXANE</synonyms></drug><drug><molecule_synonym>Nalidixate</molecule_synonym><syn_type>OTHER</syn_type><synonyms>NALIDIXATE</synonyms></drug><drug><molecule_synonym>Nalidixic acid</molecule_synonym><syn_type>ATC</syn_type><synonyms>NALIDIXIC ACID</synonyms></drug><drug><molecule_synonym>Nalidixic acid</molecule_synonym><syn_type>BAN</syn_type><synonyms>NALIDIXIC ACID</synonyms></drug><drug><molecule_synonym>Nalidixic acid</molecule_synonym><syn_type>BNF</syn_type><synonyms>NALIDIXIC ACID</synonyms></drug><drug><molecule_synonym>Nalidixic acid</molecule_synonym><syn_type>FDA</syn_type><synonyms>NALIDIXIC ACID</synonyms></drug><drug><molecule_synonym>Nalidixic acid</molecule_synonym><syn_type>INN</syn_type><synonyms>NALIDIXIC ACID</synonyms></drug><drug><molecule_synonym>Nalidixic acid</molecule_synonym><syn_type>JAN</syn_type><synonyms>NALIDIXIC ACID</synonyms></drug><drug><molecule_synonym>Nalidixic acid</molecule_synonym><syn_type>MERCK_INDEX</syn_type><synonyms>NALIDIXIC ACID</synonyms></drug><drug><molecule_synonym>Nalidixic acid</molecule_synonym><syn_type>OTHER</syn_type><synonyms>NALIDIXIC ACID</synonyms></drug><drug><molecule_synonym>Nalidixic acid</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>NALIDIXIC ACID</synonyms></drug><drug><molecule_synonym>Nalidixic acid</molecule_synonym><syn_type>USAN</syn_type><synonyms>NALIDIXIC ACID</synonyms></drug><drug><molecule_synonym>Nalidixic acid</molecule_synonym><syn_type>USP</syn_type><synonyms>NALIDIXIC ACID</synonyms></drug><drug><molecule_synonym>Nalix</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>NALIX</synonyms></drug><drug><molecule_synonym>Neg gram</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>Neg Gram</synonyms></drug><drug><molecule_synonym>Neggram</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>NEGGRAM</synonyms></drug><drug><molecule_synonym>Negram</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>NEGRAM</synonyms></drug><drug><molecule_synonym>NSC-82174</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>NSC-82174</synonyms></drug><drug><molecule_synonym>Uriben</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>URIBEN</synonyms></drug><drug><molecule_synonym>Uroneg</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>Uroneg</synonyms></drug><drug><molecule_synonym>WIN 18,320</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>WIN 18,320</synonyms></drug><drug><molecule_synonym>WIN-18320</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>WIN-18320</synonyms></drug></molecule_synonyms><ob_patent/><oral>1</oral><parenteral/><prodrug/><research_codes><value>NSC-82174</value><value>WIN-18320</value><value>WIN 18,320-3</value><value>WIN-18320-3</value><value>WIN 18,320</value></research_codes><rule_of_five>1</rule_of_five><sc_patent/><synonyms><value>Nalidixate sodium (USAN)</value><value>Nalidixic acid (BAN, INN, JAN, MI, USAN, USP)</value><value/></synonyms><topical/><usan_stem>nal-</usan_stem><usan_stem_definition>narcotic agonists/antagonists (normorphine type)</usan_stem_definition><usan_stem_substem>nal-(nal-)</usan_stem_substem><usan_year>1962</usan_year><withdrawn_flag>0</withdrawn_flag></drug><drug><applicants/><atc_code_description/><availability_type/><biotherapeutic/><black_box/><black_box_warning>0</black_box_warning><chirality>2</chirality><drug_type>1</drug_type><first_approval/><first_in_class/><helm_notation/><max_phase>2.0</max_phase><molecule_chembl_id>CHEMBL6246</molecule_chembl_id><molecule_properties><alogp>1.31</alogp><aromatic_rings>4</aromatic_rings><full_molformula>C14H6O8</full_molformula><full_mwt>302.19</full_mwt><hba>8</hba><hbd>4</hbd><heavy_atoms>22</heavy_atoms><mw_freebase>302.19</mw_freebase><np_likeness_score>1.07</np_likeness_score><num_ro5_violations/><psa>141.34</psa><qed_weighted>0.22</qed_weighted><ro3_pass>N</ro3_pass><rtb/></molecule_properties><molecule_structures><canonical_smiles>O=c1oc2c(O)c(O)cc3c(=O)oc4c(O)c(O)cc1c4c23</canonical_smiles><molfile>
     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
   -0.4750   -0.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5750    0.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4750   -1.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5750    1.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5333    0.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6292   -0.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5750   -2.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4750    2.2083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5333    1.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6292   -1.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6292    2.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5333   -2.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5833   -0.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6792    0.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5833   -1.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6792    1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5625    2.2208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6625   -2.1042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6292    3.4000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5333   -3.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6375   -2.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7375    2.1208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  2  0
  5  1  2  0
  6  2  1  0
  7  3  1  0
  8  9  1  0
  9  5  1  0
 10  7  1  0
 11  4  1  0
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 15 13  2  0
 16 14  1  0
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 18 10  2  0
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 21 15  1  0
 22 16  1  0
 12 15  1  0
  4  8  1  0
  6 10  1  0
 11 16  2  0
M  END
</molfile><standard_inchi>InChI=1S/C14H6O8/c15-5-1-3-7-8-4(14(20)22-11(7)9(5)17)2-6(16)10(18)12(8)21-13(3)19/h1-2,15-18H</standard_inchi><standard_inchi_key>AFSDNFLWKVMVRB-UHFFFAOYSA-N</standard_inchi_key></molecule_structures><molecule_synonyms><drug><molecule_synonym>Acide ellagique</molecule_synonym><syn_type>INN_FRENCH</syn_type><synonyms>ACIDE ELLAGIQUE</synonyms></drug><drug><molecule_synonym>Acido elagico</molecule_synonym><syn_type>INN_SPANISH</syn_type><synonyms>ACIDO ELAGICO</synonyms></drug><drug><molecule_synonym>Ellagic acid</molecule_synonym><syn_type>INN</syn_type><synonyms>ELLAGIC ACID</synonyms></drug><drug><molecule_synonym>Ellagic acid</molecule_synonym><syn_type>OTHER</syn_type><synonyms>ELLAGIC ACID</synonyms></drug><drug><molecule_synonym>NSC-407286</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>NSC-407286</synonyms></drug><drug><molecule_synonym>NSC-656272</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>NSC-656272</synonyms></drug></molecule_synonyms><ob_patent/><oral/><parenteral/><prodrug/><research_codes><value>NSC-656272</value><value>NSC-407286</value></research_codes><rule_of_five>1</rule_of_five><sc_patent/><synonyms><value>Ellagic acid (INN)</value><value/></synonyms><topical/><usan_stem/><usan_stem_definition/><usan_stem_substem/><usan_year/><withdrawn_flag>0</withdrawn_flag></drug><drug><applicants/><atc_code_description/><availability_type/><biotherapeutic/><black_box/><black_box_warning>0</black_box_warning><chirality>2</chirality><drug_type>1</drug_type><first_approval/><first_in_class/><helm_notation/><max_phase>3.0</max_phase><molecule_chembl_id>CHEMBL204021</molecule_chembl_id><molecule_properties><alogp>7.22</alogp><aromatic_rings>4</aromatic_rings><full_molformula>C36H38F4N4O2S</full_molformula><full_mwt>666.79</full_mwt><hba>6</hba><hbd/><heavy_atoms>47</heavy_atoms><mw_freebase>666.79</mw_freebase><np_likeness_score>-1.74</np_likeness_score><num_ro5_violations>2</num_ro5_violations><psa>58.44</psa><qed_weighted>0.09</qed_weighted><ro3_pass>N</ro3_pass><rtb>13</rtb></molecule_properties><molecule_structures><canonical_smiles>CCN(CC)CCN(Cc1ccc(-c2ccc(C(F)(F)F)cc2)cc1)C(=O)Cn1c(SCc2ccc(F)cc2)nc(=O)c2c1CCC2</canonical_smiles><molfile>
     RDKit          2D

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M  END
</molfile><standard_inchi>InChI=1S/C36H38F4N4O2S/c1-3-42(4-2)20-21-43(22-25-8-12-27(13-9-25)28-14-16-29(17-15-28)36(38,39)40)33(45)23-44-32-7-5-6-31(32)34(46)41-35(44)47-24-26-10-18-30(37)19-11-26/h8-19H,3-7,20-24H2,1-2H3</standard_inchi><standard_inchi_key>WDPFJWLDPVQCAJ-UHFFFAOYSA-N</standard_inchi_key></molecule_structures><molecule_synonyms><drug><molecule_synonym>Darapladib</molecule_synonym><syn_type>INN</syn_type><synonyms>DARAPLADIB</synonyms></drug><drug><molecule_synonym>Darapladib</molecule_synonym><syn_type>JAN</syn_type><synonyms>DARAPLADIB</synonyms></drug><drug><molecule_synonym>Darapladib</molecule_synonym><syn_type>MERCK_INDEX</syn_type><synonyms>DARAPLADIB</synonyms></drug><drug><molecule_synonym>Darapladib</molecule_synonym><syn_type>OTHER</syn_type><synonyms>DARAPLADIB</synonyms></drug><drug><molecule_synonym>Darapladib</molecule_synonym><syn_type>USAN</syn_type><synonyms>DARAPLADIB</synonyms></drug><drug><molecule_synonym>SB-480848</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>SB-480848</synonyms></drug></molecule_synonyms><ob_patent/><oral/><parenteral/><prodrug/><research_codes><value>SB-480848</value></research_codes><rule_of_five/><sc_patent/><synonyms><value>Darapladib (INN, JAN, MI, USAN)</value><value/></synonyms><topical/><usan_stem>-pladib</usan_stem><usan_stem_definition>phospholipase A2 inhibitors</usan_stem_definition><usan_stem_substem>-pladib(-pladib)</usan_stem_substem><usan_year>2005</usan_year><withdrawn_flag>0</withdrawn_flag></drug><drug><applicants><value>Novitium Pharma Llc</value><value>Cosette Pharmaceuticals Inc</value><value>Genus Lifesciences Inc</value><value>Heritage Pharma Labs Inc</value><value>Aurobindo Pharma Ltd</value><value>Teva Pharmaceuticals Usa Inc</value><value>Mutual Pharmaceutical Co Inc</value><value>Cycle Pharmaceuticals Ltd</value><value>Inwood Laboratories Inc Sub Forest Laboratories Inc</value><value>Rising Pharma Holdings Inc</value></applicants><atc_classification><drug><code>S01BC01</code><description>SENSORY ORGANS: OPHTHALMOLOGICALS: ANTIINFLAMMATORY AGENTS: Antiinflammatory agents, non-steroid</description></drug><drug><code>C01EB03</code><description>CARDIOVASCULAR SYSTEM: CARDIAC THERAPY: OTHER CARDIAC PREPARATIONS: Other cardiac preparation</description></drug><drug><code>M01AB01</code><description>MUSCULO-SKELETAL SYSTEM: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS: Acetic acid derivatives and related substance</description></drug><drug><code>M02AA23</code><description>MUSCULO-SKELETAL SYSTEM: TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN: TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN: Antiinflammatory preparations, non-steroids for topical us</description></drug><drug><code>M01AB51</code><description>MUSCULO-SKELETAL SYSTEM: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS: Acetic acid derivatives and related substances</description></drug></atc_classification><availability_type>1</availability_type><biotherapeutic/><black_box>1</black_box><black_box_warning>1</black_box_warning><chirality>2</chirality><drug_type>1</drug_type><first_approval>1965</first_approval><first_in_class/><helm_notation/><max_phase>4.0</max_phase><molecule_chembl_id>CHEMBL6</molecule_chembl_id><molecule_properties><alogp>3.93</alogp><aromatic_rings>3</aromatic_rings><full_molformula>C19H16ClNO4</full_molformula><full_mwt>357.79</full_mwt><hba>4</hba><hbd>1</hbd><heavy_atoms>25</heavy_atoms><mw_freebase>357.79</mw_freebase><np_likeness_score>-0.72</np_likeness_score><num_ro5_violations/><psa>68.53</psa><qed_weighted>0.77</qed_weighted><ro3_pass>N</ro3_pass><rtb>4</rtb></molecule_properties><molecule_structures><canonical_smiles>COc1ccc2c(c1)c(CC(=O)O)c(C)n2C(=O)c1ccc(Cl)cc1</canonical_smiles><molfile>
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
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M  END
</molfile><standard_inchi>InChI=1S/C19H16ClNO4/c1-11-15(10-18(22)23)16-9-14(25-2)7-8-17(16)21(11)19(24)12-3-5-13(20)6-4-12/h3-9H,10H2,1-2H3,(H,22,23)</standard_inchi><standard_inchi_key>CGIGDMFJXJATDK-UHFFFAOYSA-N</standard_inchi_key></molecule_structures><molecule_synonyms><drug><molecule_synonym>Aconip</molecule_synonym><syn_type>OTHER</syn_type><synonyms>ACONIP</synonyms></drug><drug><molecule_synonym>Artracin</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>ARTRACIN</synonyms></drug><drug><molecule_synonym>Artracin sr</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>ARTRACIN SR</synonyms></drug><drug><molecule_synonym>Berlind 75 ret</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>BERLIND 75 RET</synonyms></drug><drug><molecule_synonym>Durametacin</molecule_synonym><syn_type>OTHER</syn_type><synonyms>DURAMETACIN</synonyms></drug><drug><molecule_synonym>Flexin-25 continus</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>FLEXIN-25 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SR</synonyms></drug><drug><molecule_synonym>Indometacin</molecule_synonym><syn_type>ATC</syn_type><synonyms>INDOMETACIN</synonyms></drug><drug><molecule_synonym>Indometacin</molecule_synonym><syn_type>BAN</syn_type><synonyms>INDOMETACIN</synonyms></drug><drug><molecule_synonym>Indometacin</molecule_synonym><syn_type>BNF</syn_type><synonyms>INDOMETACIN</synonyms></drug><drug><molecule_synonym>Indometacin</molecule_synonym><syn_type>DCF</syn_type><synonyms>INDOMETACIN</synonyms></drug><drug><molecule_synonym>Indometacin</molecule_synonym><syn_type>INN</syn_type><synonyms>INDOMETACIN</synonyms></drug><drug><molecule_synonym>Indometacin</molecule_synonym><syn_type>JAN</syn_type><synonyms>INDOMETACIN</synonyms></drug><drug><molecule_synonym>Indometacin</molecule_synonym><syn_type>OTHER</syn_type><synonyms>INDOMETACIN</synonyms></drug><drug><molecule_synonym>Indometacina</molecule_synonym><syn_type>INN_SPANISH</syn_type><synonyms>INDOMETACINA</synonyms></drug><drug><molecule_synonym>Indometacine</molecule_synonym><syn_type>INN_FRENCH</syn_type><synonyms>INDOMETACINE</synonyms></drug><drug><molecule_synonym>Indometacin farnesil</molecule_synonym><syn_type>JAN</syn_type><synonyms>INDOMETACIN FARNESIL</synonyms></drug><drug><molecule_synonym>Indometacinum</molecule_synonym><syn_type>OTHER</syn_type><synonyms>INDOMETACINUM</synonyms></drug><drug><molecule_synonym>Indomethacin</molecule_synonym><syn_type>FDA</syn_type><synonyms>INDOMETHACIN</synonyms></drug><drug><molecule_synonym>Indomethacin</molecule_synonym><syn_type>MERCK_INDEX</syn_type><synonyms>INDOMETHACIN</synonyms></drug><drug><molecule_synonym>Indomethacin</molecule_synonym><syn_type>OTHER</syn_type><synonyms>INDOMETHACIN</synonyms></drug><drug><molecule_synonym>Indomethacin</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>INDOMETHACIN</synonyms></drug><drug><molecule_synonym>Indomethacin</molecule_synonym><syn_type>USAN</syn_type><synonyms>INDOMETHACIN</synonyms></drug><drug><molecule_synonym>Indomethacin</molecule_synonym><syn_type>USP</syn_type><synonyms>INDOMETHACIN</synonyms></drug><drug><molecule_synonym>Indomod</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>INDOMOD</synonyms></drug><drug><molecule_synonym>Indo-paed</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>INDO-PAED</synonyms></drug><drug><molecule_synonym>Indoptol</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>INDOPTOL</synonyms></drug><drug><molecule_synonym>Indotard mr 75</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>INDOTARD MR 75</synonyms></drug><drug><molecule_synonym>Ledmecin</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>LEDMECIN</synonyms></drug><drug><molecule_synonym>Maximet sr</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>MAXIMET SR</synonyms></drug><drug><molecule_synonym>Mobilan</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>MOBILAN</synonyms></drug><drug><molecule_synonym>NSC-757061</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>NSC-757061</synonyms></drug><drug><molecule_synonym>NSC-77541</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>NSC-77541</synonyms></drug><drug><molecule_synonym>Pardelprin mr</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>PARDELPRIN MR</synonyms></drug><drug><molecule_synonym>Reumacide</molecule_synonym><syn_type>OTHER</syn_type><synonyms>REUMACIDE</synonyms></drug><drug><molecule_synonym>Rheumacin la</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>RHEUMACIN LA</synonyms></drug><drug><molecule_synonym>Rimacid</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>RIMACID</synonyms></drug><drug><molecule_synonym>Slo-indo</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>SLO-INDO</synonyms></drug><drug><molecule_synonym>Tivorbex</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>TIVORBEX</synonyms></drug></molecule_synonyms><ob_patent>8734847</ob_patent><oral>1</oral><parenteral>1</parenteral><prodrug/><research_codes><value>NSC-77541</value><value>NSC-757061</value></research_codes><rule_of_five>1</rule_of_five><sc_patent>US-8734847-B2</sc_patent><synonyms><value>Indometacin sodium (JAN)</value><value>Indometacin sodium hydrate (JAN)</value><value>Indomethacin sodium (USAN, USP)</value><value>Indomethacin sodium salt trihydrate (MI)</value><value>Indometacin (BAN, DCF, INN, JAN)</value><value>Indometacin farnesil (JAN)</value><value>Indomethacin (MI, USAN, USP)</value><value/></synonyms><topical>1</topical><usan_stem/><usan_stem_definition/><usan_stem_substem/><usan_year>1963</usan_year><withdrawn_flag>0</withdrawn_flag></drug><drug><applicants><value>Antibiotice Sa</value><value>Istituto Biochimico Italiano Spa</value><value>Sandoz Inc</value><value>Acs Dobfar Spa</value><value>Hospira Inc</value><value>Entasis Therapeutics Inc</value><value>Pfizer Inc</value><value>Steriscience Specialities Pte Ltd</value><value>Pfizer Laboratories Div Pfizer Inc</value><value>Hq Specialty Pharma Corp</value></applicants><atc_classification><drug><code>J01CG01</code><description>ANTIINFECTIVES FOR SYSTEMIC USE: ANTIBACTERIALS FOR SYSTEMIC USE: BETA-LACTAM ANTIBACTERIALS, PENICILLINS: Beta-lactamase inhibitors</description></drug></atc_classification><availability_type>1</availability_type><biotherapeutic/><black_box/><black_box_warning>0</black_box_warning><chirality>1</chirality><drug_type>1</drug_type><first_approval>1986</first_approval><first_in_class/><helm_notation/><max_phase>4.0</max_phase><molecule_chembl_id>CHEMBL403</molecule_chembl_id><molecule_properties><alogp>-0.79</alogp><aromatic_rings/><full_molformula>C8H11NO5S</full_molformula><full_mwt>233.24</full_mwt><hba>4</hba><hbd>1</hbd><heavy_atoms>15</heavy_atoms><mw_freebase>233.24</mw_freebase><np_likeness_score>0.77</np_likeness_score><num_ro5_violations/><psa>91.75</psa><qed_weighted>0.60</qed_weighted><ro3_pass>N</ro3_pass><rtb>1</rtb></molecule_properties><molecule_structures><canonical_smiles>CC1(C)[C@H](C(=O)O)N2C(=O)C[C@H]2S1(=O)=O</canonical_smiles><molfile>
     RDKit          2D

 16 17  0  0  1  0  0  0  0  0999 V2000
    3.9417   -0.6292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2667   -1.5542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3583   -1.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2667   -0.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9417   -1.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625   -1.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625   -0.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9375   -2.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5792   -0.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2917   -0.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0583   -2.0583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5458   -2.8417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3167   -2.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9667   -1.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9667   -0.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2625   -0.1375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  1  1  0
  4  1  1  0
  5  3  1  0
  6  7  1  0
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  5  8  1  6
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 10  1  2  0
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  4 16  1  6
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M  END</molfile><standard_inchi>InChI=1S/C8H11NO5S/c1-8(2)6(7(11)12)9-4(10)3-5(9)15(8,13)14/h5-6H,3H2,1-2H3,(H,11,12)/t5-,6+/m1/s1</standard_inchi><standard_inchi_key>FKENQMMABCRJMK-RITPCOANSA-N</standard_inchi_key></molecule_structures><molecule_synonyms><drug><molecule_synonym>CP-458992</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>CP-458992</synonyms></drug><drug><molecule_synonym>NSC-759886</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>NSC-759886</synonyms></drug><drug><molecule_synonym>Sulbactam</molecule_synonym><syn_type>ATC</syn_type><synonyms>SULBACTAM</synonyms></drug><drug><molecule_synonym>Sulbactam</molecule_synonym><syn_type>BAN</syn_type><synonyms>SULBACTAM</synonyms></drug><drug><molecule_synonym>Sulbactam</molecule_synonym><syn_type>INN</syn_type><synonyms>SULBACTAM</synonyms></drug><drug><molecule_synonym>Sulbactam</molecule_synonym><syn_type>MERCK_INDEX</syn_type><synonyms>SULBACTAM</synonyms></drug><drug><molecule_synonym>Sulbactam</molecule_synonym><syn_type>OTHER</syn_type><synonyms>SULBACTAM</synonyms></drug><drug><molecule_synonym>Sulbactam</molecule_synonym><syn_type>USP</syn_type><synonyms>SULBACTAM</synonyms></drug></molecule_synonyms><ob_patent>9309245</ob_patent><oral/><parenteral>1</parenteral><prodrug/><research_codes><value>CP-45899-2</value><value>CP-45899-99</value><value>NSC-759886</value><value>CP-45,899-99</value><value>CP-45,899-2</value><value>CP-458992</value></research_codes><rule_of_five>1</rule_of_five><sc_patent>US-9309245-B2</sc_patent><synonyms><value>Sulbactam sodium (JAN, USAN, USP)</value><value>Sulbactam sodium salt (MI)</value><value>Sulbactam (BAN, INN, MI, USP)</value><value>Sulbactam benzathine (USAN)</value><value/></synonyms><topical/><usan_stem>-bactam</usan_stem><usan_stem_definition>beta-lactamase inhibitors</usan_stem_definition><usan_stem_substem>-bactam(-bactam)</usan_stem_substem><usan_year>1980</usan_year><withdrawn_flag>0</withdrawn_flag></drug><drug><applicants/><atc_code_description/><availability_type/><biotherapeutic/><black_box/><black_box_warning>0</black_box_warning><chirality>2</chirality><drug_type>1</drug_type><first_approval/><first_in_class/><helm_notation/><max_phase>2.0</max_phase><molecule_chembl_id>CHEMBL6259</molecule_chembl_id><molecule_properties><alogp>2.72</alogp><aromatic_rings>3</aromatic_rings><full_molformula>C21H19F2N3O3</full_molformula><full_mwt>399.40</full_mwt><hba>5</hba><hbd>1</hbd><heavy_atoms>29</heavy_atoms><mw_freebase>399.40</mw_freebase><np_likeness_score>-1.08</np_likeness_score><num_ro5_violations/><psa>65.78</psa><qed_weighted>0.73</qed_weighted><ro3_pass>N</ro3_pass><rtb>3</rtb></molecule_properties><molecule_structures><canonical_smiles>CN1CCN(c2cc3c(cc2F)c(=O)c(C(=O)O)cn3-c2ccc(F)cc2)CC1</canonical_smiles><molfile>
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   -1.7985   -1.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0840    0.0284    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3696   -1.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3696   -0.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0840   -1.6216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7985   -0.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3449    0.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0594   -0.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3449   -1.6216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7739    0.0284    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5130   -1.6216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0594   -1.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0840    0.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2028    0.8534    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0840   -2.4466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7739    0.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4883   -0.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2274   -1.2091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7985    1.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3696    1.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2028    0.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4883    1.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7739   -1.6216    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5130   -2.4466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0840    2.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3696    2.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7985    2.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0840    3.3284    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.9173    1.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  4  2  0
  1  5  1  0
  3  5  1  0
  1  6  2  0
  2  6  1  0
  4  7  1  0
  7  8  2  0
  3  9  1  0
  8 10  1  0
  1 11  1  0
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  9 12  2  0
  2 13  1  0
  5 15  2  0
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M  END</molfile><standard_inchi>InChI=1S/C21H19F2N3O3/c1-24-6-8-25(9-7-24)19-11-18-15(10-17(19)23)20(27)16(21(28)29)12-26(18)14-4-2-13(22)3-5-14/h2-5,10-12H,6-9H2,1H3,(H,28,29)</standard_inchi><standard_inchi_key>NOCJXYPHIIZEHN-UHFFFAOYSA-N</standard_inchi_key></molecule_structures><molecule_synonyms><drug><molecule_synonym>Dicural</molecule_synonym><syn_type>OTHER</syn_type><synonyms>DICURAL</synonyms></drug><drug><molecule_synonym>Difloxacin</molecule_synonym><syn_type>EMA</syn_type><synonyms>DIFLOXACIN</synonyms></drug><drug><molecule_synonym>Difloxacin</molecule_synonym><syn_type>INN</syn_type><synonyms>DIFLOXACIN</synonyms></drug><drug><molecule_synonym>Difloxacine</molecule_synonym><syn_type>INN_FRENCH</syn_type><synonyms>DIFLOXACINE</synonyms></drug><drug><molecule_synonym>Difloxacino</molecule_synonym><syn_type>INN_SPANISH</syn_type><synonyms>DIFLOXACINO</synonyms></drug><drug><molecule_synonym>Pulsaflox</molecule_synonym><syn_type>OTHER</syn_type><synonyms>PULSAFLOX</synonyms></drug><drug><molecule_synonym>Pulsaflox</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>PULSAFLOX</synonyms></drug></molecule_synonyms><ob_patent/><oral/><parenteral/><prodrug/><research_codes><value>NSC-759646</value><value>ABBOTT-56619</value></research_codes><rule_of_five>1</rule_of_five><sc_patent/><synonyms><value>Difloxacin (INN)</value><value>Difloxacin hydrochloride (USAN)</value><value>Difloxacin monohydrochloride (MI)</value><value/></synonyms><topical/><usan_stem>-oxacin</usan_stem><usan_stem_definition>antibacterials (quinolone derivatives)</usan_stem_definition><usan_stem_substem>-oxacin(-oxacin)</usan_stem_substem><usan_year>1986</usan_year><withdrawn_flag>0</withdrawn_flag></drug><drug><applicants><value>Sandoz Inc</value><value>Istituto Biochimico Italiano Spa</value><value>Fresenius Kabi Usa Llc</value><value>Provepharm Sas</value><value>Fresenius Kabi Anti Infectives Srl</value><value>Hospira Inc</value><value>Astral Steritech Pvt Ltd</value><value>Baxter Healthcare Corp</value><value>Cubist Pharmaceuticals Llc</value><value>Steriscience Specialities Pte Ltd</value></applicants><atc_classification><drug><code>J01CG02</code><description>ANTIINFECTIVES FOR SYSTEMIC USE: ANTIBACTERIALS FOR SYSTEMIC USE: BETA-LACTAM ANTIBACTERIALS, PENICILLINS: Beta-lactamase inhibitors</description></drug></atc_classification><availability_type>1</availability_type><biotherapeutic/><black_box/><black_box_warning>0</black_box_warning><chirality>1</chirality><drug_type>1</drug_type><first_approval>1993</first_approval><first_in_class/><helm_notation/><max_phase>4.0</max_phase><molecule_chembl_id>CHEMBL404</molecule_chembl_id><molecule_properties><alogp>-1.52</alogp><aromatic_rings>1</aromatic_rings><full_molformula>C10H12N4O5S</full_molformula><full_mwt>300.30</full_mwt><hba>7</hba><hbd>1</hbd><heavy_atoms>20</heavy_atoms><mw_freebase>300.30</mw_freebase><np_likeness_score>-0.31</np_likeness_score><num_ro5_violations/><psa>122.46</psa><qed_weighted>0.67</qed_weighted><ro3_pass>N</ro3_pass><rtb>3</rtb></molecule_properties><molecule_structures><canonical_smiles>C[C@]1(Cn2ccnn2)[C@H](C(=O)O)N2C(=O)C[C@H]2S1(=O)=O</canonical_smiles><molfile>
     RDKit          2D

 21 23  0  0  1  0  0  0  0  0999 V2000
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    4.7042  -10.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  4  1  0
  3  1  1  0
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M  END
</molfile><standard_inchi>InChI=1S/C10H12N4O5S/c1-10(5-13-3-2-11-12-13)8(9(16)17)14-6(15)4-7(14)20(10,18)19/h2-3,7-8H,4-5H2,1H3,(H,16,17)/t7-,8+,10+/m1/s1</standard_inchi><standard_inchi_key>LPQZKKCYTLCDGQ-WEDXCCLWSA-N</standard_inchi_key></molecule_structures><molecule_synonyms><drug><molecule_synonym>CL 298,741</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>CL 298,741</synonyms></drug><drug><molecule_synonym>CL-298741</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>CL-298741</synonyms></drug><drug><molecule_synonym>NSC-759887</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>NSC-759887</synonyms></drug><drug><molecule_synonym>Tazobactam</molecule_synonym><syn_type>ATC</syn_type><synonyms>TAZOBACTAM</synonyms></drug><drug><molecule_synonym>Tazobactam</molecule_synonym><syn_type>BAN</syn_type><synonyms>TAZOBACTAM</synonyms></drug><drug><molecule_synonym>Tazobactam</molecule_synonym><syn_type>INN</syn_type><synonyms>TAZOBACTAM</synonyms></drug><drug><molecule_synonym>Tazobactam</molecule_synonym><syn_type>JAN</syn_type><synonyms>TAZOBACTAM</synonyms></drug><drug><molecule_synonym>Tazobactam</molecule_synonym><syn_type>MERCK_INDEX</syn_type><synonyms>TAZOBACTAM</synonyms></drug><drug><molecule_synonym>Tazobactam</molecule_synonym><syn_type>OTHER</syn_type><synonyms>TAZOBACTAM</synonyms></drug><drug><molecule_synonym>Tazobactam</molecule_synonym><syn_type>USAN</syn_type><synonyms>TAZOBACTAM</synonyms></drug><drug><molecule_synonym>Tazobactam</molecule_synonym><syn_type>USP</syn_type><synonyms>TAZOBACTAM</synonyms></drug><drug><molecule_synonym>YTR-830H</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>YTR-830H</synonyms></drug></molecule_synonyms><ob_patent>7129232</ob_patent><oral/><parenteral>1</parenteral><prodrug/><research_codes><value>CL 307,579</value><value>YTR-830H</value><value>CL-307579</value><value>CL-298741</value><value>NSC-759887</value><value>CL 298,741</value></research_codes><rule_of_five>1</rule_of_five><sc_patent>US-7129232-B2</sc_patent><synonyms><value>Tazobactam sodium (USAN)</value><value>Tazobactam sodium salt (MI)</value><value>Tazobactam (BAN, INN, JAN, MI, USAN, USP)</value><value/></synonyms><topical/><usan_stem>-bactam</usan_stem><usan_stem_definition>beta-lactamase inhibitors</usan_stem_definition><usan_stem_substem>-bactam(-bactam)</usan_stem_substem><usan_year>1989</usan_year><withdrawn_flag>0</withdrawn_flag></drug><drug><applicants/><atc_classification><drug><code>J01MA08</code><description>ANTIINFECTIVES FOR SYSTEMIC USE: ANTIBACTERIALS FOR SYSTEMIC USE: QUINOLONE ANTIBACTERIALS: Fluoroquinolones</description></drug></atc_classification><availability_type/><biotherapeutic/><black_box/><black_box_warning>0</black_box_warning><chirality>2</chirality><drug_type>1</drug_type><first_approval/><first_in_class/><helm_notation/><max_phase>2.0</max_phase><molecule_chembl_id>CHEMBL6273</molecule_chembl_id><molecule_properties><alogp>1.70</alogp><aromatic_rings>2</aromatic_rings><full_molformula>C17H18F3N3O3</full_molformula><full_mwt>369.34</full_mwt><hba>5</hba><hbd>1</hbd><heavy_atoms>26</heavy_atoms><mw_freebase>369.34</mw_freebase><np_likeness_score>-0.86</np_likeness_score><num_ro5_violations/><psa>65.78</psa><qed_weighted>0.89</qed_weighted><ro3_pass>N</ro3_pass><rtb>4</rtb></molecule_properties><molecule_structures><canonical_smiles>CN1CCN(c2c(F)cc3c(=O)c(C(=O)O)cn(CCF)c3c2F)CC1</canonical_smiles><molfile>
     RDKit          2D

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M  END
</molfile><standard_inchi>InChI=1S/C17H18F3N3O3/c1-21-4-6-22(7-5-21)15-12(19)8-10-14(13(15)20)23(3-2-18)9-11(16(10)24)17(25)26/h8-9H,2-7H2,1H3,(H,25,26)</standard_inchi><standard_inchi_key>XBJBPGROQZJDOJ-UHFFFAOYSA-N</standard_inchi_key></molecule_structures><molecule_synonyms><drug><molecule_synonym>AM-833</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>AM-833</synonyms></drug><drug><molecule_synonym>Fleroxacin</molecule_synonym><syn_type>ATC</syn_type><synonyms>FLEROXACIN</synonyms></drug><drug><molecule_synonym>Fleroxacin</molecule_synonym><syn_type>BAN</syn_type><synonyms>FLEROXACIN</synonyms></drug><drug><molecule_synonym>Fleroxacin</molecule_synonym><syn_type>INN</syn_type><synonyms>FLEROXACIN</synonyms></drug><drug><molecule_synonym>Fleroxacin</molecule_synonym><syn_type>JAN</syn_type><synonyms>FLEROXACIN</synonyms></drug><drug><molecule_synonym>Fleroxacin</molecule_synonym><syn_type>USAN</syn_type><synonyms>FLEROXACIN</synonyms></drug><drug><molecule_synonym>Fleroxacine</molecule_synonym><syn_type>INN_FRENCH</syn_type><synonyms>FLEROXACINE</synonyms></drug><drug><molecule_synonym>Fleroxacino</molecule_synonym><syn_type>INN_SPANISH</syn_type><synonyms>FLEROXACINO</synonyms></drug><drug><molecule_synonym>Megalocin</molecule_synonym><syn_type>OTHER</syn_type><synonyms>MEGALOCIN</synonyms></drug><drug><molecule_synonym>Megalone</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>MEGALONE</synonyms></drug><drug><molecule_synonym>RO-236240</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>RO-236240</synonyms></drug><drug><molecule_synonym>RO 23-6240/000</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>RO 23-6240/000</synonyms></drug><drug><molecule_synonym>RO-23-6240/000</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>RO-23-6240/000</synonyms></drug><drug><molecule_synonym>RO-236240000</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>RO-236240000</synonyms></drug></molecule_synonyms><ob_patent/><oral/><parenteral/><prodrug/><research_codes><value>AM-833</value><value>RO-236240000</value><value>RO-236240</value><value>RO-23-6240/000</value><value>RO 23-6240/000</value></research_codes><rule_of_five>1</rule_of_five><sc_patent/><synonyms><value>Fleroxacin (BAN, INN, JAN, USAN)</value><value/></synonyms><topical/><usan_stem>-oxacin</usan_stem><usan_stem_definition>antibacterials (quinolone derivatives)</usan_stem_definition><usan_stem_substem>-oxacin(-oxacin)</usan_stem_substem><usan_year>1987</usan_year><withdrawn_flag>0</withdrawn_flag></drug><drug><applicants/><atc_code_description/><availability_type/><biotherapeutic/><black_box/><black_box_warning>0</black_box_warning><chirality/><drug_type>1</drug_type><first_approval/><first_in_class/><helm_notation/><max_phase>2.0</max_phase><molecule_chembl_id>CHEMBL6209</molecule_chembl_id><molecule_properties><alogp>2.43</alogp><aromatic_rings>2</aromatic_rings><full_molformula>C19H23F2N3O3</full_molformula><full_mwt>379.41</full_mwt><hba>5</hba><hbd>2</hbd><heavy_atoms>27</heavy_atoms><mw_freebase>379.41</mw_freebase><np_likeness_score>-0.80</np_likeness_score><num_ro5_violations/><psa>74.57</psa><qed_weighted>0.81</qed_weighted><ro3_pass>N</ro3_pass><rtb>6</rtb></molecule_properties><molecule_structures><canonical_smiles>CCNCC1CCN(c2c(F)cc3c(=O)c(C(=O)O)cn(CC)c3c2F)C1</canonical_smiles><molfile>
     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
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M  END
</molfile><standard_inchi>InChI=1S/C19H23F2N3O3/c1-3-22-8-11-5-6-24(9-11)17-14(20)7-12-16(15(17)21)23(4-2)10-13(18(12)25)19(26)27/h7,10-11,22H,3-6,8-9H2,1-2H3,(H,26,27)</standard_inchi><standard_inchi_key>BAYYCLWCHFVRLV-UHFFFAOYSA-N</standard_inchi_key></molecule_structures><molecule_synonyms><drug><molecule_synonym>CI-934</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>CI-934</synonyms></drug><drug><molecule_synonym>Merafloxacin</molecule_synonym><syn_type>INN</syn_type><synonyms>MERAFLOXACIN</synonyms></drug><drug><molecule_synonym>Merafloxacine</molecule_synonym><syn_type>INN_FRENCH</syn_type><synonyms>MERAFLOXACINE</synonyms></drug><drug><molecule_synonym>Merafloxacino</molecule_synonym><syn_type>INN_SPANISH</syn_type><synonyms>MERAFLOXACINO</synonyms></drug></molecule_synonyms><ob_patent/><oral/><parenteral/><prodrug/><research_codes><value>CI-934</value></research_codes><rule_of_five>1</rule_of_five><sc_patent/><synonyms><value>Merafloxacin (INN)</value><value/></synonyms><topical/><usan_stem>-oxacin</usan_stem><usan_stem_definition>antibacterials (quinolone derivatives)</usan_stem_definition><usan_stem_substem>-oxacin(-oxacin)</usan_stem_substem><usan_year/><withdrawn_flag>0</withdrawn_flag></drug><drug><applicants/><atc_code_description/><availability_type/><biotherapeutic/><black_box/><black_box_warning>0</black_box_warning><chirality>2</chirality><drug_type>1</drug_type><first_approval/><first_in_class/><helm_notation/><max_phase>2.0</max_phase><molecule_chembl_id>CHEMBL6231</molecule_chembl_id><molecule_properties><alogp>0.76</alogp><aromatic_rings>2</aromatic_rings><full_molformula>C16H19FN4O3</full_molformula><full_mwt>334.35</full_mwt><hba>6</hba><hbd>2</hbd><heavy_atoms>24</heavy_atoms><mw_freebase>334.35</mw_freebase><np_likeness_score>-0.94</np_likeness_score><num_ro5_violations/><psa>77.81</psa><qed_weighted>0.86</qed_weighted><ro3_pass>N</ro3_pass><rtb>3</rtb></molecule_properties><molecule_structures><canonical_smiles>CNn1cc(C(=O)O)c(=O)c2cc(F)c(N3CCN(C)CC3)cc21</canonical_smiles><molfile>
     RDKit          2D

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M  END
</molfile><standard_inchi>InChI=1S/C16H19FN4O3/c1-18-21-9-11(16(23)24)15(22)10-7-12(17)14(8-13(10)21)20-5-3-19(2)4-6-20/h7-9,18H,3-6H2,1-2H3,(H,23,24)</standard_inchi><standard_inchi_key>RUXPNBWPIRDVTH-UHFFFAOYSA-N</standard_inchi_key></molecule_structures><molecule_synonyms><drug><molecule_synonym>Amifloxacin</molecule_synonym><syn_type>BAN</syn_type><synonyms>AMIFLOXACIN</synonyms></drug><drug><molecule_synonym>Amifloxacin</molecule_synonym><syn_type>INN</syn_type><synonyms>AMIFLOXACIN</synonyms></drug><drug><molecule_synonym>Amifloxacin</molecule_synonym><syn_type>USAN</syn_type><synonyms>AMIFLOXACIN</synonyms></drug><drug><molecule_synonym>Amifloxacine</molecule_synonym><syn_type>INN_FRENCH</syn_type><synonyms>AMIFLOXACINE</synonyms></drug><drug><molecule_synonym>Amifloxacino</molecule_synonym><syn_type>INN_SPANISH</syn_type><synonyms>AMIFLOXACINO</synonyms></drug><drug><molecule_synonym>WIN 49,375</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>WIN 49,375</synonyms></drug><drug><molecule_synonym>WIN-49,375</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>WIN-49,375</synonyms></drug><drug><molecule_synonym>WIN-49375</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>WIN-49375</synonyms></drug></molecule_synonyms><ob_patent/><oral/><parenteral/><prodrug/><research_codes><value>WIN 49,375-3</value><value>WIN-49375</value><value>WIN-49375-3</value><value>WIN 49,375</value><value>WIN-49,375</value></research_codes><rule_of_five>1</rule_of_five><sc_patent/><synonyms><value>Amifloxacin mesylate (USAN)</value><value>Amifloxacin (BAN, INN, USAN)</value><value/></synonyms><topical/><usan_stem>-oxacin</usan_stem><usan_stem_definition>antibacterials (quinolone derivatives)</usan_stem_definition><usan_stem_substem>-oxacin(-oxacin)</usan_stem_substem><usan_year>1984</usan_year><withdrawn_flag>0</withdrawn_flag></drug><drug><applicants><value>Yiling Pharmaceutical Ltd</value><value>Laboratorios Salvat Sa</value><value>Depomed Inc</value><value>Teva Pharmaceuticals Usa</value><value>Identirx Llc</value><value>Aurobindo Pharma Ltd</value><value>Bayer Healthcare Pharmaceuticals Inc</value><value>Aiping Pharmaceutical Inc</value><value>Nostrum Laboratories Inc</value><value>Teva Pharmaceuticals Usa Inc</value></applicants><atc_classification><drug><code>S01AE03</code><description>SENSORY ORGANS: OPHTHALMOLOGICALS: ANTIINFECTIVES: Fluoroquinolone</description></drug><drug><code>S02AA15</code><description>SENSORY ORGANS: OTOLOGICALS: ANTIINFECTIVES: Antiinfective</description></drug><drug><code>S03AA07</code><description>SENSORY ORGANS: OPHTHALMOLOGICAL AND OTOLOGICAL PREPARATIONS: ANTIINFECTIVES: Antiinfective</description></drug><drug><code>J01MA02</code><description>ANTIINFECTIVES FOR SYSTEMIC USE: ANTIBACTERIALS FOR SYSTEMIC USE: QUINOLONE ANTIBACTERIALS: Fluoroquinolones</description></drug></atc_classification><availability_type>1</availability_type><biotherapeutic/><black_box>1</black_box><black_box_warning>1</black_box_warning><chirality>2</chirality><drug_type>1</drug_type><first_approval>1987</first_approval><first_in_class/><helm_notation/><max_phase>4.0</max_phase><molecule_chembl_id>CHEMBL8</molecule_chembl_id><molecule_properties><alogp>1.58</alogp><aromatic_rings>2</aromatic_rings><full_molformula>C17H18FN3O3</full_molformula><full_mwt>331.35</full_mwt><hba>5</hba><hbd>2</hbd><heavy_atoms>24</heavy_atoms><mw_freebase>331.35</mw_freebase><np_likeness_score>-0.72</np_likeness_score><num_ro5_violations/><psa>74.57</psa><qed_weighted>0.89</qed_weighted><ro3_pass>N</ro3_pass><rtb>3</rtb></molecule_properties><molecule_structures><canonical_smiles>O=C(O)c1cn(C2CC2)c2cc(N3CCNCC3)c(F)cc2c1=O</canonical_smiles><molfile>
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    2.1792   -0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2625    0.6625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3542   -0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3542    0.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5583    0.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4708    0.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5583   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1167   -1.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3833    1.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2083    0.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2958    2.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  1  0
  3  5  1  0
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 14 15  1  0
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 23 17  1  0
M  END
</molfile><standard_inchi>InChI=1S/C17H18FN3O3/c18-13-7-11-14(8-15(13)20-5-3-19-4-6-20)21(10-1-2-10)9-12(16(11)22)17(23)24/h7-10,19H,1-6H2,(H,23,24)</standard_inchi><standard_inchi_key>MYSWGUAQZAJSOK-UHFFFAOYSA-N</standard_inchi_key></molecule_structures><molecule_synonyms><drug><molecule_synonym>BAY O 9867 FREE BASE</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>BAY O 9867 FREE BASE</synonyms></drug><drug><molecule_synonym>BAY-O-9867 FREE BASE</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>BAY-O-9867 FREE BASE</synonyms></drug><drug><molecule_synonym>BAY Q 3939</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>BAY Q 3939</synonyms></drug><drug><molecule_synonym>BAY-Q-3939</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>BAY-Q-3939</synonyms></drug><drug><molecule_synonym>BAYQ3939</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>BAYQ3939</synonyms></drug><drug><molecule_synonym>Cetraxal</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>CETRAXAL</synonyms></drug><drug><molecule_synonym>Cipro</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>CIPRO</synonyms></drug><drug><molecule_synonym>Ciprofloxacin</molecule_synonym><syn_type>ATC</syn_type><synonyms>CIPROFLOXACIN</synonyms></drug><drug><molecule_synonym>Ciprofloxacin</molecule_synonym><syn_type>BAN</syn_type><synonyms>CIPROFLOXACIN</synonyms></drug><drug><molecule_synonym>Ciprofloxacin</molecule_synonym><syn_type>BNF</syn_type><synonyms>CIPROFLOXACIN</synonyms></drug><drug><molecule_synonym>Ciprofloxacin</molecule_synonym><syn_type>FDA</syn_type><synonyms>CIPROFLOXACIN</synonyms></drug><drug><molecule_synonym>Ciprofloxacin</molecule_synonym><syn_type>INN</syn_type><synonyms>CIPROFLOXACIN</synonyms></drug><drug><molecule_synonym>Ciprofloxacin</molecule_synonym><syn_type>JAN</syn_type><synonyms>CIPROFLOXACIN</synonyms></drug><drug><molecule_synonym>Ciprofloxacin</molecule_synonym><syn_type>MERCK_INDEX</syn_type><synonyms>CIPROFLOXACIN</synonyms></drug><drug><molecule_synonym>Ciprofloxacin</molecule_synonym><syn_type>OTHER</syn_type><synonyms>CIPROFLOXACIN</synonyms></drug><drug><molecule_synonym>Ciprofloxacin</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>CIPROFLOXACIN</synonyms></drug><drug><molecule_synonym>Ciprofloxacin</molecule_synonym><syn_type>USAN</syn_type><synonyms>CIPROFLOXACIN</synonyms></drug><drug><molecule_synonym>Ciprofloxacin</molecule_synonym><syn_type>USP</syn_type><synonyms>CIPROFLOXACIN</synonyms></drug><drug><molecule_synonym>Ciprofloxacin component of ciprodex</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>CIPROFLOXACIN COMPONENT OF CIPRODEX</synonyms></drug><drug><molecule_synonym>Ciprofloxacine</molecule_synonym><syn_type>INN_FRENCH</syn_type><synonyms>CIPROFLOXACINE</synonyms></drug><drug><molecule_synonym>Ciprofloxacino</molecule_synonym><syn_type>INN_SPANISH</syn_type><synonyms>CIPROFLOXACINO</synonyms></drug><drug><molecule_synonym>Ciprofloxacinum</molecule_synonym><syn_type>OTHER</syn_type><synonyms>CIPROFLOXACINUM</synonyms></drug><drug><molecule_synonym>NSC-758467</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>NSC-758467</synonyms></drug><drug><molecule_synonym>Otiprio</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>OTIPRIO</synonyms></drug><drug><molecule_synonym>Velmonit</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>Velmonit</synonyms></drug></molecule_synonyms><ob_patent>8318817</ob_patent><oral>1</oral><parenteral>1</parenteral><prodrug/><research_codes><value>BAY-O-9867 MONOHYDRATE</value><value>BAY O 9867</value><value>BAY Q 3939</value><value>BAY O 9867 FREE BASE</value><value>BAYQ3939</value><value>BAY O 9867 MONOHYDRATE</value><value>BAY-O-9867 FREE BASE</value><value>NSC-758467</value><value>BAY-O-9867</value><value>BAY-Q-3939</value></research_codes><rule_of_five>1</rule_of_five><sc_patent>US-8318817-B2</sc_patent><synonyms><value>Ciprofloxacin (BAN, INN, JAN, MI, USAN, USP)</value><value>Ciprofloxacin hydrochloride (JAN, USAN, USP)</value><value>Ciprofloxacin hydrochloride hydrate (JAN)</value><value>Ciprofloxacin hydrochloride monohydrate (MI)</value><value/></synonyms><topical>1</topical><usan_stem>-oxacin</usan_stem><usan_stem_definition>antibacterials (quinolone derivatives)</usan_stem_definition><usan_stem_substem>-oxacin(-oxacin)</usan_stem_substem><usan_year>1987</usan_year><withdrawn_flag>0</withdrawn_flag></drug><drug><applicants><value>Merck Research Laboratories Div Merck Co Inc</value></applicants><atc_classification><drug><code>J01MA06</code><description>ANTIINFECTIVES FOR SYSTEMIC USE: ANTIBACTERIALS FOR SYSTEMIC USE: QUINOLONE ANTIBACTERIALS: Fluoroquinolone</description></drug><drug><code>S01AE02</code><description>SENSORY ORGANS: OPHTHALMOLOGICALS: ANTIINFECTIVES: Fluoroquinolones</description></drug></atc_classification><availability_type/><biotherapeutic/><black_box>1</black_box><black_box_warning>1</black_box_warning><chirality>2</chirality><drug_type>1</drug_type><first_approval>1986</first_approval><first_in_class/><helm_notation/><max_phase>4.0</max_phase><molecule_chembl_id>CHEMBL9</molecule_chembl_id><molecule_properties><alogp>1.27</alogp><aromatic_rings>2</aromatic_rings><full_molformula>C16H18FN3O3</full_molformula><full_mwt>319.34</full_mwt><hba>5</hba><hbd>2</hbd><heavy_atoms>23</heavy_atoms><mw_freebase>319.34</mw_freebase><np_likeness_score>-0.97</np_likeness_score><num_ro5_violations/><psa>74.57</psa><qed_weighted>0.89</qed_weighted><ro3_pass>N</ro3_pass><rtb>3</rtb></molecule_properties><molecule_structures><canonical_smiles>CCn1cc(C(=O)O)c(=O)c2cc(F)c(N3CCNCC3)cc21</canonical_smiles><molfile>
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    6.6500   -5.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4000   -5.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0250   -5.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4000   -4.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6500   -4.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0250   -4.4875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7792   -4.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1542   -4.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7792   -5.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5417   -4.4917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0
  3  1  1  0
  4  6  1  0
  5  1  2  0
  6  5  1  0
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  8  7  1  0
  9  2  2  0
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M  END
</molfile><standard_inchi>InChI=1S/C16H18FN3O3/c1-2-19-9-11(16(22)23)15(21)10-7-12(17)14(8-13(10)19)20-5-3-18-4-6-20/h7-9,18H,2-6H2,1H3,(H,22,23)</standard_inchi><standard_inchi_key>OGJPXUAPXNRGGI-UHFFFAOYSA-N</standard_inchi_key></molecule_structures><molecule_synonyms><drug><molecule_synonym>Baccidal</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>Baccidal</synonyms></drug><drug><molecule_synonym>Chibroxin</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>CHIBROXIN</synonyms></drug><drug><molecule_synonym>MK-366</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>MK-366</synonyms></drug><drug><molecule_synonym>Norfloxacin</molecule_synonym><syn_type>ATC</syn_type><synonyms>NORFLOXACIN</synonyms></drug><drug><molecule_synonym>Norfloxacin</molecule_synonym><syn_type>BAN</syn_type><synonyms>NORFLOXACIN</synonyms></drug><drug><molecule_synonym>Norfloxacin</molecule_synonym><syn_type>BNF</syn_type><synonyms>NORFLOXACIN</synonyms></drug><drug><molecule_synonym>Norfloxacin</molecule_synonym><syn_type>FDA</syn_type><synonyms>NORFLOXACIN</synonyms></drug><drug><molecule_synonym>Norfloxacin</molecule_synonym><syn_type>INN</syn_type><synonyms>NORFLOXACIN</synonyms></drug><drug><molecule_synonym>Norfloxacin</molecule_synonym><syn_type>JAN</syn_type><synonyms>NORFLOXACIN</synonyms></drug><drug><molecule_synonym>Norfloxacin</molecule_synonym><syn_type>MERCK_INDEX</syn_type><synonyms>NORFLOXACIN</synonyms></drug><drug><molecule_synonym>Norfloxacin</molecule_synonym><syn_type>OTHER</syn_type><synonyms>NORFLOXACIN</synonyms></drug><drug><molecule_synonym>Norfloxacin</molecule_synonym><syn_type>USAN</syn_type><synonyms>NORFLOXACIN</synonyms></drug><drug><molecule_synonym>Norfloxacin</molecule_synonym><syn_type>USP</syn_type><synonyms>NORFLOXACIN</synonyms></drug><drug><molecule_synonym>Norfloxacine</molecule_synonym><syn_type>INN_FRENCH</syn_type><synonyms>NORFLOXACINE</synonyms></drug><drug><molecule_synonym>Norfloxacino</molecule_synonym><syn_type>INN_SPANISH</syn_type><synonyms>NORFLOXACINO</synonyms></drug><drug><molecule_synonym>Noroxin</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>NOROXIN</synonyms></drug><drug><molecule_synonym>NSC-757250</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>NSC-757250</synonyms></drug><drug><molecule_synonym>Quinabic</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>Quinabic</synonyms></drug><drug><molecule_synonym>Utinor</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>UTINOR</synonyms></drug></molecule_synonyms><ob_patent/><oral>1</oral><parenteral/><prodrug/><research_codes><value>NSC-757250</value><value>MK-366</value></research_codes><rule_of_five>1</rule_of_five><sc_patent/><synonyms><value>Norfloxacin (BAN, INN, JAN, MI, USAN, USP)</value><value/></synonyms><topical>1</topical><usan_stem>-oxacin</usan_stem><usan_stem_definition>antibacterials (quinolone derivatives)</usan_stem_definition><usan_stem_substem>-oxacin(-oxacin)</usan_stem_substem><usan_year>1984</usan_year><withdrawn_flag>0</withdrawn_flag></drug><drug><applicants/><atc_code_description/><availability_type/><biotherapeutic/><black_box/><black_box_warning>0</black_box_warning><chirality>2</chirality><drug_type>1</drug_type><first_approval/><first_in_class/><helm_notation/><max_phase>1.0</max_phase><molecule_chembl_id>CHEMBL269538</molecule_chembl_id><molecule_properties><alogp>3.03</alogp><aromatic_rings>3</aromatic_rings><full_molformula>C13H12N2O</full_molformula><full_mwt>212.25</full_mwt><hba>2</hba><hbd>1</hbd><heavy_atoms>16</heavy_atoms><mw_freebase>212.25</mw_freebase><np_likeness_score>0.29</np_likeness_score><num_ro5_violations/><psa>37.91</psa><qed_weighted>0.67</qed_weighted><ro3_pass>N</ro3_pass><rtb>1</rtb></molecule_properties><molecule_structures><canonical_smiles>COc1ccc2c(c1)[nH]c1c(C)nccc12</canonical_smiles><molfile>
     RDKit          2D

 16 18  0  0  0  0  0  0  0  0999 V2000
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    3.8532   -0.5260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3012    0.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5561    0.8717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0991    0.8717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0570   -1.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2393   -0.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0
  1 16  1  0
  2  6  1  0
  2  7  1  0
  3  8  1  0
  3 14  2  0
  4  5  1  0
  4  6  1  0
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 10 13  1  0
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M  END</molfile><standard_inchi>InChI=1S/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H3</standard_inchi><standard_inchi_key>BXNJHAXVSOCGBA-UHFFFAOYSA-N</standard_inchi_key></molecule_structures><molecule_synonyms><drug><molecule_synonym>Harmine</molecule_synonym><syn_type>MERCK_INDEX</syn_type><synonyms>HARMINE</synonyms></drug><drug><molecule_synonym>Harmine</molecule_synonym><syn_type>OTHER</syn_type><synonyms>HARMINE</synonyms></drug></molecule_synonyms><ob_patent/><oral/><parenteral/><prodrug/><research_codes/><rule_of_five>1</rule_of_five><sc_patent/><synonyms><value>Harmine (MI)</value><value/></synonyms><topical/><usan_stem/><usan_stem_definition/><usan_stem_substem/><usan_year/><withdrawn_flag>0</withdrawn_flag></drug><drug><applicants/><atc_code_description/><availability_type/><biotherapeutic/><black_box/><black_box_warning>0</black_box_warning><chirality>2</chirality><drug_type>1</drug_type><first_approval/><first_in_class/><helm_notation/><max_phase>2.0</max_phase><molecule_chembl_id>CHEMBL6318</molecule_chembl_id><molecule_properties><alogp>7.13</alogp><aromatic_rings>3</aromatic_rings><full_molformula>C28H30INO</full_molformula><full_mwt>523.46</full_mwt><hba>2</hba><hbd/><heavy_atoms>31</heavy_atoms><mw_freebase>523.46</mw_freebase><np_likeness_score>-0.83</np_likeness_score><num_ro5_violations>2</num_ro5_violations><psa>12.47</psa><qed_weighted>0.23</qed_weighted><ro3_pass>N</ro3_pass><rtb>8</rtb></molecule_properties><molecule_structures><canonical_smiles>CC/C(=C(\c1ccc(I)cc1)c1ccc(OCCN2CCCC2)cc1)c1ccccc1</canonical_smiles><molfile>
     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   -1.2458   -0.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0833   -0.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5208    0.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2458    0.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2458   -1.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0125   -1.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0125    0.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0125   -2.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0125    1.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4000   -1.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8333   -2.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8333    1.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4000    0.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4000   -3.4375    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4958   -1.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4000    2.2833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    2.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0042    3.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8792    2.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1083    0.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3375    0.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5083   -1.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7417    3.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5208    1.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7458    0.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3375    1.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  1  1  0
  5 20  1  0
  6  2  1  0
  7  3  1  0
  8  4  2  0
  9  4  1  0
 10  3  2  0
 11 13  1  0
 12 16  2  0
 13  9  2  0
 14  8  1  0
 15  7  2  0
 16 10  1  0
 17 11  1  0
 18  2  1  0
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 20 21  1  0
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 22  5  1  0
 23  5  1  0
 24  6  2  0
 25  6  1  0
 26 18  1  0
 27 22  1  0
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 29 24  1  0
 30 25  2  0
 31 30  1  0
 14 11  2  0
 15 12  1  0
 29 31  2  0
 27 28  1  0
M  END
</molfile><standard_inchi>InChI=1S/C28H30INO/c1-2-27(22-8-4-3-5-9-22)28(23-10-14-25(29)15-11-23)24-12-16-26(17-13-24)31-21-20-30-18-6-7-19-30/h3-5,8-17H,2,6-7,18-21H2,1H3/b28-27-</standard_inchi><standard_inchi_key>JJKOTMDDZAJTGQ-DQSJHHFOSA-N</standard_inchi_key></molecule_structures><molecule_synonyms><drug><molecule_synonym>CB 7432</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>CB 7432</synonyms></drug><drug><molecule_synonym>CB-7432</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>CB-7432</synonyms></drug><drug><molecule_synonym>CB7432</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>CB7432</synonyms></drug><drug><molecule_synonym>Idoxifene</molecule_synonym><syn_type>USAN</syn_type><synonyms>Idoxifene</synonyms></drug><drug><molecule_synonym>Idoxifene</molecule_synonym><syn_type>BAN</syn_type><synonyms>IDOXIFENE</synonyms></drug><drug><molecule_synonym>Idoxifene</molecule_synonym><syn_type>INN</syn_type><synonyms>IDOXIFENE</synonyms></drug><drug><molecule_synonym>Idoxifeno</molecule_synonym><syn_type>INN_SPANISH</syn_type><synonyms>IDOXIFENO</synonyms></drug><drug><molecule_synonym>SB-223030</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>SB-223030</synonyms></drug><drug><molecule_synonym>SB223030</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>SB223030</synonyms></drug></molecule_synonyms><ob_patent/><oral/><parenteral/><prodrug/><research_codes><value>CB 7432</value><value>CB-7432</value><value>CB7432</value><value>SB-223030</value><value>SB223030</value></research_codes><rule_of_five/><sc_patent/><synonyms><value>Idoxifene (BAN, INN, USAN, USAN)</value><value/></synonyms><topical/><usan_stem>-ifene</usan_stem><usan_stem_definition>antiestrogens of the clomifene and tamoxifen groups</usan_stem_definition><usan_stem_substem>-ifene(-ifene)</usan_stem_substem><usan_year>1996</usan_year><withdrawn_flag>0</withdrawn_flag></drug><drug><applicants><value>Prinston Pharmaceutical Inc</value><value>Granules Pharmaceuticals Inc</value><value>Neos Therapeutics Inc</value><value>Tris Pharma Inc</value><value>Alkem Laboratories Ltd</value><value>Teva Pharmaceuticals Usa</value><value>Actavis Laboratories Fl Inc</value><value>Impax Laboratories Inc</value><value>Aurolife Pharma Llc</value><value>Teva Pharmaceuticals Usa Inc</value></applicants><atc_classification><drug><code>N06BA01</code><description>NERVOUS SYSTEM: PSYCHOANALEPTICS: PSYCHOSTIMULANTS, AGENTS USED FOR ADHD AND NOOTROPICS: Centrally acting sympathomimetics</description></drug></atc_classification><availability_type>1</availability_type><biotherapeutic/><black_box>1</black_box><black_box_warning>1</black_box_warning><chirality/><drug_type>1</drug_type><first_approval>1955</first_approval><first_in_class/><helm_notation/><max_phase>4.0</max_phase><molecule_chembl_id>CHEMBL405</molecule_chembl_id><molecule_properties><alogp>1.58</alogp><aromatic_rings>1</aromatic_rings><full_molformula>C9H13N</full_molformula><full_mwt>135.21</full_mwt><hba>1</hba><hbd>1</hbd><heavy_atoms>10</heavy_atoms><mw_freebase>135.21</mw_freebase><np_likeness_score>-0.02</np_likeness_score><num_ro5_violations/><psa>26.02</psa><qed_weighted>0.65</qed_weighted><ro3_pass>Y</ro3_pass><rtb>2</rtb></molecule_properties><molecule_structures><canonical_smiles>CC(N)Cc1ccccc1</canonical_smiles><molfile>
     RDKit          2D

 10 10  0  0  0  0  0  0  0  0999 V2000
    1.5625    0.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7792    0.7208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9500    0.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792    0.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9542   -0.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3292    0.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792   -0.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3375   -0.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2833    0.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2833   -0.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  1  1  0
  4  1  1  0
  5  3  2  0
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 10  8  2  0
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M  END</molfile><standard_inchi>InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3</standard_inchi><standard_inchi_key>KWTSXDURSIMDCE-UHFFFAOYSA-N</standard_inchi_key></molecule_structures><molecule_synonyms><drug><molecule_synonym>Adzenys er</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>ADZENYS ER</synonyms></drug><drug><molecule_synonym>Adzenys xr-odt</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>ADZENYS XR-ODT</synonyms></drug><drug><molecule_synonym>Amfetamin</molecule_synonym><syn_type>OTHER</syn_type><synonyms>AMFETAMIN</synonyms></drug><drug><molecule_synonym>Amfetamine</molecule_synonym><syn_type>ATC</syn_type><synonyms>AMFETAMINE</synonyms></drug><drug><molecule_synonym>Amfetamine</molecule_synonym><syn_type>INN</syn_type><synonyms>AMFETAMINE</synonyms></drug><drug><molecule_synonym>Amfetamine</molecule_synonym><syn_type>OTHER</syn_type><synonyms>AMFETAMINE</synonyms></drug><drug><molecule_synonym>Amphetamine</molecule_synonym><syn_type>FDA</syn_type><synonyms>AMPHETAMINE</synonyms></drug><drug><molecule_synonym>Amphetamine</molecule_synonym><syn_type>MERCK_INDEX</syn_type><synonyms>AMPHETAMINE</synonyms></drug><drug><molecule_synonym>Amphetamine</molecule_synonym><syn_type>OTHER</syn_type><synonyms>AMPHETAMINE</synonyms></drug><drug><molecule_synonym>Amphetamine, dl-</molecule_synonym><syn_type>OTHER</syn_type><synonyms>AMPHETAMINE, DL-</synonyms></drug><drug><molecule_synonym>Amphetamine resin complex</molecule_synonym><syn_type>FDA</syn_type><synonyms>AMPHETAMINE RESIN COMPLEX</synonyms></drug><drug><molecule_synonym>Anfetamina</molecule_synonym><syn_type>INN_SPANISH</syn_type><synonyms>ANFETAMINA</synonyms></drug><drug><molecule_synonym>Dyanavel</molecule_synonym><syn_type>OTHER</syn_type><synonyms>DYANAVEL</synonyms></drug><drug><molecule_synonym>Dyanavel xr</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>DYANAVEL XR</synonyms></drug><drug><molecule_synonym>Mydayis (mixed salts of a single entity)</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>MYDAYIS (MIXED SALTS OF A SINGLE ENTITY)</synonyms></drug><drug><molecule_synonym>Norephedrane</molecule_synonym><syn_type>OTHER</syn_type><synonyms>NOREPHEDRANE</synonyms></drug><drug><molecule_synonym>NSC-27159</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>NSC-27159</synonyms></drug></molecule_synonyms><ob_patent>8062667</ob_patent><oral>1</oral><parenteral/><prodrug/><research_codes><value>NSC-27159</value><value>NSC-170999</value></research_codes><rule_of_five>1</rule_of_five><sc_patent>US-8062667-B2</sc_patent><synonyms><value>Amphetamine sulfate (MI)</value><value>Amfetamine (INN)</value><value>Amphetamine (MI)</value><value/></synonyms><topical/><usan_stem/><usan_stem_definition/><usan_stem_substem/><usan_year/><withdrawn_flag>0</withdrawn_flag></drug><drug><applicants><value>Sandoz Inc</value><value>Endo Operations Ltd</value><value>Ani Pharmaceuticals Inc</value><value>Watson Laboratories Inc An Indirect Wholly Owned Sub Of Teva Pharmaceuticals Usa Inc</value><value>Watson Laboratories Inc</value><value>Astrazeneca Pharmaceuticals Lp</value><value>Zydus Lifesciences Global Fze</value><value>Hikma International Pharmaceuticals Llc</value><value>Riconpharma Llc</value><value>Rubicon Research Private Ltd</value></applicants><atc_classification><drug><code>C05AE02</code><description>CARDIOVASCULAR SYSTEM: VASOPROTECTIVES: AGENTS FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE: Muscle relaxant</description></drug><drug><code>C01DA58</code><description>CARDIOVASCULAR SYSTEM: CARDIAC THERAPY: VASODILATORS USED IN CARDIAC DISEASES: Organic nitrate</description></drug><drug><code>C01DA08</code><description>CARDIOVASCULAR SYSTEM: CARDIAC THERAPY: VASODILATORS USED IN CARDIAC DISEASES: Organic nitrates</description></drug></atc_classification><availability_type>1</availability_type><biotherapeutic/><black_box/><black_box_warning>0</black_box_warning><chirality>1</chirality><drug_type>1</drug_type><first_approval>1986</first_approval><first_in_class/><helm_notation/><max_phase>4.0</max_phase><molecule_chembl_id>CHEMBL6622</molecule_chembl_id><molecule_properties><alogp>-1.06</alogp><aromatic_rings/><full_molformula>C6H8N2O8</full_molformula><full_mwt>236.14</full_mwt><hba>8</hba><hbd/><heavy_atoms>16</heavy_atoms><mw_freebase>236.14</mw_freebase><np_likeness_score>-0.02</np_likeness_score><num_ro5_violations/><psa>123.20</psa><qed_weighted>0.45</qed_weighted><ro3_pass>N</ro3_pass><rtb>4</rtb></molecule_properties><molecule_structures><canonical_smiles>O=[N+]([O-])O[C@H]1CO[C@H]2[C@@H]1OC[C@H]2O[N+](=O)[O-]</canonical_smiles><molfile>
     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
   10.7582  -23.3680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7582  -22.5466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9775  -23.6194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4929  -22.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9755  -22.2873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4874  -21.6213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7032  -21.8796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7066  -22.7053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0439  -23.1908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1331  -24.0074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8881  -24.3412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4738  -24.4957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9078  -23.5464    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4242  -22.0656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3848  -21.5799    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1737  -22.4018    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8432  -21.9191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  5  1  0
  4  3  1  0
  3  1  1  0
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  8  4  1  0
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 10 11  2  0
 10 12  1  0
  2 14  1  1
 14 16  1  0
 16 17  2  0
 16 18  1  0
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M  CHG  4  10   1  12  -1  16   1  18  -1
M  END</molfile><standard_inchi>InChI=1S/C6H8N2O8/c9-7(10)15-3-1-13-6-4(16-8(11)12)2-14-5(3)6/h3-6H,1-2H2/t3-,4+,5-,6-/m1/s1</standard_inchi><standard_inchi_key>MOYKHGMNXAOIAT-JGWLITMVSA-N</standard_inchi_key></molecule_structures><molecule_synonyms><drug><molecule_synonym>Angitak</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>ANGITAK</synonyms></drug><drug><molecule_synonym>C01DA08</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>C01DA08</synonyms></drug><drug><molecule_synonym>Carvasin</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>CARVASIN</synonyms></drug><drug><molecule_synonym>Cedocard</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>CEDOCARD</synonyms></drug><drug><molecule_synonym>Cedocard-10</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>CEDOCARD-10</synonyms></drug><drug><molecule_synonym>Cedocard-20</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>CEDOCARD-20</synonyms></drug><drug><molecule_synonym>Cedocard-40</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>CEDOCARD-40</synonyms></drug><drug><molecule_synonym>Cedocard-5</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>CEDOCARD-5</synonyms></drug><drug><molecule_synonym>Cedocard ret</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>CEDOCARD RET</synonyms></drug><drug><molecule_synonym>Dilatrate</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>DILATRATE</synonyms></drug><drug><molecule_synonym>Dilatrate-sr</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>DILATRATE-SR</synonyms></drug><drug><molecule_synonym>Diluted isosorbide dinitrate</molecule_synonym><syn_type>USP</syn_type><synonyms>DILUTED ISOSORBIDE DINITRATE</synonyms></drug><drug><molecule_synonym>Diluted-isosorbide dinitrate</molecule_synonym><syn_type>OTHER</syn_type><synonyms>DILUTED-ISOSORBIDE DINITRATE</synonyms></drug><drug><molecule_synonym>Diluted isosorbide dinitrate rs</molecule_synonym><syn_type>USP</syn_type><synonyms>DILUTED ISOSORBIDE DINITRATE RS</synonyms></drug><drug><molecule_synonym>Dinitrate d'isosorbide</molecule_synonym><syn_type>INN_FRENCH</syn_type><synonyms>DINITRATE D'ISOSORBIDE</synonyms></drug><drug><molecule_synonym>Dinitrato de isosorbida</molecule_synonym><syn_type>INN_SPANISH</syn_type><synonyms>DINITRATO DE ISOSORBIDA</synonyms></drug><drug><molecule_synonym>Imtack</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>IMTACK</synonyms></drug><drug><molecule_synonym>Isocard</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>ISOCARD</synonyms></drug><drug><molecule_synonym>Isoket 10</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>ISOKET 10</synonyms></drug><drug><molecule_synonym>Isoket 20</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>ISOKET 20</synonyms></drug><drug><molecule_synonym>Isoket 5</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>ISOKET 5</synonyms></drug><drug><molecule_synonym>Isoket ret 20</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>ISOKET RET 20</synonyms></drug><drug><molecule_synonym>Isoket ret 40</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>ISOKET RET 40</synonyms></drug><drug><molecule_synonym>Iso mack</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>ISO MACK</synonyms></drug><drug><molecule_synonym>Isomannide dinitrate</molecule_synonym><syn_type>OTHER</syn_type><synonyms>ISOMANNIDE DINITRATE</synonyms></drug><drug><molecule_synonym>Isomannide-dinitrate</molecule_synonym><syn_type>OTHER</syn_type><synonyms>ISOMANNIDE-DINITRATE</synonyms></drug><drug><molecule_synonym>Isordil</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>ISORDIL</synonyms></drug><drug><molecule_synonym>Isordil tembids</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>ISORDIL TEMBIDS</synonyms></drug><drug><molecule_synonym>Isosorbide dinitrate</molecule_synonym><syn_type>ATC</syn_type><synonyms>ISOSORBIDE DINITRATE</synonyms></drug><drug><molecule_synonym>Isosorbide dinitrate</molecule_synonym><syn_type>BAN</syn_type><synonyms>ISOSORBIDE DINITRATE</synonyms></drug><drug><molecule_synonym>Isosorbide dinitrate</molecule_synonym><syn_type>BNF</syn_type><synonyms>ISOSORBIDE DINITRATE</synonyms></drug><drug><molecule_synonym>Isosorbide dinitrate</molecule_synonym><syn_type>FDA</syn_type><synonyms>ISOSORBIDE DINITRATE</synonyms></drug><drug><molecule_synonym>Isosorbide dinitrate</molecule_synonym><syn_type>INN</syn_type><synonyms>ISOSORBIDE DINITRATE</synonyms></drug><drug><molecule_synonym>Isosorbide dinitrate</molecule_synonym><syn_type>JAN</syn_type><synonyms>ISOSORBIDE DINITRATE</synonyms></drug><drug><molecule_synonym>Isosorbide dinitrate</molecule_synonym><syn_type>MERCK_INDEX</syn_type><synonyms>ISOSORBIDE DINITRATE</synonyms></drug><drug><molecule_synonym>Isosorbide dinitrate</molecule_synonym><syn_type>OTHER</syn_type><synonyms>ISOSORBIDE DINITRATE</synonyms></drug><drug><molecule_synonym>Isosorbide dinitrate</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>ISOSORBIDE DINITRATE</synonyms></drug><drug><molecule_synonym>Isosorbide dinitrate</molecule_synonym><syn_type>USAN</syn_type><synonyms>ISOSORBIDE DINITRATE</synonyms></drug><drug><molecule_synonym>Isosorbide dinitrate</molecule_synonym><syn_type>USP</syn_type><synonyms>ISOSORBIDE DINITRATE</synonyms></drug><drug><molecule_synonym>Isosorbide dinitrate component of bidil</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>ISOSORBIDE DINITRATE COMPONENT OF BIDIL</synonyms></drug><drug><molecule_synonym>Isosorbide dinitrate, diluted</molecule_synonym><syn_type>OTHER</syn_type><synonyms>ISOSORBIDE DINITRATE, DILUTED</synonyms></drug><drug><molecule_synonym>Isosorbide dinitrate, diluted-</molecule_synonym><syn_type>OTHER</syn_type><synonyms>ISOSORBIDE DINITRATE, DILUTED-</synonyms></drug><drug><molecule_synonym>Isosorbidi dinitras dilutes</molecule_synonym><syn_type>OTHER</syn_type><synonyms>ISOSORBIDI DINITRAS DILUTES</synonyms></drug><drug><molecule_synonym>Isosorbidi dinitras dilutus</molecule_synonym><syn_type>OTHER</syn_type><synonyms>ISOSORBIDI DINITRAS DILUTUS</synonyms></drug><drug><molecule_synonym>Jeridin</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>JERIDIN</synonyms></drug><drug><molecule_synonym>NSC-80038</molecule_synonym><syn_type>RESEARCH_CODE</syn_type><synonyms>NSC-80038</synonyms></drug><drug><molecule_synonym>Soni-slo</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>SONI-SLO</synonyms></drug><drug><molecule_synonym>Sorbichew</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>SORBICHEW</synonyms></drug><drug><molecule_synonym>Sorbid-20 sa</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>SORBID-20 SA</synonyms></drug><drug><molecule_synonym>Sorbid-40 sa</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>SORBID-40 SA</synonyms></drug><drug><molecule_synonym>Sorbide nitrate</molecule_synonym><syn_type>OTHER</syn_type><synonyms>SORBIDE NITRATE</synonyms></drug><drug><molecule_synonym>Sorbidilat</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>SORBIDILAT</synonyms></drug><drug><molecule_synonym>Sorbid sa</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>SORBID SA</synonyms></drug><drug><molecule_synonym>Sorbitrate</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>SORBITRATE</synonyms></drug><drug><molecule_synonym>Vascardin</molecule_synonym><syn_type>TRADE_NAME</syn_type><synonyms>VASCARDIN</synonyms></drug></molecule_synonyms><ob_patent/><oral>1</oral><parenteral/><prodrug>1</prodrug><research_codes><value>C01DA08</value><value>NSC-80038</value></research_codes><rule_of_five>1</rule_of_five><sc_patent/><synonyms><value>Diluted isosorbide dinitrate (USP)</value><value>Diluted isosorbide dinitrate rs (USP)</value><value>Isosorbide dinitrate (BAN, INN, JAN, MI, USAN, USP)</value><value/></synonyms><topical>1</topical><usan_stem/><usan_stem_definition/><usan_stem_substem/><usan_year>1966</usan_year><withdrawn_flag>0</withdrawn_flag></drug></drugs><page_meta><limit>20</limit><next>/chembl/api/data/drug?limit=20&amp;offset=20</next><offset/><previous/><total_count>16093</total_count></page_meta></response>