Marvin  10230612332D          
 
 25 28  0  0  1  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280   -0.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280   -1.4925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4130   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 23  1  1  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  2  4  2  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  5  6  2  0  0  0  0
  8  9  1  0  0  0  0
 24 10  1  0  0  0  0
 24 11  1  0  0  0  0
 24 12  1  0  0  0  0
 10 13  1  1  0  0  0
 10 14  1  0  0  0  0
 11 15  1  0  0  0  0
 11 16  2  0  0  0  0
 12 17  1  0  0  0  0
 14 18  1  0  0  0  0
 15 19  2  0  0  0  0
 16 20  1  0  0  0  0
 17 18  1  0  0  0  0
 19 21  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 23 13  1  0  0  0  0
 24 25  1  1  0  0  0
M  END
> <ID>
CHEBI:7936

> <NAME>
paroxetine

> <DEFINITION>
A benzodioxole that consists of piperidine bearing 1,3-benzodioxol-5-yloxy)methyl and 4-fluorophenyl substituents at positions 3 and 4 respectively; the (3S,4R)-diastereomer. Highly potent and selective 5-HT uptake inhibitor that binds with high affinity to the serotonin transporter (Ki = 0.05 nM). Ki values are 1.1, 350 and 1100 nM for inhibition of [3H]-5-HT, [3H]-l-NA and [3H]-DA uptake respectively. Displays minimal affinity for ?1-, ?2- or ?-adrenoceptors, 5-HT2A, 5-HT1A, D2 or H1 receptors at concentrations below 1000 nM, however displays weak affinity for muscarinic ACh receptors (Ki = 42 nM). Antidepressant and anxiolytic in vivo.

> <STAR>
3

> <SYNONYM>
Paroxetine; (3S-trans)-3-((1,3-benzodioxol-5-yloxy)methyl)-4-(4-fluorophenyl)piperidine; (-)-(3S,4R)-4-(p-fluorophenyl)-3-((3,4-(methylenedioxy)phenoxy)methyl)piperidine

> <IUPAC_NAME>
(3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine

> <INN>
paroxetinum; paroxetina

> <FORMULA>
C19H20FNO3

> <MASS>
329.36540

> <MONOISOTOPIC_MASS>
329.14272

> <CHARGE>
0

> <SMILES>
[H][C@]1(CCNC[C@H]1COc1ccc2OCOc2c1)c1ccc(F)cc1

> <INCHI>
InChI=1S/C19H20FNO3/c20-15-3-1-13(2-4-15)17-7-8-21-10-14(17)11-22-16-5-6-18-19(9-16)24-12-23-18/h1-6,9,14,17,21H,7-8,10-12H2/t14-,17-/m0/s1

> <INCHIKEY>
AHOUBRCZNHFOSL-YOEHRIQHSA-N

> <BEILSTEIN_REGISTRY_NUMBER>
7467879

> <CAS_REGISTRY_NUMBER>
61869-08-7

> <REAXYS_REGISTRY_NUMBER>
7467879

> <CHEMIDPLUS>
61869-08-7

> <DRUGBANK_ACCESSION>
DB00715

> <KEGG_COMPOUND_ACCESSION>
C07415

> <KEGG_DRUG_ACCESSION>
D02362

> <LINCS_ACCESSION>
LSM-2843

> <WIKIPEDIA_ACCESSION>
Paroxetine

> <PUBMED_CITATION>
11009210; 11169163; 11271409; 11281965; 11324355; 11360029; 11513198; 11563413; 11565622; 11819027; 11893234; 11910269; 12027788; 12088162; 12369443; 12421645; 12818234; 12820211; 12906023; 12920419; 14516531; 14521492; 14566196; 14566200; 14619895; 14624192; 14673053; 14689334; 14978354; 15048901; 15199661; 15241233; 15264994; 15374134; 15376524; 15544025; 15613191; 15845695; 15853570; 15903129; 15963219; 15992089; 16395417; 16397315; 16426087; 16765127; 16822276; 16913391; 17122538; 17162096; 17219219; 17286545; 17452166; 17559097; 17612590; 17652957; 17874333; 18273418; 18345955; 18808757; 18983224; 19687003; 19851065; 21404089; 21452176; 21739267; 21908494; 21909633; 21922171; 21939725; 22153922; 22198456; 22212003; 22240860; 22263916; 22283559; 22353759; 22377745

$$$$