CHEBI:50845 - doxycycline

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ChEBI Name doxycycline
ChEBI ID CHEBI:50845
Definition Tetracycline in which the 5β-hydrogen is replaced by a hydroxy group, while the 6α-hydroxy group is replaced by hydrogen. A semi-synthetic tetracycline antibiotic, it is used to inhibit bacterial protein synthesis and treat non-gonococcal urethritis and cervicitis, exacerbations of bronchitis in patients with chronic obstructive pulmonary disease (COPD), and adult periodontitis.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:42135, CHEBI:4713
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Formula C22H24N2O8
Net Charge 0
Average Mass 444.43464
Monoisotopic Mass 444.153
InChI InChI=1S/C22H24N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-7,10,14-15,17,25,27-29,32H,1-3H3,(H2,23,31)/t7-,10+,14+,15-,17-,22-/m0/s1
InChIKey JBIWCJUYHHGXTC-AKNGSSGZSA-N
SMILES [H][C@@]12[C@@H](C)c3cccc(O)c3C(=O)C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@]1([H])[C@H]2O
Roles Classification
Biological Role(s): antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
antibacterial drug
A drug used to treat or prevent bacterial infections.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via tetracyclines )
Application(s): antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
antibacterial drug
A drug used to treat or prevent bacterial infections.
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ChEBI Ontology
Outgoing doxycycline (CHEBI:50845) has role antibacterial drug (CHEBI:36047)
doxycycline (CHEBI:50845) has role antimalarial (CHEBI:38068)
doxycycline (CHEBI:50845) is a tetracyclines (CHEBI:26895)
Incoming doxycycline HCl (CHEBI:652992) has part doxycycline (CHEBI:50845)
doxycycline monohydrate (CHEBI:60648) has part doxycycline (CHEBI:50845)
IUPAC Name
(4S,4aR,5S,5aR,6R,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
INNs Sources
doxiciclina ChemIDplus
doxycycline KEGG DRUG
doxycyclinum ChemIDplus
Synonyms Sources
(4S,4AR,5S,5AR,6R,12AS)-4-(DIMETHYLAMINO)-3,5,10,12,12A-PENTAHYDROXY-6-METHYL-1,11-DIOXO-1,4,4A,5,5A,6,11,12A-OCTAHYDROTETRACENE-2-CARBOXAMIDE PDBeChem
5-hydroxy-α-6-deoxytetracycline ChemIDplus
6α-deoxy-5-oxytetracycline ChemIDplus
Doxycyclin ChEBI
Doxycycline KEGG COMPOUND
doxycycline (anhydrous) ChemIDplus
Brand Names Sources
Jenacyclin DrugBank
Supracyclin DrugBank
Vibramycin DrugBank
Database Links Databases
C00017127 KNApSAcK
C06973 KEGG COMPOUND
D07876 KEGG DRUG
DB00254 DrugBank
Doxycycline Wikipedia
DXT PDBeChem
US3019260 Patent
US3200149 Patent
View more database links
Registry Numbers Types Sources
3041790 Reaxys Registry Number Reaxys
3041790 Beilstein Registry Number Beilstein
564-25-0 CAS Registry Number KEGG COMPOUND
564-25-0 CAS Registry Number ChemIDplus
Citation Waiting for Citations Type Source
1650428 PubMed citation Europe PMC
Last Modified
28 July 2014