Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0396)
Drug Name
Cyproterone acetate
Synonyms
Cyprosterone acetate; Cyproteron acetate; Cyproteron-R acetate; Cyproterone 17-O-acetate; Cyproterone 17.alpha.-acetate; Cyproterone 17alpha-acetate; Cyproterone acetate [USAN:JAN]; Androcur; CYPROTERONE ACETATE; Cyproteroneacetate; SH 714; SH 80714; SH-714; 3'H-Cyclopropa(1,2)pregna-1,4,6-triene-3,20-dione, 17-(acetyloxy)-6-chloro-1,2-dihydro-, (1beta,2beta)-; 427-51-0; 4KM2BN5JHF; C24H29ClO4; CCRIS 4385; CHEBI:50743; CHEMBL139835; EINECS 207-048-3; HSDB 3592; MLS000859908; NSC 81430; NSC-81430; UNII-4KM2BN5JHF
Indication Polycystic ovary syndrome [ICD11: 5A80] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 416.9 Topological Polar Surface Area 60.4
Heavy Atom Count 29 Rotatable Bond Count 3
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
9880
ChEBI ID
CHEBI:50743
CAS Number
427-51-0
Formula
C24H29ClO4
Canonical SMILES
CC(=O)C1(CCC2C1(CCC3C2C=C(C4=CC(=O)C5CC5C34C)Cl)C)OC(=O)C
InChI
1S/C24H29ClO4/c1-12(26)24(29-13(2)27)8-6-16-14-10-20(25)19-11-21(28)15-9-18(15)23(19,4)17(14)5-7-22(16,24)3/h10-11,14-18H,5-9H2,1-4H3/t14-,15+,16-,17-,18-,22-,23-,24-/m0/s1
InChIKey
UWFYSQMTEOIJJG-FDTZYFLXSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
15beta-hydroxycyproterone acetate DM006555 N. A. Oxidation - Hydrolyzationn 1 [4]
Cyproterone acetate Metabolite T1 DM006546 N. A. Hydrolysis - Hydrolysis 1 [4]
Cyproterone acetate Metabolite T2 DM006551 N. A. Reduction - Dechlorination 1 [4]
Cyproterone acetate Metabolite D1 DM006552 N. A. Reduction - Hydrogenation 2 [4]
Cyproterone acetate Metabolite D2 DM006549 N. A. Reduction - Hydrogenation 2 [4]
Cyproterone acetate Metabolite D3 DM006550 N. A. Reduction - Hydrogenation 2 [4]
Cyproterone acetate Metabolite P1 DM006547 N. A. Oxidation - Hydrolyzationn 2 [4]
Cyproterone acetate Metabolite P2 DM006553 N. A. Oxidation - Hydrolyzationn 2 [4]
Cyproterone acetate Metabolite P3 DM006548 N. A. Reduction - Hydrogenation 2 [4]
Cyproterone acetate Metabolite P4 DM006554 N. A. Oxidation - Hydrolyzationn 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007057 Cyproterone acetate Cyproterone acetate Metabolite T1 Hydrolysis - Hydrolysis Unclear [4]
MR007062 Cyproterone acetate Cyproterone acetate Metabolite T2 Reduction - Dechlorination Unclear [4]
MR007066 Cyproterone acetate 15beta-hydroxycyproterone acetate Oxidation - Hydrolyzationn CYP3A4 [4]
MR007058 Cyproterone acetate Metabolite T1 Cyproterone acetate Metabolite P1 Oxidation - Hydrolyzationn Non-ME [4]
MR007059 Cyproterone acetate Metabolite T1 Cyproterone acetate Metabolite P3 Reduction - Hydrogenation Non-ME [4]
MR007060 Cyproterone acetate Metabolite T1 Cyproterone acetate Metabolite D2 Reduction - Hydrogenation Unclear [4]
MR007061 Cyproterone acetate Metabolite T1 Cyproterone acetate Metabolite D3 Reduction - Hydrogenation Unclear [4]
MR007063 Cyproterone acetate Metabolite T2 Cyproterone acetate Metabolite D1 Reduction - Hydrogenation Unclear [4]
MR007064 Cyproterone acetate Metabolite T2 Cyproterone acetate Metabolite P2 Oxidation - Hydrolyzationn Non-ME [4]
MR007065 Cyproterone acetate Metabolite T2 Cyproterone acetate Metabolite P4 Oxidation - Hydrolyzationn Non-ME [4]
⏷ Show the Full List of 10 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1366 Bacteroides eggerthii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1445 Parabacteroides distasonis Not Available Not Available [3]
⏷ Show the Full List of 12  DME(s)
References
1 ClinicalTrials.gov (NCT01752270) the Effect of Diane-35 Pretreatment on In-vitro Fertilization Outcome for Patients With Polycystic Ovary Syndrome.
2 Progestogens in menopausal hormone therapy. Prz Menopauzalny. 2015 Jun;14(2):134-43.
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
4 Uptake, Elimination, and Biotransformation Potential of a Progestagen (Cyproterone Acetate) in Tilapia Exposed at an Environmental Concentration

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