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

General Information of Drug (ID: DR0030)
Drug Name
Abiraterone acetate
Prodrug Info Abiraterone acetate is the prodrug of Abiraterone
Synonyms
Abiraterone (acetate); Abiraterone acetate; Abiraterone; Abiraterone (CB-7598); CB 7598; CB-7598; CB7598; CB 7630; CB-7630; CB7630; CHEBI:68639; EM5OCB9YJ6; UNII-EM5OCB9YJ6; Yonsa; Zytiga; CHEBI:68642; CHEMBL254328; G819A456D0; MFCD00924100; UNII-G819A456D0; [(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-pyridin-3-yl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate; (3S,8R,9S,10R,13S,14S)-10,13-DIMETHYL-17-(PYRIDIN-3-YL)-2,3,4,7,8,9,10,11,12,13,14,15-DODECAHYDRO-1H-CYCLOPENTA[A]PHENANTHREN-3-YL ACETATE; 154229-18-2; 17-(3-Pyridyl)-5,16-androstadien-3beta-acetate; 17-(pyridin-3-yl)androsta-5,16-dien-3beta-yl acetate; (3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-(pyridin-3-yl)-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol; (3beta)-17-(3-pyridinyl)-androsta-5,16-dien-3-ol; (3beta)-17-(pyridin-3-yl)androsta-5,16-dien-3-ol; 154229-19-3; 17-(3-Pyridyl)androsta-5,16-dien-3beta-ol
Indication Prostate cancer [ICD11: 2C82] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 391.5 Topological Polar Surface Area 39.2
Heavy Atom Count 29 Rotatable Bond Count 3
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
9821849
ChEBI ID
CHEBI:68639
CAS Number
154229-18-2
TTD Drug ID
D06CNP
Formula
C26H33NO2
Canonical SMILES
CC(=O)OC1CCC2(C3CCC4(C(C3CC=C2C1)CC=C4C5=CN=CC=C5)C)C
InChI
1S/C26H33NO2/c1-17(28)29-20-10-12-25(2)19(15-20)6-7-21-23-9-8-22(18-5-4-14-27-16-18)26(23,3)13-11-24(21)25/h4-6,8,14,16,20-21,23-24H,7,9-13,15H2,1-3H3/t20-,21-,23-,24-,25-,26+/m0/s1
InChIKey
UVIQSJCZCSLXRZ-UBUQANBQSA-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
Abiraterone DM000585
132971
Hydrolysis - Hydrolysis 1 [2]
D4A DM000588
196941
Oxidation - Dehydrogenation 1 [3]
Abiraterone sulfate DM000586
91827106
Conjugation - Hydroxyl Sulphation 2 [2]
N-oxide abiraterone sulfate DM000587
91826892
Oxidation - Oxidation 3 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000013 Abiraterone acetate Abiraterone Hydrolysis - Hydrolysis Unclear [2]
MR000014 Abiraterone acetate D4A Oxidation - Dehydrogenation HSD3B1 [3]
MR000011 Abiraterone Abiraterone sulfate Conjugation - Hydroxyl Sulphation SULT2A1 [2]
MR000012 Abiraterone sulfate N-oxide abiraterone sulfate Oxidation - Oxidation SULT2A1 ... [3]
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]
Dihydrotestosterone oxidoreductase (HSD3B1) DME0221 Homo sapiens
3BHS1_HUMAN
1.1.1.145
[3]
Sulfotransferase 2A1 (SULT2A1) DME0074 Homo sapiens
ST2A1_HUMAN
2.8.2.14
[2]
References
1 Abiraterone Acetate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Abiraterone for the treatment of metastatic castrate-resistant prostate cancer. Ann Pharmacother. 2012 Jul-Aug;46(7-8):1016-24.
3 Conversion of abiraterone to D4A drives anti-tumour activity in prostate cancer Nature. 2015 Jul 16;523(7560):347-51. doi: 10.1038/nature14406.

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