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CHEBI:68639 - abiraterone acetate

ChEBI IDCHEBI:68639
ChEBI Nameabiraterone acetate
Stars
DefinitionA sterol ester obtained by formal condensation of the 3-hydroxy group of abiraterone with the carboxy group of acetic acid. A prodrug that is converted in vivo into abiraterone. Used for treatment of metastatic castrate-resistant prostate cancer.
Last Modified28 April 2020
SubmitterSteve
DownloadsMolfile
FormulaC26H33NO2
Net Charge0
Average Mass391.555
Monoisotopic Mass391.25113
SMILES[H][C@@]12CC=C3C[C@@H](OC(C)=O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)C(c3cccnc3)=CC[C@@]21[H]
InChIInChI=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
InChIKeyUVIQSJCZCSLXRZ-UBUQANBQSA-N
Roles Classification
Biological Role:
EC 1.14.99.9 (steroid 17alpha-monooxygenase) inhibitor  An EC 1.14.99.* (miscellaneous oxidoreductase acting on paired donors, with incorporation or reduction of molecular oxygen) inhibitor that interferes with the action of cytochrome P450 17-α-hydroxylase/C17,20-lyase (EC 1.14.99.9).
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
prodrug  A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
ChEBI Ontology
Outgoing Relation(s)
abiraterone acetate (CHEBI:68639) has functional parent abiraterone (CHEBI:68642)
abiraterone acetate (CHEBI:68639) has role antineoplastic agent (CHEBI:35610)
abiraterone acetate (CHEBI:68639) has role EC 1.14.99.9 (steroid 17α-monooxygenase) inhibitor (CHEBI:68640)
abiraterone acetate (CHEBI:68639) has role prodrug (CHEBI:50266)
abiraterone acetate (CHEBI:68639) is a pyridines (CHEBI:26421)
abiraterone acetate (CHEBI:68639) is a sterol ester (CHEBI:35915)
IUPAC Name 
17-(pyridin-3-yl)androsta-5,16-dien-3β-yl acetate
Synonyms  Source
17-(3-Pyridyl)-5,16-androstadien-3beta-acetateChemIDplus
(3β)-17-(pyridin-3-yl)androsta-5,16-dien-3-yl acetateIUPAC
Brand Name  Source
ZytigaChEBI
Manual XrefsDatabases
D09701KEGG DRUG
WO2012083112Patent
WO2006021776Patent
US2011201563Patent
US2008051380Patent
4176DrugCentral
Registry NumbersSources
Reaxys:7314563Reaxys
CAS:154229-18-2KEGG DRUG
CAS:154229-18-2ChemIDplus
Citations