CHEBI:68639 - abiraterone acetate

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ChEBI Name abiraterone acetate
ChEBI ID CHEBI:68639
Definition A 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 to abiraterone. Used for treatment of metastatic castrate-resistant prostate cancer.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C26H33NO2
Net Charge 0
Average Mass 391.54570
Monoisotopic Mass 391.251
InChI 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
SMILES [H][C@@]12CC=C3C[C@H](CC[C@]3(C)[C@@]1([H])CC[C@]1(C)C(=CC[C@@]21[H])c1cccnc1)OC(C)=O
Roles Classification
Biological Role(s): 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-alpha-hydroxylase/C17,20-lyase (EC 1.14.99.9).
Application(s): 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.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing 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 Sources
(3β)-17-(pyridin-3-yl)androsta-5,16-dien-3-yl acetate IUPAC
17-(3-Pyridyl)-5,16-androstadien-3beta-acetate ChemIDplus
Brand Name Source
Zytiga ChEBI
Database Links Databases
4176 DrugCentral
D09701 KEGG DRUG
US2008051380 Patent
US2011201563 Patent
WO2006021776 Patent
WO2012083112 Patent
View more database links
Registry Numbers Types Sources
154229-18-2 CAS Registry Number ChemIDplus
154229-18-2 CAS Registry Number KEGG DRUG
7314563 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017