Abiraterone

Abiraterone

Identifiers
IUPAC name (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-ol
Synonyms	CB-7598; 17-(3-pyridyl)androsta-5,16-dien-3β-ol
CAS Number	154229-19-3
PubChem (CID)	132971
ChemSpider	117349
UNII	G819A456D0
Chemical and physical data
Formula	C24H31NO
Molar mass	349.52 g·mol−1
3D model (Jmol)	Interactive image
SMILES C[C@]12CC[C@@H](CC1=CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC=C4C5=CN=CC=C5)C)O
InChI InChI=1S/C24H31NO/c1-23-11-9-18(26)14-17(23)5-6-19-21-8-7-20(16-4-3-13-25-15-16)24(21,2)12-10-22(19)23/h3-5,7,13,15,18-19,21-22,26H,6,8-12,14H2,1-2H3/t18-,19-,21-,22-,23-,24+/m0/s1 Key:GZOSMCIZMLWJML-VJLLXTKPSA-N

Abiraterone (INN, BAN) (developmental code name CB-7598), also known as 17-(3-pyridyl)androsta-5,16-dien-3β-ol, is a synthetic, steroidal CYP17A1 inhibitor and the active metabolite of abiraterone acetate, an ester and prodrug of abiraterone that is used in the treatment of prostate cancer. In addition to acting as an irreversible inhibitor of CYP17A1 (17α-hydroxylase/17,20-lyase), abiraterone has also been found to inhibit 3β-hydroxysteroid dehydrogenase (3β-HSD), steroid 11β-hydroxylase (CYP11B1), 5α-reductase (via a metabolite), and certain hepatic enzymes (e.g., CYP1A2, CYP2C9, and CYP3A4). The drug has been found to act as a partial antagonist of the androgen receptor and as an agonist of the estrogen receptor as well, and a metabolite of abiraterone has been found to act as an agonist of the androgen receptor.

Clinically, it is used in the form of abiraterone acetate (trade name Zytiga, among others).