3-Keto-5α-abiraterone

3-Keto-5α-abiraterone

Clinical data
Other names	17-(3-Pyridyl)-5α-androst-16-en-3-one
Identifiers
IUPAC name (5S,8R,9S,10S,13S,14S)-10,13-Dimethyl-17-pyridin-3-yl-1,2,4,5,6,7,8,9,11,12,14,15-dodecahydrocyclopenta[a]phenanthren-3-one
CAS Number	154229-26-2^Y
PubChem CID	11725391
UNII	675L8BAG4G
CompTox Dashboard (EPA)	DTXSID00471175
Chemical and physical data
Formula	C24H31NO
Molar mass	349.518 g·mol^−1
3D model (JSmol)	Interactive image
SMILES C[C@]12CCC(=O)C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC=C4C5=CN=CC=C5)C
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/h3-4,7,13,15,17,19,21-22H,5-6,8-12,14H2,1-2H3/t17-,19-,21-,22-,23-,24+/m0/s1 Key:FKNZCFYWNHCQGE-IRMBCWQZSA-N

3-Keto-5α-abiraterone, also known as 17-(3-pyridyl)-5α-androst-16-en-3-one, is an active metabolite of abiraterone acetate that has been found to possess androgenic activity and to stimulate prostate cancer progression.^[1][2] It is formed as follows: abiraterone acetate to abiraterone by esterases; abiraterone to Δ⁴-abiraterone by 3β-hydroxysteroid dehydrogenase/Δ^5-4 isomerase; and Δ⁴-abiraterone to 3-keto-5α-abiraterone by 5α-reductase.^[1][2] 3-Keto-5α-abiraterone may counteract the clinical effectiveness of abiraterone acetate, and so inhibition of its formation using the 5α-reductase inhibitor dutasteride is being investigated as an adjunct to abiraterone acetate in the treatment of prostate cancer.^[1][2]

References

1. Li Z, Alyamani M, Li J, Rogacki K, Abazeed M, Upadhyay SK, Balk SP, Taplin ME, Auchus RJ, Sharifi N (May 2016). "Redirecting abiraterone metabolism to fine-tune prostate cancer anti-androgen therapy" (PDF). Nature. 533 (7604): 547–51. Bibcode:2016Natur.533..547L. doi:10.1038/nature17954. PMC 5111629. PMID 27225130.
2. Obst JK, Sadar MD (2016). "Directing abiraterone metabolism: balancing the scales between clinical relevance and experimental observation". Translational Cancer Research. 3 (5): S529–S531. doi:10.21037/tcr.2016.07.35. PMC 6388702. PMID 30815377.