3-Keto-5α-abiraterone

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3-Keto-5α-abiraterone
3-Keto-5α-abiraterone.svg
Clinical data
Synonyms 17-(3-Pyridyl)-5α-androst-16-en-3-one
Identifiers
PubChem CID
Chemical and physical data
Formula C24H31NO
Molar mass 349.52 g·mol−1
3D model (JSmol)

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/Δ5-4 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[edit]

  1. ^ a b c 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". Nature. 533 (7604): 547–51. doi:10.1038/nature17954. PMID 27225130. 
  2. ^ a b c Obst, J. K., & Sadar, M. D. (2016). Directing abiraterone metabolism: balancing the scales between clinical relevance and experimental observation. Translational Cancer Research, 3(5), S529-S531.