3-keto-5α-abiraterone

3-Keto-5α-abiraterone

3-Keto-5α-abiraterone

Chemical compound

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]

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References

  1. [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. [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.


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