Cannabaceae

3-Keto-5α-abiraterone
Clinical data
Other names17-(3-Pyridyl)-5α-androst-16-en-3-one
Identifiers
  • (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
PubChem CID
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC24H31NO
Molar mass349.518 g·mol−1
3D model (JSmol)
  • 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=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/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" (PDF). Nature. 533 (7604): 547–51. Bibcode:2016Natur.533..547L. doi:10.1038/nature17954. PMC 5111629. PMID 27225130.
  2. ^ a b c 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.


One thought on “Cannabaceae

  1. Well, that’s interesting to know that Psilotum nudum are known as whisk ferns. Psilotum nudum is the commoner species of the two. While the P. flaccidum is a rare species and is found in the tropical islands. Both the species are usually epiphytic in habit and grow upon tree ferns. These species may also be terrestrial and grow in humus or in the crevices of the rocks.
    View the detailed Guide of Psilotum nudum: Detailed Study Of Psilotum Nudum (Whisk Fern), Classification, Anatomy, Reproduction

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