3-Keto-5α-abiraterone

{{Short description|Chemical compound}}

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| 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

| image = 3-Keto-5α-abiraterone.svg

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| CAS_number = 154229-26-2

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| UNII = 675L8BAG4G

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| PubChem = 11725391

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| C=24 | H=31 | N=1 | O=1

| 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

| StdInChI_Ref =

| StdInChI = 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

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| StdInChIKey = FKNZCFYWNHCQGE-IRMBCWQZSA-N

| synonyms = 17-(3-Pyridyl)-5α-androst-16-en-3-one

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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.{{cite journal | vauthors = Li Z, Alyamani M, Li J, Rogacki K, Abazeed M, Upadhyay SK, Balk SP, Taplin ME, Auchus RJ, Sharifi N | title = Redirecting abiraterone metabolism to fine-tune prostate cancer anti-androgen therapy | journal = Nature | volume = 533 | issue = 7604 | pages = 547–51 | date = May 2016 | pmid = 27225130 | doi = 10.1038/nature17954 | url = https://dash.harvard.edu/bitstream/handle/1/29626087/5111629.pdf?sequence=1 | pmc=5111629| bibcode = 2016Natur.533..547L }}{{cite journal | vauthors = Obst JK, Sadar MD | year = 2016 | title = Directing abiraterone metabolism: balancing the scales between clinical relevance and experimental observation | journal = Translational Cancer Research | volume = 3 | issue = 5| pages = S529–S531 | doi = 10.21037/tcr.2016.07.35 | pmid = 30815377 | pmc = 6388702 | doi-access = free }} 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. 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.