From Wikipedia, the free encyclopedia
Chemical compound
3-Keto-5α-abiraterone
|
|
Other names | 17-(3-Pyridyl)-5α-androst-16-en-3-one |
---|
|
(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) | |
---|
|
Formula | C24H31NO |
---|
Molar mass | 349.518 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
- ^
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.
- ^
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.
|
---|
ARTooltip Androgen receptor | Agonists | |
---|
SARMsTooltip Selective androgen receptor modulator | |
---|
Antagonists | |
---|
|
---|
GPRC6A | |
---|
|