Compound: 154229-21-7
SMILES: O=C1C=C2[C@]([C@@H]3[C@H]([C@H]4[C@](C(c5cnccc5)=CC4)(C)CC3)CC2)(C)CC1
InChIKey: GYJZZAJJENTSTP-NHFPKVKZSA-N
Synonyms: 154229-21-7, Delta4-abiraterone, Androsta-4,16-dien-3-one, 17-(3-pyridinyl)-, CB-7627, 17-(3-Pyridyl)androsta-5,16-dien-3-one, Z2L6XS2R7H, DTXSID90934961, 17-(3-PYRIDINYL)ANDROSTA-4,16-DIEN-3-ONE, CB7627, RefChem:908232, DTXCID201363598, D4-abiraterone, 17-(3-pyridinyl)-androsta-4,16-diene-3-one, 17-(3-Pyridinyl)-androsta-4,16-dien-3-one, CHEMBL132778, (8R,9S,10R,13S,14S)-10,13-dimethyl-17-pyridin-3-yl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-one, 17-(3-Pyridyl)androsta-4,16-dien-3-one, (8R,9S,10R,13S,14S)-10,13-Dimethyl-17-(pyridin-3-yl)-6,7,8,9,10,11,12,13,14,15-decahydro-1H-cyclopenta[a]phenanthren-3(2H)-one, (8alpha)-17-(pyridin-3-yl)androsta-4,16-dien-3-one, (8R,9S,10R,13S,14S)-10,13-dimethyl-17-(pyridin-3-yl)-1,2,6,7,8,9,10,11,12,13,14,15-dodecahydro-3H-cyclopenta[a]phenanthren-3-one, CB 7627, C24H29NO, U7P, MFCD31544313, Abiraterone (D4A)?, Abiraterone D4A metabolite, UNII-Z2L6XS2R7H, 17-(pyridin-3-yl)androsta-4,16-dien-3-one, .DELTA.4-ABIRATERONE, orb611912, orb3132233, SCHEMBL1961409, SCHEMBL29767924, GYJZZAJJENTSTP-NHFPKVKZSA-N, BDBM50216168, AKOS028109269, DA-62627, FP158433, MS-25350, HY-109619, CS-0033729, A11351, T10946, F795058, Q30647364, (8R,9S,10R,13S,14S)-10,13-dimethyl-17-(3-pyridyl)-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-one
Theoretical properties:
molecular_formula: C24H29NO
molecular_weight: 347.5 g/mol
exact_mass: 347.224914549 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 1
heavy_atom_count: 26
topological_polar_surface_area: 30 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Δ4-Abiraterone (D4A; code name CB-7627), also known as 17-(3-pyridyl)androsta-4,16-dien-3-one, is a steroidogenesis inhibitor and active metabolite of abiraterone acetate, a drug which is used in the treatment of prostate cancer and is itself a prodrug of abiraterone (another active metabolite of abiraterone acetate). D4A is formed from abiraterone by 3β-hydroxysteroid dehydrogenase/Δ5-4 isomerase (3β-HSD). It is said to be a more potent inhibitor of steroidogenesis than abiraterone, and is partially responsible for the activity of abiraterone acetate.
D4A is specifically an inhibitor of CYP17A1 (17α-hydroxylase/17,20-lyase), 3β-HSD, and 5α-reductase. In addition, it has also been found to act as a competitive antagonist of the androgen receptor (AR), with potency reportedly comparable to that of enzalutamide. However, the initial 5α-reduced metabolite of D4A, 3-keto-5α-abiraterone, is an agonist of the AR, and has been found to stimulate prostate cancer progression. The formation of this metabolite can be blocked by the coadministration of dutasteride, a selective and highly potent 5α-reductase inhibitor, and the addition of this medication may improve the effectiveness of abiraterone acetate in the treatment of prostate cancer.