Abiraterone acetateProduct ingredient for Abiraterone

Name
Abiraterone acetate
Drug Entry
Abiraterone

Abiraterone is a derivative of steroidal progesterone and is an innovative drug that offers clinical benefit to patients with hormone refractory prostate cancer. Abiraterone is administered as an acetate salt prodrug because it has a higher bioavailability and less susceptible to hydrolysis than abiraterone itself. FDA approved on April 28, 2011.

Accession Number
DBSALT001173
Structure
Thumb
Synonyms
(3β)-17-(pyridin-3-yl)androsta-5,16-dien-3-yl acetate / 17-(3-Pyridyl)-5,16-androstadien-3beta-acetate / Abiraterone (as acetate)
External IDs
CB-7630 / CB7630 / JNJ-212082
UNII
EM5OCB9YJ6
CAS Number
154229-18-2
Weight
Average: 391.555
Monoisotopic: 391.251129307
Chemical Formula
C26H33NO2
InChI Key
UVIQSJCZCSLXRZ-UBUQANBQSA-N
InChI
InChI=1S/C26H33NO2/c1-17(28)29-20-10-12-25(2)19(15-20)6-7-21-23-9-8-22(18-5-4-14-27-16-18)26(23,3)13-11-24(21)25/h4-6,8,14,16,20-21,23-24H,7,9-13,15H2,1-3H3/t20-,21-,23-,24-,25-,26+/m0/s1
IUPAC Name
(3aS,3bR,7S,9aR,9bS,11aS)-9a,11a-dimethyl-1-(pyridin-3-yl)-3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-yl acetate
SMILES
[H][[email protected]@]12CC=C(C3=CC=CN=C3)[[email protected]@]1(C)CC[[email protected]@]1([H])[[email protected]@]2([H])CC=C2C[[email protected]](CC[[email protected]]12C)OC(C)=O
KEGG Drug
D09701
ChemSpider
7997598
BindingDB
50407398
ChEBI
68639
ChEMBL
CHEMBL271227
ZINC
ZINC000003809191
Wikipedia
Abiraterone_acetate
Predicted Properties
PropertyValueSource
Water Solubility0.00101 mg/mLALOGPS
logP5.63ALOGPS
logP4.41ChemAxon
logS-5.6ALOGPS
pKa (Strongest Basic)4.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area39.19 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity116.45 m3·mol-1ChemAxon
Polarizability46.53 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon