Abiraterone acetateProduct ingredient for Abiraterone
- Name
- Abiraterone acetate
- Drug Entry
- Abiraterone
Abiraterone is a potent, irreversible, and selective inhibitor of 17 αhydroxylase/C17,20-lyase (CYP17), an enzyme expressed in testicular, adrenal, and prostatic tumour tissues, to regulate androgen biosynthesis.2,7,9 Abiraterone was first approved by the FDA and EMA on April,7 July,14 and September 2011,7 respectively. It is used to treat metastatic castration-resistant prostate cancer and hormone-sensitive high-risk metastatic prostate cancer.9,10,13,14
As abiraterone has poor oral bioavailability and is susceptible to hydrolysis by esterases, abiraterone acetate was developed as an orally bioavailable prodrug with enhanced stability and absorption.2,4
- Accession Number
- DBSALT001173
- Structure
Structure for Abiraterone acetate (DBSALT001173)
- 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][C@@]12CC=C(C3=CC=CN=C3)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](CC[C@]12C)OC(C)=O
- External Links
- KEGG Drug
- D09701
- ChemSpider
- 7997598
- BindingDB
- 50407398
- ChEBI
- 68639
- ChEMBL
- CHEMBL271227
- ZINC
- ZINC000003809191
- Wikipedia
- Abiraterone_acetate
- Predicted Properties
Property Value Source Water Solubility 0.00101 mg/mL ALOGPS logP 5.63 ALOGPS logP 4.41 Chemaxon logS -5.6 ALOGPS pKa (Strongest Basic) 4.81 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 39.19 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 116.45 m3·mol-1 Chemaxon Polarizability 46.53 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon