Abiraterone acetate

Base Information

• Chemical Name: Abiraterone acetate
• CAS No.: 154229-18-2
• Molecular Formula: C26H33NO2
• Molecular Weight: 391.554
• Hs Code.: 2937290000
• European Community (EC) Number: 620-314-7
• NSC Number: 748121,749227
• UNII: EM5OCB9YJ6
• DSSTox Substance ID: DTXSID3049043
• Nikkaji Number: J617.458B
• Wikipedia: Abiraterone_acetate
• NCI Thesaurus Code: C68845
• RXCUI: 1100071
• Pharos Ligand ID: 84J8P9Z9HM33
• Metabolomics Workbench ID: 65143
• ChEMBL ID: CHEMBL271227
• Mol file: 154229-18-2.mol

Synonyms:17-(3-pyridyl)-5,16-androstadien-3beta-acetate;abiraterone acetate;CB 7630;CB-7630;CB7630;Zytiga

Chemical Property of Abiraterone acetate

Chemical Property:

• Vapor Pressure: 2.17E-10mmHg at 25°C
• Melting Point: 127-130°C
• Refractive Index: 1.583
• Boiling Point: 506.709 °C at 760 mmHg
• PKA: 5.31±0.12(Predicted)
• Flash Point: 260.249 °C
• PSA: 39.19000
• Density: 1.14 g/cm³
• LogP: 5.96940
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), DMSO (Sparingly), Methanol (Sparingly)
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 391.251129295
• Heavy Atom Count: 29
• Complexity: 739

Purity/Quality:

98% ,99% , ^*data from raw suppliers

Abiraterone acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1CCC2(C3CCC4(C(C3CC=C2C1)CC=C4C5=CN=CC=C5)C)C
• Isomeric SMILES: CC(=O)O[C@H]1CC[C@@]2([C@H]3CC[C@]4([C@H]([C@@H]3CC=C2C1)CC=C4C5=CN=CC=C5)C)C
• Recent ClinicalTrials: Enzalutamide vs. Abiraterone in Chemotherapy-na?ve Metastatic Castration-resistant Prostate Cancer (mCRPC)
• Recent EU Clinical Trials: SPLASH: Study Evaluating Metastatic Castrate Resistant Prostate Cancer Treatment Using 177Lu-PNT2002 PSMA Therapy After Second-line Hormonal Treatment
• Recent NIPH Clinical Trials: A Study of Abiraterone Acetate Plus Prednisone With or Without Abemaciclib (LY2835219) in Participants With Prostate Cancer
• Description: In April 2011, the United States FDA approved abiraterone acetate (CB7630) in combination with the steroid prednisone for the treatment of metastatic castration-resistant prostate cancer (mCRPC) for patients who were previously treated with a docetaxel containing regimen for late-stage disease. Abiraterone acetate affects prostate, testicular, and adrenal androgens by irreversibly inhibiting both the lyase and hydroxylase activity of cytochrome P450 17A (CYP17) signaling pathways (IC50's of 2.9 and 4 nM, respectively) thereby decreasing testosterone levels.Most common serious adverse events for abiraterone acetate versus placebo included fluid retention (30.5% vs. 22.3%), hypokalemia (17.1% vs. 8.4%), hypertension (9.7% vs. 7.9%), hepatic transaminase abnormalities (10.4% vs. 8.1%), and cardiac abnormalities (13.3% vs. 10.4%).
• Uses: Abiraterone acetate is a novel steroidal inhibitor of human Cytochrome P450 (17α-Hydroxylase-C17,20-lyase): potential agent for the treatment of prostatic cancer. Abiraterone acetate was approved by the U.S. Food and Drug Administration (FDA) in April 2011 for the treatment of castrationresistant prostate cancer. The drug, marketed under the trade name Zytiga, was originally discovered by researchers at the Cancer Research UK Centre for Cancer Therapeutics in 1990, developed by Cougar Biotechnology, and ultimately commercialized by Johnson & Johnson after its acquisition of Cougar in 2009. Abiraterone acetate inhibits CYP17A1—an enzyme expressed in testicular, adrenal, and prostatic tumor tissues—which has been implied in the production of testosterone and the proliferation of such tumor cell lines. A novel steroidal inhibitor of human Cytochrome P450(17a-Hydroxylase-C17,20-lyase): potential agent for the treatment of prostatic cancer.
• Clinical Use: Hormone antagonist: Treatment of metastatic prostate cancer
• Drug interactions: Potentially hazardous interactions with other drugs Antibacterials: concentration possibly reduced by rifabutin and rifampicin - avoid. Antidepressants: concentration possibly reduced by St John’s wort - avoid. Antiepileptics: concentration possibly reduced by carbamazepine, fosphenytoin, phenobarbital, phenytoin and primidone - avoid.

Technology Process of Abiraterone acetate

There total 80 articles about Abiraterone acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

C28H40O4 → abiraterone acetate (154229-18-2)

Guidance literature:

With hydroxylamine hydrochloride; In acetonitrile;

Reference yield: 95.3%

acetic anhydride (108-24-7) + abiraterone (154229-19-3) → abiraterone acetate (154229-18-2)

Guidance literature:

With dmap; In acetone; at 20 - 65 ℃; for 1h;

Reference yield: 95.0%

3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate (115375-60-5) + 3-Diethylboranylpyridine (89878-14-8) → abiraterone acetate (154229-18-2)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In tetrahydrofuran; at 65 ℃; for 4h; Reflux;

upstream raw materials:

3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate

3-Diethylboranylpyridine

acetic anhydride

abiraterone

Downstream raw materials:

17-(3-pyridine)-4,16-dieneandrost-3-one

abiraterone

Refernces

• 1、 Ma, Siyue,Li, Jianheng,Tang, Huayang,Xu, Feng. "Synthesis of the anti-prostate cancer drug abiraterone acetate". . p. 461 - 469. Retrieved 2018.
• 2、 Cheong, Eleanor Jing Yi,Nair, Pramod C.,Neo, Rebecca Wan Yi,Tu, Ho Thanh,Lin, Fu,Chiong, Edmund,Esuvaranathan, Kesavan,Fan, Hao,Szmulewitz, Russell Z.,Peer, Cody J.,Figg, William D.,Chai, Christina Li Lin,Miners, John O.,Chan, Eric Chun Yong. "Slow-, tight-binding inhibition of CYP17A1 by abiraterone redefines its kinetic selectivity and dosing regimen". supporting information. p. 438 - 451. Retrieved 2020/09/04.
• 3、 -. "Synthetic method of abiraterone acetate and intermediate thereof (by machine translation)". . . Retrieved 2021/01/04.