851895-79-9

Basic information

• Product Name: (3beta)-17-(1H-Benzimidazol-1-yl)androsta-5,16-dien-3-ol 3-acetate
• Synonyms: (3beta)-17-(1H-Benzimidazol-1-yl)androsta-5,16-dien-3-ol 3-acetate;(3S,8R,9S,10R,13S,14S)-17-(1H-benzo[d]iMidazol-1-yl)-10,13-diMethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate;(3S,8R,9S,10R,13S)-17-(1H-benzo[d]imidazol-1-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate
• CAS NO: 851895-79-9
• Molecular Formula: C28H34N2O2
• Molecular Weight: 430.58176
• Mol File: 851895-79-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 159-160℃
• Appearance: /
• Density: 1.26
• CAS DataBase Reference: (3beta)-17-(1H-Benzimidazol-1-yl)androsta-5,16-dien-3-ol 3-acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (3beta)-17-(1H-Benzimidazol-1-yl)androsta-5,16-dien-3-ol 3-acetate(851895-79-9)
• EPA Substance Registry System: (3beta)-17-(1H-Benzimidazol-1-yl)androsta-5,16-dien-3-ol 3-acetate(851895-79-9)

Safety Data

• Hazardous Substances Data: 851895-79-9(Hazardous Substances Data)

Usage

General Description

The chemical (3beta)-17-(1H-Benzimidazol-1-yl)androsta-5,16-dien-3-ol 3-acetate, also known as benzimidazole androsta, is a synthetic compound that belongs to the class of androstanes. It is a derivative of androstenol, a pheromone found in humans and animals. This chemical has a benzimidazole group attached to the 17th carbon of the androstenol structure, as well as an acetate group attached to the 3rd carbon. (3beta)-17-(1H-Benzimidazol-1-yl)androsta-5,16-dien-3-ol 3-acetate has been studied for its potential medical applications, including its role as an anti-inflammatory and analgesic agent. It may also have uses in the field of hormone replacement therapy and as a potential treatment for certain types of cancers.

Upstream product

• 1865-56-1 3β-acetoxy-17-chloro-16-formylandrost-5,16-diene 
• 51-17-2 benzoimidazole 
• 851895-78-8 3-β-acetoxy-17-(1H-benzimidazol-1-yl)-16-formyl-androsta-5,16-diene 

Downstream Products

• 851983-85-2 Galeterone 
• 1441047-09-1 3β-(6-(cyclohex-3-enecaboxylic acid)carboxylate)-17-(1H-benzimidazol-1-yl)-androsta-5,16-diene 
• 1441047-08-0 3β-(3-(oxycarbonyl)phenylacetic acid)-17-(1H-benzimidazol-1-yl)-androsta-5,16-diene 
• 1441047-00-2 3β-tosyloxy-17-(1H-benzimidazol-1-yl)-androsta-5,16-diene 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF GALETERONE

A process for the synthesis of 3β-hydroxy-17-(1H-benzimidazol-1-yl)androsta-5,16-diene is described, a compound also known as Galeterone and used in the treatment of prostate cancer, having the formula (I) given below.

Discovery and development of galeterone (TOK-001 or VN/124-1) for the treatment of all stages of prostate cancer

In our effort to discover potent and specific inhibitors of 17α-hydroxylase/17,20-lyase (CYP17), the key enzyme which catalyzes the biosynthesis of androgens from progestins, 3β-(hydroxy)-17-(1H-benzimidazole-1-yl)androsta-5,16-diene (Galeterone or TOK-001, formerly called VN/124-1) was identified as a selective development candidate which modulates multiple targets in the androgen receptor (AR) signaling pathway. This drug annotation summarizes the mechanisms of action, scientific rationale, medicinal chemistry, pharmacokinetic properties, and human efficacy data for galeterone, which has successfully completed phase II clinical development in men with castration resistant (advanced) prostate cancer (CRPC). Phase III clinical studies in CRPC patients are scheduled to begin in early 2015.

ANDROGEN RECEPTOR DOWN-REGULATING AGENTS AND USES THEREOF

The present disclosure provides the design and synthesis of novel steroidal compounds that cause down-regulation of the androgen receptor (AR), both full length and splice variant. The compounds are potential agents for the treatment of all forms of prostate cancer and other diseases that depend on functional AR.