104239-97-6

Basic information

• Product Name: 4-Aza-5a-androstan-1-ene-3-one-17b-carboxylic acid
• Synonyms: 4-AZA-5ALPHA-ANDROSTA-1-EN-3-ONE-17BETA-CARBOXYLIC ACID;(5APHA,17BETA)-3-OXO-4-AZAANDROST-1-ENE-17-CARBOXYLIC ACID;3-Oxo-4-aza-5a-androst-1-ene-17b-carboxylicAcid;(5alpha,17beta)-3-Oxo-4-azaandrost-1-ene-17-carboxylic acid;4-Aza-5a-androstan-1-ene-3-one-17b-carboxylic acid;4-AZA-5A-ANDROSTAN-1-ENE-3-ONE-17β-CARBOXYLIC ACID;3-Oxo-4-aza-5a-androst-1-ene-17-carboxylic Acid;3-Oxo-4-aza-5α-αndrost-1-ene-17β-carboxylic Acid
• CAS NO: 104239-97-6
• Molecular Formula: C₁₉H₂₇NO₃
• Molecular Weight: 317.42
• EINECS: 1592732-453-0
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroids;Intermediates
• Mol File: 104239-97-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: 295-297 °C
• Boiling Point: 527.3 °C at 760 mmHg
• Flash Point: 272.7 °C
• Appearance: off-white powder
• Density: 1.166
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.547
• Storage Temp.: 2-8°C
• Solubility: Acetonitrile (Slightly), DMSO (Slightly), Methanol (Slightly, Sonicated)
• PKA: 4.80±0.60(Predicted)
• CAS DataBase Reference: 4-Aza-5a-androstan-1-ene-3-one-17b-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Aza-5a-androstan-1-ene-3-one-17b-carboxylic acid(104239-97-6)
• EPA Substance Registry System: 4-Aza-5a-androstan-1-ene-3-one-17b-carboxylic acid(104239-97-6)

Safety Data

• Hazardous Substances Data: 104239-97-6(Hazardous Substances Data)

Usage

Description

4-Aza-5a-androstan-1-ene-3-one-17b-carboxylic acid is an off-white powder that serves as a novel intermediate in the synthesis of Finasteride and Dutasteride. These are 5α-reductase inhibitors, which are used to treat various hyperandrogenetic related disorders.
Used in Pharmaceutical Industry:
4-Aza-5a-androstan-1-ene-3-one-17b-carboxylic acid is used as an intermediate in the synthesis of Finasteride and Dutasteride for the treatment of benign prostatic hyperplasia, acne, seborrhea, female hirsutism, prostatitis, and prostatic carcinoma, as well as other hyperandrogenetic related disorders. Its role in the synthesis process is crucial for the development of these medications that help manage and alleviate symptoms associated with excessive androgen levels.

InChI:InChI=1/C19H27NO3/c1-18-9-7-13-11(12(18)4-5-14(18)17(22)23)3-6-15-19(13,2)10-8-16(21)20-15/h8,10-15H,3-7,9H2,1-2H3,(H,20,21)(H,22,23)/t11-,12-,13-,14+,15+,18-,19+/m0/s1

Upstream product

• 103335-41-7 methyl 3-oxo-4-aza-5α-androst-1-ene-17β-carboxylate 
• 75-09-2 dichloromethane 
• 21149-38-2 2,2,2-trifluoro-N,N-bis(trimethylsilyl)-acetamide 
• 504-02-9 1,3-cylohexanedione 
• 103335-55-3 3-oxo-4-aza-5α-androstane-17β-carboxylic acid 
• 98319-26-7 finasteride 
• 1416955-18-4 3,5-seco-4-norpregn-5,20-dioxo-3-(ethoxycarbonyl)carboxylate 
• 149198-45-8 methyl (2α,5α,17β)-2-iodo-3-oxo-4-aza-5-androstane-17-carboxylate 
• 3510-20-1 3,5-seco-4-norpregn-5,20-dion-3-carboxylic acid 
• 57-83-0 Progesterone 
• 73711-89-4 3,20-dioxo-4-aza-5α-pregnane 
• 1416955-23-1 C₂₀H₃₁NO₃ 
• 20283-95-8 3,20-dioxo-4-aza-pregnan-5-ene 
• 73671-92-8 3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester 

Downstream Products

• 1796930-46-5 dutasteride 
• 103335-41-7 methyl 3-oxo-4-aza-5α-androst-1-ene-17β-carboxylate 
• 142139-60-4 N-[1-methyl-1-(4-methoxyphenyl)ethyl]-3-oxo-4-aza-5α-androst-1-ene-17β-carboxamide 

Relevant articles and documents

A scaleable synthesis of dutasteride: A selective 5α-reductase inhibitor

An improved and scaleable process for Dutasteride (1), a synthetic 4-azasteroid derivative essentially used for the treatment of prostate diseases, is described

Production process of high-purity dutasteride

The invention discloses a purification production process of high-purity dutasteride. The problems to be solved are that the purity of the dutasteride is improved while the production cost is reduced.According to the method, after a dutasteride crude product is obtained, twice crystallization is carried out, so that the dutasteride with high yield and high purity can be obtained. The production process provided by the invention has the advantages of high efficiency and clean production, and the operability is high. An intermediate is refined, so that the quality of the dutasteride finished product is more easily controlled, the purity of the obtained dutasteride product is not lower than 99.5%, and any single impurity in the product is not higher than 0. 1%.

PROCESS FOR PREPARING ANDROSTENONE DERIVATIVES

Provided is a process for preparing androstenone derivatives, specifically 3-oxo-4-aza-5α-androstene-17β-carboxylic acid of Formula I, a key intermediate for dutasteride.