103335-41-7

Basic information

• Product Name: METHYL 4-AZA-5ALPHA-ANDROSTA-1-EN-3-ONE-17BETA-CARBOXYLATE
• Synonyms: METHYL 3-OXO-4-AZA-5-ALPHA-ANDROST-1-ENE-17-BETA-CARBOXYLATE;3-Oxo-4-aza-5α-αndrost-1-ene-17β-carboxylic Acid Methyl Ester;(4aR,4bS,6aS,7S,9aS,9bS,11aR)-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-Tetradecahydro-4a,6a-diMethyl-2-oxo-;Finasteride Methyl Ester Analog;(4aR,4bS,6aS,7S,9aS,9bS,11aR)-Methyl 4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7, 8,9,9a,9b,10,11,11a-t;(4aR,4bS,6aS,7S,9aS,9bS,11aR);-Methyl 4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxylate;(4aR,4bS,6aS,7S,9aS,9bS,11aR)-Methyl 4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a
• CAS NO: 103335-41-7
• Molecular Formula: C₂₀H₂₉NO₃
• Molecular Weight: 331.46
• Product Categories: Intermediates;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 103335-41-7.mol
• Article Data: 19

Chemical Properties

• Melting Point: 280-282°C (dec.)
• Boiling Point: 478.615 °C at 760 mmHg
• Flash Point: 243.258 °C
• Appearance: Off-White Solid
• Density: 1.114 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.525
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly, Heated), Methanol (Slightly, Heated)
• PKA: 14.15±0.70(Predicted)
• CAS DataBase Reference: METHYL 4-AZA-5ALPHA-ANDROSTA-1-EN-3-ONE-17BETA-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 4-AZA-5ALPHA-ANDROSTA-1-EN-3-ONE-17BETA-CARBOXYLATE(103335-41-7)
• EPA Substance Registry System: METHYL 4-AZA-5ALPHA-ANDROSTA-1-EN-3-ONE-17BETA-CARBOXYLATE(103335-41-7)

Safety Data

• Hazardous Substances Data: 103335-41-7(Hazardous Substances Data)

Usage

Description

METHYL 4-AZA-5ALPHA-ANDROSTA-1-EN-3-ONE-17BETA-CARBOXYLATE, also known as 3-Oxo-4-aza-5α-αndrost-1-ene-17β-carboxylic Acid Methyl Ester, is an intermediate in the synthesis of Finasteride and Dutasteride. These are 5α-reductase inhibitors used for the treatment of various hyperandrogenetic related disorders. It is an off-white solid.

Uses

Used in Pharmaceutical Industry:
METHYL 4-AZA-5ALPHA-ANDROSTA-1-EN-3-ONE-17BETA-CARBOXYLATE is used as an intermediate in the synthesis of Finasteride (F342000) and Dutasteride (D735000) for the treatment of benign prostatic hyperplasia, acne, seborrhea, female hirsutism, prostatitis, and prostatic carcinoma, and other hyperandrogenetic related disorders.
Used as Impurity:
METHYL 4-AZA-5ALPHA-ANDROSTA-1-EN-3-ONE-17BETA-CARBOXYLATE is also used as an impurity in Finasteride (F342000) and Dutasteride (D735000) to ensure the quality and purity of the final product.

InChI:InChI=1/C20H29NO3/c1-19-10-8-14-12(13(19)5-6-15(19)18(23)24-3)4-7-16-20(14,2)11-9-17(22)21-16/h9,11-16H,4-8,10H2,1-3H3,(H,21,22)/t12-,13-,14-,15+,16+,19-,20+/m0/s1

Upstream product

• 67-56-1 methanol 
• 104239-97-6 3-Oxo-4-aza-5α-androst-1-ene-17β-carboxylic acid 
• 149198-45-8 methyl (2α,5α,17β)-2-iodo-3-oxo-4-aza-5-androstane-17-carboxylate 
• 17697-12-0 benzeneseleninic anhydride 
• 73671-92-8 3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester 

Downstream Products

• 104239-97-6 3-Oxo-4-aza-5α-androst-1-ene-17β-carboxylic acid 
• 1796930-46-5 dutasteride 
• 606101-78-4 2-Fluoro-4-methyl-3-oxo-4-aza-5α-androst-1-ene-17β-carboxylic acid methyl ester 
• 606101-79-5 (5α,17β)-2-Fluoro-3-oxo-4-methyl-4-azaandrost-1-ene-17-carboxylic acid 
• 827589-62-8 Methyl 4-p-methoxybenzyl-3-oxo-4-aza-5α-androst-1-ene-17β-carboxylate 
• 103335-44-0 Methyl 4-methyl-3-oxo-4-aza-5alpha-androst-1-ene-17beta-carboxamide 
• 73671-92-8 3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester 
• 98319-26-7 finasteride 
• 496947-19-4 3-Oxo-4-phenyl-4-aza-5α-androst-1-ene-17β-carboxylic acid 
• 166896-63-5 Methyl 3-oxo-4-azaandrosta-1,5,7-triene-17β-carboxylate 
• 166896-62-4 Methyl 3-oxo-4-azaandrosta-1,5-diene-17β-carboxylate 
• 1026013-15-9 (4aR,4bS,6aS,7S,9aS,9bS)-11a-Methoxy-4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxylic acid methyl ester 
• 138689-15-3 (5α,17β)-N-Methoxy-N-methyl-3-oxo-4-aza-androst-1-ene-17β-carboxamide 

Relevant articles and documents

A method of preparation he male amine

The invention belongs to the field of pharmaceutical chemistry, and relates to a high-yield method for preparing dutasteride, which comprises the following steps: (1) under the action of a catalyst, reacting aza-5-androst-1-alkenyl-3-keto-17beta-carboxylic acid (I) with alcohol to generate 4-aza-5-androst-1-alkenyl-3-keto-17beta-carboxylate (II); and (2) in the presence of a catalyst, reacting the 4-aza-5-androst-1-alkenyl-3-keto-17beta-carboxylate (II) with 2,5-ditrifluoromethylaniline in an organic solvent at certain reaction temperature to obtain the dutasteride (III) at high yield. The method has the characteristics of accessible raw material, mild reaction conditions and high product yield, and is easy to control.

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.

Method of prevention of prostatic carcinoma with 17β-N-monosubstituted-carbamoyl-4-aza-5α-androst-1-en-3-ones

17β-N-monosubstituted-carbamoyl-4-aza-5α-androst-1-en-3-ones of the formula wherein R1is selected from hydrogen, methyl and ethyl and R2is a straight or branched chain alkyl, cycloalkyl, aralkyl of from 1-12 carbons, or monocyclic aryl optionally containing 1 or more lower alkyl substituents of 1-2 carbon atoms and/or 1 or more halogens, and R′, R″, R″′ are hydrogen or methyl are useful for the prevention of prostatic carcinoma.