98319-24-5

Basic information

• Product Name: Dihydroproscar
• Synonyms: N-TERT-BUTYL-3-OXO-4-AZA-5ALPHA-ANDROSTANE-17BETA-CARBOXAMIDE;N-T-BUTYL-4-AZA-5-ALPHA-ANDROSTA-3-ONE-17BETA-CARBOXAMIDE;N-(1,1-DIMETHYLETHYL)-3-OXO-4-AZA-5A-ANDRO-STANE-17B-CARBOXAMIDE;(4AR,4BS,6AS,7S,9AS,9BS,11AR)-4A,6A-DIMETHYL-2-OXO-HEXADECAHYDRO-INDENO[5,4-F]QUINOLINE-7-CARBOXYLIC ACID TERT-BUTYLAMIDE;4A,6A,11A-TRIMETHYL-2-OXO-HEXADECAHYDRO-INDENO[5,4-F]QUINOLINE-7-CARBOXYLIC ACID TERT-BUTYLAMIDE;3-OXO-4-AZA-5A-ANDROSTANE-17-BETA-(N-TERT-BUTYLCARBOXAMIDE);3-oxo-4-aza-5a-androstane-17b-(n-tert-butylcarboxamide);3-OXO-4-AZA-5-ALPHA-ANDROSTANE-17-BETA-N-T-BUTYLCARBOXAMIDE
• CAS NO: 98319-24-5
• Molecular Formula: C₂₃H₃₈N₂O₂
• Molecular Weight: 374.56
• Product Categories: INTERMEDIATESOFFINASTERIDE;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 98319-24-5.mol

Chemical Properties

• Melting Point: 273-275 °C
• Boiling Point: 569.397 °C at 760 mmHg
• Flash Point: 171.728 °C
• Appearance: yellow/powder
• Density: 1.051 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.514
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Methanol
• PKA: 15.94±0.70(Predicted)
• CAS DataBase Reference: Dihydroproscar(CAS DataBase Reference)
• NIST Chemistry Reference: Dihydroproscar(98319-24-5)
• EPA Substance Registry System: Dihydroproscar(98319-24-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 98319-24-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Dihydroproscar is used as a pharmaceutical agent for the treatment of benign prostatic hyperplasia (BPH) and androgenetic alopecia (male pattern baldness). It works by inhibiting the conversion of testosterone to dihydrotestosterone (DHT), thereby reducing the size of the prostate and promoting hair growth.
Used in Research Applications:
Dihydroproscar is used as a research tool for studying the role of 5α-reductase enzymes in various biological processes, including prostate growth, hair loss, and hormone regulation. It helps researchers understand the mechanisms of action and potential therapeutic applications of 5α-reductase inhibitors.

InChI:InChI=1/C23H38N2O2/c1-21(2,3)25-20(27)17-8-7-15-14-6-9-18-23(5,13-11-19(26)24-18)16(14)10-12-22(15,17)4/h14-18H,6-13H2,1-5H3,(H,24,26)(H,25,27)/t14-,15-,16-,17+,18+,22-,23+/m0/s1

Upstream product

• 75-64-9 tert-butylamine 
• 103335-50-8 S-2-pyridyl 3-oxo-4-aza-5α-androstane-17β-thiocarboxylate 
• 104214-27-9 benzotriazol-1'-yl 3-oxo-4-aza-5α-androstane-17β-carboxylate 
• 166896-74-8 N-tert-butyl-3-oxo-4-aza-5-androsten-17β-formamide 
• 167982-07-2 3-oxo-4-azaandrosta-5,16-diene-17-(N-tert-butylcarboxamide) 
• 877080-59-6 4-aza-androst-5,16-diene-17-cyano-3-one 
• 877080-58-5 4-aza-5-androstene-17α-hydroxy-17β-cyano-3-one 
• 63-05-8 Androstenedione 
• 6857-88-1 3-((3aS,5aS,6R,9aR,9bS)-3a,6-dimethyl-3,7-dioxododecahydro-1H-cyclopenta[a]naphthalen-6-yl)propanoic acid 
• 51478-09-2 4-aza-5α-androstene-3,17-dione 
• 302-97-6 androst-4-en-3-one-17β-carboxylic acid 
• 131267-80-6 N-(1,1-dimethylethyl)-3-oxoandrost-4-ene-17β-carboxamide 
• 57072-90-9 3-oxoandrost-4-ene-17β-carboxylic acid chloride 
• 103335-55-3 3-oxo-4-aza-5α-androstane-17β-carboxylic acid 

Downstream Products

• 98319-26-7 finasteride 
• 684215-49-4 N-tert-butyl-2-phenylsulfenyl-3-oxo-4-aza-5α-androstane-17β-carboxamide 
• 123-31-9 hydroquinone 
• 943823-26-5 C₃₁H₄₄N₂O₄ 
• 943823-24-3 C₃₀H₄₁N₃O₅ 
• 943823-23-2 C₃₀H₄₁N₃O₅ 
• 943823-22-1 C₃₀H₄₁N₃O₅ 
• 943823-27-6 C₃₁H₄₄N₂O₃ 
• 1329611-51-9 C₂₃H₃₄N₂O₂ 

Relevant articles and documents

Synthesis and comprehensive structural and physicochemical characterization of dutasteride hydrochloride hydrate solvates

Four crystalline dutasteride hydrochloride hydrate solvates containing respectively methanol, ethanol, acetone and acetonitrile molecules were obtained. All samples were characterized by extensive spectroscopic analysis with infrared spectroscopy (FT-IR), differential scanning calorimetry (DSC) and 1H as well as 13C NMR techniques. For three solvates, i.e. methanol, ethanol and acetone solvates, the single crystal X-ray diffraction (SCXRD) experiments were possible, and their respective crystal and molecular structures were determined. The present study allowed to unambiguously establish the molecular composition of solvates as consisting of a dutasteride: hydrogen chloride: water: solvent in a molar ratio of 1:1:1:1 and confirm that they are isostructural. Beyond providing the full spectroscopic characteristic of the compounds, the results obtained have also allowed clarifying of some appearing inconsistencies in published literature regarding the appropriate attribution of IR absorption bands to the relevant molecular vibrations.

A synthetic 3-carbonyl-4-nitrogen mixed male steroid -17 β derivative method

The invention discloses a method for synthesizing 3-carbonyl-4-azaandrost-17beta derivative I, which comprises the following steps: (1) in the presence of an acidic catalyst, dissolving A-norandrostane-3,5-cracked-androst-5-one-3-carboxylic acid-17beta derivative II in dioxane aqua ammonia, heating, and slowly and dropwisely adding reducer-dissolved aqua ammonia to simultaneously perform reduction amination reaction and ring-closing reaction; (2) adding acid to destroy the reducer, concentrating under normal pressure, and recovering dioxane; (3) cooling, and carrying out centrifugal filtration to obtain a filter cake; washing the filter cake with water to a neutral state, and carrying out centrifugal drying to obtain a 3-carbonyl-4-azaandrost-17beta derivative I crude product; and (4) pulping the 3-carbonyl-4-azaandrost-17beta derivative I crude product with methanol, carrying out centrifugal filtration to obtain a filter cake, washing the filter cake with methanol, carrying out centrifugal drying, and baking to obtain the 3-carbonyl-4-azaandrost-17beta derivative refined product. By completing the reduction amination reaction and ring-closing reaction in one step, the method has the advantages of low reaction temperature, high product yield and good product quality, is economical and environment-friendly, and is suitable for industrialization.

Impurities in finasteride: Identification, synthesis, characterization and control of potential carry-over impurities from reagents used for the process

An assessment of the impurity profile of finasteride and possible carry-over related substances likely to arise during the synthesis of finasteride is described in this article. Impurities in reaction mass were monitored by HPLC, potential impurities isolated with preparative HPLC and structures were substantiated by 1H NMR, MS and MS-MS. Impurities RRT's were established by HPLC co-injection. Based on the spectral data structure of impurity I and impurity II were characterized as cyclohexyl and phenyl analog of finasteride.

PROCESS FOR THE PREPARATION OF 17-N-SUBSTITUTED-CARBAMOYL-4-AZA-ANDROST-1 -EN-3-ONES

The present invention relates to a process for producing 17-N-substituted-carbamoyl-4-aza-androst-1-en-3-ones of formula (1) , including Finasteride and Dutasteride.

PROCESSES TO PREPARE FINASTERIDE POLYMORPHS

Processes for preparing polymorphic crystalline Form I and Form III of finasteride.

Process for the preparation of 17-N-substituted-carbamoyl-4-aza-androst-1-en-3-ones

The present invention relates to a process for producing 17-N-substituted-carbamoyl-4-aza-androst-1-en-3-ones of formula 1, including Finasteride and Dutasteride.

New approach to 3-oxo-4-aza-5α-androst-1-ene-17β-(N-tert- butylcarboxamide)

We describe the synthesis of 3-oxo-4-aza-5α-androst-1-ene-17β- (N-tert-butylcarboxamide) (finasteride) from 4-androstene-3,17-dione (AD) in seven steps in an overall yield of 18.6% via oxidation, ammoniumation, dehydration, and dehydrogenation.

METHOD FOR THE PREPARATION OF HIGHLY PURE 1-ANDROSTENE DERIVATIVES

A method for preparing a 1-androstene derivative which comprises reacting a 2-iodo-androstane derivative with an oxidizing agent while maintaining the pH of the reaction mixture at a specific range gives the 1-androstene derivative with high purity and yield.

PROCESS FOR THE PREPARATION OF 17?-SUBSTITUTED-3-OXO-4-AZA-5ALPHA-ANDROSTANE DERIVATIVES

Process for the preparation of 17?-substituted-3-oxo-4-aza-5α-androstane derivatives, which are useful intermediates for the synthesis of 3-oxo-4-aza-5α-androst-1-ene derivatives including finasteride, is provided.

Process for obtaining 17 beta-(N-tert-butylcarbamoyl)-3-one4-aza-steroids

17β-(N-tert-butylcarbamoyl)-3-one-4-aza-steroids (I) can be obtained by a process which comprises the reaction of 17β-(alkoxycarbonyl)-3-one-4-aza-steroid with lithium tert-butylamide in an organic solvent. Some compounds of formula (I), for example, finasteride, are useful as inhibitors of 5α-reductase, and can be used in the treatment of benign prostatic hyperplasia and alopecia.