131267-80-6

Basic information

• Product Name: N-T-BUTYL-4-ANDROSTEN-3-ONE-17BETA-CARBOXAMIDE
• Synonyms: 17b-(N-tert-butylcarbamoyl)-3-oxo-androstene;N-tert-butyl-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-17-carboxamide
• CAS NO: 131267-80-6
• Molecular Formula: C₂₄H₃₇NO₂
• Molecular Weight: 371.55608
• Mol File: 131267-80-6.mol

Chemical Properties

• Boiling Point: 540.0±50.0 °C(Predicted)
• Appearance: /
• Density: 1.07±0.1 g/cm3(Predicted)
• PKA: 16.10±0.60(Predicted)
• CAS DataBase Reference: N-T-BUTYL-4-ANDROSTEN-3-ONE-17BETA-CARBOXAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-T-BUTYL-4-ANDROSTEN-3-ONE-17BETA-CARBOXAMIDE(131267-80-6)
• EPA Substance Registry System: N-T-BUTYL-4-ANDROSTEN-3-ONE-17BETA-CARBOXAMIDE(131267-80-6)

Safety Data

• Hazardous Substances Data: 131267-80-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-T-BUTYL-4-ANDROSTEN-3-ONE-17BETA-CARBOXAMIDE is used as a potential treatment for growth hormone deficiency and muscle wasting conditions. It is employed for its anabolic properties, which can promote muscle growth and improve muscle strength by stimulating the release of growth hormone and IGF-1.
Used in Geriatric Care:
In the geriatric care industry, N-T-BUTYL-4-ANDROSTEN-3-ONE-17BETA-CARBOXAMIDE is used for its potential role in promoting bone density and reducing the risk of fractures in older individuals. This can help improve the quality of life and reduce the incidence of bone-related injuries in the elderly population.

Upstream product

• 302-97-6 androst-4-en-3-one-17β-carboxylic acid 
• 75-64-9 tert-butylamine 
• 57072-90-9 3-oxoandrost-4-ene-17β-carboxylic acid chloride 
• 73672-02-3 pregnenolone 21-pyridinium iodide 
• 15173-68-9 etienic acid 
• 1778-02-5 Pregnenolone acetate 
• 146175-29-3 S-(2-pyridyl)-androst-4-ene-3-one-17β-thiocarboxylate 
• 979-02-2 16-dehydropregnenolone acetate 
• 57-83-0 Progesterone 
• 2681-55-2 3-oxo-androst-4-ene-17β-carboxylic acid methyl ester 
• 85541-82-8 methyl 5-androsten-3β-ol-17β-carboxylate 
• 145-13-1 Pregnenolone 

Downstream Products

• 98319-26-7 finasteride 
• 98319-24-5 dihydro-finasteride 
• 166896-74-8 N-tert-butyl-3-oxo-4-aza-5-androsten-17β-formamide 
• 119169-78-7 epristeride 
• 151338-11-3 N-t-butyl-3-cyanoandrosta-3,5-diene-17β-carboxamide 

Relevant articles and documents

Design, synthesis and biological evaluation of novel 3-oxo-4-oxa-5α-androst-17β-amide derivatives as dual 5α-reductase inhibitors and androgen receptor antagonists

Prostate cancer (PCa) is the second leading cause of death in men. Recently, some researches have showed that 5α-reductase inhibitors were beneficial in PCa treatment as well. In this study, a series of novel 3-oxo-4-oxa-5α-androst-17β-amide derivatives have been designed and synthesized in a more simple and convenient method. Most of the synthesized compounds displayed good 5α-reductase inhibitory activities and androgen receptor binding affinities. Their anti-proliferation activities in PC-3 and LNCaP cell lines were also evaluated and the results indicated that most of the synthesized compounds exhibited potent anti-proliferative activities. It is obvious that the androgen-dependent cell line LNCaP was much more sensitive than the androgen-independent cell line PC-3. Among all the synthesized compounds, 11d and 11k displayed the best inhibition activity with 4-fold more sensitive toward LNCaP than PC-3, which was consistent with their high affinities observed in AR binding assay. Molecular modeling studies suggested that 11k could bind to AR in a manner similar to the binding of dihydrotestosterone to AR. Compared to the finasteride, 11k showed a longer plasma half-life (4 h) and a better bioavailability. Overall, based on biological activities data, compound 11d and 11k can be identified as potential dual 5α-reductase inhibitors and AR antagonists which might be of therapeutic importance for prostate cancer treatment.

Epristeride intermediate, preparation method of Epristeride intermediate, and preparation method of Epristeride

The invention relates to the field of medicine, in particular to an Epristeride intermediate, a preparation method of the Epristeride intermediate, and a preparation method of Epristeride. The preparation method of the Epristeride intermediate comprises the following steps that a compound 3 takes a sulfonation reaction with an alkaline reagent to produce a compound 4; the reaction conversion is single; the column chromatography isolation is avoided; the alkaline reagent used in the reaction process can be easily obtained; the reaction conditions are mild. The unit operation is reduced; the production period is shortened; the production efficiency is improved; the production efficiency is high; the economic benefits are improved.

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.

Treatment of hyperandrogenic conditions

The invention concerns the treatment of hyperandrogenic conditions in humans by the formation of a novel mechanism-based irreversible inhibitor of human 5α-reductase enzymes from 3-oxo-4-oxa and 4-thiasteroids having a 1,2-double bond and the pyridine-nuc

4-Oxa and 4-thia steroids

The compounds of the present invention are those of structural formula (I) STR1 wherein X is oxygen or sulfur. Pharmaceutical compositions and methods of use of the compounds in the treatment of hyperandrogenic conditions are disclosed. In addition, the combination of the compounds with other active agents such as finasteride, minoxidil and retinoic acid or a derivative thereof is disclosed.

Anti-AIDS agents. Part 36: 17-carboxylated steroids as potential anti-HIV agents

In our search for novel anti-HIV agents, seven 17-carboxylated steroid derivatives were synthesized and evaluated as potential anti-HIV agents. Compound 13 exhibited potent anti-HIV activity in acutely infected H9 lymphocytes with EC50 and therapeutic index values of 0.8 μM and 300, respectively.

Treatment of hyperandrogenic conditions

The invention concerns the treatment of hyperandrogenic conditions in humans by the formation of a novel mechanism-based irreversible inhibitor of human 5α-reductase enzymes from 3-oxo-4-oxa end 4-thiasteroids having a 1,2-double bond and the pyridine-nuc

Synthesis of N-substituted 3-oxo-17β -carboxamide-4-aza-5α-androstanes and the tautomerism of 3-oxo-4-aza-5-androstenes

An N-aryl-3-oxo-4-aza-5α -androst-1-ene-17β carboxamide and three N-aryl or alkyl substituted 17α -hydroxy-3-oxo-4-aza-5α -androstane-17β -carboxamides were synthesized as antiandrogen candidates from 3-oxoandrost-4-ene-17β - carboxylic acid and androst-4-ene-3,17-dione respectively. The chemo- and stereoselective reduction of 3-oxo-4-aza-5-ene intermediates with formic acid and their tautomerism in a solution of chloroform and methanol were described.

Synthesis of 4-trifluoromethylsteroids: A novel class of steroid 5α-reductase inhibitors

A concise synthetic approach to 4-trifluoromethyl steroids, a novel class of steroid 5α-reductase inhibitors, is described. Direct trifluoromethylation of steroid olefinic bromide with methyl fluorosulfonyldifluoroacetate was used as a key step in the synthesis. The compound 4 exhibited highly inhibitory activity than Finasteride in in vitro assay.