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
• Article Data: 12

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

General Description

N-T-BUTYL-4-ANDROSTEN-3-ONE-17BETA-CARBOXAMIDE, also known as ibutamoren mesylate or MK-677, is a synthetic compound with potential anabolic and growth hormone-releasing properties. This chemical is commonly used as a potential treatment for growth hormone deficiency and muscle wasting conditions. It is believed that N-T-BUTYL-4-ANDROSTEN-3-ONE-17BETA-CARBOXAMIDE works by stimulating the release of growth hormone and insulin-like growth factor 1 (IGF-1), which can promote muscle growth and improve muscle strength. Moreover, this compound has also been studied for its potential role in promoting bone density and reducing the risk of fractures in older individuals. However, further research is needed to fully understand the potential benefits and risks associated with its use.

Upstream product

• 57072-90-9 3-oxoandrost-4-ene-17β-carboxylic acid chloride 
• 75-64-9 tert-butylamine 
• 57-83-0 Progesterone 
• 979-02-2 16-dehydropregnenolone acetate 
• 146175-29-3 S-(2-pyridyl)-androst-4-ene-3-one-17β-thiocarboxylate 
• 1778-02-5 Pregnenolone acetate 
• 15173-68-9 etienic acid 
• 73672-02-3 pregnenolone 21-pyridinium iodide 
• 302-97-6 androst-4-en-3-one-17β-carboxylic acid 
• 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

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

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.

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.

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.