153546-23-7

Basic information

• Product Name: 7β,17α-Dimethyl-5β-androstane-3α,17β-diol
• Synonyms: 7β,17α-Dimethyl-5β-androstane-3α,17β-diol
• CAS NO: 153546-23-7
• Molecular Formula: C21H36O2
• Molecular Weight: 320.50934
• Mol File: 153546-23-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 7β,17α-Dimethyl-5β-androstane-3α,17β-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 7β,17α-Dimethyl-5β-androstane-3α,17β-diol(153546-23-7)
• EPA Substance Registry System: 7β,17α-Dimethyl-5β-androstane-3α,17β-diol(153546-23-7)

Safety Data

• Hazardous Substances Data: 153546-23-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
7β,17α-Dimethyl-5β-androstane-3α,17β-diol is used as a pharmaceutical compound for treating breast cancer. As a metabolite of calusterone, it plays a role in the treatment of this specific type of cancer, potentially offering an alternative or complementary approach to existing therapies.
Additionally, due to its structural similarity to Bolasterone M, it may have potential applications in further research and development of new drugs targeting hormone-related conditions or cancers.

Relevant articles and documents

17-Epimerization of 17α-methyl anabolic steroids in humans: metabolism and synthesis of 17α-hydroxy-17β-methyl steroids

The 17-epimers of the anabolic steroids bolasterone (I), 4-chlorodehydromethyltestosterone (II), fluoxymesterone (III), furazabol (IV), methanedienone (V), mestanolone (VI), methyltestosterone (VII), methandriol (VIII), oxandrolone (IX), oxymesterone (X), oxymetholone (XI), stanozolol (XII), and the human metabolites 7α,17α-dimethyl-5β-androstane-3α,17β-diol (XIII) (metabolite of I), 6β-hydroxymetandienone (XIV) (metabolite of V), 17α-methyl-5β-androst-1-ene-3α,17β-diol (XV) (metabolite of V), 3'-hydroxystanozolol (XVI) (metabolite of XII), as well as the reference substances 17β-hydroxy-17α-methyl-5β-androstan-3-one (XVII), 17β-hydroxy-17α-methyl-5β-androst-1-en-3-one (XVIII) (also a metabolite of V), the four isomers 17α-methyl-5α-androstane-3α,17β-diol (XIX) (also a metabolite of VI, VII, and XI), 17α-methyl-5α-androstane-3β,17β-diol (XX), 17α-methyl-5β-androstane-3α,17β-diol (XXI) (also a metabolite of V, VII, and VIII), 17α-methyl-5β-androstane-3β,17β-diol (XXII), and 17β-hydroxy-7α,17α-dimethyl-5β-androstan-3-one (XXIII) were synthesized via a 17β-sulfate that spontaneously hydrolyzed in water to several dehydration products, and to the 17α-hydroxy-17β-methyl epimer.The 17β-sulfate was prepared by reaction of the 17β-hydroxy-17α-methyl steroid with sulfur trioxide pyridine complex.The 17β-methyl epimers are eluted in gas chromatography as trimethylsilyl derivatives from a capillary SE-54 or OV-1 column 70-170 methylen units before the corresponding 17α-methyl epimer.The electron impact mass spectra of the underivatized and trimethylsilylated epimers are in most cases identical and only for I, II, and V was a differentiation between the 17-epimers possible. 1H nuclear magnetic resonance (NMR) spectra show for the 17β-methyl epimer a chemical shift for the C-18 protons (singlet) of about 0.175 ppm (in deuterochloroform) to a lower field. 13C NMR spectra display differences for the 17-epimeric steroids in shielding effects for carbons 12-18 and 20.Excretion studies with I-XII with identification and quantification of 17-epimeric metabolites indicate that the extent of 17-epimerization depends on the A-ring structure and shows a great variation for the different 17α-methyl anabolic steroids.Keywords: anabolic steroids; 17-epimerization; nuclear magnetic resonance; Kovats indices; mass spectrometry; metabolism; gas chromatography