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Structure Database (LMSD)

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Common Name

Mesterolone

Systematic Name

1α-Methyl-5α-androstan-17β-hydroxy-3-one

Synonyms

1alpha-Methyl-5alpha-androstan-17beta-ol-3-one

LM ID

LMST02020107

Formula

C₂₀H₃₂O₂

Exact Mass

Calculate m/z

304.24023

Sum Composition

ST 20:1;O2

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

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Classification

Biological Context

Mesterolone is an analytical reference standard categorized as an anabolic androgenic steroid. Formulations containing mesterolone have been used in patients with low testosterone or symptoms of aging male syndrome.^1,2 Mesterolone cannot be aromatized to estrogens, unlike other androgens.^1,3 This compound is the active ingredient in different pharmaceutical preparations that have been used medically but have also been widely applied in sports in order to improve athlete performance.⁴ Mesterolone is regulated as a Schedule III drug in the United States. This product is intended for research and forensic applications.

This information has been provided by Cayman Chemical

References

1. Dugeroglu, H., Ozturk, M., Atmaca, M., et al. Mesterolone treatment of aging male syndrome improves lower urinary tract symptoms. J. Pak. Med. Assoc. 64(12), 1366-1369 (2014).

2. Dołowy, M., Pyka-Pająk, A., Filip, K., et al. A validated TLC-densitometric method for the determination of mesterolone in bulk material and in tablets. Biomed Res. Int. 230104 (2015).

3. Carruthers, M., Cathcart, P., and Feneley, M.R. Evolution of testosterone treatment over 25 years: Symptom responses, endocrine profiles and cardiovascular changes. Aging Male 18(4), 217-227 (2015).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

[Experimental animal studies with a new androgen--mesterolone (1-alpha-methyl-5-alpha-androstan-17-beta-ol-one)].,
Arzneimittelforschung, 1966

Pubmed ID: 6014248

String Representations

InChiKey (Click to copy)

UXYRZJKIQKRJCF-TZPFWLJSSA-N

InChi (Click to copy)

InChI=1S/C20H32O2/c1-12-10-14(21)11-13-4-5-15-16-6-7-18(22)19(16,2)9-8-17(15)20(12,13)3/h12-13,15-18,22H,4-11H2,1-3H3/t12-,13-,15-,16-,17-,18-,19-,20-/m0/s1

SMILES (Click to copy)

[C@@]12([H])CC[C@@]3([H])CC(=O)C[C@H](C)[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@@H](O)CC[C@@]21[H]