اپی‌تستوسترون

Also known as epi-testosterone, 17a-cis-Testosterone, 17-Epitestosterone, cis-Testosterone, Isotestosterone, (1S,2R,10R,11S,14R,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one, (10ALPHA,13ALPHA,14BETA,17ALPHA)-17-HYDROXYANDROST-4-EN-3-ONE

Epitestosterone, or isotestosterone, also known as 17α-testosterone or as androst-4-en-17α-ol-3-one, is an endogenous steroid and an epimer of the androgen sex hormone testosterone. It is a weak competitive antagonist of the androgen receptor (AR) and a potent 5α-reductase inhibitor.

Chemical data

Formula: C19H28O2
Molecular weight: 288.4 g/mol
IUPAC name: (8R,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Research

596 papers

Epitestosterone.The Journal of steroid biochemistry and molecular biology · 2003
Epitestosterone--a hormone or not.Endocrine regulations · 1993
Evaluation of testosterone/epitestosterone ratio influential factors as determined in doping analysis.Journal of analytical toxicology · 2000
Epitestosterone- and testosterone-replacement in immature castrated rats changes main testicular developmental characteristics.Molecular and cellular endocrinology · 2018
5α-reduction of epitestosterone is catalysed by human SRD5A1 and SRD5A2 and increases androgen receptor transactivation.The Journal of steroid biochemistry and molecular biology · 2024

via PubMed

Wikidata facts

Has part: carbon
Mass: 288.209

Show 5 more facts

chemical formula: C₁₉H₂₈O₂
canonical SMILES: CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C
isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@H]2O)CCC4=CC(=O)CC[C@]34C
found in taxon: Vitex agnus-castus
stereoisomer of: testosterone

Sources (4)

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