Epitestosterone

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.

Epitestosterone
Names
IUPAC name
17α-Hydroxyandrost-4-en-3-one
Systematic IUPAC name
(1R,3aS,3bR,9aR,9bS,11aS)-1-Hydroxy-9a,11a-dimethyl-1,2,3,3a,3b,4,5,8,9,9a,9b,10,11,11a-tetradecahydro-7H-cyclopenta[a]phenanthren-7-one
Other names
Isotestosterone; 17α-Testosterone; Androst-4-en-17α-ol-3-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.169.813
PubChem CID
UNII
  • InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17+,18-,19-/m0/s1
    Key: MUMGGOZAMZWBJJ-KZYORJDKSA-N
SMILES
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@H]2O)CCC4=CC(=O)CC[C@]34C
Properties
C19H28O2
Molar mass 288.431 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Structurally, epitestosterone differs from testosterone only in the configuration at the hydroxy-bearing carbon, C17. Epitestosterone is believed to form in a similar way to testosterone; a 1993 study found that around 50% of epitestosterone production in human males can be ascribed to the testis, although the exact pathway of its formation is still the subject of research. It has been shown to accumulate in mammary cyst fluid and in the prostate. Epitestosterone levels are typically highest in young males; however, by adulthood, most healthy males exhibit a testosterone to epitestosterone ratio (T/E ratio) of about 1:1.

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