 | |
| Names | |
|---|---|
| IUPAC name 17β-Hydroxy-5β-androstan-3-one | |
| Systematic IUPAC name (1S,3aS,3bR,5aR,9aS,9bS,11aS)-1-Hydroxy-9a,11a-dimethylhexadecahydro-7H-cyclopenta[a]phenanthren-7-one | |
| Other names 5β-Androstan-17β-ol-3-one; Etiocholan-17β-ol-3-one; 5β-Dihydrotestosterone; 5β-DHT | |
| Identifiers | |
| |
3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.164.933 |
| EC Number |
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| KEGG | |
| UNII | |
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| Properties | |
| C19H30O2 | |
| Molar mass | 290.447 g·mol−1 |
| Hazards | |
| GHS labelling:[1] | |
  | |
| Danger | |
| H302,H312,H332,H350,H360 | |
| P203,P261,P264,P270,P271,P280,P301+P317,P302+P352,P304+P340,P317,P318,P321,P330,P362+P364,P405,P501 | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
5β-Dihydrotestosterone (5β-DHT), also known as5β-androstan-17β-ol-3-one or asetiocholan-17β-ol-3-one, is anetiocholane (5β-androstane)steroid as well as an inactivemetabolite oftestosterone formed by5β-reductase in theliver andbone marrow[1][2] and anintermediate in the formation of3α,5β-androstanediol and3β,5β-androstanediol (by3α- and3β-hydroxysteroid dehydrogenase) and, from them, respectively,etiocholanolone andepietiocholanolone (by17β-hydroxysteroid dehydrogenase).[3][4] Unlike itsisomer5α-dihydrotestosterone (5α-DHT or simply DHT), 5β-DHT either does not bind to or binds only very weakly to theandrogen receptor.[1] 5β-DHT is notable among metabolites of testosterone in that, due to the fusion of the A and B rings in thecis orientation, it has an extremely angularmolecular shape, and this could be related to its lack ofandrogenic activity.[5] 5β-DHT, unlike 5α-DHT, is also inactive in terms ofneurosteroid activity,[6][7] although its metabolite, etiocholanolone, does possess such activity.[8][9]
