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Dihydrotestosterone information


This article is about dihydrotestosterone as a hormone. For its use as a medication, see Androstanolone.
This article is about 5α-dihydrotestosterone, an androgen. For the inactive 5β isomer, see 5β-Dihydrotestosterone.

Dihydrotestosterone
The chemical structure of dihydrotestosterone.
A ball-and-stick model of dihydrotestosterone.
Names
IUPAC name
17β-Hydroxy-5α-androstan-3-one
Systematic IUPAC name
(1S,3aS,3bR,5aS,9aS,9bS,11aS)-1-Hydroxy-9a,11a-dimethylhexadecahydro-7H-cyclopenta[a]phenanthren-7-one
Other names
DHT; 5α-Dihydrotestosterone; 5α-DHT; Androstanolone; Stanolone; 5α-Androstan-17β-ol-3-one
Identifiers
CAS Number
  • 521-18-6 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:16330 checkY
ChEMBL
  • ChEMBL27769 ☒N
ChemSpider
  • 10189 checkY
DrugBank
  • DB02901 checkY
ECHA InfoCard 100.007.554 Edit this at Wikidata
KEGG
  • C03917 checkY
PubChem CID
  • 10635
UNII
  • 08J2K08A3Y checkY
CompTox Dashboard (EPA)
  • DTXSID9022364 Edit this at Wikidata
InChI
  • InChI=1S/C19H30O2/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/h12,14-17,21H,3-11H2,1-2H3/t12-,14-,15-,16-,17-,18-,19-/m0/s1 checkY
    Key: NVKAWKQGWWIWPM-ABEVXSGRSA-N checkY
SMILES
  • O=C4C[C@@H]3CC[C@@H]2[C@H](CC[C@]1(C)[C@@H](O)CC[C@H]12)[C@@]3(C)CC4
Properties
Chemical formula
 C19H30O2
Molar mass 290.447 g·mol−1
Pharmacology
ATC code
 A14AA01 (WHO)
Routes of
administration
 Transdermal (gel), in the cheek, under the tongue, intramuscular injection (as esters)
Pharmacokinetics:
Bioavailability
 Oral: very low (due to extensive first pass metabolism)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Dihydrotestosterone (DHT, 5α-dihydrotestosterone, 5α-DHT, androstanolone or stanolone) is an endogenous androgen sex steroid and hormone primarily involved in the growth and repair of the prostate and the penis, as well as the production of sebum and body hair composition.

The enzyme 5α-reductase catalyzes the formation of DHT from testosterone in certain tissues including the prostate gland, seminal vesicles, epididymides, skin, hair follicles, liver, and brain. This enzyme mediates reduction of the C4-5 double bond of testosterone. DHT may also be synthesized from progesterone and 17α-hydroxyprogesterone via the androgen backdoor pathway in the absence of testosterone. Relative to testosterone, DHT is considerably more potent as an agonist of the androgen receptor (AR).

In addition to its role as a natural hormone, DHT has been used as a medication, for instance in the treatment of low testosterone levels in men; for information on DHT as a medication, see the androstanolone article.

  1. ^ Coutts SB, Kicman AT, Hurst DT, Cowan DA (November 1997). "Intramuscular administration of 5 alpha-dihydrotestosterone heptanoate: changes in urinary hormone profile". Clinical Chemistry. 43 (11): 2091–2098. doi:10.1093/clinchem/43.11.2091. PMID 9365393.

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