Dihydrotestosterone

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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16330 ;
ChEMBL	ChEMBL27769 ;
ChemSpider	10189 ;
DrugBank	DB02901 ;
ECHA InfoCard	100.007.554
KEGG	C03917 ;
PubChem CID	10635;
UNII	08J2K08A3Y ;
CompTox Dashboard (EPA)	DTXSID9022364 ;
	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 Key: NVKAWKQGWWIWPM-ABEVXSGRSA-N ;
	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)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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.

^ 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.

[pmid9365393-1] 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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