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 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16330 Y
ChEMBL	ChEMBL27769 N
ChemSpider	10189 Y
DrugBank	DB02901 Y
ECHA InfoCard	100.007.554
KEGG	C03917 Y
PubChem CID	10635
UNII	08J2K08A3Y Y
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 Y Key: NVKAWKQGWWIWPM-ABEVXSGRSA-N Y
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). Y verify (what is YN ?) 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.