DHEA

Dehydroepiandrosterone

Clinical data
Trade names	Astenile, Cetovister, 17-Chetovis, Dastonil S, Deandros, Diandrone, Hormobago, 17-Hormoforin, 17-Ketovis, Mentalormon, Psicosterone
Routes of administration	By mouth, intramuscular injection (as prasterone enanthate)
ATC code	A14AA07 (WHO) G03EA03 (WHO) (combination with estrogen)
Pharmacokinetic data
Bioavailability	50%
Metabolism	Hepatic
Metabolites	• Androsterone • Etiocholanolone • DHEA sulfate • Androstenedione • Androstenediol • Testosterone • Androstanediol
Biological half-life	DHEA: 25 minutes DHEA-S: 11 hours
Excretion	Urinary
Legal status
Legal status	AU: S4 (Prescription only) CA: Schedule IV US: OTC
ECHA InfoCard	100.000.160
Identifiers
IUPAC name (3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one; (1S,2R,5S,10R,11S,15S)-5-Hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-7-en-14-one
Synonyms	Androst-5-en-3β-ol-17-one; 3β-Hydroxyandrost-5-en-17-one; 5,6-Didehydroepiandrosterone; Dehydroisoepiandrosterone
CAS Number	53-43-0 Y
PubChem CID	5881
IUPHAR/BPS	2370
DrugBank	DB01708 Y
ChemSpider	5670 Y
UNII	459AG36T1B
ChEBI	CHEBI:28689 Y
ChEMBL	CHEMBL90593 Y
Chemical and physical data
Formula	C19H28O2
Molar mass	288.424 g/mol
3D model (Jmol)	Interactive image
Melting point	148.5 °C (299.3 °F)
SMILES O=C3[C@]2(CC[C@@H]1[C@@]4(C(=C/C[C@H]1[C@@H]2CC3)\C[C@@H](O)CC4)C)C
InChI 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/h3,13-16,20H,4-11H2,1-2H3/t13-,14-,15-,16-,18-,19-/m0/s1 Y Key:FMGSKLZLMKYGDP-USOAJAOKSA-N Y

Dehydroepiandrosterone (DHEA), also known as androstenolone or prasterone (INN), is an endogenous steroid hormone. It is the most abundant circulating steroid hormone in humans, in whom it is produced in the adrenal glands, the gonads, and the brain, where it functions predominantly as a metabolic intermediate in the biosynthesis of the androgen and estrogen sex steroids. However, DHEA also has a variety of potential biological effects in its own right, binding to an array of nuclear and cell surface receptors, and acting as a neurosteroid.

In women with adrenal insufficiency and the healthy elderly there is insufficient evidence to support the use of DHEA.

DHEA is sometimes used as an androgen in hormone replacement therapy (HRT) for menopause. A long-lasting ester prodrug of DHEA, prasterone enanthate, is used in combination with estradiol valerate for this indication.

DHEA is produced naturally in the human body, but the long-term effects of its use are largely unknown. In the short term, several studies have noted few adverse effects. In a study by Chang et al., DHEA was administered at a dose of 200 mg/day for 24 weeks with slight androgenic effects noted. Another study utilized a dose up to 400 mg/day for 8 weeks with few adverse events reported. A longer term study followed patients dosed with 50 mg of DHEA for 12 months with the number and severity of side effects reported to be small. Another study delivered a dose of 50 mg of DHEA for 10 months with no serious adverse events reported.