Dehydroepiandrosterone

Dehydroepiandrosterone (DHEA), also known as androstenolone, is an endogenous steroid hormone precursor. It is one of the most abundant circulating steroids in humans. DHEA is produced in the adrenal glands, the gonads, and the brain. It functions as a metabolic intermediate in the biosynthesis of the androgen and estrogen sex steroids both in the gonads and in various other tissues. 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 and modulator of neurotrophic factor receptors.

This article is about DHEA as a hormone. For its use as a medication or supplement, see Prasterone. For other uses, see DHEA (disambiguation). For the precursor hormone of DHEA produced mainly in the adrenal cortex, DHEA sulfate or DHEA-S, see Dehydroepiandrosterone sulfate.
Dehydroepiandrosterone
Names
IUPAC name
3β-Hydroxyandrost-5-en-17-one
Systematic IUPAC name
(3aS,3bR,7S,9aR,9bS,11aS)-7-Hydroxy-9a,11a-dimethyl-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-1-one
Other names
Androstenolone; Prasterone; Androst-5-en-3β-ol-17-one; 5,6-Didehydroepiandrosterone; Dehydroisoepiandrosterone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.160
UNII
  • 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
  • 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
Properties
C19H28O2
Molar mass 288.424 g/mol
Melting point 148.5
Pharmacology
QA14AA07 (WHO)
G03EA03 (WHO) (combination with estrogen)
By mouth, vaginal (insert), intramuscular injection (as prasterone enanthate), injection (as prasterone sodium sulfate)
Pharmacokinetics:
50%
Hepatic
DHEA: 25 minutes
DHEA-S: 11 hours
Urine
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

In the United States, DHEA is sold as an over-the-counter supplement, and medication called prasterone.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.