Dehydroepiandrosterone
Chemical compound / From Wikipedia, the free encyclopedia
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Dehydroepiandrosterone (DHEA), also known as androstenolone, is an endogenous steroid hormone precursor.[4] It is one of the most abundant circulating steroids in humans.[5] DHEA is produced in the adrenal glands,[6] the gonads, and the brain.[7] 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.[4][8][9] However, DHEA also has a variety of potential biological effects in its own right, binding to an array of nuclear and cell surface receptors,[10] and acting as a neurosteroid and modulator of neurotrophic factor receptors.[11]
Names | |
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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;[1] Dehydroisoepiandrosterone | |
Identifiers | |
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3D model (JSmol) |
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ChEBI | |
ChEMBL | |
ChemSpider |
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DrugBank |
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ECHA InfoCard | 100.000.160 |
PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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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%[2] | |
Hepatic[2] | |
DHEA: 25 minutes[3] DHEA-S: 11 hours[3] | |
Urine | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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In the United States, DHEA is sold as an over-the-counter supplement, and medication called prasterone.