7α-Hydroxy-DHEA
Chemical compound / From Wikipedia, the free encyclopedia
7α-Hydroxydehydroepiandrosterone (7α-hydroxy-DHEA; 7α-OH-DHEA), also known as 3β,7α-dihydroxyandrost-5-ene-17-one, is an endogenous, naturally occurring steroid and a major metabolite of dehydroepiandrosterone (DHEA) that is formed by CYP7B1 (steroid 7α-hydroxylase) in tissues such as the prostate gland and by CYP3A4 in the liver.[1][2] The major metabolic pathway of DHEA outside the liver is via 7-hydroxylation into 7α-OH-DHEA and 7β-OH-DHEA.[3] 7α-OH-DHEA has weak estrogenic activity, selectively activating the estrogen receptor ERβ.[2] In addition, 7α-OH-DHEA may be responsible for the known antiglucocorticoid effects of DHEA.[4][5]
Names | |
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IUPAC name
3β,7α-Dihydroxyandrost-5-ene-17-one | |
Systematic IUPAC name
(3aS,3bR,4S,7S,9aR,9bS,11aS)-4,7-Dihydroxy-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
7α-OH-DHEA; Androst-5-en-3β,7α-diol-17-one | |
Identifiers | |
3D model (JSmol) |
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Properties | |
C19H28O3 | |
Molar mass | 304.430 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Serum levels of 7α-OH-DHEA have been found to be significantly elevated in patients with Alzheimer's disease.[4] It is unclear what significance this may have, if any.[6]
7α-OH-DHEA is on the World Anti-Doping Agency list of prohibited substances in sporting.[7]