7β-Hydroxy-DHEA

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7β-Hydroxy-DHEA
7β-Hydroxy-DHEA.svg
Names
IUPAC name
(3S,7R,8R,9S,10R,13S,14S)-3,7-Dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one
Other names
7β-OH-DHEA; 3β,7β-Dihydroxyandrost-4-ene-17-one; Androst-4-en-3β,7β-diol-17-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
Properties
C19H28O3
Molar mass 304.43 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

7β-Hydroxydehydroepiandrosterone (7β-hydroxy-DHEA; 7β-OH-DHEA), also known as 3β,7β-dihydroxyandrost-4-ene-17-one, is an endogenous, naturally occurring steroid and a metabolite of dehydroepiandrosterone (DHEA). The major metabolic pathway of DHEA outside the liver is via 7-hydroxylation into 7α-OH-DHEA and 7β-OH-DHEA.[1] 7β-OH-DHEA has weak antiestrogenic activity, selectively antagonizing the estrogen receptor ERβ.[2][2]

7β-OH-DHEA is on the World Anti-Doping Agency list of prohibited substances in sporting.[3]

See also[edit]

References[edit]

  1. ^ Li H, Liu HM, Ge W, Huang L, Shan L (2005). "Synthesis of 7alpha-hydroxy-dehydroepiandrosterone and 7beta-hydroxy-dehydroepiandrosterone". Steroids. 70 (14): 970–3. doi:10.1016/j.steroids.2005.07.006. PMID 16143359. he major metabolic pathway for DHEA in extra-hepatic tissues is via 7-hydroxylation [18], [19] and [20]. 
  2. ^ a b Miller KK, Al-Rayyan N, Ivanova MM, Mattingly KA, Ripp SL, Klinge CM, Prough RA (2013). "DHEA metabolites activate estrogen receptors alpha and beta". Steroids. 78 (1): 15–25. doi:10.1016/j.steroids.2012.10.002. PMC 3529809Freely accessible. PMID 23123738. 
  3. ^ http://list.wada-ama.org/list/s1-anabolic-agents/7b-hydroxy-dhea/