7β-Hydroxy-DHEA

7β-Hydroxydehydroepiandrosterone (7β-hydroxy-DHEA; 7β-OH-DHEA), also known as 3β,7β-dihydroxyandrost-5-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]

7β-Hydroxy-DHEA
Names
IUPAC name
3β,7β-Dihydroxyandrost-5-en-17-one
Systematic IUPAC name
(3aS,3bR,4R,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
7β-OH-DHEA; Androst-5-en-3β,7β-diol-17-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)10-15(21)17-13-3-4-16(22)19(13,2)8-6-14(17)18/h10,12-15,17,20-21H,3-9H2,1-2H3/t12-,13-,14-,15-,17-,18-,19-/m0/s1
    Key: OLPSAOWBSPXZEA-GCNMQWDSSA-N
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)[C@H](C=C4[C@@]3(CC[C@@H](C4)O)C)O
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).
Infobox references

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

See also

References
  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. S2CID 53294855. he major metabolic pathway for DHEA in extra-hepatic tissues is via 7-hydroxylation [18], [19] and [20].
  2. 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 3529809. PMID 23123738.
  3. "What is Prohibited". Archived from the original on 2020-11-12. Retrieved 2020-01-09.
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