7β-Hydroxy-DHEA

7β-Hydroxy-DHEA
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
CAS Number	2487-48-1;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1082098;
ChemSpider	7993704;
PubChem CID	9817954;
UNII	923RBW7OJQ;
CompTox Dashboard (EPA)	DTXSID50431284 ;
	InChI 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;
	SMILES 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
Chemical formula	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-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]

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

References

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].
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.
https://www.wada-ama.org/en/content/what-is-prohibited/prohibited-at-all-times/anabolic-agents

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