7β-Hydroxy-DHEA - Misplaced Pages

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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-cyclopentaphenanthren-1-one
Other names 7β-OH-DHEA; Androst-5-en-3β,7β-diol-17-one
Identifiers
CAS Number	2487-48-1
3D model (JSmol)	Interactive image
ChEBI	CHEBI:183368
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/s1Key: OLPSAOWBSPXZEA-GCNMQWDSSA-N
SMILES C12CC3(1CCC2=O)(C=C43(CC(C4)O)C)O
Properties
Chemical formula	C₁₉H₂₈O₃
Molar mass	304.430 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

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. 7β-OH-DHEA has weak antiestrogenic activity, selectively antagonizing the estrogen receptor ERβ.

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

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 , and .
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.
"What is Prohibited". Archived from the original on 2020-11-12. Retrieved 2020-01-09.

Others

ERTooltip Estrogen receptor

Agonists

Mixed
(SERMsTooltip Selective estrogen receptor modulators)

Antagonists

GPERTooltip G protein-coupled estrogen receptor

Agonists	2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Aldosterone Atrazine Bisphenol A Daidzein DDT (p,p'-DDT, o',p'-DDE) Diarylpropionitrile Equol Estradiol Ethinylestradiol Fulvestrant (ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Nicotinic acid Nicotinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol STX Tamoxifen Tectoridin
Antagonists	CCL18 Estriol G-15 G-36 MIBE
Unknown	Diethylstilbestrol Zearalenone

See also: Receptor/signaling modulators; Estrogens and antiestrogens; Androgen receptor modulators; Progesterone receptor modulators; List of estrogens

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