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7α-Hydroxy-DHEA

Names
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-cyclopentaphenanthren-1-one
Other names 7α-OH-DHEA; Androst-5-en-3β,7α-diol-17-one
Identifiers
CAS Number	53-00-9
3D model (JSmol)	Interactive image
ChEBI	CHEBI:81471
ChEMBL	ChEMBL1079392
ChemSpider	58963
KEGG	C18045
PubChem CID	65517
UNII	CL15H93XTM
CompTox Dashboard (EPA)	DTXSID901018916
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-JIEICEMKSA-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

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. The major metabolic pathway of DHEA outside the liver is via 7-hydroxylation into 7α-OH-DHEA and 7β-OH-DHEA. 7α-OH-DHEA has weak estrogenic activity, selectively activating the estrogen receptor ERβ. In addition, 7α-OH-DHEA may be responsible for the known antiglucocorticoid effects of DHEA.

Serum levels of 7α-OH-DHEA have been found to be significantly elevated in patients with Alzheimer's disease. It is unclear what significance this may have, if any.

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

See also

• 7-Keto-DHEA
• 7α-Hydroxyepiandrosterone
• 7β-Hydroxyepiandrosterone

References

1. "Metabocard for 7α-Hydroxydehydroepiandrosterone (HMDB04611)". Human Metabolome Database.
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. 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 .
4. ^ Attal-Khémis S, Dalmeyda V, Michot JL, Roudier M, Morfin R (1998). "Increased total 7 alpha-hydroxy-dehydroepiandrosterone in serum of patients with Alzheimer's disease". J. Gerontol. A Biol. Sci. Med. Sci. 53 (2): B125–32. doi:10.1093/gerona/53a.2.b125. PMID 9520908.
5. Neurosteroids and Brain Function. Academic Press. 12 December 2001. pp. 84–. ISBN 978-0-08-054423-6.
6. Ronald Ross Watson (22 July 2011). DHEA in Human Health and Aging. CRC Press. pp. 437–. ISBN 978-1-4398-3883-9.
7. "World Anti-Doping Agency Prohibited List 2019" (PDF).

External links

• Diols
• Androstanes
• Antiglucocorticoids
• Estrogens
• Ketones
• World Anti-Doping Agency prohibited substances