7α-Hydroxy-DHEA

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-cyclopenta[a]phenanthren-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/s1 Key: OLPSAOWBSPXZEA-JIEICEMKSA-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

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.^[1]^[2] The major metabolic pathway of DHEA outside the liver is via 7-hydroxylation into 7α-OH-DHEA and 7β-OH-DHEA.^[3] 7α-OH-DHEA has weak estrogenic activity, selectively activating the estrogen receptor ERβ.^[2] In addition, 7α-OH-DHEA may be responsible for the known antiglucocorticoid effects of DHEA.^[4]^[5]

Serum levels of 7α-OH-DHEA have been found to be significantly elevated in patients with Alzheimer's disease.^[4] It is unclear what significance this may have, if any.^[6]

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

References

^ "Metabocard for 7α-Hydroxydehydroepiandrosterone (HMDB04611)". Human Metabolome Database.
^ ^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 3529809. PMID 23123738.
^ 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].
^ ^a ^b 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.
^ Neurosteroids and Brain Function. Academic Press. 12 December 2001. pp. 84–. ISBN 978-0-08-054423-6.
^ Ronald Ross Watson (22 July 2011). DHEA in Human Health and Aging. CRC Press. pp. 437–. ISBN 978-1-4398-3883-9.
^ "World Anti-Doping Agency Prohibited List 2019" (PDF).

External links

[HMDB-1] "Metabocard for 7α-Hydroxydehydroepiandrosterone (HMDB04611)". Human Metabolome Database.

[pmid23123738-2] 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.

[pmid16143359-3] 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 [18], [19] and [20].

[pmid9520908-4] 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.

[Watson2011-6] Ronald Ross Watson (22 July 2011). DHEA in Human Health and Aging. CRC Press. pp. 437–. ISBN 978-1-4398-3883-9.

[DHEA-7] "World Anti-Doping Agency Prohibited List 2019" (PDF).

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[3]

[4]

[5]

[6]

[7]

7α-Hydroxy-DHEA

See also

References

External links