7α-Hydroxy-DHEA

7α-Hydroxy-DHEA
Names
IUPAC name
(3S,7S,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
7α-OH-DHEA; 3β,7α-Dihydroxyandrost-4-ene-17-one; Androst-4-en-3β,7α-diol-17-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
Properties
C19H28O3
Molar mass 304.43 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-4-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 of 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]

See also

References

  1. ↑ http://www.hmdb.ca/metabolites/HMDB04611
  2. 1 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. PMC 3529809 Freely accessible. PMID 23123738. doi:10.1016/j.steroids.2012.10.002.
  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. PMID 16143359. doi:10.1016/j.steroids.2005.07.006. he major metabolic pathway for DHEA in extra-hepatic tissues is via 7-hydroxylation [18], [19] and [20].
  4. 1 2 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. 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. ↑ http://list.wada-ama.org/list/s1-anabolic-agents/7a-hydroxy-dhea/



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