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Contents

   



(Top)
  


1 See also  




2 References  




3 External links  













7α-Hydroxy-DHEA






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From Wikipedia, the free encyclopedia
  

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

3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG

PubChem CID
UNII

CompTox Dashboard (EPA)

  • 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

  • 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 metaboliteofdehydroepiandrosterone (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]

See also[edit]

References[edit]

  1. ^ "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[edit]


    Retrieved from "https://en.wikipedia.org/w/index.php?title=7α-Hydroxy-DHEA&oldid=1152058375"
    Categories: 
    ●Diols
     ●Androstanes
     ●Antiglucocorticoids
     ●Estrogens
     ●Ketones
     ●World Anti-Doping Agency prohibited substances
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