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7α-Hydroxy-DHEA

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]

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
  • 53-00-9
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:81471
ChEMBL
  • ChEMBL1079392
ChemSpider
  • 58963
KEGG
  • C18045
  • 65517
UNII
  • CL15H93XTM
  • 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
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).

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.
  2. ^ 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.
  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].
  4. ^ 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.
  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 edit

hydroxy, dhea, hydroxydehydroepiandrosterone, hydroxy, dhea, dhea, also, known, dihydroxyandrost, endogenous, naturally, occurring, steroid, major, metabolite, dehydroepiandrosterone, dhea, that, formed, cyp7b1, steroid, hydroxylase, tissues, such, prostate, g. 7a Hydroxydehydroepiandrosterone 7a hydroxy DHEA 7a OH DHEA also known as 3b 7a dihydroxyandrost 5 ene 17 one is an endogenous naturally occurring steroid and a major metabolite of dehydroepiandrosterone DHEA that is formed by CYP7B1 steroid 7a 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 7a OH DHEA and 7b OH DHEA 3 7a OH DHEA has weak estrogenic activity selectively activating the estrogen receptor ERb 2 In addition 7a OH DHEA may be responsible for the known antiglucocorticoid effects of DHEA 4 5 7a Hydroxy DHEA Names IUPAC name 3b 7a 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 7a OH DHEA Androst 5 en 3b 7a 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 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 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 C 19H 28O 3 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 Serum levels of 7a 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 7a OH DHEA is on the World Anti Doping Agency list of prohibited substances in sporting 7 See also edit7 Keto DHEA 7a Hydroxyepiandrosterone 7b HydroxyepiandrosteroneReferences edit Metabocard for 7a 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 Khemis 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 7a Hydroxy DHEA amp oldid 1152058375, wikipedia, wiki, book, books, library,

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