7α-Hydroxy-DHEA

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| ImageFile = 7α-Hydroxy-DHEA.svg

| ImageSize = 200px

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| IUPACName = 3β,7α-Dihydroxyandrost-5-ene-17-one

| SystematicName = (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

| OtherNames = 7α-OH-DHEA; Androst-5-en-3β,7α-diol-17-one

| Section1 = {{Chembox Identifiers

| CASNo = 53-00-9

| ChEBI = 81471

| ChEMBL = 1079392

| ChemSpiderID = 58963

| KEGG = C18045

| PubChem = 65517

| StdInChI = 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

| StdInChIKey = 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

| UNII = CL15H93XTM

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| Section2 = {{Chembox Properties

| C=19 | H=28 | O=3

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| Section3 = {{Chembox Hazards

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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.{{cite web | url = http://www.hmdb.ca/metabolites/HMDB04611 | title = Metabocard for 7α-Hydroxydehydroepiandrosterone (HMDB04611)| work = Human Metabolome Database }}{{cite journal | vauthors = Miller KK, Al-Rayyan N, Ivanova MM, Mattingly KA, Ripp SL, Klinge CM, Prough RA | title = DHEA metabolites activate estrogen receptors alpha and beta | journal = Steroids | volume = 78 | issue = 1 | pages = 15–25 | year = 2013 | pmid = 23123738 | pmc = 3529809 | doi = 10.1016/j.steroids.2012.10.002 }} The major metabolic pathway of DHEA outside the liver is via 7-hydroxylation into 7α-OH-DHEA and 7β-OH-DHEA.{{cite journal | vauthors = Li H, Liu HM, Ge W, Huang L, Shan L | title = Synthesis of 7alpha-hydroxy-dehydroepiandrosterone and 7beta-hydroxy-dehydroepiandrosterone | journal = Steroids | volume = 70 | issue = 14 | pages = 970–3 | year = 2005 | pmid = 16143359 | doi = 10.1016/j.steroids.2005.07.006 | s2cid = 53294855 | quote = he major metabolic pathway for DHEA in extra-hepatic tissues is via 7-hydroxylation [18], [19] and [20].}} 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.{{cite journal | vauthors = Attal-Khémis S, Dalmeyda V, Michot JL, Roudier M, Morfin R | title = Increased total 7 alpha-hydroxy-dehydroepiandrosterone in serum of patients with Alzheimer's disease | journal = J. Gerontol. A Biol. Sci. Med. Sci. | volume = 53 | issue = 2 | pages = B125–32 | year = 1998 | pmid = 9520908 | doi = 10.1093/gerona/53a.2.b125| doi-access = free }}{{cite book|title=Neurosteroids and Brain Function|url=https://books.google.com/books?id=BJumUEbiaPYC&pg=PA84|date=12 December 2001|publisher=Academic Press|isbn=978-0-08-054423-6|pages=84–}}

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.{{cite book|author=Ronald Ross Watson|title=DHEA in Human Health and Aging|url=https://books.google.com/books?id=COZH22RYMT4C&pg=PA437|date=22 July 2011|publisher=CRC Press|isbn=978-1-4398-3883-9|pages=437–}}

7α-OH-DHEA is on the World Anti-Doping Agency list of prohibited substances in sporting.{{cite web | url = https://www.wada-ama.org/sites/default/files/wada_2019_english_prohibited_list.pdf | title = World Anti-Doping Agency Prohibited List 2019 }}