:7β-Hydroxy-DHEA

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| ImageFile = 7β-Hydroxy-DHEA.svg

| ImageSize = 200px

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

| SystematicName = (3aS,3bR,4R,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 = 7β-OH-DHEA; Androst-5-en-3β,7β-diol-17-one

| Section1 = {{Chembox Identifiers

| CASNo = 2487-48-1

| ChEMBL = 1082098

| ChemSpiderID = 7993704

| ChEBI = 183368

| PubChem = 9817954

| 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-GCNMQWDSSA-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 = 923RBW7OJQ

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| Section2 = {{Chembox Properties

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

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7β-Hydroxydehydroepiandrosterone (7β-hydroxy-DHEA; 7β-OH-DHEA), also known as 3β,7β-dihydroxyandrost-5-ene-17-one, is an endogenous, naturally occurring steroid and a metabolite of dehydroepiandrosterone (DHEA). 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].}} 7β-OH-DHEA has weak antiestrogenic activity, selectively antagonizing the estrogen receptor ERβ.{{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 }}

7β-OH-DHEA is on the World Anti-Doping Agency list of prohibited substances in sporting.{{Cite web|url=https://www.wada-ama.org/en/content/what-is-prohibited/prohibited-at-all-times/anabolic-agents|title=What is Prohibited|access-date=2020-01-09|archive-date=2020-11-12|archive-url=https://web.archive.org/web/20201112011132/https://www.wada-ama.org/en/content/what-is-prohibited/prohibited-at-all-times/anabolic-agents|url-status=dead}}

See also

References

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{{Steroid hormones}}

{{Estrogen receptor modulators}}

{{DEFAULTSORT:Hydroxy-DHEA, 7β-}}

Category:Diols

Category:Androstanes

Category:Antiestrogens

Category:Ketones

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