7β-Hydroxy-DHEA
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Names | |
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IUPAC name 3β,7β-Dihydroxyandrost-5-en-17-one | |
Systematic IUPAC name (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 | |
Other names 7β-OH-DHEA; Androst-5-en-3β,7β-diol-17-one | |
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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 |
Chemical compound
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.[1] 7β-OH-DHEA has weak antiestrogenic activity, selectively antagonizing the estrogen receptor ERβ.[2]
7β-OH-DHEA is on the World Anti-Doping Agency list of prohibited substances in sporting.[3]
See also
References
- ^ 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].
- ^ 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.
- ^ "What is Prohibited". Archived from the original on 2020-11-12. Retrieved 2020-01-09.
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- Cholesterol
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
- Pregnenolone
- 11β-Hydroxypregnenolone
- 17α-Hydroxypregnenolone
- 21-Hydroxypregnenolone
- 17α,21-Dihydroxypregnenolone
- 11β,17α,21-Trihydroxypregnenolone
- Cholestanes: 24S-Hydroxycholesterol
- Cholesterol
- Pregnanes: 3α-Dihydroprogesterone
- 3β-Dihydroprogesterone
- 5α-Dihydrocorticosterone
- 5α-Dihydroprogesterone
- 5β-Dihydroprogesterone
- Allopregnanolone
- Corticosterone
- DHC
- DHDOC
- 11-Deoxycorticosterone
- Epipregnanolone
- Isopregnanolone
- Pregnanolone
- Pregnenolone
- Pregnenolone sulfate
- Progesterone
- THB
- THDOC
- Androstanes: 3α-Androstanediol
- 3α-Androstenol
- 7-Keto-DHEA
- 7α-Hydroxy-DHEA
- 7β-Hydroxy-DHEA
- 7α-Hydroxyepiandrosterone
- 7β-Hydroxyepiandrosterone
- Androsterone
- DHEA
- DHEA sulfate
- Etiocholanolone
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