7β-Hydroxyepiandrosterone
Names | |
---|---|
IUPAC name 3β,7β-Dihydroxy-5α-androstan-17-one | |
Systematic IUPAC name (3aS,3bR,4S,5aR,7S,9aS,9bS,11aS)-4,7-Dihydroxy-9a,11a-dihydroxyhexadecahydro-1H-cyclopenta[a]phenanthren-1-one | |
Other names 7β-OH-EPIA; 5α-Androstan-3β,7β-diol-17-one | |
Identifiers | |
CAS Number |
|
3D model (JSmol) |
|
ChEBI |
|
ChemSpider |
|
PubChem CID |
|
UNII |
|
CompTox Dashboard (EPA) |
|
InChI
| |
| |
Properties | |
Chemical formula | C19H30O3 |
Molar mass | 306.446 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-Hydroxyepiandrosterone (7β-OH-EPIA), also known as 5α-androstan-3β,7β-diol-17-one, is an endogenous androgen, estrogen, and neurosteroid that is produced from dehydroepiandrosterone and epiandrosterone.[1][2][3] It has neuroprotective effects and, along with 7α-hydroxyepiandrosterone, may mediate the neuroprotective effects of DHEA.[1] 7β-OH-EPIA may act as a highly potent antagonist of the G protein-coupled estrogen receptor (GPER) (affinity of <1 nM).[4]
References
- ^ a b Dudas B, Hanin I, Rose M, Wülfert E (2004). "Protection against inflammatory neurodegeneration and glial cell death by 7beta-hydroxy epiandrosterone, a novel neurosteroid". Neurobiol. Dis. 15 (2): 262–8. doi:10.1016/j.nbd.2003.11.001. PMID 15006696. S2CID 24078411.
- ^ Sandra N, Ester P, Marie-Agnès P, Robert M, Olivier H (2012). "The DHEA metabolite 7β-hydroxy-epiandrosterone exerts anti-estrogenic effects on breast cancer cell lines" (PDF). Steroids. 77 (5): 542–51. doi:10.1016/j.steroids.2012.01.019. PMID 22342541. S2CID 140140008.
- ^ 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.
- ^ Prossnitz ER, Arterburn JB (July 2015). "International Union of Basic and Clinical Pharmacology. XCVII. G Protein-Coupled Estrogen Receptor and Its Pharmacologic Modulators". Pharmacol. Rev. 67 (3): 505–40. doi:10.1124/pr.114.009712. PMC 4485017. PMID 26023144.
- v
- t
- e
- 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
This article about a steroid is a stub. You can help Wikipedia by expanding it. |
- v
- t
- e