7β-Hydroxyepiandrosterone - Misplaced Pages

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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-cyclopentaphenanthren-1-one
Other names 7β-OH-EPIA; 5α-Androstan-3β,7β-diol-17-one
Identifiers
CAS Number	25848-69-5
3D model (JSmol)	Interactive image
ChEBI	CHEBI:183809
ChemSpider	8011902
PubChem CID	9836181
UNII	OCP3E5KD08
CompTox Dashboard (EPA)	DTXSID701293235
InChI InChI=1S/C19H30O3/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/h11-15,17,20-21H,3-10H2,1-2H3/t11-,12+,13+,14+,15+,17+,18+,19+/m1/s1Key: VFPMCLQMAUVEHD-UCPSWNCLSA-N
SMILES C12CC(C1C(32CC4(3CCC4=O)C)O)O
Properties
Chemical formula	C₁₉H₃₀O₃
Molar mass	306.446 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 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. It has neuroprotective effects and, along with 7α-hydroxyepiandrosterone, may mediate the neuroprotective effects of DHEA. 7β-OH-EPIA may act as a highly potent antagonist of the G protein-coupled estrogen receptor (GPER) (affinity of <1 nM).

References

^ 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.

Others

ARTooltip Androgen receptor

Agonists

17α-Alkylated 5α-dihydro-19-nortestosterone derivatives: 5α-Dihydronorethandrolone
5α-Dihydronormethandrone

5α-Dihydro-17α-ethynyl-19-nortestosterone derivatives: 5α-Dihydrolevonorgestrel
5α-Dihydronorethisterone

SARMsTooltip Selective androgen receptor modulator

Antagonists

Agonists	Cations (incl. aluminium, calcium, gadolinium, magnesium, strontium, zinc) Dehydroandrosterone Dihydrotestosterone Estradiol L-α-Amino acids (incl. L-arginine, L-lysine, L-ornithine) Osteocalcin SHBGTooltip Sex hormone-binding globulin Testosterone

See also: Receptor/signaling modulators; Androgens and antiandrogens; Estrogen receptor modulators; Progesterone receptor modulators; List of androgens and anabolic steroids

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