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3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
Clinical data
Other names3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
Identifiers
  • (8R,9S,10S,13S,14S,17S)-10-Ethenyl-3,13-dimethyl-2,7,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-ol
CAS Number
PubChemCID
ChemSpider
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC21H30O
Molar mass298.470 g·mol−1
3D model (JSmol)
  • CC1=CC2=CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@]2(CC1)C=C)C)O
  • InChI=1S/C21H30O/c1-4-21-12-9-14(2)13-15(21)5-6-16-17-7-8-19(22)20(17,3)11-10-18(16)21/h4-5,13,16-19,22H,1,6-12H2,2-3H3/t16-,17-,18-,19-,20-,21-/m0/s1
  • Key:PPGVWCDLIZEUNC-PXQJOHHUSA-N

3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol is asynthetic,steroidalestrogen and aselectiveagonist of theERβ.[1] It was discovered serendipitously and was thelead compound among a series ofandrosta-3,5-dienes as ERβligands.[1][2] Itsaffinity (IC50) for the ERβ was found to be 9 nM and it showed 62- and 160-fold binding selectivity for this receptor over theARTooltip androgen receptor and theERα, respectively.[1] TheEC50 of the compound for the ERβ was found to be 69 nM and itsintrinsic activity was 92% (relative to that ofestradiol).[1] As such, it is apotent ERβ agonist with high affinity and selectivity.[1]

References

[edit]
  1. ^abcdeBlizzard TA, Gude C, Morgan JD, Chan W, Birzin ET, Mojena M, Tudela C, Chen F, Knecht K, Su Q, Kraker B, Mosley RT, Holmes MA, Rohrer SP, Hammond ML (2007). "Androstene-3,5-dienes as ER-beta selective SERMs".Bioorg. Med. Chem. Lett.17 (22):6295–8.doi:10.1016/j.bmcl.2007.09.001.PMID 17890084.
  2. ^Khalil RA (2013)."Estrogen, vascular estrogen receptor and hormone therapy in postmenopausal vascular disease".Biochem. Pharmacol.86 (12):1627–42.doi:10.1016/j.bcp.2013.09.024.PMC 3840081.PMID 24099797.
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown


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