Просмотр кода страницы Английская Википедия:3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol

{{Английская Википедия/Панель перехода}}
{{Short description|Chemical compound}}
{{Infobox drug
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| IUPAC_name = (8''R'',9''S'',10''S'',13''S'',14''S'',17''S'')-10-Ethenyl-3,13-dimethyl-2,7,8,9,11,12,14,15,16,17-decahydro-1''H''-cyclopenta[''a'']phenanthren-17-ol
| image = 3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol.svg
| width =

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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B            / C / D / X -->
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
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<!-- Identifiers -->
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| PubChem = 24896626
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| ChemSpiderID = 23306322
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| ChEMBL = 398456

<!--Chemical data-->
| C=21 | H=30 | O=1
| SMILES = CC1=CC2=CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@]2(CC1)C=C)C)O
| StdInChI_Ref = 
| StdInChI = 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
| StdInChIKey_Ref = 
| StdInChIKey = PPGVWCDLIZEUNC-PXQJOHHUSA-N
| synonyms = 3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
}}

'''3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol''' is a [[synthetic compound|synthetic]], [[steroid]]al [[estrogen]] and a [[binding selectivity|selective]] [[agonist]] of the [[ERβ]].<ref name="pmid17890084">{{cite journal | vauthors = Blizzard 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 | title = Androstene-3,5-dienes as ER-beta selective SERMs | journal = Bioorg. Med. Chem. Lett. | volume = 17 | issue = 22 | pages = 6295–8 | year = 2007 | pmid = 17890084 | doi = 10.1016/j.bmcl.2007.09.001 }}</ref> It was discovered serendipitously and was the [[lead compound]] among a series of [[androstane|androsta-3,5-diene]]s as ERβ [[ligand (biochemistry)|ligand]]s.<ref name="pmid17890084" /><ref name="pmid24099797">{{cite journal | vauthors = Khalil RA | title = Estrogen, vascular estrogen receptor and hormone therapy in postmenopausal vascular disease | journal = Biochem. Pharmacol. | volume = 86 | issue = 12 | pages = 1627–42 | year = 2013 | pmid = 24099797 | pmc = 3840081 | doi = 10.1016/j.bcp.2013.09.024 }}</ref> Its [[affinity (pharmacology)|affinity]] ([[IC50|IC<sub>50</sub>]]) for the ERβ was found to be 9&nbsp;nM and it showed 62- and 160-fold binding selectivity for this receptor over the {{abbrlink|AR|androgen receptor}} and the [[ERα]], respectively.<ref name="pmid17890084" /> The [[EC50|EC<sub>50</sub>]] of the compound for the ERβ was found to be 69&nbsp;nM and its [[intrinsic activity]] was 92% (relative to that of [[estradiol]]).<ref name="pmid17890084" /> As such, it is a [[potency (pharmacology)|potent]] ERβ agonist with high affinity and selectivity.<ref name="pmid17890084" />

==References==
{{reflist}}

{{Estrogen receptor modulators}}

{{DEFAULTSORT:Methyl-19-methyleneandrosta-3, 5-dien-17β-ol, 3-}}
[[Category:Secondary alcohols]]
[[Category:Androstanes]]
[[Category:Selective ERβ agonists]]
[[Category:Synthetic estrogens]]


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{{genito-urinary-drug-stub}}
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