11β-Methoxyestradiol

{{Short description|Chemical compound}}

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| IUPAC_name = (8S,9S,11S,13S,14S,17S)-11-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol

| image = 11β-Methoxyestradiol.svg

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| class = Estrogen

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| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 21507-14-2

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| UNII = R3M9HHJ34D

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| PubChem = 68568

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| ChemSpiderID = 61838

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| ChEMBL = 368703

| synonyms = 11β-MeOE2; 11βOMeEST; RU-2504; 11β-Methoxyestra-1,3,5(10)-triene-3,17β-diol

| C=19 | H=26 | O=3

| SMILES = C[C@]12C[C@@H]([C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)O)OC

| StdInChI_Ref =

| StdInChI = 1S/C19H26O3/c1-19-10-16(22-2)18-13-6-4-12(20)9-11(13)3-5-14(18)15(19)7-8-17(19)21/h4,6,9,14-18,20-21H,3,5,7-8,10H2,1-2H3/t14-,15-,16-,17-,18+,19-/m0/s1

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| StdInChIKey = OAHDOJSNKCCHJM-VIUKOLAESA-N

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11β-Methoxyestradiol (11β-MeOE2; developmental code name RU-2504) is a synthetic steroidal estrogen which was never marketed.{{cite journal | vauthors = Wolohan P, Reichert DE | title = CoMSIA and docking study of rhenium based estrogen receptor ligand analogs | journal = Steroids | volume = 72 | issue = 3 | pages = 247–260 | date = March 2007 | pmid = 17280694 | pmc = 1964785 | doi = 10.1016/j.steroids.2006.11.011 }}{{cite journal| vauthors = Katzenellenbogen JA, Muthyala R |title=Interactions of exogenous endocrine active substances with nuclear receptors|journal=Pure and Applied Chemistry|volume=75|issue=11–12|year=2003|pages=1797–1817|issn=1365-3075|doi=10.1351/pac200375111797|s2cid=86680540|doi-access=free}}{{cite journal | vauthors = Azadian-Boulanger G, Bertin D | title = Synthèse et activité utérotrophique des 11β-méthoxy estradiol 11β-méthoxy estriol et 11β-méthoxy 17α-éthynyl estradiol | trans-title = Synthesis and uterotropic activity of 11β-methoxyestradiol, 11β-methoxyestriol, and 11β-methoxy-17α-ethynylestradiol | journal = Chimica Therapeutica | year = 1973 | volume = 8 | issue = 4 | pages = 451–454 | issn = 0009-4374 | quote = The prepn. and estrogenic activity of the 11β-methoxylated derivs. of estradiol, estriol, and 17α-ethynylestradiol were described. When administered orally to mice, the 3 compds. were from 10 to 1000 times more active than the corresponding nonmethoxylated estrogens.}} It has about 86% of the relative binding affinity of estradiol for the estrogen receptor. 11β-MeOE2 is structurally related to moxestrol (11β-methoxy-17α-ethynylestradiol). 11β-MeOE2 and moxestrol are substantially more potent than their non-methoxylated analogues (estradiol and ethinylestradiol, respectively) in mice.