11β-Methoxyestradiol

11β-Methoxyestradiol (11β-MeOE2; developmental code name RU-2504) is a synthetic steroidal estrogen which was never marketed.[1][2][3] It has about 86% of the relative binding affinity of estradiol for the estrogen receptor.[1][2] 11β-MeOE2 is structurally related to moxestrol (11β-methoxy-17α-ethynylestradiol).[3][2] 11β-MeOE2 and moxestrol are substantially more potent than their non-methoxylated analogues (estradiol and ethinylestradiol, respectively) in mice.[3]

11β-Methoxyestradiol
Clinical data
Other names11β-MeOE2; 11βOMeEST; RU-2504; 11β-Methoxyestra-1,3,5(10)-triene-3,17β-diol
Drug classEstrogen
Identifiers
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
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H26O3
Molar mass302.414 g·mol−1
3D model (JSmol)
SMILES
  • C[C@]12C[C@@H]([C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)O)OC
InChI
  • InChI=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
  • Key:OAHDOJSNKCCHJM-VIUKOLAESA-N

See also

References
  1. Wolohan P, Reichert DE (March 2007). "CoMSIA and docking study of rhenium based estrogen receptor ligand analogs". Steroids. 72 (3): 247–60. doi:10.1016/j.steroids.2006.11.011. PMC 1964785. PMID 17280694.
  2. Katzenellenbogen, J. A.; Muthyala, R. (2003). "Interactions of exogenous endocrine active substances with nuclear receptors". Pure and Applied Chemistry. 75 (11–12): 1797–1817. doi:10.1351/pac200375111797. ISSN 1365-3075. S2CID 86680540.
  3. Azadian-Boulanger G, Bertin D (1973). "Synthèse et activité utérotrophique des 11β-méthoxy estradiol 11β-méthoxy estriol et 11β-méthoxy 17α-éthynyl estradiol" [Synthesis and uterotropic activity of 11β-methoxyestradiol, 11β-methoxyestriol, and 11β-methoxy-17α-ethynylestradiol]. Chimica Therapeutica. 8 (4): 451–454. ISSN 0009-4374. 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.



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