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Chemical compound
11β-Methoxyestradiol Other names 11β-MeOE2; 11βOMeEST; RU-2504; 11β-Methoxyestra-1,3,5(10)-triene-3,17β-diol Drug class Estrogen
(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 ) Formula C 19 H 26 O 3 Molar mass −1 3D model (JSmol )
C[C@]12C[C@@H]([C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)O)OC
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
11β-Methoxyestradiol (11β-MeOE2 ; developmental code name RU-2504 ) is a synthetic steroidal estrogen which was never marketed.[ 1] [ 2] [ 3] relative binding affinity of estradiol for the estrogen receptor .[ 1] [ 2] moxestrol (11β-methoxy-17α-ethynylestradiol).[ 3] [ 2] potent than their non-methoxylated analogues (estradiol and ethinylestradiol , respectively) in mice.[ 3]
See also
References
^ a b 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 . ^ a b c 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 . ^ a b c 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.
ER Tooltip Estrogen receptor
Agonists
Steroidal: 2-Hydroxyestradiol 2-Hydroxyestrone 3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol 3α-Androstanediol 3α,5α-Dihydrolevonorgestrel 3β,5α-Dihydrolevonorgestrel 3α-Hydroxytibolone 3β-Hydroxytibolone 3β-Androstanediol 4-Androstenediol 4-Androstenedione 4-Fluoroestradiol 4-Hydroxyestradiol 4-Hydroxyestrone 4-Methoxyestradiol 4-Methoxyestrone 5-Androstenediol 7-Oxo-DHEA 7α-Hydroxy-DHEA 7α-Methylestradiol 7β-Hydroxyepiandrosterone 8,9-Dehydroestradiol 8,9-Dehydroestrone 8β-VE2 10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED) 11β-Chloromethylestradiol 11β-Methoxyestradiol 15α-Hydroxyestradiol 16-Ketoestradiol 16-Ketoestrone 16α-Fluoroestradiol 16α-Hydroxy-DHEA 16α-Hydroxyestrone 16α-Iodoestradiol 16α-LE2 16β-Hydroxyestrone 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol) 17α-Estradiol (alfatradiol )17α-Dihydroequilenin 17α-Dihydroequilin 17α-Epiestriol (16α-hydroxy-17α-estradiol) 17α-Ethynyl-3α-androstanediol 17α-Ethynyl-3β-androstanediol 17β-Dihydroequilenin 17β-Dihydroequilin 17β-Methyl-17α-dihydroequilenin Abiraterone Abiraterone acetate Alestramustine Almestrone Anabolic steroids (e.g., testosterone and esters , methyltestosterone , metandienone (methandrostenolone) , nandrolone and esters , many others; via estrogenic metabolites)Atrimustine Bolandiol Bolandiol dipropionate Butolame Clomestrone Cloxestradiol
Conjugated estriol Conjugated estrogens Cyclodiol Cyclotriol DHEA DHEA-S ent -EstradiolEpiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol) Epimestrol Equilenin Equilin ERA-63 (ORG-37663) Esterified estrogens Estetrol Estradiol
Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol
Estrofurate Estrogenic substances Estromustine Estrone
Etamestrol (eptamestrol) Ethinylandrostenediol
Ethinylestradiol
Ethinylestriol Ethylestradiol Etynodiol Etynodiol diacetate Hexolame Hippulin Hydroxyestrone diacetate Lynestrenol Lynestrenol phenylpropionate Mestranol Methylestradiol Moxestrol Mytatrienediol Nilestriol Norethisterone Noretynodrel Orestrate Pentolame Prodiame Prolame Promestriene RU-16117 Quinestradol Quinestrol Tibolone Xenoestrogens: Anise -related (e.g., anethole , anol , dianethole , dianol , photoanethole )Chalconoids (e.g., isoliquiritigenin , phloretin , phlorizin (phloridzin) , wedelolactone )Coumestans (e.g., coumestrol , psoralidin )Flavonoids (incl. 7,8-DHF , 8-prenylnaringenin , apigenin , baicalein , baicalin , biochanin A , calycosin , catechin , daidzein , daidzin , ECG , EGCG , epicatechin , equol , formononetin , glabrene , glabridin , genistein , genistin , glycitein , kaempferol , liquiritigenin , mirificin , myricetin , naringenin , penduletin , pinocembrin , prunetin , puerarin , quercetin , tectoridin , tectorigenin )Lavender oil Lignans (e.g., enterodiol , enterolactone , nyasol (cis -hinokiresinol) )Metalloestrogens (e.g., cadmium )Pesticides (e.g., alternariol , dieldrin , endosulfan , fenarimol , HPTE , methiocarb , methoxychlor , triclocarban , triclosan )Phytosteroids (e.g., digitoxin (digitalis ), diosgenin , guggulsterone )Phytosterols (e.g., β-sitosterol , campesterol , stigmasterol )Resorcylic acid lactones (e.g., zearalanone , α-zearalenol , β-zearalenol , zearalenone , zeranol (α-zearalanol) , taleranol (teranol, β-zearalanol) )Steroid -like (e.g., deoxymiroestrol , miroestrol )Stilbenoids (e.g., resveratrol , rhaponticin )Synthetic xenoestrogens (e.g., alkylphenols , bisphenols (e.g., BPA , BPF , BPS ), DDT , parabens , PBBs , PHBA , phthalates , PCBs )Others (e.g., agnuside , rotundifuran ) MixedSERMs Tooltip Selective estrogen receptor modulators ) Antagonists
Coregulator-binding modulators: ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown
