11β-Chloromethylestradiol

Chemical compound (8S,9R,11S,13S,14S,17S)-11-(chloromethyl)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol 11β-Chloromethylestradiol.svg skin-invert-image Estrogen correct CAS 71794-60-0 correct FDA BRP4DW4SEE 67088 60438 C14307 34142 11β-CME2; CME; ORG-4333; 11β-(Chloromethyl)estra-1,3,5(10)-trien-3,17β-diol 19 25 1 2 C[C@]12C[C@@H]([C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)O)CCl 1S/C19H25ClO2/c1-19-9-12(10-20)18-14-5-3-13(21)8-11(14)2-4-15(18)16(19)6-7-17(19)22/h3,5,8,12,15-18,21-22H,2,4,6-7,9-10H2,1H3/t12-,15+,16+,17+,18-,19+/m1/s1 CADGCTOWBAPSFQ-OQFXVXKWSA-N 11β-Chloromethylestradiol (11β-CME2; developmental code name ORG-4333) is a synthetic steroidal estrogen which was never marketed. Sasson S Equilibrium binding analysis of estrogen agonists and antagonists: relation to the activation of the estrogen receptor Pathologie-Biologie 39 1 59–69 January 1991 2011412 Bindal RD, Carlson KE, Reiner GC, Katzenellenbogen JA 11 beta-chloromethyl-[3H]estradiol-17 beta: a very high affinity, reversible ligand for the estrogen receptor Journal of Steroid Biochemistry 28 4 361–370 October 1987 3669657 10.1016/0022-4731(87)91052-1 Ratajczak T, Atrache V, Antes P, Comber M, Hähnel R A comparison of 11 beta-chloromethylestradiol and tamoxifen aziridine as affinity labeling reagents for estrogen receptors Steroids 51 5–6 499–518 1988 3242173 10.1016/0039-128x(88)90047-5 11598932 Ratajczak T, Sheppard PN, Capon RJ, Hähnel R The synthesis and study of some potential affinity labeling reagents for estrogen receptors Steroids 38 5 537–555 November 1981 7324085 10.1016/0039-128x(81)90053-2 37503105 Reiner GC, Katzenellenbogen BS, Bindal RD, Katzenellenbogen JA Biological activity and receptor binding of a strongly interacting estrogen in human breast cancer cells Cancer Research 44 6 2302–2308 June 1984 6547074 https://cancerres.aacrjournals.org/content/44/6/2302.short Soto AM, Sonnenschein C, Chung KL, Fernandez MF, Olea N, Serrano FO The E-SCREEN assay as a tool to identify estrogens: an update on estrogenic environmental pollutants Environmental Health Perspectives 103 Suppl 7 113–122 October 1995 8593856 1518887 10.1289/ehp.95103s7113 It has very high affinity for the estrogen receptor and dissociates from it relatively slowly. Sasson S, Katzenellenbogen JA Reversible, positive cooperative interaction of 11 beta-chloromethyl-[3H]estradiol-17 beta with the calf uterine estrogen receptor Journal of Steroid Biochemistry 33 5 859–865 November 1989 2601330 10.1016/0022-4731(89)90233-1 Katzenellenbogen JA, Muthyala R Interactions of exogenous endocrine active substances with nuclear receptors Pure and Applied Chemistry 75 11–12 2003 1797–1817 1365-3075 10.1351/pac200375111797 86680540 free It was originally thought that 11β-CME2 might be a covalent ligand of the estrogen receptors, but its binding was subsequently shown to be fully reversible. The relative binding affinity of 11β-CME2 for the estrogen receptors ranges from 230 to 3,320% of that of estradiol depending on the study. Fink BE, Mortensen DS, Stauffer SR, Aron ZD, Katzenellenbogen JA Novel structural templates for estrogen-receptor ligands and prospects for combinatorial synthesis of estrogens Chemistry & Biology 6 4 205–219 April 1999 10099132 10.1016/S1074-5521(99)80037-4 free Sasson S, Katzenellenbogen JA Reversible, positive cooperative interaction of 11 beta-chloromethyl-[3H]estradiol-17 beta with the calf uterine estrogen receptor Journal of Steroid Biochemistry 33 5 859–865 November 1989 2601330 10.1016/0022-4731(89)90233-1 Wolohan P, Reichert DE CoMSIA and docking study of rhenium based estrogen receptor ligand analogs Steroids 72 3 247–260 March 2007 17280694 1964785 10.1016/j.steroids.2006.11.011 Quivy J, Leclercq G, Deblaton M, Henrot P, Velings N, Norberg B, Evrard G, Zeicher M 6 Synthesis, structure and biological properties of Z-17alpha-(2-iodovinyl)-11beta-chloromethyl estradiol-17beta (Z-CMIV), a high affinity ligand for the characterization of estrogen receptor-positive tumors The Journal of Steroid Biochemistry and Molecular Biology 59 1 103–117 September 1996 9009243 10.1016/s0960-0760(96)00007-6 54359888 11β-CME2 also has about 14% of the relative binding affinity of estradiol for sex hormone-binding globulin (SHBG). The compound has been developed as a radiolabel for the ERs. See also 11β-Methoxyestradiol Moxestrol References Category:Abandoned drugs Category:Secondary alcohols Category:Estranes Category:Chloromethyl compounds Category:Synthetic estrogens