Movatterモバイル変換

[0]ホーム
URL:

Jump to content
WikipediaThe Free Encyclopedia
Search

11β-Chloromethylestradiol

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
11β-Chloromethylestradiol
Clinical data
Other names11β-CME2; CME; ORG-4333; 11β-(Chloromethyl)estra-1,3,5(10)-trien-3,17β-diol
Drug classEstrogen
Identifiers
  • (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
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
ChEBI
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC19H25ClO2
Molar mass320.86 g·mol−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)CCl
  • InChI=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
  • Key:CADGCTOWBAPSFQ-OQFXVXKWSA-N

11β-Chloromethylestradiol (11β-CME2; developmental code nameORG-4333) is asyntheticsteroidalestrogen which was never marketed.[1][2][3][4][5][6] It has very highaffinity for theestrogen receptor and dissociates from it relatively slowly.[1][2][4][5][7][8] 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.[3] Therelative binding affinity of 11β-CME2 for theestrogen receptors ranges from 230 to 3,320% of that ofestradiol depending on the study.[5][9][7][8][10][11] 11β-CME2 also has about 14% of the relative binding affinity of estradiol forsex hormone-binding globulin (SHBG).[11] The compound has been developed as aradiolabel for the ERs.[3][4]

See also

[edit]

References

[edit]
  1. ^abSasson S (January 1991). "Equilibrium binding analysis of estrogen agonists and antagonists: relation to the activation of the estrogen receptor".Pathologie-Biologie.39 (1):59–69.PMID 2011412.
  2. ^abBindal RD, Carlson KE, Reiner GC, Katzenellenbogen JA (October 1987). "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.doi:10.1016/0022-4731(87)91052-1.PMID 3669657.
  3. ^abcRatajczak T, Atrache V, Antes P, Comber M, Hähnel R (1988). "A comparison of 11 beta-chloromethylestradiol and tamoxifen aziridine as affinity labeling reagents for estrogen receptors".Steroids.51 (5–6):499–518.doi:10.1016/0039-128x(88)90047-5.PMID 3242173.S2CID 11598932.
  4. ^abcRatajczak T, Sheppard PN, Capon RJ, Hähnel R (November 1981). "The synthesis and study of some potential affinity labeling reagents for estrogen receptors".Steroids.38 (5):537–555.doi:10.1016/0039-128x(81)90053-2.PMID 7324085.S2CID 37503105.
  5. ^abcReiner GC, Katzenellenbogen BS, Bindal RD, Katzenellenbogen JA (June 1984)."Biological activity and receptor binding of a strongly interacting estrogen in human breast cancer cells".Cancer Research.44 (6):2302–2308.PMID 6547074.
  6. ^Soto AM, Sonnenschein C, Chung KL, Fernandez MF, Olea N, Serrano FO (October 1995)."The E-SCREEN assay as a tool to identify estrogens: an update on estrogenic environmental pollutants".Environmental Health Perspectives.103 (Suppl 7):113–122.doi:10.1289/ehp.95103s7113.PMC 1518887.PMID 8593856.
  7. ^abSasson S, Katzenellenbogen JA (November 1989). "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.doi:10.1016/0022-4731(89)90233-1.PMID 2601330.
  8. ^abKatzenellenbogen JA, 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.
  9. ^Fink BE, Mortensen DS, Stauffer SR, Aron ZD, Katzenellenbogen JA (April 1999)."Novel structural templates for estrogen-receptor ligands and prospects for combinatorial synthesis of estrogens".Chemistry & Biology.6 (4):205–219.doi:10.1016/S1074-5521(99)80037-4.PMID 10099132.
  10. ^Wolohan P, Reichert DE (March 2007)."CoMSIA and docking study of rhenium based estrogen receptor ligand analogs".Steroids.72 (3):247–260.doi:10.1016/j.steroids.2006.11.011.PMC 1964785.PMID 17280694.
  11. ^abQuivy J, Leclercq G, Deblaton M, Henrot P, Velings N, Norberg B, et al. (September 1996). "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.doi:10.1016/s0960-0760(96)00007-6.PMID 9009243.S2CID 54359888.
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown

This article about anestrane is astub. You can help Wikipedia byexpanding it.

Stub icon

Thisdrug article relating to thegenito-urinary system is astub. You can help Wikipedia byexpanding it.

Retrieved from "https://en.wikipedia.org/w/index.php?title=11β-Chloromethylestradiol&oldid=1308581269"
Categories:
Hidden categories:
[8]ページ先頭
©2009-2025 Movatter.jp