(R,R)-Tetrahydrochrysene

Chemical compound (R,R)-Tetrahydrochrysene (5R,11R)-5,11-Diethyl-5,6,11,12-tetrahydrochrysene-2,8-diol Tetrahydrochrysene.svg skin-invert-image 250 correct CAS 138090-06-9 correct FDA 89HTC2NWF3 446849 42371 394097 22 24 2 CCC1CC2=C(C=CC(=C2)O)C3=C1C4=C(CC3CC)C=C(C=C4)O 1S/C22H24O2/c1-3-13-9-15-11-17(23)6-8-20(15)22-14(4-2)10-16-12-18(24)5-7-19(16)21(13)22/h5-8,11-14,23-24H,3-4,9-10H2,1-2H3/t13-,14-/m1/s1 MASYAWHPJCQLSW-ZIAGYGMSSA-N (R,R)-Tetrahydrochrysene ((R,R)-THC) is a drug used to study the estrogen receptors (ERs) in scientific research. It is an ERβ antagonist and an ERα agonist with 10-fold higher affinity for ERβ relative to ERα.Ying Chen The Role of Steroids in the Regulation of Oocyte Cyst Breakdown and Primordial Follicle Assembly in the Neonatal Mouse Ovary https://books.google.com/books?id=uf2VdCOO6moC&pg=PA101 2008 978-0-549-74620-1 101– Syracuse University Shiau AK, Barstad D, Radek JT, Meyers MJ, Nettles KW, Katzenellenbogen BS, Katzenellenbogen JA, Agard DA, Greene GL Structural characterization of a subtype-selective ligand reveals a novel mode of estrogen receptor antagonism Nat. Struct. Biol. 9 5 359–64 2002 11953755 10.1038/nsb787 452305 (R,R)-THC is a silent antagonist of ERβ, Sun J, Meyers MJ, Fink BE, Rajendran R, Katzenellenbogen JA, Katzenellenbogen BS Novel ligands that function as selective estrogens or antiestrogens for estrogen receptor-alpha or estrogen receptor-beta Endocrinology 140 2 800–4 1999 9927308 10.1210/endo.140.2.6480 free and, uniquely relative to other known ERβ antagonists, a passive antagonist of the receptor. (S,S)-Tetrahydrochrysene ((S,S)-THC) also binds to the ERs, but in contrast to (R,R)-THC, (S,S)-THC is an agonist of both ERα and ERβ and has 20-fold lower affinity for ERβ relative to (R,R)-THC. See also Propylpyrazoletriol (PPT) PHTPP Methylpiperidinopyrazole (MPP) Diarylpropionitrile (DPN) Prinaberel (ERB-041) Liquiritigenin Menerba 2,8-DHHHC Chrysene References 30em Category:Estrogens Category:Antiestrogens