16α-LE2

Chemical compound 3,17β-Dihydroxy-16α,21-epoxy-19-nor-17α-pregna-1,3,5(10)-trien-21-one 16aLE2_structure.png skin-invert-image 250 correct CAS 406483-39-4 9862250 8037946 correct FDA Z7DNN9U8AE 20 24 4 O=C1O[C@@]2([H])[C@]([C@@]3(C)CC[C@]4([H])C5=CC=C(C=C5CC[C@@]4([H])[C@]3([H])C2)O)(C1)O InChI=1S/C20H24O4/c1-19-7-6-14-13-5-3-12(21)8-11(13)2-4-15(14)16(19)9-17-20(19,23)10-18(22)24-17/h3,5,8,14-17,21,23H,2,4,6-7,9-10H2,1H3/t14-,15-,16+,17-,19+,20+/m1/s1 NLUGVTJBNRSIKH-UQZPWQSVSA-N 16α-LE2, or 16α-lactone-estradiol, also known as 3,17β-dihydroxy-19-nor-17α-pregna-1,3,5-(10)-triene-21,16α-lactone, is a synthetic, steroidal estrogen featuring an estradiol core. It is a highly potent and selective agonist of the ERα that is used in scientific research to study the function of the ERα. Pakdel F, Kah O, Jégou B Mechanisms of action of particular endocrine-disrupting chemicals Shaw I Endocrine-Disrupting Chemicals in Food https://books.google.com/books?id=x6ejAgAAQBAJ&pg=PA550 31 March 2009 Elsevier 978-1-84569-574-3 550– Hegele-Hartung C, Siebel P, Peters O, Kosemund D, Müller G, Hillisch A, Walter A, Kraetzschmar J, Fritzemeier KH 6 Impact of isotype-selective estrogen receptor agonists on ovarian function Proceedings of the National Academy of Sciences of the United States of America 101 14 5129–5134 April 2004 15037755 387385 10.1073/pnas.0306720101 free 2004PNAS..101.5129H It has 265-fold higher potency in transactivation assays of the ERα relative to the ERβ and 70-fold preference in binding affinity for the ERα over the ERβ. In rodents, 16α-LE2 has no effect on ovarian follicle development, whereas the highly ERβ-selective agonist 8β-VE2 stimulates follicular growth and to a comparable extent as estradiol, indicating that the ERβ and not the ERα is involved in the effects of estrogen on ovarian follicles. Binder K, Winuthayanon W, Hewitt SC, Couse JF, Korach KS Steroid Receptors in the Uterus and Ovary Plant TM, Zeleznik AJ Knobil and Neill's Physiology of Reproduction https://books.google.com/books?id=I1ACBAAAQBAJ&pg=PA1150 15 November 2014 Academic Press 978-0-12-397769-4 1150– In contrast, 16α-LE2 stimulates uterine weight, whereas 8β-VE2 has no effect, indicating that the ERα and not the ERβ is involved in the effects of estrogen on the uterus. Research has determined through experimental rodent studies with estradiol, 16α-LE2, and 8β-VE2 that the positive, protective effects of estrogens on bone formation resorption and bone mineral density are mediated via the ERα, whereas the ERβ does not appear to be involved. Hertrampf T, Schleipen B, Velders M, Laudenbach U, Fritzemeier KH, Diel P Estrogen receptor subtype-specific effects on markers of bone homeostasis Molecular and Cellular Endocrinology 291 1–2 104–108 September 2008 18433985 10.1016/j.mce.2008.03.003 1774519 https://hal.archives-ouvertes.fr/hal-00532015/file/PEER_stage2_10.1016%252Fj.mce.2008.03.003.pdf See also ERA-45 ERA-63 Propylpyrazoletriol Methylpiperidinopyrazole GTx-758 Diarylpropionitrile WAY-200070 16α-Iodo-E2 References 30em Category:Estranes Category:Lactones Category:Synthetic estrogens Category:Hydroxyarenes Category:Tertiary alcohols