17α-Epiestriol

epiestriol (set index) 17α-Epiestriol.svg skin-invert-image Estra-1,3,5(10)-triene-3,16α,17α-triol (1S,2R,3aS,3bR,9bS,11aS)-11a-Methyl-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H-cyclopenta[a]phenanthrene-1,2,7-triol 17-Epiestriol; 16α-Hydroxy-17α-estradiol; 3,16α,17α-Trihydroxy-1,3,5(10)-estratriene 1228-72-4 256737 225189 DB07702 Oc1ccc2[C@H]3CC[C@]4(C)[C@@]5([C@@]6C[C@H]4[C@@H]3CCc2c1).O6.O5 1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17-,18+/m1/s1 PROQIPRRNZUXQM-PNVOZDDCSA-N 4G7IHY560Z 42156 1232445 18 24 3 288.38136 g/mol 17α-Epiestriol, or simply 17-epiestriol, also known as 16α-hydroxy-17α-estradiol or estra-1,3,5(10)-triene-3,16α,17α-triol, is a minor and weak endogenous estrogen, and the 17α-epimer of estriol (which is 16α-hydroxy-17β-estradiol). Ashutosh K Tewari vanc Prostate Cancer: A Comprehensive Perspective https://books.google.com/books?id=8VI_AAAAQBAJ&pg=PA373 5 April 2013 Springer Science & Business Media 978-1-4471-2864-9 373– Labhart A Clinical Endocrinology: Theory and Practice https://books.google.com/books?id=DAgJCAAAQBAJ&pg=PA522 6 December 2012 Springer Science & Business Media 978-3-642-96158-8 522– Assali NS The Maternal Organism https://books.google.com/books?id=mSzLBAAAQBAJ&pg=PA341 3 September 2013 Elsevier 978-1-4832-6380-9 341– It is formed from 16α-hydroxyestrone. Von Euler US Comparative Endocrinology https://books.google.com/books?id=rAJX4z_oQrkC&pg=PA135 2 December 2012 Elsevier Science 978-0-323-14609-8 135– Norbert W. Tietz vanc Fundamentals of clinical chemistry https://books.google.com/books?id=Keg6AAAAMAAJ 1 August 1976 Saunders 978-0-7216-8866-4 773 In contrast to other endogenous estrogens like estradiol, 17α-epiestriol is a selective agonist of the ERβ. Gajanan V. Sherbet vanc Therapeutic Strategies in Cancer Biology and Pathology https://books.google.com/books?id=vSSES5WRdZ4C&pg=PA83 26 July 2013 Elsevier 978-0-12-416590-8 83– It is described as a relatively weak estrogen, which is in accordance with its relatively low affinity for the ERα. Ralph I. Dorfman vanc Steroidal Activity in Experimental Animals and Man https://books.google.com/books?id=BbLfBAAAQBAJ&pg=PA13 22 October 2013 Elsevier Science 978-1-4832-7299-3 13– 17α-Epiestriol has been found to be approximately 400-fold more potent than estradiol in inhibiting tumor necrosis factor α (TNFα)-induced vascular cell adhesion molecule 1 (VCAM-1) expression in vitro. Mukherjee TK, Nathan L, Dinh H, Reddy ST, Chaudhuri G 17-epiestriol, an estrogen metabolite, is more potent than estradiol in inhibiting vascular cell adhesion molecule 1 (VCAM-1) mRNA expression The Journal of Biological Chemistry 278 14 11746–52 April 2003 12547825 10.1074/jbc.M207800200 free Relative affinities (%) of 17α-epiestriol and related steroidsRaynaud J.P. Ojasoo T. Bouton M.M. Philibert D. Drug Design Receptor Binding as a Tool in the Development of New Bioactive Steroids 1979 169–214 10.1016/B978-0-12-060308-4.50010-X 9780120603084 https://books.google.com/books?id=bhAlBQAAQBAJ&pg=PA169 Ojasoo T, Raynaud JP Unique steroid congeners for receptor studies Cancer Research 38 11 Pt 2 4186–98 November 1978 359134 http://cancerres.aacrjournals.org/content/38/11_Part_2/4186.short Ojasoo T, Delettré J, Mornon JP, Turpin-VanDycke C, Raynaud JP Towards the mapping of the progesterone and androgen receptors Journal of Steroid Biochemistry 27 1–3 255–69 1987 3695484 10.1016/0022-4731(87)90317-7 Raynaud JP, Bouton MM, Moguilewsky M, Ojasoo T, Philibert D, Beck G, Labrie F, Mornon JP Steroid hormone receptors and pharmacology Journal of Steroid Biochemistry 12 143–57 January 1980 7421203 10.1016/0022-4731(80)90264-2 Compound PR Progesterone receptor AR Androgen receptor ER Estrogen receptor GR Glucocorticoid receptor MR Mineralocorticoid receptor SHBG Sex hormone-binding globulin CBG Corticosteroid binding globulin Estradiol 2.6 7.9 100 0.6 0.13 8.7 <0.1 Alfatradiol <1 <1 15 <1 <1 ? ? Estriol <1 <1 15 <1 <1 ? ? 16β-Epiestriol <1 <1 20 <1 <1 ? ? 17α-Epiestriol <1 <1 31 <1 <1 ? ? Values are percentages (%). Reference ligands (100%) were progesterone for the PR progesterone receptor, testosterone for the AR androgen receptor, E2 estradiol for the ER estrogen receptor, DEXA dexamethasone for the GR glucocorticoid receptor, aldosterone for the MR mineralocorticoid receptor, DHT dihydrotestosterone for SHBG sex hormone-binding globulin, and cortisol for CBG Corticosteroid-binding globulin. See also Epimestrol 16β,17α-Epiestriol 16β-Epiestriol 17α-Estradiol 2-Methoxyestradiol References 30em Category:Estranes Category:Estrogens Category:Hormones of the hypothalamus-pituitary-gonad axis Category:Selective ERβ agonists Category:Sex hormones