10β,17β-Dihydroxyestra-1,4-dien-3-one

Chemical compound 93% 10β,17β-Dihydroxyestra-1,4-dien-3-one (8S,9S,10S,13S,14S,17S)-10,17-dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one (17β)-10,17-Dihydroxyestra-1,4-dien-3-one.svg skin-invert-image 250px By mouth Estrogen correct CAS 549-02-0 correct FDA UR9WW8CA3J 11851170 10025642 DHED; Estradiol paraquinol; Estra-1,4-diene-10β,17β-diol-3-one 18 24 3 C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=CC(=O)C=C[C@]34O 1S/C18H24O3/c1-17-8-7-15-13(14(17)4-5-16(17)20)3-2-11-10-12(19)6-9-18(11,15)21/h6,9-10,13-16,20-21H,2-5,7-8H2,1H3/t13-,14-,15-,16-,17-,18+/m0/s1 UIKDFTLKOKNUJP-UGDFAFBOSA-N 10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED), also known as estradiol paraquinol, is an orally active, centrally selective estrogen and a biosynthetic prodrug of estradiol. Prokai L, Nguyen V, Szarka S, Garg P, Sabnis G, Bimonte-Nelson HA, McLaughlin KJ, Talboom JS, Conrad CD, Shughrue PJ, Gould TD, Brodie A, Merchenthaler I, Koulen P, Prokai-Tatrai K The prodrug DHED selectively delivers 17β-estradiol to the brain for treating estrogen-responsive disorders Sci Transl Med 7 297 297ra113 2015 26203081 4591937 10.1126/scitranslmed.aab1290 Merchenthaler I, Lane M, Sabnis G, Brodie A, Nguyen V, Prokai L, Prokai-Tatrai K Treatment with an orally bioavailable prodrug of 17β-estradiol alleviates hot flushes without hormonal effects in the periphery Sci Rep 6 30721 2016 27477453 4967894 10.1038/srep30721 free 2016NatSR...630721M Tschiffely AE, Schuh RA, Prokai-Tatrai K, Prokai L, Ottinger MA A comparative evaluation of treatments with 17β-estradiol and its brain-selective prodrug in a double-transgenic mouse model of Alzheimer's disease Horm Behav 83 39–44 2016 27210479 10.1016/j.yhbeh.2016.05.009 4950979 Cappelletti Maurand M. 2016 Estrogens, androgens, and the hormonal modulation of female primate sexual motivation in rhesus monkeys 1835777256 Upon systemic administration, regardless of route of administration, DHED has been found to rapidly and selectively convert into estradiol in the brain, whereas no such conversion occurs in the rest of the body. Moreover, DHED itself possesses no estrogenic activity, requiring transformation into estradiol for its estrogenicity. As such, the drug shows selective estrogenic effects in the brain (e.g., alleviation of hot flashes, neuroprotection) that are said to be identical to those of estradiol, whereas estrogenic effects elsewhere in the body are not observed. DHED has been proposed as a possible novel estrogenic treatment for neurological and psychiatric conditions associated with hypoestrogenism (e.g., menopausal hot flashes, depression, cognitive decline, Alzheimer's disease, and stroke) that uniquely lacks potentially detrimental estrogenic side effects in the periphery. References Category:Centrally selective drugs Category:Conjugated dienes Category:Estranes Category:Enones Category:Sex hormone esters and conjugates Category:Synthetic estrogens Category:Secondary alcohols Category:Tertiary alcohols