Estradiol 3-tetrahydropyranyl ether

{{Short description|Chemical compound}}

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| IUPAC_name = (8R,9S,13S,14S,17S)-13-Methyl-3-(oxan-2-yloxy)-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-ol

| image = Estradiol 3-tetrahydropyranyl ether.svg

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| routes_of_administration = By mouth

| class = Estrogen; Estrogen ether

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| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 41781-86-6

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| UNII = 2UC9XAN8CV

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| PubChem = 257864

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| ChemSpiderID = 226239

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| ChEMBL = 472508

| synonyms = NSC-86473; Estra-1,3,5(10)-triene-17β-diol 3-(tetrahydropyran-2-yl) ether; 3-(Tetrahydro-2H-pyran-2-yloxy)estra-1,3,5(10)-trien-3-ol

| C=23 | H=32 | O=3

| SMILES = C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)OC5CCCCO5

| StdInChI_Ref =

| StdInChI = 1S/C23H32O3/c1-23-12-11-18-17-8-6-16(26-22-4-2-3-13-25-22)14-15(17)5-7-19(18)20(23)9-10-21(23)24/h6,8,14,18-22,24H,2-5,7,9-13H2,1H3/t18-,19-,20+,21+,22?,23+/m1/s1

| StdInChIKey_Ref =

| StdInChIKey = BOLMNLJKDBCJIB-CUFSGNDSSA-N

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Estradiol 3-tetrahydropyranyl ether is a synthetic estrogen and estrogen ether which was never marketed.{{cite book| vauthors = Lemke TL, Williams DA |title=Foye's Principles of Medicinal Chemistry|url=https://books.google.com/books?id=Sd6ot9ul-bUC&pg=PA1395|date=24 January 2012|publisher=Lippincott Williams & Wilkins|isbn=978-1-60913-345-0|pages=1395–}}{{cite journal| vauthors = Cross AD, Harrison IT, Kincl FA, Farkas E, Kraay R, Dorfman RI|title=Steroids CCLXX. Biologically-active labile ethers II. A new group of potent orally-active estrogens|journal=Steroids|volume=4|issue=3|year=1964|pages=423–432|issn=0039-128X|doi=10.1016/0039-128X(64)90155-2}}{{cite journal | vauthors = Kincl FA, Dorfman RI | title = Antifertility activity of various steroids in the female rat | journal = Journal of Reproduction and Fertility | volume = 10 | pages = 105–113 | date = August 1965 | pmid = 14337800 | doi = 10.1530/jrf.0.0100105 | s2cid = 32111383 }}{{cite journal | vauthors = Locardi G | title = [Clinical pharmacology and biological characteristics of 3-tetrahydropyranyl ether of 17-beta-estradiol] | language = it | journal = Minerva Ginecologica | volume = 24 | issue = 2 | pages = 70–81 | date = February 1972 | pmid = 4603402 | url = https://www.popline.org/node/486526 }}{{cite journal | vauthors = Plancher G | title = [On some pharmacobiological characteristics of a new estrogen derivative (3-tetrahydropyranyl ether of 17-beta-estradiol)] | language = it | journal = Minerva Ginecologica | volume = 23 | issue = 17 | pages = 671–678 | date = September 1971 | pmid = 5131894 }}{{cite journal | vauthors = Andreoli C, Lenzi G | title = [Clinical pharmacological aspects of a new hormone derivative (3-tetrahydropyranyl ether of 17-beta-estradiol)] | language = it | journal = Minerva Ginecologica | volume = 23 | issue = 18 | pages = 711–724 | date = September 1971 | pmid = 5131179 }}{{cite journal | vauthors = Boucheau V, Renaud M, Rolland de Ravel M, Mappus E, Cuilleron CY | title = Proton and carbon-13 nuclear magnetic resonance spectroscopy of diastereoisomeric 3- and 17 beta-tetrahydropyranyl ether derivatives of estrone and estradiol | journal = Steroids | volume = 55 | issue = 5 | pages = 209–221 | date = May 1990 | pmid = 2163125 | doi = 10.1016/0039-128X(90)90018-7 | s2cid = 1476967 }} It has been reported to possess improved oral activity relative to estradiol. One study in animals found that it had 15 times the oral activity of estradiol.