Estradiol 3-tetrahydropyranyl ether

Estradiol 3-tetrahydropyranyl ether is a synthetic estrogen and estrogen ether which was never marketed.[1][3][4][2][5][6][7] It has been reported to possess improved oral activity relative to estradiol.[1][3][4] One study in animals found that it had 15 times the oral activity of estradiol.[1][3]

Estradiol 3-tetrahydropyranyl ether
Clinical data
Other namesNSC-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
Routes of
administration		By mouth[1][2][3][4]
Drug classEstrogen; Estrogen ether
Identifiers
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
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC23H32O3
Molar mass356.506 g·mol−1
3D model (JSmol)
SMILES
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)OC5CCCCO5
InChI
  • InChI=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
  • Key:BOLMNLJKDBCJIB-CUFSGNDSSA-N

See also

References
  1. Thomas L. Lemke; David A. Williams (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 1395–. ISBN 978-1-60913-345-0.
  2. Locardi G (February 1972). "[Clinical pharmacology and biological characteristics of 3-tetrahydropyranyl ether of 17-beta-estradiol]". Minerva Ginecol (in Italian). 24 (2): 70–81. PMID 4603402.
  3. Cross, A.D.; Harrison, I.T.; Kincl, F.A.; Farkas, E.; Kraay, R.; Dorfman, R.I. (1964). "Steroids CCLXX. Biologically-active labile ethers II. A new group of potent orally-active estrogens". Steroids. 4 (3): 423–432. doi:10.1016/0039-128X(64)90155-2. ISSN 0039-128X.
  4. Kincl FA, Dorfman RI (August 1965). "Antifertility activity of various steroids in the female rat" (PDF). J. Reprod. Fertil. 10: 105–13. doi:10.1530/jrf.0.0100105. PMID 14337800. S2CID 32111383.
  5. Plancher G (September 1971). "[On some pharmacobiological characteristics of a new estrogen derivative (3-tetrahydropyranyl ether of 17-beta-estradiol)]". Minerva Ginecol (in Italian). 23 (17): 671–8. PMID 5131894.
  6. Andreoli C, Lenzi G (September 1971). "[Clinical pharmacological aspects of a new hormone derivative (3-tetrahydropyranyl ether of 17-beta-estradiol)]". Minerva Ginecol (in Italian). 23 (18): 711–24. PMID 5131179.
  7. Boucheau V, Renaud M, Rolland de Ravel M, Mappus E, Cuilleron CY (May 1990). "Proton and carbon-13 nuclear magnetic resonance spectroscopy of diastereoisomeric 3- and 17 beta-tetrahydropyranyl ether derivatives of estrone and estradiol". Steroids. 55 (5): 209–21. doi:10.1016/0039-128X(90)90018-7. PMID 2163125. S2CID 1476967.



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