Estradiol 17β-tetrahydropyranyl ether

Chemical compound Pharmaceutical compound

Estradiol 17β-tetrahydropyranyl ether
Clinical data

Other names	RS-2290; NSC-99694; Estra-1,3,5(10)-triene-17β-diol 17β-(tetrahydropyran-2-yl) ether; 17β-(Tetrahydro-2H-pyran-2-yloxy)estra-1,3,5(10)-trien-3-ol
Routes of administration	By mouth
Drug class	Estrogen; Estrogen ether
Identifiers
IUPAC name (8R,9S,13S,14S,17S)-13-methyl-17-(oxan-2-yloxy)-6,7,8,9,11,12,14,15,16,17-decahydrocyclopentaphenanthren-3-ol
CAS Number	3589-90-0
PubChem CID	23618059
ChemSpider	19955297
UNII	OEU4S60XOJ
Chemical and physical data
Formula	C₂₃H₃₂O₃
Molar mass	356.506 g·mol
3D model (JSmol)	Interactive image
SMILES C12CC3(1CC2OC4CCCCO4)CCC5=C3C=CC(=C5)O
InChI InChI=1S/C23H32O3/c1-23-12-11-18-17-8-6-16(24)14-15(17)5-7-19(18)20(23)9-10-21(23)26-22-4-2-3-13-25-22/h6,8,14,18-22,24H,2-5,7,9-13H2,1H3/t18-,19-,20+,21+,22?,23+/m1/s1 Key:DRRJWMXJIVWKKW-CUFSGNDSSA-N

Estradiol 17β-tetrahydropyranyl ether is a synthetic estrogen and estrogen ether which was never marketed. 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.

References

^ Lemke TL, Williams DA (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 1395–. ISBN 978-1-60913-345-0.
^ Locardi G (February 1972). "[Clinical pharmacology and biological characteristics of 3-tetrahydropyranyl ether of 17-beta-estradiol]". Minerva Ginecologica (in Italian). 24 (2): 70–81. PMID 4603402.
^ Cross AD, Harrison IT, Kincl FA, Farkas E, Kraay R, Dorfman RI (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.
^ Kincl FA, Dorfman RI (August 1965). "Antifertility activity of various steroids in the female rat". Journal of Reproduction and Fertility. 10: 105–113. doi:10.1530/jrf.0.0100105. PMID 14337800. S2CID 32111383.
Plancher G (September 1971). "". Minerva Ginecologica (in Italian). 23 (17): 671–678. PMID 5131894.
Andreoli C, Lenzi G (September 1971). "". Minerva Ginecologica (in Italian). 23 (18): 711–724. PMID 5131179.
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): 209–221. doi:10.1016/0039-128X(90)90018-7. PMID 2163125. S2CID 1476967.

Estrogen receptor modulators

ERTooltip Estrogen receptor

Agonists

Unknown/unsorted: ERB-26
ERA-45
ERB-79
ZK-283197

Xenoestrogens: Anise-related (e.g., anethole, anol, dianethole, dianol, photoanethole)
Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone)
Coumestans (e.g., coumestrol, psoralidin)
Flavonoids (incl. 7,8-DHF, 8-prenylnaringenin, apigenin, baicalein, baicalin, biochanin A, calycosin, catechin, daidzein, daidzin, ECG, EGCG, epicatechin, equol, formononetin, glabrene, glabridin, genistein, genistin, glycitein, kaempferol, liquiritigenin, mirificin, myricetin, naringenin, penduletin, pinocembrin, prunetin, puerarin, quercetin, tectoridin, tectorigenin)
Lavender oil
Lignans (e.g., enterodiol, enterolactone, nyasol (cis-hinokiresinol))
Metalloestrogens (e.g., cadmium)
Pesticides (e.g., alternariol, dieldrin, endosulfan, fenarimol, HPTE, methiocarb, methoxychlor, triclocarban, triclosan)
Phytosteroids (e.g., digitoxin (digitalis), diosgenin, guggulsterone)
Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol)
Resorcylic acid lactones (e.g., zearalanone, α-zearalenol, β-zearalenol, zearalenone, zeranol (α-zearalanol), taleranol (teranol, β-zearalanol))
Steroid-like (e.g., deoxymiroestrol, miroestrol)
Stilbenoids (e.g., resveratrol, rhaponticin)
Synthetic xenoestrogens (e.g., alkylphenols, bisphenols (e.g., BPA, BPF, BPS), DDT, parabens, PBBs, PHBA, phthalates, PCBs)
Others (e.g., agnuside, rotundifuran)

Mixed
(SERMsTooltip Selective estrogen receptor modulators)

Antagonists

Coregulator-binding modulators: ERX-11

Noncompetitive inhibitors: Trilostane

GPERTooltip G protein-coupled estrogen receptor

Agonists	2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Aldosterone Atrazine Bisphenol A Daidzein DDT (p,p'-DDT, o',p'-DDE) Diarylpropionitrile Equol Estradiol Ethinylestradiol Fulvestrant (ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Niacin Niacinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol STX Tamoxifen Tectoridin
Antagonists	CCL18 Estriol G-15 G-36 MIBE
Unknown	Diethylstilbestrol Zearalenone

See also: Receptor/signaling modulators; Estrogens and antiestrogens; Androgen receptor modulators; Progesterone receptor modulators; List of estrogens

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See also

References