From Wikipedia, the free encyclopedia
Chemical compound
Estradiol 17β-tetrahydropyranyl ether 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 [ 1] [ 2] [ 3] [ 4] Drug class Estrogen ; Estrogen ether
(8R ,9S ,13S ,14S ,17S )-13-methyl-17-(oxan-2-yloxy)-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a ]phenanthren-3-ol
CAS Number PubChem CID ChemSpider UNII Formula C 23 H 32 O 3 Molar mass 356.506 g·mol−1 3D model (JSmol )
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC4CCCCO4)CCC5=C3C=CC(=C5)O
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.[ 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]
^ a b c d Lemke TL, Williams DA (24 January 2012). Foye's Principles of Medicinal Chemistry . Lippincott Williams & Wilkins. pp. 1395–. ISBN 978-1-60913-345-0 .
^ a b 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 .
^ a b c d 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 .
^ a b c 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). "[On some pharmacobiological characteristics of a new estrogen derivative (3-tetrahydropyranyl ether of 17-beta-estradiol)]". Minerva Ginecologica (in Italian). 23 (17): 671–678. PMID 5131894 .
^ Andreoli C, Lenzi G (September 1971). "[Clinical pharmacological aspects of a new hormone derivative (3-tetrahydropyranyl ether of 17-beta-estradiol)]". 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 .
ER Tooltip Estrogen receptor
Agonists
Steroidal: 2-Hydroxyestradiol
2-Hydroxyestrone
3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
3α-Androstanediol
3α,5α-Dihydrolevonorgestrel
3β,5α-Dihydrolevonorgestrel
3α-Hydroxytibolone
3β-Hydroxytibolone
3β-Androstanediol
4-Androstenediol
4-Androstenedione
4-Fluoroestradiol
4-Hydroxyestradiol
4-Hydroxyestrone
4-Methoxyestradiol
4-Methoxyestrone
5-Androstenediol
7-Oxo-DHEA
7α-Hydroxy-DHEA
7α-Methylestradiol
7β-Hydroxyepiandrosterone
8,9-Dehydroestradiol
8,9-Dehydroestrone
8β-VE2
10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)
11β-Chloromethylestradiol
11β-Methoxyestradiol
15α-Hydroxyestradiol
16-Ketoestradiol
16-Ketoestrone
16α-Fluoroestradiol
16α-Hydroxy-DHEA
16α-Hydroxyestrone
16α-Iodoestradiol
16α-LE2
16β-Hydroxyestrone
16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
17α-Estradiol (alfatradiol )
17α-Dihydroequilenin
17α-Dihydroequilin
17α-Epiestriol (16α-hydroxy-17α-estradiol)
17α-Ethynyl-3α-androstanediol
17α-Ethynyl-3β-androstanediol
17β-Dihydroequilenin
17β-Dihydroequilin
17β-Methyl-17α-dihydroequilenin
Abiraterone
Abiraterone acetate
Alestramustine
Almestrone
Anabolic steroids (e.g., testosterone and esters , methyltestosterone , metandienone (methandrostenolone) , nandrolone and esters , many others; via estrogenic metabolites)
Atrimustine
Bolandiol
Bolandiol dipropionate
Butolame
Clomestrone
Cloxestradiol
Conjugated estriol
Conjugated estrogens
Cyclodiol
Cyclotriol
DHEA
DHEA-S
ent -Estradiol
Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)
Epimestrol
Equilenin
Equilin
ERA-63 (ORG-37663)
Esterified estrogens
Estetrol
Estradiol
Estramustine
Estramustine phosphate
Estrapronicate
Estrazinol
Estriol
Estrofurate
Estrogenic substances
Estromustine
Estrone
Etamestrol (eptamestrol)
Ethinylandrostenediol
Ethinylestradiol
Ethinylestriol
Ethylestradiol
Etynodiol
Etynodiol diacetate
Hexolame
Hippulin
Hydroxyestrone diacetate
Lynestrenol
Lynestrenol phenylpropionate
Mestranol
Methylestradiol
Moxestrol
Mytatrienediol
Nilestriol
Norethisterone
Noretynodrel
Orestrate
Pentolame
Prodiame
Prolame
Promestriene
RU-16117
Quinestradol
Quinestrol
Tibolone
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 (SERMs Tooltip Selective estrogen receptor modulators ) Antagonists
Coregulator-binding modulators: ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown