[{"@context":"http:\/\/schema.org\/","@type":"BlogPosting","@id":"https:\/\/wiki.edu.vn\/en\/wiki41\/estradiol-3-saccharinylmethyl-ether-wikipedia\/#BlogPosting","mainEntityOfPage":"https:\/\/wiki.edu.vn\/en\/wiki41\/estradiol-3-saccharinylmethyl-ether-wikipedia\/","headline":"Estradiol 3-saccharinylmethyl ether – Wikipedia","name":"Estradiol 3-saccharinylmethyl ether – Wikipedia","description":"before-content-x4 From Wikipedia, the free encyclopedia after-content-x4 Chemical compound Estradiol 3-saccharinylmethyl ether Clinical data Other names E2SME; 3-O-(Saccharinylmethyl)-17\u03b2-estradiol; 3-O-(Saccharinylmethyl)estra-1,3,5(10)-triene-3,17\u03b2-diol Routes","datePublished":"2022-12-09","dateModified":"2022-12-09","author":{"@type":"Person","@id":"https:\/\/wiki.edu.vn\/en\/wiki41\/author\/lordneo\/#Person","name":"lordneo","url":"https:\/\/wiki.edu.vn\/en\/wiki41\/author\/lordneo\/","image":{"@type":"ImageObject","@id":"https:\/\/secure.gravatar.com\/avatar\/c9645c498c9701c88b89b8537773dd7c?s=96&d=mm&r=g","url":"https:\/\/secure.gravatar.com\/avatar\/c9645c498c9701c88b89b8537773dd7c?s=96&d=mm&r=g","height":96,"width":96}},"publisher":{"@type":"Organization","name":"Enzyklop\u00e4die","logo":{"@type":"ImageObject","@id":"https:\/\/wiki.edu.vn\/wiki4\/wp-content\/uploads\/2023\/08\/download.jpg","url":"https:\/\/wiki.edu.vn\/wiki4\/wp-content\/uploads\/2023\/08\/download.jpg","width":600,"height":60}},"image":{"@type":"ImageObject","@id":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/thumb\/7\/77\/Saccharinylmethylestradiol.svg\/250px-Saccharinylmethylestradiol.svg.png","url":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/thumb\/7\/77\/Saccharinylmethylestradiol.svg\/250px-Saccharinylmethylestradiol.svg.png","height":"144","width":"250"},"url":"https:\/\/wiki.edu.vn\/en\/wiki41\/estradiol-3-saccharinylmethyl-ether-wikipedia\/","about":["Wiki"],"wordCount":3772,"articleBody":"     (adsbygoogle = window.adsbygoogle || []).push({});before-content-x4From Wikipedia, the free encyclopedia       (adsbygoogle = window.adsbygoogle || []).push({});after-content-x4Chemical compoundEstradiol 3-saccharinylmethyl etherClinical dataOther namesE2SME; 3-O-(Saccharinylmethyl)-17\u03b2-estradiol; 3-O-(Saccharinylmethyl)estra-1,3,5(10)-triene-3,17\u03b2-diolRoutes ofadministrationBy mouth[1]Drug classEstrogenIdentifiers2-[[(8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl]oxymethyl]-1,1-dioxo-1,2-benzothiazol-3-oneCAS NumberPubChem CIDChemSpiderUNIICompTox Dashboard (EPA)Chemical and physical dataFormulaC26H29NO5SMolar mass467.58\u00a0g\u00b7mol\u221213D model (JSmol)C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)OCN5C(=O)C6=CC=CC=C6S5(=O)=O       (adsbygoogle = window.adsbygoogle || []).push({});after-content-x4InChI=1S\/C26H29NO5S\/c1-26-13-12-19-18-9-7-17(14-16(18)6-8-20(19)22(26)10-11-24(26)28)32-15-27-25(29)21-4-2-3-5-23(21)33(27,30)31\/h2-5,7,9,14,19-20,22,24,28H,6,8,10-13,15H2,1H3\/t19-,20-,22+,24+,26+\/m1\/s1Key:QNUCLUWOICXPIY-QETBJLDASA-NEstradiol 3-saccharinylmethyl ether (E2SME), also known as 3-O-(saccharinylmethyl)-17\u03b2-estradiol, is a synthetic estrogen and estrogen ether \u2013 specifically, the C3 saccharinylmethyl ether of estradiol \u2013 which was described in the mid-1990s and was never marketed.[2][1][3][4] It is a prodrug of estradiol and appears to be partially protected from first-pass metabolism in the liver and intestines with oral administration, showing greatly improved oral potency compared to estradiol.[1][3][4]E2SME has been found to be 9-fold as potent as estradiol by the oral route in rats.[1][4] Similarly, its bioavailability (16%) was 5-fold greater than that of estradiol via the oral route in rats, and the elimination half-life of released estradiol was 5- to 7-fold longer than that of regular estradiol.[1][3][4] Conversely, when E2SME and estradiol were given intravenously in rats, there was no difference between them in terms of potency.[1]In vitro studies revealed that E2SME is not hydrolyzed to estradiol enzymatically but rather is hydrolyzed chemically in biological media such as plasma, apparently dependent on the concentration of protein.[1]       (adsbygoogle = window.adsbygoogle || []).push({});after-content-x4See also[edit]References[edit]^ a b c d e f g Patel J, Katovich MJ, Sloan KB, Curry SH, Prankerd RJ (February 1995). “A prodrug approach to increasing the oral potency of a phenolic drug. Part 2. Pharmacodynamics and preliminary bioavailability of an orally administered O-(imidomethyl) derivative of 17 beta-estradiol”. J Pharm Sci. 84 (2): 174\u20138. doi:10.1002\/jps.2600840210. PMID\u00a07738796.^ Patel JU, Prankerd RJ, Sloan KB (October 1994). “A prodrug approach to increasing the oral potency of a phenolic drug. 1. Synthesis, characterization, and stability of an O-(imidomethyl) derivative of 17 beta-estradiol”. J Pharm Sci. 83 (10): 1477\u201381. doi:10.1002\/jps.2600831022. PMID\u00a07884673.^ a b c Michael Oettel; Ekkehard Schillinger (6 December 2012). Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen. Springer Science & Business Media. pp.\u00a0263\u2013. ISBN\u00a0978-3-642-60107-1.^ a b c d Aungst, Bruce J.; Matz, Nicole (2007). “Prodrugs to Reduce Presystemic Metabolism”. Prodrugs. Biotechnology: Pharmaceutical Aspects. Vol.\u00a0V. pp.\u00a0339\u2013355. doi:10.1007\/978-0-387-49785-3_8. ISBN\u00a0978-0-387-49782-2.li{counter-increment:listitem}.mw-parser-output .hlist ol>li::before{content:\" \"counter(listitem)\"a0 \"}.mw-parser-output .hlist dd ol>li:first-child::before,.mw-parser-output .hlist dt ol>li:first-child::before,.mw-parser-output .hlist li ol>li:first-child::before{content:\" (\"counter(listitem)\"a0 \"}]]>.navbox-abovebelow,.mw-parser-output tr+tr>.navbox-group,.mw-parser-output tr+tr>.navbox-image,.mw-parser-output tr+tr>.navbox-list{border-top:2px solid #fdfdfd}.mw-parser-output .navbox-title{background-color:#ccf}.mw-parser-output .navbox-abovebelow,.mw-parser-output .navbox-group,.mw-parser-output .navbox-subgroup .navbox-title{background-color:#ddf}.mw-parser-output .navbox-subgroup .navbox-group,.mw-parser-output .navbox-subgroup .navbox-abovebelow{background-color:#e6e6ff}.mw-parser-output .navbox-even{background-color:#f7f7f7}.mw-parser-output .navbox-odd{background-color:transparent}.mw-parser-output .navbox .hlist td dl,.mw-parser-output .navbox .hlist td ol,.mw-parser-output .navbox .hlist td ul,.mw-parser-output .navbox td.hlist dl,.mw-parser-output .navbox td.hlist ol,.mw-parser-output .navbox td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}]]>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}]]>ERAgonistsSteroidal: 2-Hydroxyestradiol2-Hydroxyestrone3-Methyl-19-methyleneandrosta-3,5-dien-17\u03b2-ol3\u03b1-Androstanediol3\u03b1,5\u03b1-Dihydrolevonorgestrel3\u03b2,5\u03b1-Dihydrolevonorgestrel3\u03b1-Hydroxytibolone3\u03b2-Hydroxytibolone3\u03b2-Androstanediol4-Androstenediol4-Androstenedione4-Fluoroestradiol4-Hydroxyestradiol4-Hydroxyestrone4-Methoxyestradiol4-Methoxyestrone5-Androstenediol7-Oxo-DHEA7\u03b1-Hydroxy-DHEA7\u03b1-Methylestradiol7\u03b2-Hydroxyepiandrosterone8,9-Dehydroestradiol8,9-Dehydroestrone8\u03b2-VE210\u03b2,17\u03b2-Dihydroxyestra-1,4-dien-3-one (DHED)11\u03b2-Chloromethylestradiol11\u03b2-Methoxyestradiol15\u03b1-Hydroxyestradiol16-Ketoestradiol16-Ketoestrone16\u03b1-Fluoroestradiol16\u03b1-Hydroxy-DHEA16\u03b1-Hydroxyestrone16\u03b1-Iodoestradiol16\u03b1-LE216\u03b2-Hydroxyestrone16\u03b2,17\u03b1-Epiestriol (16\u03b2-hydroxy-17\u03b1-estradiol)17\u03b1-Estradiol (alfatradiol)17\u03b1-Dihydroequilenin17\u03b1-Dihydroequilin17\u03b1-Epiestriol (16\u03b1-hydroxy-17\u03b1-estradiol)17\u03b1-Ethynyl-3\u03b1-androstanediol17\u03b1-Ethynyl-3\u03b2-androstanediol17\u03b2-Dihydroequilenin17\u03b2-Dihydroequilin17\u03b2-Methyl-17\u03b1-dihydroequileninAbirateroneAbiraterone acetateAlestramustineAlmestroneAnabolic steroids (e.g., testosterone and esters, methyltestosterone, metandienone (methandrostenolone), nandrolone and esters, many others; via estrogenic metabolites)AtrimustineBolandiolBolandiol dipropionateButolameClomestroneCloxestradiolConjugated estriolConjugated estrogensCyclodiolCyclotriolDHEADHEA-Sent-EstradiolEpiestriol (16\u03b2-epiestriol, 16\u03b2-hydroxy-17\u03b2-estradiol)EpimestrolEquileninEquilinERA-63 (ORG-37663)Esterified estrogensEstetrolEstradiolEstramustineEstramustine phosphateEstrapronicateEstrazinolEstriolEstrofurateEstrogenic substancesEstromustineEstroneEtamestrol (eptamestrol)EthinylandrostenediolEthinylestradiolEthinylestriolEthylestradiolEtynodiolEtynodiol diacetateHexolameHippulinHydroxyestrone diacetateLynestrenolLynestrenol phenylpropionateMestranolMethylestradiolMoxestrolMytatrienediolNilestriolNorethisteroneNoretynodrelOrestratePentolameProdiameProlamePromestrieneRU-16117QuinestradolQuinestrolTiboloneXenoestrogens: 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 oilLignans (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., \u03b2-sitosterol, campesterol, stigmasterol)Resorcylic acid lactones (e.g., zearalanone, \u03b1-zearalenol, \u03b2-zearalenol, zearalenone, zeranol (\u03b1-zearalanol), taleranol (teranol, \u03b2-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)AntagonistsCoregulator-binding modulators: ERX-11GPER     (adsbygoogle = window.adsbygoogle || []).push({});after-content-x4"},{"@context":"http:\/\/schema.org\/","@type":"BreadcrumbList","itemListElement":[{"@type":"ListItem","position":1,"item":{"@id":"https:\/\/wiki.edu.vn\/en\/wiki41\/#breadcrumbitem","name":"Enzyklop\u00e4die"}},{"@type":"ListItem","position":2,"item":{"@id":"https:\/\/wiki.edu.vn\/en\/wiki41\/estradiol-3-saccharinylmethyl-ether-wikipedia\/#breadcrumbitem","name":"Estradiol 3-saccharinylmethyl ether – Wikipedia"}}]}]