Etacstil

Etacstil (developmental code names GW-5638, DPC974) is an orally active, nonsteroidal, combined selective estrogen receptor modulator (SERM) and selective estrogen receptor degrader (SERD) that was developed for the treatment of estrogen receptor-positive breast cancer.[1][2][3] It was shown to overcome antiestrogen (tamoxifen, aromatase inhibitor, fulvestrant) resistance in breast cancer by altering the shape of the estrogen receptor, thus exhibiting SERD properties.[11] Etacstil was developed in the early 1990s by Duke University, Glaxo Wellcome, and later, Dupont.[12][13] In 2001, Bristol Myers-Squibb (BMS) acquired Dupont, and for non-scientific, corporate reasons, closed the trial and abandoned the release of etacstil and its metabolite GW-7604.[6][9][12] After many dormant years, a recent resurgence of interest in SERDs has led to the development of brilanestrant, a structural analogue of etacstil.
IUPAC nameCAS NumberChemSpiderChEMBLFormulaMolar massSMILESorally activenonsteroidalselective estrogen receptor modulatorselective estrogen receptor degraderestrogen receptorbreast cancerantiestrogentamoxifenaromatase inhibitorfulvestrantmetaboliteafimoxifeneDuke UniversityGlaxo WellcomeDupontBristol Myers-SquibbbrilanestrantBazedoxifeneElacestrantTimeline of cancer treatment developmentmodulators2-Hydroxyestradiol2-Hydroxyestrone3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol3α-Androstanediol3α-Hydroxytibolone3β-Hydroxytibolone3β-Androstanediol4-Androstenediol4-Androstenedione4-Fluoroestradiol4-Hydroxyestradiol4-Hydroxyestrone4-Methoxyestradiol4-Methoxyestrone5-Androstenediol7-Oxo-DHEA7α-Hydroxy-DHEA7α-Methylestradiol7β-Hydroxyepiandrosterone8,9-Dehydroestradiol8,9-Dehydroestrone8β-VE210β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)11β-Chloromethylestradiol11β-Methoxyestradiol15α-Hydroxyestradiol16-Ketoestradiol16-Ketoestrone16α-Fluoroestradiol16α-Hydroxy-DHEA16α-Hydroxyestrone16α-Iodoestradiol16α-LE216β-Hydroxyestrone16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)17α-Estradiolalfatradiol17α-Dihydroequilenin17α-Dihydroequilin17α-Epiestriol (16α-hydroxy-17α-estradiol)17α-Ethynyl-3α-androstanediol17α-Ethynyl-3β-androstanediol17β-Dihydroequilenin17β-Dihydroequilin17β-Methyl-17α-dihydroequileninAbirateroneAbiraterone acetateAlestramustineAlmestroneAnabolic steroidstestosteronemethyltestosteronemetandienone (methandrostenolone)nandroloneAtrimustineBolandiolBolandiol dipropionateButolameClomestroneCloxestradiolCloxestradiol acetateConjugated estriolConjugated estrogensCyclodiolCyclotriolDHEA-Sent-EstradiolEpiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)EpimestrolEquileninEquilinERA-63 (ORG-37663)Esterified estrogensEstetrolEstradiolLipoidal estradiolPolyestradiol phosphateEstramustineEstramustine phosphateEstrapronicateEstrazinolEstriolPolyestriol phosphateEstrofurateEstrogenic substancesEstromustineEstroneEstrone methyl etherEstropipateEtamestrol (eptamestrol)EthinylandrostenediolEthandrostateEthinylestradiolEthinylestradiol 3-benzoateEthinylestradiol sulfonateEthinylestriolEthylestradiolEtynodiolEtynodiol diacetateHexolameHippulinHydroxyestrone diacetateLynestrenolLynestrenol phenylpropionateMestranolMethylestradiolMoxestrolMytatrienediolNilestriolNorethisteroneNoretynodrelOrestratePentolameProdiameProlamePromestrieneRU-16117QuinestradolQuinestrolTibolone(R,R)-THC(S,S)-THC2,8-DHHHCβ-LGND2 (GTx-878)AllenestrolAllenolic acidBenzestrolBifluranolBisdehydrodoisynolic acidButestrolCarbestrolD-15414DCW234DiarylpropionitrileDienestrolDienestrol diacetateDiethylstilbestrolDimestrol (dianisylhexene)DimethylstilbestrolDoisynoestrol (fenocycline)Doisynolic acidEfavirenzERB-196 (WAY-202196)Erteberel (SERBA-1, LY-500307)Estrobin (DBE)FenestrelFERb 033Fosfestrol (diethylstilbestrol diphosphate)Furostilbestrol (diethylstilbestrol difuroate)GTx-758HexestrolICI-85966 (Stilbostat)meso-Butestrolmeso-HexestrolMestilbolMethallenestrilMethestrolMethestrol dipropionateParoxypropionePentafluranolPhenestrolPrinaberel (ERB-041, WAY-202041)PropylpyrazoletriolQuadrosilanSC-4289SERBA-2SKF-82,958TerfluranolTriphenylbromoethyleneTriphenylchloroethyleneTriphenyliodoethyleneTriphenylmethylethylene (triphenylpropene)WAY-166818WAY-200070WAY-204688 (SIM-688)WAY-214156ERB-26ERA-45ERB-79ZK-283197anetholedianetholedianolphotoanetholeChalconoidsisoliquiritigeninphloretinphlorizin (phloridzin)wedelolactoneCoumestanscoumestrolpsoralidinFlavonoids7,8-DHF8-prenylnaringeninapigeninbaicaleinbaicalinbiochanin AcalycosincatechindaidzeindaidzinepicatechinformononetinglabreneglabridingenisteingenistinglyciteinkaempferolliquiritigeninmirificinmyricetinnaringeninpinocembrinprunetinpuerarinquercetintectoridintectorigeninLavender oilLignansenterodiolenterolactonenyasol (cis-hinokiresinol)MetalloestrogenscadmiumPesticidesalternarioldieldrinendosulfanfenarimolmethiocarbmethoxychlortriclocarbantriclosanPhytosteroidsdigitoxindigitalisdiosgeninguggulsteronePhytosterolsβ-sitosterolcampesterolstigmasterolResorcylic acid lactoneszearalanoneα-zearalenolβ-zearalenolzearalenonezeranol (α-zearalanol)taleranol (teranol, β-zearalanol)SteroiddeoxymiroestrolmiroestrolStilbenoidsresveratrolrhaponticinSynthetic xenoestrogensalkylphenolsbisphenolsparabensphthalatesagnuside2-Phenylbenzofuran4'-Hydroxynorendoxifen27-HydroxycholesterolAcefluranolAcolbifeneAnordiolAnordrinArzoxifeneBroparestrolCamizestrantChlorotrianiseneClomifeneClomifenoxideCyclofenilDesmethylchlorotrianiseneDroloxifeneEnclomifeneEndoxifenEthamoxytriphetol (MER-25)FemarelleFispemifeneICI-55548IdoxifeneLasofoxifeneLevormeloxifeneLN-1643LN-2299MenerbaMiproxifeneMiproxifene phosphateNafoxidineNitromifeneNNC 45-0095OrmeloxifeneOspemifenePanomifenePipendoxifeneRaloxifeneRimostil (P-081)SpironolactoneTAS-108 (SR-16234)ToremifeneTrioxifeneZindoxifeneZuclomifene7β-Hydroxy-DHEACytestrol acetateEpitiostanolFulvestrant (ICI-182780)GlyceollinsICI-164384MepitiostaneMethylepitiostanolMethylpiperidinopyrazolePhenytoinProchlorazERX-11Trilostane2-MethoxyestradiolAfimoxifene (4-hydroxytamoxifen)AldosteroneAtrazineBisphenol Ap,p'-DDTHydroxytyrosolKeponeNicotinic acidNicotinamideNonylphenolOleuropeinList of estrogens