Bifluranol

Bifluranol (INNTooltip International Nonproprietary Name, BANTooltip British Approved Name; brand name Prostarex; former developmental code name BX-341) is a synthetic nonsteroidal estrogen of the stilbestrol group related to diethylstilbestrol that has been used as an antiandrogen in the United Kingdom in the treatment of benign prostatic hyperplasia.[1][2][3][4][5][6][7][8] The drug is described as a weak estrogen, and possesses about one-eighth the potency of diethylstilbestrol.[3][7][9] In spite of the fact that it is widely referred to as an antiandrogen in the literature, bifluranol is actually a pure estrogen and does not significantly bind to the androgen receptor or directly antagonize the action of androgens.[3] It exerts functional antiandrogen effects by binding to and activating the estrogen receptor in the pituitary gland, consequently suppressing the secretion of luteinizing hormone (and hence acting as an antigonadotropin) and thereby reducing gonadal androgen production and systemic androgen levels.[3] Bifluranol has also been found to act as a 17α-hydroxylase/17,20 lyase inhibitor, though with less potency than ketoconazole, and this action may contribute to its efficacy in benign prostatic hyperplasia by further helping to lower androgen levels.
Drug classNonsteroidal estrogenIUPAC nameCAS NumberChemSpiderChEMBLFormulaMolar massSMILESsyntheticstilbestroldiethylstilbestrolantiandrogenUnited Kingdombenign prostatic hyperplasiaandrogen receptorantagonizeandrogensestrogen receptorpituitary glandluteinizing hormoneantigonadotropingonadal17α-hydroxylase/17,20 lyaseinhibitorpotencyketoconazolepentafluranolterfluranolAcefluranolParoxypropioneMetallibureEstrogensantiestrogensAlfatradiolanabolic steroidstestosteronemethyltestosteronemetandienoneprogestinsnorethisteronenoretynodreletynodiol diacetatetiboloneClomestroneCloxestradiol acetateConjugated estriolConjugated estrogensEpiestriolEpimestrolEsterified estrogensEstetrolEstradiolestradiol acetateestradiol benzoateestradiol cypionateestradiol enanthateestradiol undecylateestradiol valeratepolyestradiol phosphateestradiol ester mixturesClimacteronEstramustine phosphateEstriolestriol succinatepolyestriol phosphateEstrogenic substancesEstroneEstrone sulfateEstropipate (piperazine estrone sulfate)EthinylestradiolEthinylestradiol sulfonateHydroxyestrone diacetateMestranolMethylestradiolMoxestrolNilestriolPrasterone (dehydroepiandrosterone; DHEA)Prasterone enanthatePrasterone sulfatePromestrieneQuinestradolQuinestrolBenzestrolChlorotrianiseneDienestrolDienestrol diacetateDiethylstilbestrol (stilbestrol)Dimestrol (diethylstilbestrol dimethyl ether)Fosfestrol (diethylstilbestrol diphosphate)Mestilbol (diethylstilbestrol monomethyl ether)Doisynoestrol (fenocycline)HexestrolMethallenestrilMethestrol (promethestrol)Methestrol dipropionate (promethestrol dipropionate)QuadrosilanTriphenylbromoethyleneTriphenylchloroethyleneZeranolProgonadotropinsAntiandrogensbicalutamideGnRH agonistsGnRH (gonadorelin)leuprorelinGonadotropinsAcolbifeneAnordrinBazedoxifeneBroparestrolClomifeneCyclofenilEnclomifeneEpitiostanolLasofoxifeneMepitiostaneOrmeloxifeneOspemifeneRaloxifeneTamoxifenToremifeneElacestrantFulvestrantTrilostaneAromatase inhibitorsAminoglutethimideTestolactoneFadrozoleFormestaneAnastrozoleExemestaneLetrozoleAntigonadotropinsoxandrolonefluoxymesteroneD2 receptorantagonistsprolactindomperidonemetoclopramiderisperidonehaloperidolchlorpromazinesulpiridegoserelinGnRH antagonistscetrorelixelagolixProgestogenschlormadinone acetatecyproterone acetategestonorone caproatehydroxyprogesterone caproatemedroxyprogesterone acetatemegestrol acetateDanazolGestrinoneAndrovax (androstenedione albumin)Ovandrotone albumin (Fecundin)WHO-EMWithdrawnClinical trialsList of estrogensagonistsAndrostenediol dipropionateBoldenone undecylenateClostebolClostebol acetateClostebol caproateClostebol propionateCloxotestosterone acetatePrasterone (dehydroepiandrosterone, DHEA)Prasterone enanthate (DHEA enanthate)Prasterone sulfate (DHEA sulfate)Quinbolonetestosterone cypionatetestosterone enanthatetestosterone propionatetestosterone undecanoatetestosterone ester mixturesDeposteronaOmnadrenSustanonTestoviron DepotAndrostanolone (stanolone, dihydrotestosterone, DHT)Bolazine capronateDrostanolone propionate (dromostanolone propionate)MesteroloneMetenolone acetate (methenolone acetate)Metenolone enanthate (methenolone enanthate)Stenbolone acetateBolandiol dipropionatenandrolone decanoatenandrolone phenylpropionateNorclostebolNorclostebol acetateOxabolone cipionate (oxabolone cypionate)Trenbolone acetateTrenbolone hexahydrobenzylcarbonate (trenbolone cyclohexylmethylcarbonate)BolasteroneCalusteroneChlorodehydromethyltestosterone (CDMT)FormeboloneMetandienone (methandienone, methandrostenolone)Methandriol (methylandrostenediol)Methandriol bisenanthoyl acetateMethandriol dipropionateMethandriol propionateMethyltestosterone 3-hexyl etherOxymesteronePenmesterolTiomesterone (thiomesterone)AndroisoxazoleFurazabolMebolazine (dimethazine)MestanoloneOxymetholoneStanozololEthylestrenolMiboleroneNorethandroloneNormethandrone (methylestrenolone, normethisterone)Propetandrol (propethandrol)Norvinisterone (vinylnortestosterone)ethisterone (ethynyltestosterone)levonorgestrelnorgestrelnorethisterone (norethindrone)lynestrenolnorgestrienoneAbiraterone acetate+niraparibCanrenoneDelmadinone acetateDienogestDrospirenoneMedrogestoneNomegestrol acetateOsaterone acetateOxendolonePotassium canrenoateSpironolactoneApalutamideCimetidineDarolutamideEnzalutamideFlutamideNilutamideSeviteronelTopilutamide (fluridil)Steroidogenesisinhibitors5α-ReductaseDutasterideEpristerideFinasterideSaw palmetto extractprolactin releasersList of androgens/anabolic steroidsmodulators2-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-Estradiol17α-Dihydroequilenin17α-Dihydroequilin17α-Epiestriol (16α-hydroxy-17α-estradiol)17α-Ethynyl-3α-androstanediol17α-Ethynyl-3β-androstanediol17β-Dihydroequilenin17β-Dihydroequilin17β-Methyl-17α-dihydroequileninAbirateroneAlestramustineAlmestronemetandienone (methandrostenolone)nandroloneAtrimustineBolandiolButolameCloxestradiolCyclodiolCyclotriolDHEA-Sent-EstradiolEpiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)EquileninEquilinERA-63 (ORG-37663)Lipoidal estradiolEstramustineEstrapronicateEstrazinolEstrofurateEstromustineEstrone methyl etherEstropipateEtamestrol (eptamestrol)EthinylandrostenediolEthandrostateEthinylestradiol 3-benzoateEthinylestriolEthylestradiolEtynodiolHexolameHippulinLynestrenol phenylpropionateMytatrienediolOrestratePentolameProdiameProlameRU-16117(R,R)-THC(S,S)-THC2,8-DHHHCβ-LGND2 (GTx-878)AllenestrolAllenolic acidBisdehydrodoisynolic acidButestrolCarbestrolD-15414DCW234DiarylpropionitrileDimestrol (dianisylhexene)DimethylstilbestrolDoisynolic acidEfavirenzERB-196 (WAY-202196)Erteberel (SERBA-1, LY-500307)Estrobin (DBE)FenestrelFERb 033Furostilbestrol (diethylstilbestrol difuroate)GTx-758ICI-85966 (Stilbostat)meso-Butestrolmeso-HexestrolMestilbolMethestrolMethestrol dipropionatePhenestrolPrinaberel (ERB-041, WAY-202041)PropylpyrazoletriolSC-4289SERBA-2SKF-82,958TriphenyliodoethyleneTriphenylmethylethylene (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-HydroxycholesterolAfimoxifeneAnordiolArzoxifeneBrilanestrantCamizestrantClomifenoxideDesmethylchlorotrianiseneDroloxifeneEndoxifenEtacstil (GW-5638, DPC-974)Ethamoxytriphetol (MER-25)FemarelleFispemifeneICI-55548IdoxifeneLevormeloxifeneLN-1643LN-2299MenerbaMiproxifeneMiproxifene phosphateNafoxidineNitromifeneNNC 45-0095PanomifenePipendoxifeneRimostil (P-081)TAS-108 (SR-16234)TrioxifeneZindoxifeneZuclomifene7β-Hydroxy-DHEACytestrol acetateFulvestrant (ICI-182780)GlyceollinsICI-164384MethylepitiostanolMethylpiperidinopyrazolePhenytoinProchlorazERX-112-MethoxyestradiolAfimoxifene (4-hydroxytamoxifen)AldosteroneAtrazineBisphenol Ap,p'-DDTHydroxytyrosolKeponeNicotinic acidNicotinamideNonylphenolOleuropein