Varenicline - Wikipedia

Varenicline (trade name Chantix and Champix) is a medication used for smoking cessation. Varenicline is also used for the treatment of dry eye disease. Varenicline FromWikipedia,thefreeencyclopedia Jumptonavigation Jumptosearch Nicotinicreceptoragonist VareniclineClinicaldataTradenamesChampix,Chantix,Tyrvaya,othersOthernamesOC-01AHFS/Drugs.comMonographMedlinePlusa606024Licensedata EU EMA: byINN US DailyMed: Varenicline Pregnancycategory AU:B3 RoutesofadministrationBymouth,NasalsprayATCcodeN07BA03(WHO)LegalstatusLegalstatus AU:S4(Prescriptiononly)[1][2] CA:℞-only UK:POM(Prescriptiononly)[3] US:℞-only[4][5] EU:Rx-only[6] PharmacokineticdataProteinbinding<20%MetabolismLimited(<10%)Eliminationhalf-life24hoursExcretionKidney(81–92%)Identifiers IUPACname 7,8,9,10-Tetrahydro-6,10-methano-6H-pyrazino[2,3-h][3]benzazepine CASNumber249296-44-4 Y375815-87-5PubChemCID5310966IUPHAR/BPS5459DrugBankDB01273 YChemSpider4470510 YUNIIW6HS99O8ZOKEGGD08669 NChEBICHEBI:84500 NChEMBLChEMBL1076903 YCompToxDashboard(EPA)DTXSID70891447ChemicalandphysicaldataFormulaC13H13N3Molarmass211.268 g·mol−13Dmodel(JSmol)Interactiveimage SMILES n1c2cc3c(cc2ncc1)[C@@H]4CNC[C@H]3C4 InChI InChI=1S/C13H13N3/c1-2-16-13-5-11-9-3-8(6-14-7-9)10(11)4-12(13)15-1/h1-2,4-5,8-9,14H,3,6-7H2/t8-,9+ YKey:JQSHBVHOMNKWFT-DTORHVGOSA-N Y  NY (whatisthis?)  (verify) Varenicline(tradenameChantixandChampix)isamedicationusedforsmokingcessation.[4][6]Vareniclineisalsousedforthetreatmentofdryeyedisease.[5][7] Themostcommonside-effectsincludenausea(feelingsick),insomnia(difficultysleeping),abnormaldreams,headacheandnasopharyngitis(inflammationofthenoseandthroat).[6] Itisahigh-affinitypartialagonistfortheα4β2nicotinicacetylcholinereceptorsubtype(nACh)thatleadstothereleaseoftheneurotransmitterdopamineinthenucleusaccumbensrewardcenterofthebrainwhenactivated,andtherefore,hasthecapacitytoreducethefeelingsofcravingandwithdrawalcausedbysmokingcessation.[8]Inthisrespectitissimilartocytisineanddifferentfromthenicotinicantagonistbupropionandnicotinereplacementtherapies(NRTs)likenicotinepatchesandnicotinegum.Itisestimatedthatvareniclinesuccessfullyhelpsoneofeveryelevenpeoplewhosmokeremainabstinentfromtobaccoatsixmonths.[9]ItisontheWorldHealthOrganization'sListofEssentialMedicines.[10][11]Itisavailableasagenericmedication.[12] Contents 1Medicaluses 2Sideeffects 2.1Depressionandsuicide 2.2Cardiovasculardisease 3Mechanismofaction 4Pharmacokinetics 5History 6References 7Externallinks Medicaluses[edit] Vareniclineisusedtohelppeoplestopsmokingtobacco(smokingcessation).Ameta-analysisfoundthatlessthan20%ofpeopletreatedwithvareniclineremainabstinentfromsmokingatoneyear.[13]Ina2009meta-analysisvareniclinewasfoundtobemoreeffectivethanbupropion(oddsratio1.40)andnicotinereplacementtherapies(NRT)(oddsratio1.56).[14] A2013Cochraneoverviewandnetworkmeta-analysisconcludedthatvareniclineisthemosteffectivemedicationfortobaccocessationandthatsmokerswerenearlythreetimesmorelikelytoquittobaccousewhileonvareniclinethanwithplacebotreatment.VareniclinewasmoreefficaciousthanbupropionorNRTandaseffectiveascombinationNRTfortobaccosmokingcessation.[15][16] Vareniclinehasnotbeentestedinthoseunder18yearsoldorpregnantwomenandthereforeisnotrecommendedforusebythesegroups.[17]VareniclineisconsideredaclassCpregnancydrug,asanimalstudieshaveshownnoincreasedriskofcongenitalanomalies;however,nodatafromhumanstudiesisavailable.[18]Anobservationalstudyiscurrentlybeingconductedassessingformalformationsrelatedtovareniclineexposure,buthasnoresultsyet.[19]Analternatedrugispreferredforsmokingcessationduringbreastfeedingduetolackofinformationandbasedontheanimalstudiesonnicotine.[20] Sideeffects[edit] Mildnauseaisthemostcommonsideeffectandisseeninapproximately30%ofpeopletakingvareniclinethoughthisrarely(<3%)resultsindiscontinuationofthemedication.[16]Otherlesscommonsideeffectsincludeheadache,difficultysleeping,andvividdreams.Raresideeffectsreportedbypeopletakingvareniclinecomparedtoplaceboincludechangeintaste,vomiting,abdominalpain,flatulence,andconstipation.Ithasbeenestimatedthatforeveryfivesubjectstakingvareniclineatmaintenancedoses,therewillbeaneventofnausea,andforevery24of35treatedsubjects,therewillbeaneventofconstipationandflatulence,respectively.Gastrointestinalside-effectsleadtodiscontinuationofthedrugin2%to8%ofpeopleusingvarenicline.[21][22]Incidenceofnauseaisdose-dependent:incidenceofnauseawashigherinpeopletakingalargerdose(30%)versusplacebo(10%)ascomparedtopeopletakingasmallerdose(16%)versusplacebo(11%).[4] Depressionandsuicide[edit] In2007,theUSFDAhadannouncedithadreceivedpost-marketingreportsofthoughtsofsuicideandoccasionalsuicidalbehavior,erraticbehavior,anddrowsinessamongpeopleusingvareniclineforsmokingcessation.In2009,theUSFDArequiredvareniclinetocarryaboxedwarningthatthedrugshouldbestoppedifanyofthesesymptomsareexperienced.[23] A2014systematicreviewdidnotfindevidenceofanincreasedsuiciderisk.[24]Otheranalyseshavereachedthesameconclusionandfoundnoincreasedriskofneuropsychiatricsideeffectswithvarenicline.[15][16]Noevidenceforincreasedrisksofcardiovascularevents,depression,orself-harmwithvareniclineversusnicotinereplacementtherapywasfoundinonepost-marketingsurveillancestudy.[25] In2016theFDAremovedtheblackboxwarning.[26]Peoplearestilladvisedtostopthemedicationifthey"noticeanysideeffectsonmood,behavior,orthinking."[26][27][28] Cardiovasculardisease[edit] InJune2011,theUSFDAissuedasafetyannouncementthatvareniclinemaybeassociatedwith"asmall,increasedriskofcertaincardiovascularadverseeventsinpeoplewhohavecardiovasculardisease."[29] Aprior2011reviewhadfoundincreasedriskofcardiovasculareventscomparedwithplacebo.[30]Expertcommentaryinthesamejournalraiseddoubtsaboutthemethodologyofthereview,[31][32]concernswhichwereechoedbytheEuropeanMedicinesAgencyandsubsequentreviews.[33][34]Ofspecificconcernwere"thelownumberofeventsseen,thetypesofeventscounted,thehigherdrop-outrateinpeoplereceivingplacebo,thelackofinformationonthetimingofevents,andtheexclusionofstudiesinwhichno-onehadanevent." Incontrast,multiplerecentsystematicreviewsandmeta-analyseshavefoundnoincreaseinoverallorseriousadversecardiovascularevents(includingforindividualsatriskofdevelopingcardiovasculardisease)associatedwithvareniclineuse.[34][35][36][37] Mechanismofaction[edit] Vareniclinedisplaysfullagonismonα7nicotinicacetylcholinereceptorsandisapartialagonistontheα4β2,α3β4,andα6β2subtypes.[38][39][40]Inaddition,itisaweakagonistontheα3β2containingreceptors. Varenicline'spartialagonismontheα4β2receptorsratherthannicotine'sfullagonismproduceslesseffectofdopaminereleasethannicotine's.Thisα4β2competitivebindingreducestheabilityofnicotinetobindandstimulatethemesolimbicdopaminesystem—similartothemethodofactionofbuprenorphineinthetreatmentofopioidaddiction.[16] Pharmacokinetics[edit] Mostoftheactivecompoundisexcretedbythekidneys(92–93%).Asmallproportionisglucuronidated,oxidised,N-formylatedorconjugatedtoahexose.[41]Theeliminationhalf-lifeisabout24hours. History[edit] UseofCytisusplantsasasmokingsubstitutesduringWorldWarII[42]ledtouseasacessationaidineasternEuropeandextractionofcytisine.[43]CytisineanalogsledtovareniclineatPfizer.[44][45][46] Vareniclinereceiveda"priorityreview"bytheUSFDAinFebruary2006,shorteningtheusualten-monthreviewperiodtosixmonthsbecauseofitsdemonstratedeffectivenessinclinicaltrialsandperceivedlackofsafetyissues.[47]Theagency'sapprovalofthedrugcameonMay11,2006.[48][49]OnSeptember29,2006,itwasapprovedforsaleintheEuropeanUnion.[6] OnSeptember16,2021,Pfizerannouncedarecallof"alllotsofitsanti-smokingtreatment,Chantix[Varenicline],duetohighlevelsofcancer-causingagentscallednitrosaminesinthepills".[50]ThisfollowedaJuly2,2021announcementbytheFDAthatitwas"alertingpatientsandhealthcareprofessionalstoPfizer’svoluntaryrecallofninelotsofthesmokingcessationdrug"andfurtherrecallsbyPfizeronJuly19andAug.8.[51]OnJune24,PfizerhadpauseddistributionofChantixworldwide;[52]"[t]hedistributionhalt[wa]soutofanabundanceofcaution,pendingfurthertesting,thecompanysaidinanemail.[53]AccordingtothePfizerInc.2020Form10-KAnnualReport,high-revenueproductsbythecompanyinclude[d]Chantix/Champix(varenicline)totreatnicotineaddiction,[which]had$919millionin2020revenues.[54] InOctober2021,USFDAapprovedOysterPointPharmatomarketTyrvayaasanewrouteofvareniclineadministrationthroughnasalsprayforthetreatmentofdryeyedisease.[55] References[edit] ^"ChampixProductInformation".TherapeuticGoodsAdministration(TGA).26September2021.Retrieved26September2021. 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^Crawford,P;Cieslak,D(September2017)."VareniclineforSmokingCessation".AmericanFamilyPhysician.96(5):Online.PMID 28925657. ^WorldHealthOrganization(2019).WorldHealthOrganizationmodellistofessentialmedicines:21stlist2019.Geneva:WorldHealthOrganization.hdl:10665/325771.WHO/MVP/EMP/IAU/2019.06.License:CCBY-NC-SA3.0IGO. ^WorldHealthOrganization(2021).WorldHealthOrganizationmodellistofessentialmedicines:22ndlist(2021).Geneva:WorldHealthOrganization.hdl:10665/345533.WHO/MHP/HPS/EML/2021.02. ^"Varenicline:FDA-ApprovedDrugs".U.S.FoodandDrugAdministration(FDA).Retrieved24September2021. ^RosenLJ,GaliliT,KottJ,GoodmanM,FreedmanLS(May2018)."Diminishingbenefitofsmokingcessationmedicationsduringthefirstyear:ameta-analysisofrandomizedcontrolledtrials".Addiction.113(5):805–816.doi:10.1111/add.14134.PMC 5947828.PMID 29377409. 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^PalmerG,MasseyV(May1969)."Electronparamagneticresonanceandcirculardichroismstudiesonmilkxanthineoxidase".TheJournalofBiologicalChemistry.244(10):2614–20.doi:10.1186/1753-6561-9-S1-A31.PMC 4306032.PMID 4306032. ^YeungE,BachiB,LongB,LeeJ,ChaoY(2015)."VareniclineandDepression:aLiteratureReview"(PDF).WorldJournalofMedicalEducationandResearch.9(1):24–29. ^"FDADrugSafetyCommunication:Chantix(varenicline)mayincreasetheriskofcertaincardiovascularadverseeventsinpatientswithcardiovasculardisease".2011-06-16. ^SinghS,LokeYK,SpanglerJG,FurbergCD(September2011)."Riskofseriousadversecardiovasculareventsassociatedwithvarenicline:asystematicreviewandmeta-analysis".CMAJ.183(12):1359–66.doi:10.1503/cmaj.110218.PMC 3168618.PMID 21727225. ^TakagiH,UmemotoT(September2011)."Varenicline:quantifyingtherisk".CMAJ.183(12):1404,authorreply1405,1407.doi:10.1503/cmaj.111-2063.PMC 3168634.PMID 21896705. 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^PipeAL(October2014)."Networkmeta-analysisdemonstratesthesafetyofpharmacotherapyforsmokingcessationincardiovascularpatients".Evidence-BasedMedicine(Review&Commentary).19(5):193.doi:10.1136/eb-2014-110030.PMID 24917603.S2CID 40856313. ^RowlandK(April2014)."ACPJournalClub.Review:NicotinereplacementtherapyincreasesCVDevents;bupropionandvareniclinedonot".AnnalsofInternalMedicine(Review&Commentary).160(8):JC2.doi:10.7326/0003-4819-160-8-201404150-02002.PMID 24733219.S2CID 37165486. ^MihalakKB,CarrollFI,LuetjeCW(September2006)."Vareniclineisapartialagonistatalpha4beta2andafullagonistatalpha7neuronalnicotinicreceptors".MolecularPharmacology.70(3):801–5.doi:10.1124/mol.106.025130.PMID 16766716.S2CID 14562170. ^MineurYS,PicciottoMR(December2010)."Nicotinereceptorsanddepression:revisitingandrevisingthecholinergichypothesis".TrendsinPharmacologicalSciences.31(12):580–6.doi:10.1016/j.tips.2010.09.004.PMC 2991594.PMID 20965579. ^BordiaT,HrachovaM,ChinM,McIntoshJM,QuikM(August2012)."Vareniclineisapotentpartialagonistatα6β2*nicotinicacetylcholinereceptorsinratandmonkeystriatum".TheJournalofPharmacologyandExperimentalTherapeutics.342(2):327–34.doi:10.1124/jpet.112.194852.PMC 3400806.PMID 22550286. ^ObachRS,Reed-HagenAE,KruegerSS,ObachBJ,O'ConnellTN,ZandiKS,MillerS,CoeJW(January2006)."Metabolismanddispositionofvarenicline,aselectivealpha4beta2acetylcholinereceptorpartialagonist,invivoandinvitro".DrugMetabolismandDisposition.34(1):121–30.doi:10.1124/dmd.105.006767.PMID 16221753.S2CID 18746784. ^SeegerR(January1992)."[Cytisineasanaidforsmokingcessation]".MedizinischeMonatsschriftfürPharmazeuten.15(1):20–1.PMID 1542278. ^ProchaskaJJ,DasS,BenowitzNL(August2013)."Cytisine,theworld'soldestsmokingcessationaid".BMJ.347:f5198.doi:10.1136/bmj.f5198.PMID 23974638.S2CID 31845933. ^CoeJW,BrooksPR,VetelinoMG,WirtzMC,ArnoldEP,HuangJ,SandsSB,DavisTI,LebelLA,FoxCB,ShrikhandeA,HeymJH,SchaefferE,RollemaH,LuY,MansbachRS,ChambersLK,RovettiCC,SchulzDW,TingleyFD,O'NeillBT(May2005)."Varenicline:analpha4beta2nicotinicreceptorpartialagonistforsmokingcessation".JournalofMedicinalChemistry.48(10):3474–7.doi:10.1021/jm050069n.PMID 15887955. ^SchwartzJL(1979)."Reviewandevaluationofmethodsofsmokingcessation,1969-77.Summaryofamonograph".PublicHealthReports.94(6):558–63.PMC 1431736.PMID 515342. ^EtterJF(2006)."Cytisineforsmokingcessation:aliteraturereviewandameta-analysis".ArchivesofInternalMedicine.166(15):1553–9.doi:10.1001/archinte.166.15.1553.PMID 16908787. ^KuehnBM(February2006)."FDAspeedssmokingcessationdrugreview".JAMA.295(6):614.doi:10.1001/jama.295.6.614.PMID 16467225. ^"FDAApprovesNovelMedicationforSmokingCessation".U.S.FoodandDrugAdministration(FDA)(Pressrelease).11May2006.Archivedfromtheoriginalon10July2009.Retrieved26September2021. 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Externallinks[edit] "Varenicline".DrugInformationPortal.U.S.NationalLibraryofMedicine. ClinicaltrialnumberNCT03636061for"ClinicalTrialtoEvaluatetheEfficacyofOC-01NasalSprayonSignsandSymptomsofDryEyeDisease(TheONSET-1Study)"atClinicalTrials.gov ClinicaltrialnumberNCT04036292for"EvaluatingtheEfficacyandSafetyofOC-01(Varenicline)NasalSprayonDryEyeDisease"atClinicalTrials.gov vteStimulantsAdamantanes Adapromine Amantadine Bromantane Memantine Rimantadine Adenosineantagonists 8-Chlorotheophylline 8-Cyclopentyltheophylline 8-Phenyltheophylline Aminophylline Caffeine CGS-15943 Dimethazan Istradefylline Paraxanthine SCH-58261 Theobromine Theophylline Alkylamines Cyclopentamine Cypenamine Cyprodenate Heptaminol Isometheptene Levopropylhexedrine Methylhexaneamine Octodrine Propylhexedrine Tuaminoheptane Ampakines CX-516 CX-546 CX-614 CX-691 CX-717 IDRA-21 LY-404,187 LY-503,430 Nooglutyl Org26576 PEPA S-18986 Sunifiram Unifiram Arylcyclohexylamines Benocyclidine Dieticyclidine Esketamine Eticyclidine Gacyclidine Ketamine Phencyclamine Phencyclidine Rolicyclidine Tenocyclidine Tiletamine Benzazepines 6-Br-APB SKF-77434 SKF-81297 SKF-82958 Cathinones 3-Fluoromethcathinone 3,4-DMMC 4-BMC 4-CMC 4-Methylbuphedrone 4-Methylcathinone 4-MEAP 4-Methylpentedrone Amfepramone Benzedrone Buphedrone Bupropion Butylone Cathinone Dimethylcathinone Ethcathinone Ethylone Flephedrone Hexedrone Isoethcathinone Mephedrone Methcathinone Methedrone Methylenedioxycathinone Methylone Mexedrone N-Ethylbuphedrone N-Ethylhexedrone Pentedrone Pentylone Phthalimidopropiophenone Cholinergics A-84,543 A-366,833 ABT-202 ABT-418 AR-R17779 Altinicline Anabasine Arecoline Bradanicline Cotinine Cytisine Dianicline Epibatidine Epiboxidine GTS-21 Ispronicline Nicotine PHA-543,613 PNU-120,596 PNU-282,987 Pozanicline Rivanicline SazetidineA SIB-1553A SSR-180,711 TC-1698 TC-1827 TC-2216 Tebanicline UB-165 Varenicline WAY-317,538 Convulsants Anatoxin-a Bicuculline DMCM Flurothyl Gabazine Pentetrazol Picrotoxin Strychnine Thujone Eugeroics Adrafinil Armodafinil CRL-40,940 CRL-40,941 Fluorenol Modafinil Oxazolines 4-Methylaminorex Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone Phenethylamines 1-(4-Methylphenyl)-2-aminobutane 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane 2-Fluoroamphetamine 2-Fluoromethamphetamine 2-OH-PEA 2-Phenyl-3-aminobutane 2,3-MDA 3-Fluoroamphetamine 3-Fluoroethamphetamine 3-Methoxyamphetamine 3-Methylamphetamine 4-Fluoroamphetamine 4-Fluoromethamphetamine 4-MA 4-MMA 4-MTA 6-FNE AL-1095 Alfetamine a-Ethylphenethylamine Amfecloral Amfepentorex Amidephrine 2-Amino-1,2-dihydronaphthalene 2-Aminoindane 5-(2-Aminopropyl)indole 2-Aminotetralin Acridorex Amphetamine(Dextroamphetamine,Levoamphetamine) Amphetaminil Arbutamine β-Methylphenethylamine β-Phenylmethamphetamine Benfluorex Benzphetamine BDB BOH 3-Benzhydrylmorpholine BPAP Camfetamine Cathine Chlorphentermine Cilobamine Cinnamedrine Clenbuterol Clobenzorex Cloforex Clortermine Cypenamine D-Deprenyl Denopamine Dimethoxyamphetamine Dimethylamphetamine Dobutamine DOPA(Dextrodopa,Levodopa) Dopamine Dopexamine Droxidopa EBDB Ephedrine Epinephrine Epinine Etafedrine Ethylnorepinephrine Etilamfetamine Etilefrine Famprofazone Fencamfamin Fencamine Fenethylline Fenfluramine(Dexfenfluramine,Levofenfluramine) Fenproporex Feprosidnine Fludorex Formetorex Furfenorex Gepefrine Hexapradol HMMA Hordenine 4-Hydroxyamphetamine 5-Iodo-2-aminoindane Ibopamine Indanylamphetamine Iofetamine Isoetarine Isoprenaline L-Deprenyl(Selegiline) Lefetamine Lisdexamfetamine Lophophine MBDB MDA(tenamfetamine) MDBU MDEA MDMA(midomafetamine) MDMPEA MDOH MDPR MDPEA Mefenorex Mephentermine Metanephrine Metaraminol Mesocarb Methamphetamine(Dextromethamphetamine,Levomethamphetamine) Methoxamine Methoxyphenamine MMA Methoxyphenamine MMDA MMDMA MMMA Morforex N,alpha-Diethylphenylethylamine N,N-Dimethylphenethylamine Naphthylamphetamine Nisoxetine Norepinephrine Norfenefrine Norfenfluramine Normetanephrine L-Norpseudoephedrine Octopamine Orciprenaline Ortetamine Oxifentorex Oxilofrine PBA PCA PCMA PHA Pentorex Phenatine Phenpromethamine Phentermine Phenylalanine Phenylephrine Phenylpropanolamine Pholedrine PIA PMA PMEA PMMA PPAP Prenylamine Propylamphetamine Pseudoephedrine Ropinirole Salbutamol(Levosalbutamol) Sibutramine Solriamfetol Synephrine Theodrenaline Tiflorex Tranylcypromine Tyramine Tyrosine Xylopropamine Zylofuramine Phenylmorpholines 3-Fluorophenmetrazine Fenbutrazate Fenmetramide G-130 Manifaxine Morazone Morforex Oxaflozane PD-128,907 Phendimetrazine Phenmetrazine 2-Phenyl-3,6-dimethylmorpholine Pseudophenmetrazine Radafaxine Piperazines 2C-B-BZP 3C-PEP BZP CM156 DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 GBR-13119 MeOPP MBZP oMPP Vanoxerine Piperidines 1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine 2-Benzylpiperidine 2-Methyl-3-phenylpiperidine 3,4-Dichloromethylphenidate 4-Benzylpiperidine 4-Fluoromethylphenidate 4-Methylmethylphenidate Desoxypipradrol Difemetorex Diphenylpyraline Ethylnaphthidate Ethylphenidate Methylnaphthidate Isopropylphenidate JZ-IV-10 Methylphenidate(Dexmethylphenidate) Nocaine Phacetoperane Pipradrol Propylphenidate SCH-5472 Pyrrolidines 2-Diphenylmethylpyrrolidine 4-Cl-PVP 5-DBFPV α-PPP α-PBP α-PCYP α-PHiP α-PHP α-PHPP α-PVP α-PVT Diphenylprolinol DMPVP FPOP FPVP MDPPP MDPBP MPBP MPHP MPPP MOPVP MOPPP Indapyrophenidone MDPV Naphyrone PEP Picilorex Prolintane Pyrovalerone Racetams Oxiracetam Phenylpiracetam Phenylpiracetamhydrazide Tropanes 4-fluorotropacocaine 4'-Fluorococaine Altropane(IACFT) Brasofensine CFT(WIN35,428) β-CIT(RTI-55) Cocaethylene Cocaine Dichloropane(RTI-111) Difluoropine FE-β-CPPIT FP-β-CPPIT Ioflupane(123I) Norcocaine PIT PTT RTI-31 RTI-32 RTI-51 RTI-112 RTI-113 RTI-120 RTI-121(IPCIT) RTI-126 RTI-150 RTI-177 RTI-229 RTI-336 RTI-354 RTI-371 RTI-386 Salicylmethylecgonine Tesofensine Troparil(β-CPT,WIN35,065-2) Tropoxane WF-23 WF-33 Tryptamines 4-HO-αMT 4-Methyl-αET 4-Methyl-αMT 5-Chloro-αMT 5-Fluoro-αMT 5-MeO-αET 5-MeO-αMT 5-MeO-DIPT 6-Fluoro-αMT 7-Methyl-αET αET αMT Others 2-MDP 3,3-Diphenylcyclobutanamine Amfonelicacid Amineptine Amiphenazole Atipamezole Atomoxetine Bemegride Benzydamine BTQ BTS74,398 Centanafadine Ciclazindol Clofenciclan Cropropamide Crotetamide D-161 Desipramine Diclofensine Dimethocaine Efaroxan Etamivan Fenisorex Fenpentadiol Gamfexine Gilutensin GSK1360707F GYKI-52895 Hexacyclonate Idazoxan Indanorex Indatraline JNJ-7925476 Lazabemide Leptacline Lomevactone LR-5182 Mazindol Meclofenoxate Medifoxamine Mefexamide Methamnetamine Methastyridone Methiopropamine Naphthylaminopropane Nefopam Nikethamide Nomifensine O-2172 Oxaprotiline PNU-99,194 PRC200-SS Rasagiline Rauwolscine Rubidiumchloride Setazindol Tametraline Tandamine Thiopropamine Thiothinone Trazium UH-232 Yohimbine ATCcode:N06B vteTreatmentofdrugdependence(N07B)Nicotinedependence Bupropion# Cytisine Lobeline Mecamylamine Varenicline AA(Clonidine) Alcoholdependence ADinhibitor(Disulfiram Calciumcarbimide Hydrogencyanamide) Acamprosate Opioidantagonists Naltrexone Nalmefene Topiramate AA(Clonidine) Baclofen Phenibut Opioiddependence AA(Clonidine Lofexidine) Ibogaine Opioids Buprenorphine(+naloxone) Levacetylmethadol Methadone Dihydrocodeine Dihydroetorphine Hydromorphone(extended-release) Morphine(extended-release) Opioidantagonists(Naltrexone Nalmefene) Benzodiazepinedependence AA(Clonidine) Benzodiazepines(Diazepam Lorazepam Chlordiazepoxide Oxazepam) Barbiturates(Phenobarbital) vteNicotinicacetylcholinereceptormodulatorsnAChRsAgonists(andPAMs) 5-HIAA 6-Chloronicotine A-84,543 A-366,833 A-582,941 A-867,744 ABT-202 ABT-418 ABT-560 ABT-894 Acetylcholine Altinicline Anabasine Anatabine Anatoxin-a AR-R17779 Bepheniumhydroxynaphthoate Butinoline Butyrylcholine Carbachol Choline Cotinine Cytisine Decamethonium Desformylflustrabromine Dianicline Dimethylphenylpiperazinium Epibatidine Epiboxidine Ethanol(alcohol) Ethoxysebacylcholine EVP-4473 EVP-6124 Galantamine GTS-21 Ispronicline Ivermectin JNJ-39393406 Levamisole Lobeline MEM-63,908(RG-3487) Morantel Nicotine(tobacco) NS-1738 PHA-543,613 PHA-709,829 PNU-120,596 PNU-282,987 Pozanicline Pyrantel Rivanicline RJR-2429 SazetidineA SB-206553 Sebacylcholine SIB-1508Y SIB-1553A SSR-180,711 Suberyldicholine Suxamethonium(succinylcholine) Suxethonium(succinyldicholine) TC-1698 TC-1734 TC-1827 TC-2216 TC-5214 TC-5619 TC-6683 Tebanicline Tribendimidine Tropisetron UB-165 Varenicline WAY-317,538 XY-4083 Antagonists(andNAMs) 18-MAC 18-MC α-Neurotoxins(e.g.,α-bungarotoxin,α-cobratoxin,α-conotoxin,manyothers) ABT-126 Alcuronium Allopregnanolone Amantadine Anatruxonium AQW051 Atracurium Barbiturates(e.g.,pentobarbital,sodiumthiopental) BNC-210 Bungarotoxins(e.g.,α-bungarotoxin,κ-bungarotoxin) Bupropion BW284C51 BW-A444 Candocuroniumiodide(chandoniumiodide) Chlorisondamine Cisatracurium Coclaurine Coronaridine Curare Cyclopropane Dacuroniumbromide Decamethonium Dehydronorketamine Desflurane Dextromethorphan Dextropropoxyphene Dextrorphan Diadonium DHβE Dihydrochandonium Dimethyltubocurarine(metocurine) Dioscorine Dipyrandium Dizocilpine(MK-801) Doxacurium Encenicline Enflurane Erythravine Esketamine Fazadinium Gallamine Gantacuriumchloride Halothane Hexafluronium Hexamethonium(benzohexonium) Hydroxybupropion Hydroxynorketamine Ibogaine Isoflurane Ketamine Kynurenicacid Laudanosine Laudexium(laudolissin) Levacetylmethadol Levomethadone Malouetine ME-18-MC Mecamylamine Memantine Methadone Methorphan(racemethorphan) Methyllycaconitine Metocurine Mivacurium Morphanol(racemorphan) Neramexane Nitrousoxide Norketamine Pancuroniumbromide Pempidine Pentamine Pentolinium Phencyclidine Pipecuroniumbromide Progesterone Promegestone Radafaxine Rapacuroniumbromide Reboxetine Rocuroniumbromide Sevoflurane Stercuroniumiodide Surugatoxin Thiocolchicoside Toxiferine Tramadol Trimetaphancamsilate(trimethaphancamsylate) Tropeinium Tubocurarine Vanoxerine Vecuroniumbromide Xenon Precursors(andprodrugs) Acetyl-coA Adafenoxate Choline(lecithin) Citicoline Cyprodenate Dimethylethanolamine Glycerophosphocholine Meclofenoxate(centrophenoxine) Phosphatidylcholine Phosphatidylethanolamine Phosphorylcholine Pirisudanol Seealso:Receptor/signalingmodulators•Muscarinicacetylcholinereceptormodulators•Acetylcholinemetabolism/transportmodulators Portal:Medicine Retrievedfrom"https://en.wikipedia.org/w/index.php?title=Varenicline&oldid=1084998598" Categories:5-HT3agonistsBenzazepinesBridgedheterocycliccompoundsNicotinicagonistsNitrogenheterocyclesPfizerbrandsSmokingcessationWorldHealthOrganizationessentialmedicinesHiddencategories:AllarticleswithdeadexternallinksArticleswithdeadexternallinksfromJanuary2022ArticleswithshortdescriptionShortdescriptionisdifferentfromWikidataDrugswithnon-standardlegalstatusArticleswithchangedKEGGidentifierArticleswithchangedEBIidentifierDrughasEMAlinkDrugboxeswhichcontainchangestoverifiedfieldsDrugboxeswhichcontainchangestowatchedfields Navigationmenu Personaltools NotloggedinTalkContributionsCreateaccountLogin Namespaces 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