Pilocarpine - Wikipedia

Pilocarpine is a medication used to reduce pressure inside the eye and treat dry mouth. ... As eye drops it is used to manage angle closure glaucoma until surgery ... Pilocarpine FromWikipedia,thefreeencyclopedia Jumptonavigation Jumptosearch Medicationusedtotreatglaucomaanddrymouth PilocarpineClinicaldataTradenamesIsoptoCarpine,Salagen,Vuity,othersAHFS/Drugs.comMonographMedlinePlusa608039Licensedata US DailyMed: Pilocarpine Pregnancycategory AU:B3 RoutesofadministrationTopicaleyedrops,bymouthDrugclassMiotic(cholinergic)[1]ATCcodeN07AX01(WHO)S01EB01(WHO)LegalstatusLegalstatus AU:S4(Prescriptiononly) UK:POM(Prescriptiononly) US:℞-only[2] PharmacokineticdataEliminationhalf-life0.76hours(5mg),1.35hours(10mg)[3]ExcretionurineIdentifiers IUPACname (3S,4R)-3-Ethyl-4-((1-methyl-1H-imidazol-5-yl)methyl)dihydrofuran-2(3H)-one CASNumber92-13-7 Y54-71-7(hydrochloride)PubChemCID5910IUPHAR/BPS305DrugBankDB01085 YChemSpider5699 YUNII01MI4Q9DI3KEGGD00525 YChEBICHEBI:8207 YChEMBLChEMBL550 YCompToxDashboard(EPA)DTXSID1021162ECHAInfoCard100.001.936ChemicalandphysicaldataFormulaC11H16N2O2Molarmass208.261 g·mol−13Dmodel(JSmol)Interactiveimage SMILES O=C2OC[C@H](Cc1n(cnc1)C)[C@@H]2CC InChI InChI=1S/C11H16N2O2/c1-3-10-8(6-15-11(10)14)4-9-5-12-7-13(9)2/h5,7-8,10H,3-4,6H2,1-2H3/t8-,10-/m0/s1 YKey:QCHFTSOMWOSFHM-WPRPVWTQSA-N Y   (verify) Pilocarpineisamedicationusedtoreducepressureinsidetheeyeandtreatdrymouth.[1][4]Aseyedropsitisusedtomanageangleclosureglaucomauntilsurgerycanbeperformed,ocularhypertension,primaryopenangleglaucoma,andtobringaboutconstrictionofthepupilfollowingitsdilation.[1][5][6]However,duetoitssideeffectsitisnolongertypicallyusedinthelongtermmanagement.[7]Onsetofeffectswiththedropsistypicallywithinanhourandlastsforuptoaday.[1]BymouthitisusedfordrymouthasaresultofSjögrensyndromeorradiationtherapy.[8] Commonsideeffectsoftheeyedropsincludeirritationoftheeye,increasedtearing,headache,andblurryvision.[1]Othersideeffectsincludeallergicreactionsandretinaldetachment.[1]Useisgenerallynotrecommendedduringpregnancy.[9]Pilocarpineisinthemioticsfamilyofmedication.[10]Itworksbyactivatingcholinergicreceptorsofthemuscarinictypewhichcausethetrabecularmeshworktoopenandtheaqueoushumortodrainfromtheeye.[1] Pilocarpinewasisolatedin1874byHardyandGerrardandhasbeenusedtotreatglaucomaformorethan100years.[11][12][13]ItisontheWorldHealthOrganization'sListofEssentialMedicines.[14]ItwasoriginallymadefromtheSouthAmericanplantPilocarpus.[11] Contents 1Medicaluses 1.1Surgery 1.2Presbyopia 1.3Other 2Adverseeffects 3Pharmacology 4Societyandculture 4.1Preparation 4.2Tradenames 5Research 6Veterinary 7References 8Externallinks Medicaluses[edit] Pilocarpinestimulatesthesecretionoflargeamountsofsalivaandsweat.[15]Itisusedtopreventortreatdrymouth,particularlyinSjögrensyndrome,butalsoasasideeffectofradiationtherapyforheadandneckcancer.[16] ItmaybeusedtohelpdifferentiateAdiesyndromefromothercausesofunequalpupilsize.[17][18][clarificationneeded] Itmaybeusedtotreataformofdryeyecalledaqueousdeficientdryeye(ADDE)[19] Surgery[edit] Pilocarpineissometimesusedimmediatelybeforecertaintypesofcornealgraftsandcataractsurgery.[20][21]ItisalsousedpriortoYAGlaseriridotomy.Inophthalmology,pilocarpineisalsousedtoreducesymptomaticglareatnightfromlightswhenthepatienthasundergoneimplantationofphakicintraocularlenses;theuseofpilocarpinewouldreducethesizeofthepupils,partiallyrelievingthesesymptoms.[dubious–discuss]Themostcommonconcentrationforthisuseispilocarpine1%.[citationneeded]Pilocarpineisshowntobejustaseffectiveasapraclonidineinpreventingintraocularpressurespikesafterlasertrabeculoplasty.[22] Presbyopia[edit] In2021,theUSFoodandDrugAdministrationapprovedpilocarpinehydrochlorideasaneyedroptreatmentforpresbyopia,age-relateddifficultywithnear-invision.Itworksbycausingthepupilstoconstrict,increasingdepthoffield,similartotheeffectofpinholeglasses.MarketedasVuity,theeffectlastsformorethan6hours.[23][24] Other[edit] Pilocarpineisusedtostimulatesweatglandsinasweattesttomeasuretheconcentrationofchlorideandsodiumthatisexcretedinsweat.Itisusedtodiagnosecysticfibrosis.[25] Adverseeffects[edit] Useofpilocarpinemayresultinarangeofadverseeffects,mostofthemrelatedtoitsnon-selectiveactionasamuscarinicreceptoragonist.Pilocarpinehasbeenknowntocauseexcessivesalivation,sweating,bronchialmucussecretion,bronchospasm,bradycardia,vasodilation,anddiarrhea.Eyedropscanresultinbrowacheandchronicuseinmiosis.Itcanalsocausetemporaryblurredvisionordarknessofvision,temporaryshortsightedness,hyphemaandretinaldetachment. Pharmacology[edit] Pilocarpineisadrugthatactsasamuscarinicreceptoragonist.Itactsonasubtypeofmuscarinicreceptor(M3)foundontheirissphinctermuscle,causingthemuscletocontract-resultinginpupilconstriction(miosis).Pilocarpinealsoactsontheciliarymuscleandcausesittocontract.Whentheciliarymusclecontracts,itopensthetrabecularmeshworkthroughincreasedtensiononthescleralspur.Thisactionfacilitatestheratethataqueoushumorleavestheeyetodecreaseintraocularpressure.Paradoxically,whenpilocarpineinducesthisciliarymusclecontraction(knownasanaccommodativespasm)itcausestheeye'slenstothickenandmoveforwardwithintheeye.Thismovementcausestheiris(whichislocatedimmediatelyinfrontofthelens)toalsomoveforward,narrowingtheAnteriorchamberangle.Narrowingoftheanteriorchamberangleincreasestheriskofincreasedintraocularpressure.[26] Societyandculture[edit] Preparation[edit] PlantsinthegenusPilocarpusaretheonlyknownsourcesofpilocarpine,andcommercialproductionisderivedentirelyfromtheleavesofPilocarpusmicrophyllus(MaranhamJaborandi).ThisgenusgrowsonlyinSouthAmerica,andPilocarpusmicrophyllusisnativetoseveralstatesinnorthernBrazil.[27] Pilocarpineisextractedfromthepowderedleafmaterialinamulti-stepprocess.Firstthematerialistreatedwithethanolacidifiedwithhydrochloricacid,andthesolventsremovedunderreducedpressure.Theresultantaqueousresidueisneutralizedwithammoniaandputasideuntiltheresinhascompletelysettled.Itisthenfilteredandconcentratedbysugarsolutiontoasmallvolume,madealkalinewithammonia,andfinallyextractedwithchloroform.Thesolventisremovedunderreducedpressure.[verificationneeded] Thissectionneedstobeupdated.Pleasehelpupdatethisarticletoreflectrecenteventsornewlyavailableinformation.(September2020) [28] Tradenames[edit] Pilocarpineisavailableunderseveraltradenamessuchas:Diocarpine(Dioptic),IsoptoCarpine(Alcon),Miocarpine(CIBAVision),OcusertPilo-20and-40(Alza),PilopineHS(Alcon),Salagen(MGIPharma),ScheinpharmPilocarpine(ScheinPharmaceutical),Timpilo(MerckFrosst),andVuity(AbbVie). Research[edit] Pilocarpineisusedtoinducechronicepilepsyinrodents,commonlyrats,asameanstostudythedisorder'sphysiologyandtoexaminedifferenttreatments.[29][30]Smallerdosesmaybeusedtoinducesalivationinordertocollectsamplesofsaliva,forinstance,toobtaininformationaboutIgAantibodies. Veterinary[edit] Pilocarpineisgiveninmoderatedoses(about2 mg)toinduceemesisincatsthathaveingestedforeignplants,foods,ordrugs.Onefelinetrialdetermineditwaseffective,eventhoughtheusualchoiceofemeticisxylazine.[citationneeded] References[edit] ^abcdefg"Pilocarpine".TheAmericanSocietyofHealth-SystemPharmacists.Archivedfromtheoriginalon28December2016.Retrieved8December2016. ^"Vuity-pilocarpinehydrochloridesolution/drops".DailyMed.Retrieved19December2021. ^GornitskyM,ShenoudaG,SultanemK,KatzH,HierM,BlackM,VellyAM(July2004)."Double-blindrandomized,placebo-controlledstudyofpilocarpinetosalvagesalivaryglandfunctionduringradiotherapyofpatientswithheadandneckcancer".OralSurgery,OralMedicine,OralPathology,OralRadiology,andEndodontics.98(1):45–52.doi:10.1016/j.tripleo.2004.04.009.PMID 15243470. ^TarasconPocketPharmacopoeia2019DeluxeLab-CoatEdition.Jones&BartlettLearning.2018.p. 224.ISBN 9781284167542. ^WorldHealthOrganization(2009).StuartMC,KouimtziM,HillSR(eds.).WHOModelFormulary2008.WorldHealthOrganization.p. 439.hdl:10665/44053.ISBN 9789241547659. ^"Glaucomaandocularhypertension.NICEguideline81".NationalInstituteforHealthandCareExcellence.November2017.Retrieved19September2019.Ocularhypertension...alternativeoptionsincludecarbonicanhydraseinhibitorssuchasbrinzolamideordorzolamide,atopicalsympathomimeticsuchasapraclonidineorbrimonidinetartrate,oratopicalmioticsuchaspilocarpine,giveneitherasmonotherapyorascombinationtherapy. ^LusthausJ,GoldbergI(March2019)."Currentmanagementofglaucoma"(PDF).TheMedicalJournalofAustralia.210(4):180–187.doi:10.5694/mja2.50020.PMID 30767238.S2CID 73438590.PilocarpineisnolongerroutinelyusedforlongtermIOPcontrolduetoapoorsideeffectprofile ^HamiltonR(2015).TarasconPocketPharmacopoeia2015DeluxeLab-CoatEdition.Jones&BartlettLearning.p. 415.ISBN 9781284057560. ^"PilocarpineophthalmicUseDuringPregnancy|Drugs.com".www.drugs.com.Archivedfromtheoriginalon28December2016.Retrieved28December2016. ^Britishnationalformulary :BNF69(69 ed.).BritishMedicalAssociation.2015.p. 769.ISBN 9780857111562. ^abSneaderW(2005).DrugDiscovery:AHistory.JohnWiley&Sons.p. 98.ISBN 978-0-471-89979-2.Archivedfromtheoriginalon2016-12-29. ^RosinA(1991)."[Pilocarpine.Amioticofchoiceinthetreatmentofglaucomahaspassed110yearsofuse]".Oftalmologia(inRomanian).35(1):53–5.PMID 1811739. ^Holmstedt,B;Wassén,SH;Schultes,RE(January1979)."Jaborandi:aninterdisciplinaryappraisal".JournalofEthnopharmacology.1(1):3–21.doi:10.1016/0378-8741(79)90014-x.PMID 397371. ^WorldHealthOrganization(2019).WorldHealthOrganizationmodellistofessentialmedicines:21stlist2019.Geneva:WorldHealthOrganization.hdl:10665/325771.WHO/MVP/EMP/IAU/2019.06.License:CCBY-NC-SA3.0IGO. ^"Pilocarpine".MedLinePlus.U.S.NationalLibraryofMedicine.Archivedfromtheoriginalon2010-03-06. ^Yang,WF;Liao,GQ;Hakim,SG;Ouyang,DQ;Ringash,J;Su,YX(1March2016)."IsPilocarpineEffectiveinPreventingRadiation-InducedXerostomia?ASystematicReviewandMeta-analysis".InternationalJournalofRadiationOncology,Biology,Physics.94(3):503–11.doi:10.1016/j.ijrobp.2015.11.012.hdl:10722/229069.PMID 26867879. ^KanskiJJ,BowlingB(2015-03-24).Kanski'sClinicalOphthalmologyE-Book:ASystematicApproach.ElsevierHealthSciences.p. 812.ISBN 9780702055744. ^BartlettJD,JamesSD(October2013)."DrugAffecttheAutonomousNervousSystem".ClinicalOcularPharmacology.Elsevier.p. 118.ISBN 9781483193915. ^Mannis,MarkJ;Holland,EdwardJ(September2016)."Chapter33:DryEye".CorneaE-Book.ElsevierHealthSciences.p. 388.ISBN 978-0-323-35758-6.OCLC 960165358. ^Parker,Jack(2017).DescemetMembraneEndothelialKeratoplasty(DMEK):AReview(PDF)(Thesis).LeidenUniversity. ^AhmedE,EA(2010).ComprehensiveManualofOphthalmology.JPMedicalLtd.p. 345.ISBN 9789350251751. ^ZhangL,WeizerJS,MuschDC(February2017)."Perioperativemedicationsforpreventingtemporarilyincreasedintraocularpressureafterlasertrabeculoplasty".TheCochraneDatabaseofSystematicReviews.2017(2):CD010746.doi:10.1002/14651858.CD010746.pub2.PMC 5477062.PMID 28231380. ^Grzybowski,A;Ruamviboonsuk,V(3March2022)."PharmacologicalTreatmentinPresbyopia".JournalofClinicalMedicine.11(5):1385.doi:10.3390/jcm11051385.PMC 8910925.PMID 35268476. ^VuityLabel,Revised:10/2021.LinkedfromFDApageforVuity ^PrasadRK(2017-07-11).ChemistryandSynthesisofMedicinalAgents:(ExpandingKnowledgeofDrugChemistry).BookRix.ISBN 9783743821415. ^ShaarawyTM,SherwoodMB,HitchingsRA,CrowstonJG(September2014)."LsserPeripheralIridoplasty".GlaucomaE-Book.ElsevierHealthSciences.p. 718.ISBN 9780702055416. ^DeAbreuIN,SawayaAC,EberlinMN,MazzaferaP(November–December2005)."ProductionofPilocarpineinCallusofJaborandi(PilocarpusmicrophyllusStapf)".InVitroCellular&DevelopmentalBiology-Plant.SocietyforInVitroBiology.41(6):806–811.doi:10.1079/IVP2005711.JSTOR 4293939.S2CID 26058596. ^Schwab,Larry(2007).EyeCareinDevelopingNations.CRCPress.p. 110.ISBN 9781840765229. ^KárolyN(2018).Immunohistochemicalinvestigationsoftheneuronalchangesinducedbychronicrecurrentseizuresinapilocarpinerodentmodeloftemporallobeepilepsy(Thesis).UniversityofSzeged.doi:10.14232/phd.9734. ^MorimotoK,FahnestockM,RacineRJ(May2004)."Kindlingandstatusepilepticusmodelsofepilepsy:rewiringthebrain".ProgressinNeurobiology.73(1):1–60.doi:10.1016/j.pneurobio.2004.03.009.PMID 15193778.S2CID 36849482. Externallinks[edit] "Pilocarpine".DrugInformationPortal.U.S.NationalLibraryofMedicine. vteDrugsusedforglaucomapreparationsandmiosis(S01E)Sympathomimetics Apraclonidine Brimonidine(+timolol) Clonidine Dipivefrine Epinephrine Parasympathomimeticsmuscarinic Aceclidine Pilocarpine muscarinic/nicotinic Acetylcholine Carbachol acetylcholinesteraseinhibitors Demecarium Ecothiopate Stigmine(Fluostigmine Neostigmine Physostigmine) Paraoxon Carbonicanhydraseinhibitors/(sulfonamides) Acetazolamide Brinzolamide(+timolol,+brimonidine) Diclofenamide Dorzolamide(+timolol) Methazolamide Betablockingagents Befunolol Betaxolol Carteolol Levobunolol Metipranolol Timolol Mepindolol Prostaglandinanalogues(F2α) Bimatoprost(+timolol) Latanoprost(+netarsudil,+timolol) Latanoprostenebunod Tafluprost Travoprost(+timolol) Unoprostone Otheragents Dapiprazole Guanethidine Netarsudil(+latanoprost) Omidenepag Ripasudil vteMuscarinicacetylcholinereceptormodulatorsmAChRsAgonists 77-LH-28-1 AC-42 AC-260,584 Aceclidine Acetylcholine AF30 AF150(S) AF267B Alvameline AQRA-741 Arecoline Bethanechol Bevonium Butyrylcholine Carbachol CDD-0034 CDD-0078 CDD-0097 CDD-0098 CDD-0102 Cevimeline Choline cis-Dioxolane Clozapine Desmethylclozapine(norclozapine) Ethoxysebacylcholine Itameline LY-593,039 L-689,660 LY-2,033,298 McNA343 Methacholine Milameline Muscarine NGX-267 Ocvimeline Oxotremorine PD-151,832 Pilocarpine RS86 Sabcomeline SDZ210-086 Sebacylcholine Suberyldicholine Talsaclidine Tazomeline Thiopilocarpine Vedaclidine VU-0029767 VU-0090157 VU-0152099 VU-0152100 VU-0238429 WAY-132,983 Xanomeline YM-796 Antagonists 3-Quinuclidinylbenzilate 4-DAMP Aclidiniumbromide(+formoterol) Abediterol AF-DX250 AF-DX384 Ambutoniumbromide Anisodamine Anisodine Antihistamines(first-generation)(e.g.,brompheniramine,buclizine,captodiame,chlorphenamine(chlorpheniramine),cinnarizine,clemastine,cyproheptadine,dimenhydrinate,dimetindene,diphenhydramine,doxylamine,meclizine,mequitazine,perlapine,phenindamine,pheniramine,phenyltoloxamine,promethazine,propiomazine,triprolidine) AQ-RA741 Atropine Atropinemethonitrate Atypicalantipsychotics(e.g.,clozapine,fluperlapine,olanzapine(+fluoxetine),rilapine,quetiapine,tenilapine,zotepine) Benactyzine Benzatropine(benztropine) Benzilone Benzilylcholinemustard Benzydamine BIBN99 Biperiden Bornaprine Camylofin CAR-226,086 CAR-301,060 CAR-302,196 CAR-302,282 CAR-302,368 CAR-302,537 CAR-302,668 Caramiphen Cimetropiumbromide Clidiniumbromide Cloperastine CS-27349 Cyclobenzaprine Cyclopentolate Darifenacin DAU-5884 Desfesoterodine Dexetimide DIBD Dicycloverine(dicyclomine) Dihexyverine Difemerine Diphemanilmetilsulfate Ditran Drofenine EA-3167 EA-3443 EA-3580 EA-3834 Emeproniumbromide Etanautine Etybenzatropine(ethybenztropine) Fenpiverinium Fentoniumbromide Fesoterodine Flavoxate Glycopyrroniumbromide(+beclometasone/formoterol,+indacaterol) Hexahydrodifenidol Hexahydrosiladifenidol Hexbutinol Hexocyclium Himbacine HL-031,120 Homatropine Imidafenacin Ipratropiumbromide(+salbutamol) Isopropamide J-104,129 Hyoscyamine Mambatoxin3 Mambatoxin7 Mazaticol Mebeverine Meladrazine Mepenzolate Methantheline Methoctramine Methylatropine Methylhomatropine Methylscopolamine Metixene Muscarinictoxin7 N-Ethyl-3-piperidylbenzilate N-Methyl-3-piperidylbenzilate Nefopam Octatropinemethylbromide(anisotropinemethylbromide) Orphenadrine Otenzepad(AF-DX116) Otiloniumbromide Oxapiumiodide Oxitropiumbromide Oxybutynin Oxyphencyclimine Oxyphenoniumbromide PBID PD-102,807 PD-0298029 Penthienate Pethidine pFHHSiD Phenglutarimide Phenyltoloxamine Pipenzolatebromide Piperidolate Pirenzepine Piroheptine Pizotifen Poldine Pridinol Prifiniumbromide Procyclidine Profenamine(ethopropazine) Propanthelinebromide Propiverine Quinidine 3-Quinuclidinylthiochromane-4-carboxylate Revefenacin Rociverine RU-47,213 SCH-57,790 SCH-72,788 SCH-217,443 Scopolamine(hyoscine) Scopolaminebutylbromide(hyoscinebutylbromide) Silahexacyclium Sofpironiumbromide Solifenacin SSRIs(e.g.,femoxetine,paroxetine) Telenzepine Terodiline Tetracyclicantidepressants(e.g.,amoxapine,maprotiline,mianserin,mirtazapine) Tiemoniumiodide Timepidiumbromide Tiotropiumbromide Tiquiziumbromide Tofenacin Tolterodine Tricyclicantidepressants(e.g.,amitriptyline(+perphenazine),amitriptylinoxide,butriptyline,cidoxepin,clomipramine,desipramine,desmethyldesipramine,dibenzepin,dosulepin(dothiepin),doxepin,imipramine,lofepramine,nitroxazepine,northiaden(desmethyldosulepin),nortriptyline,protriptyline,quinupramine,trimipramine) Tridihexethyl Trihexyphenidyl Trimebutine Tripitamine(tripitramine) Tropacine Tropatepine Tropicamide Trospiumchloride Typicalantipsychotics(e.g.,chlorpromazine,chlorprothixene,cyamemazine(cyamepromazine),loxapine,mesoridazine,thioridazine) Umeclidiniumbromide(+vilanterol) WIN-2299 Xanomeline Zamifenacin Precursors(andprodrugs) Acetyl-coA Adafenoxate Choline(lecithin) Citicoline Cyprodenate Dimethylethanolamine Glycerophosphocholine Meclofenoxate(centrophenoxine) Phosphatidylcholine Phosphatidylethanolamine Phosphorylcholine Pirisudanol Seealso Receptor/signalingmodulators Nicotinicacetylcholinereceptormodulators Acetylcholinemetabolism/transportmodulators Portal: Medicine Retrievedfrom"https://en.wikipedia.org/w/index.php?title=Pilocarpine&oldid=1100338430" 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