Glycopyrrolate1.docx
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Glycopyrrolate1.docx
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Glycopyrrolate1
Glycopyrrolate
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Glycopyrrolate
Systematic(IUPAC)name
3-(2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium
Clinicaldata
AHFS/D
monograph
MedlinePlus
a602014
Pregnancycat.
B
Legalstatus
?
Routes
oral,IV
Pharmacokineticdata
Half-life
0.6–1.2hours
Excretion
85%renal,unknownamountinthebile
Identifiers
CASnumber
596-51-0
Y
ATCcode
A03AB02
PubChem
CID3494
DrugBank
APRD01000
ChemSpider
11201
Y
UNII
V92SO9WP2I
Y
KEGG
D00540
Y
ChEMBL
CHEMBL1201335
N
Chemicaldata
Formula
C19H28NO3+
Mol.mass
318.431g/mol
SMILES
eMolecules&PubChem
InChI[show]
∙InChI=1S/C19H28NO3.BrH/c1-20
(2)13-12-17(14-20)23-18(21)19(22,16-10-6-7-11-16)15-8-4-3-5-9-15;/h3-5,8-9,16-17,22H,6-7,10-14H2,1-2H3;1H/q+1;/p-1
Y
Key:
VPNYRYCIDCJBOM-UHFFFAOYSA-M
Y
N (whatisthis?
) (verify)
Glycopyrrolateisamedicationofthemuscarinicanticholinergicgroup.Itdoesnotcrossthebloodbrainbarrierandconsequentlyhasnotofewcentraleffects.Itisasyntheticquaternaryamine.Itisavailableinoralandintravenous(i.v.)forms.ItwasdevelopedbySoseiandlicensedtoNovartisin2005.
Withcounterion,itisknownasglycopyrroniumbromide.[1]
Contents
[hide]
∙1Pharmacology
∙2Medicaluses
∙3Sideeffects
∙4References
[edit]Pharmacology
Glycopyrrolateblocksmuscarinicreceptors,[2]thusinhibitingcholinergictransmission.
[edit]Medicaluses
Inanesthesia,glycopyrrolateinjectioncanbeusedasapreoperativemedicationinordertoreducesalivary,tracheobronchial,andpharyngealsecretions,aswellasdecreasingtheacidityofgastricsecretion.Itisalsousedinconjunctionwithneostigmine,aneuromuscularblockingreversalagent,topreventneostigmine'smuscariniceffectssuchasbradycardia.
Itisalsousedtoreduceexcessivesaliva(sialorrhea).[3][4][5]
Itdecreasesacidsecretioninthestomachandsomaybeusedfortreatingstomachulcers,incombinationwithothermedications.
Useintreatingasthma[6][7]andCOPD[8]hasbeendescribed.
Ithasbeenusedtopicallyandorallytotreathyperhidrosis.[9][10]
[edit]Sideeffects
Sinceglycopyrrolatereducesthebody'ssweatingability,itcanevencausefeverandheatstrokeinhotenvironments.Drymouth,difficultyurinating,headaches,diarrheaandconstipationarealsoobservedsideeffectsofthemedication.
Themedicationalsoinducesdrowsinessorblurredvisions,aneffectexacerbatedbytheconsumptionofalcohol.
[edit]References
1.^BajajV,LangtryJA(July2007)."Useoforalglycopyrroniumbromideinhyperhidrosis".Br.J.Dermatol.157
(1):
118–21.doi:
10.1111/j.1365-2133.2007.07884.x.PMID 17459043.http:
//www.blackwell-
2.^HaddadEB,PatelH,KeelingJE,YacoubMH,BarnesPJ,BelvisiMG(May1999)."Pharmacologicalcharacterizationofthemuscarinicreceptorantagonist,glycopyrrolate,inhumanandguinea-pigairways".Br.J.Pharmacol.127
(2):
413–20.doi:
10.1038/sj.bjp.0702573.PMC 1566042.PMID 10385241.http:
//www.pubmedcentral.nih.gov/articlerender.fcgi?
tool=pmcentrez&artid=1566042.
3.^MierRJ,BachrachSJ,LakinRC,BarkerT,ChildsJ,MoranM(December2000)."Treatmentofsialorrheawithglycopyrrolate:
Adouble-blind,dose-rangingstudy".ArchPediatrAdolescMed154(12):
1214–8.PMID 11115305.http:
//archpedi.ama-assn.org/cgi/pmidlookup?
view=long&pmid=11115305.
4.^TschengDZ(November2002)."Sialorrhea-therapeuticdrugoptions".AnnPharmacother36(11):
1785–90.doi:
10.1345/aph.1C019.PMID 12398577.
5.^OlsenAK,SjøgrenP(October1999)."Oralglycopyrrolatealleviatesdroolinginapatientwithtonguecancer".JPainSymptomManage18(4):
300–2.doi:
10.1016/S0885-3924(99)00080-9.PMID 10534970.
6.^HanselTT,NeighbourH,ErinEM,etal.(October2005)."Glycopyrrolatecausesprolongedbronchoprotectionandbronchodilatationinpatientswithasthma".Chest128(4):
1974–9.doi:
10.1378/chest.128.4.1974.PMID 16236844.http:
//www.chestjournal.org/cgi/pmidlookup?
view=long&pmid=16236844.
7.^GilmanMJ,MeyerL,CarterJ,SlovisC(November1990)."Comparisonofaerosolizedglycopyrrolateandmetaproterenolinacuteasthma".Chest98(5):
1095–8.doi:
10.1378/chest.98.5.1095.PMID 2225951.http:
//www.chestjournal.org/cgi/pmidlookup?
view=long&pmid=2225951.
8.^TzelepisG,KomanapolliS,TylerD,VegaD,FulambarkerA(January1996)."Comparisonofnebulizedglycopyrrolateandmetaproterenolinchronicobstructivepulmonarydisease".Eur.Respir.J.9
(1):
100–3.doi:
10.1183/09031936.96.09010100.PMID 8834341.
9.^KimWO,KilHK,YoonDM,ChoMJ(August2003)."Treatmentofcompensatorygustatoryhyperhidrosiswithtopicalglycopyrrolate"([deadlink]).YonseiMed.J.44(4):
579–82.PMID 12950111.http:
//www.eymj.org/abstracts/viewArticle.asp?
year=2003&page=579.
10.^KimWO,KilHK,YoonKB,YoonDM(May2008)."Topicalglycopyrrolateforpatientswithfacialhyperhidrosis".Br.J.Dermatol.158(5):
1094–7.doi:
10.1111/j.1365-2133.2008.08476.x.PMID 18294315.http:
//www.blackwell-
[show]
∙v
∙t
∙e
Cholinergics
[show]
Receptorligands
mAChR
∙Agonists:
77-LH-28-1
∙AC-42
∙AC-260,584
∙Aceclidine
∙Acetylcholine
∙AF30
∙AF150(S)
∙AF267B
∙AFDX-384
∙Alvameline
∙AQRA-741
∙Arecoline
∙Bethanechol
∙Butyrylcholine
∙Carbachol
∙CDD-0034
∙CDD-0078
∙CDD-0097
∙CDD-0098
∙CDD-0102
∙Cevimeline
∙cis-Dioxolane
∙Ethoxysebacylcholine
∙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
∙Suberylcholine
∙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
∙Anisodamine
∙Anisodine
∙Atropine
∙AtropineMethonitrate
∙Benactyzine
∙Benzatropine(Benztropine)
∙Benzydamine
∙BIBN99
∙Biperiden
∙Bornaprine
∙CAR-226,086
∙CAR-301,060
∙CAR-302,196
∙CAR-302,282
∙CAR-302,368
∙CAR-302,537
∙CAR-302,668
∙CS-27349
∙Cyclobenzaprine
∙Cyclopentolate
∙Darifenacin
∙DAU-5884
∙Dimethindene
∙Dexetimide
∙DIBD
∙Dicyclomine(Dicycloverine)
∙Ditran
∙EA-3167
∙EA-3443
∙EA-3580
∙EA-3834
∙Etanautine
∙Etybenzatropine(Ethylbenztropine)
∙Flavoxate
∙Himbacine
∙HL-031,120
∙Ipratropiumbromide
∙J-104,129
∙Hyoscyamine
∙MambaToxin3
∙MambaToxin7
∙Mazaticol
∙Mebeverine
∙Methoctramine
∙Metixene
∙N-Ethyl-3-PiperidylBenzilate
∙N-Methyl-3-PiperidylBenzilate
∙Orphenadrine
∙Otenzepad
∙Oxybutynin
∙PBID
∙PD-102,807
∙PD-0298029
∙Phenglutarimide
∙Phenyltoloxamine
∙Pirenzepine
∙Piroheptine
∙Procyclidine
∙Profenamine
∙RU-47,213
∙SCH-57,790
∙SCH-72,788
∙SCH-217,443
∙Scopolamine(Hyoscine)
∙Solifenacin
∙Telenzepine
∙Tiotropiumbromide
∙Tolterodine
∙Trihexyphenidyl
∙Tripitamine
∙Tropatepine
∙Tropicamide
∙WIN-2299
∙Xanomeline
∙Zamifenacin;Others:
1stGenerationAntihistamines(Brompheniramine
∙chlorphenamine
∙cyproheptadine
∙dimenhydrinate
∙diphenhydramine
∙doxylamine
∙mepyramine/pyrilamine
∙phenindamine
∙pheniramine
∙tripelennamine
∙triprolidine,etc)
∙TricyclicAntidepressants(Amitriptyline
∙doxepin
∙trimipramine,etc)
∙TetracyclicAntidepressants(Amoxapine
∙maprotiline,etc)
∙TypicalAntipsychotics(Chlorpromazine
∙thioridazine,etc)
∙AtypicalAntipsychotics(Clozapine
∙olanzapine
∙quetiapine,etc)
nAChR
∙Agonists:
5-HIAA
∙A-84,543
∙A-366,833
∙A-582,941
∙A-867,744
∙ABT-202
∙ABT-418
∙ABT-560
∙ABT-894
∙Acetylcholine
∙Altinicline
∙Anabasine
∙Anatoxin-a
∙AR-R17779
∙Butyrylcholine
∙Carbachol
∙Cotinine
∙Cytisine
∙Decamethonium
∙Desformylflustrabromine
∙Dianicline
∙Dimethylphenylpiperazinium
∙Epibatidine
∙Epiboxidine
∙Ethanol
∙Ethoxysebacylcholine
∙EVP-4473
∙EVP-6124
∙Galantamine
∙GTS-21
∙Ispronicline
∙Lobeline
∙MEM-63,908(RG-3487)
∙Nicotine
∙NS-1738
∙PHA-543,613
∙PHA-709,829
∙PNU-120,596
∙PNU-282,987
∙Pozanicline
∙Rivanicline
∙SazetidineA
∙Sebacylcholine
∙SIB-1508Y
∙SIB-1553A
∙SSR-180,711
∙Suberylcholine
∙TC-1698
∙TC-1734
∙TC-1827
∙TC-2216
∙TC-5214
∙TC-5619
∙TC-6683
∙Tebanicline
∙Tropisetron
∙UB-165
∙Varenicline
∙WAY-317,538
∙XY-4083
Antagonists:
18-Methoxycoronaridine
∙α-Bungarotoxin
∙α-Conotoxin
∙Alcuronium
∙Amantadine
∙Anatruxonium
∙Atracurium
∙Bupropion(Amfebutamone)
∙Chandonium
∙Chlorisondamine
∙Cisatracurium
∙Coclaurine
∙Coronaridine
∙Dacuronium
∙Decamethonium
∙Dextromethorphan
∙Dextropropoxyphene
∙Dextrorphan
∙Diadonium
∙DHβE
∙Dimethyltubocurarine(Metocurine)
∙Dipyrandium
∙Dizocilpine(MK-801)
∙Doxacurium
∙Duador
∙Esketamine
∙Fazadinium
∙Gallamine
∙Hexafluronium
∙Hexamethonium(Benzohexonium)
∙Ibogaine
∙Isoflurane
∙Ketamine
∙Kynurenicacid
∙Laudexium(Laudolissin)
∙Levacetylmethadol
∙Malouetine
∙Mecamylamine
∙Memantine
∙Methadone
∙Methorphan(Racemethorphan)
∙Methyllycaconitine
∙Metocurine
∙Mivacurium
∙Morphanol(Racemorphanol)
∙Neramexane
∙NitrousOxide
∙Pancuronium
∙Pempidine
∙Pentamine
∙Pentolinium
∙Phencyclidine
∙Pipecuronium
∙Rada
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