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Identification
NameGlycopyrronium
Accession NumberDB00986  (APRD01000)
TypeSmall Molecule
GroupsApproved, Investigational, Vet Approved
DescriptionGlycopyrronium (as the bromide salt glycopyrrolate) is a synthetic anticholinergic agent with a quaternary ammonium structure. A muscarinic competitive antagonist used as an antispasmodic, in some disorders of the gastrointestinal tract, and to reduce salivation with some anesthetics. In October 2015, glycopyrrolate was approved by the FDA for use as a standalone treatment for Chronic obstructive pulmonary disease (COPD), as Seebri Neohaler.
Structure
Thumb
Synonyms
Glycopyrrolate cation
Glycopyrrolate ion
Glycopyrronium cation
Glycopyrronium ion
External Identifiers
  • DRM-04
  • DRM04
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cuvposaliquid1 mg/5mLoralMerz Pharmaceuticals, LLC2013-01-01Not applicableUs
Enurev BreezhalerInhalation powder, hard capsule44 microgramsInhalation useNovartis Europharm Ltd2012-09-28Not applicableEu
Enurev BreezhalerInhalation powder, hard capsule44 microgramsInhalation useNovartis Europharm Ltd2012-09-28Not applicableEu
Enurev BreezhalerInhalation powder, hard capsule44 microgramsInhalation useNovartis Europharm Ltd2012-09-28Not applicableEu
Enurev BreezhalerInhalation powder, hard capsule44 microgramsInhalation useNovartis Europharm Ltd2012-09-28Not applicableEu
Enurev BreezhalerInhalation powder, hard capsule44 microgramsInhalation useNovartis Europharm Ltd2012-09-28Not applicableEu
Enurev BreezhalerInhalation powder, hard capsule44 microgramsInhalation useNovartis Europharm Ltd2012-09-28Not applicableEu
Enurev BreezhalerInhalation powder, hard capsule44 microgramsInhalation useNovartis Europharm Ltd2012-09-28Not applicableEu
Enurev BreezhalerInhalation powder, hard capsule44 microgramsInhalation useNovartis Europharm Ltd2012-09-28Not applicableEu
Glycopyrrolateinjection, solution.2 mg/mLintramuscular; intravenousCardinal Health2010-12-17Not applicableUs
Glycopyrrolateinjection.2 mg/mLintramuscular; intravenousWest Ward Pharmaceutical Corp.1975-02-06Not applicableUs
Glycopyrrolateinjection, solution.2 mg/mLintramuscular; intravenousCardinal Health2010-12-17Not applicableUs
Glycopyrrolateinjection.2 mg/mLintramuscular; intravenousWest Ward Pharmaceutical Corp.1975-02-06Not applicableUs
Glycopyrrolatetablet1 mg/1oralUnited Research Laboratories, Inc.2005-01-132015-12-29Us
Glycopyrrolateinjection.2 mg/mLintramuscular; intravenousWest Ward Pharmaceutical Corp.1975-02-06Not applicableUs
Glycopyrrolateinjection.2 mg/mLintramuscular; intravenousCardinal Health1975-02-06Not applicableUs
Glycopyrrolateinjection, solution.2 mg/mLintramuscular; intravenousPhysicians Total Care, Inc.2011-05-06Not applicableUs
Glycopyrrolatetablet2 mg/1oralUnited Research Laboratories, Inc.2005-01-132015-12-29Us
Glycopyrrolateinjection, powder, for solution.2 mg/mLintramuscular; intravenousGeneral Injectables & Vaccines, Inc2010-03-01Not applicableUs
Glycopyrrolateinjection.2 mg/mLintramuscular; intravenousWest Ward Pharmaceutical Corp.1975-02-06Not applicableUs
Glycopyrrolateinjection, solution.2 mg/mLintramuscular; intravenousCardinal Health2010-12-17Not applicableUs
Glycopyrrolate Injectionliquid0.2 mgintramuscular; intravenousOmega Laboratories Ltd2012-06-29Not applicableCanada
Glycopyrrolate Injection Multidoseliquid0.2 mgintramuscular; intravenousOmega Laboratories Ltd2012-07-13Not applicableCanada
Glycopyrrolate Injection USPliquid0.2 mgintramuscular; intravenousSandoz Canada Incorporated1993-12-31Not applicableCanada
Robinulinjection.2 mg/mLintramuscular; intravenousWest Ward Pharmaceutical Corp.1975-02-06Not applicableUs
Robinulinjection.2 mg/mLintramuscular; intravenousGeneral Injectables & Vaccines, Inc2012-10-11Not applicableUs
Robinulinjection.2 mg/mLintramuscular; intravenousWest Ward Pharmaceutical Corp.1975-02-06Not applicableUs
Robinulinjection, solution.2 mg/mLintramuscular; intravenousGeneral Injectables & Vaccines, Inc2010-08-01Not applicableUs
Robinulinjection.2 mg/mLintramuscular; intravenousWest Ward Pharmaceutical Corp.1975-02-06Not applicableUs
Robinulinjection.2 mg/mLintramuscular; intravenousWest Ward Pharmaceutical Corp.1975-02-06Not applicableUs
Robinultablet1 mg/1oralShionogi Inc.1961-03-28Not applicableUs
Robinul 0.2mg/ml Liq Injliquid.2 mgintramuscular; intravenousWyeth Ayerst Canada Inc.1994-12-312000-03-07Canada
Robinul Fortetablet2 mg/1oralShionogi Inc.1961-03-28Not applicableUs
Robinul Tab 1mgtablet1 mgoralWyeth Ayerst Canada Inc.1994-12-312002-07-31Canada
Robinul-forte Tab 2mgtablet2 mgoralWyeth Ayerst Canada Inc.1996-10-252000-06-27Canada
Seebri BreezhalerInhalation powder, hard capsule44 microgramsInhalation useNovartis Europharm Ltd2012-09-28Not applicableEu
Seebri BreezhalerInhalation powder, hard capsule44 microgramsInhalation useNovartis Europharm Ltd2012-09-28Not applicableEu
Seebri BreezhalerInhalation powder, hard capsule44 microgramsInhalation useNovartis Europharm Ltd2012-09-28Not applicableEu
Seebri BreezhalerInhalation powder, hard capsule44 microgramsInhalation useNovartis Europharm Ltd2012-09-28Not applicableEu
Seebri BreezhalerInhalation powder, hard capsule44 microgramsInhalation useNovartis Europharm Ltd2012-09-28Not applicableEu
Seebri BreezhalerInhalation powder, hard capsule44 microgramsInhalation useNovartis Europharm Ltd2012-09-28Not applicableEu
Seebri Breezhalercapsule50 mcginhalationNovartis Pharmaceuticals Canada Inc2013-01-14Not applicableCanada
Seebri BreezhalerInhalation powder, hard capsule44 microgramsInhalation useNovartis Europharm Ltd2012-09-28Not applicableEu
Seebri BreezhalerInhalation powder, hard capsule44 microgramsInhalation useNovartis Europharm Ltd2012-09-28Not applicableEu
Seebri Neohalercapsule15.6 ug/1respiratory (inhalation)Novartis Pharmaceuticals Corporation2015-10-29Not applicableUs
Tovanor BreezhalerInhalation powder, hard capsule44 microgramsInhalation useNovartis Europharm Ltd.2012-09-28Not applicableEu
Tovanor BreezhalerInhalation powder, hard capsule44 microgramsInhalation useNovartis Europharm Ltd.2012-09-28Not applicableEu
Tovanor BreezhalerInhalation powder, hard capsule44 microgramsInhalation useNovartis Europharm Ltd.2012-09-28Not applicableEu
Tovanor BreezhalerInhalation powder, hard capsule44 microgramsInhalation useNovartis Europharm Ltd.2012-09-28Not applicableEu
Tovanor BreezhalerInhalation powder, hard capsule44 microgramsInhalation useNovartis Europharm Ltd.2012-09-28Not applicableEu
Tovanor BreezhalerInhalation powder, hard capsule44 microgramsInhalation useNovartis Europharm Ltd.2012-09-28Not applicableEu
Tovanor BreezhalerInhalation powder, hard capsule44 microgramsInhalation useNovartis Europharm Ltd.2012-09-28Not applicableEu
Tovanor BreezhalerInhalation powder, hard capsule44 microgramsInhalation useNovartis Europharm Ltd.2012-09-28Not applicableEu
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Glycatetablet1.5 mg/1oralNuro Pharma, Inc.2012-03-12Not applicableUs
Glycopyrrolatetablet1 mg/1oralMylan Institutional Inc.2010-06-14Not applicableUs
Glycopyrrolatetablet2 mg/1oralbryant ranch prepack2006-09-26Not applicableUs
Glycopyrrolateinjection.2 mg/mLintramuscular; intravenousWest ward Pharmaceutical Corp2011-09-21Not applicableUs
Glycopyrrolatetablet2 mg/1oralQualitest Pharmaceuticals2008-12-29Not applicableUs
Glycopyrrolateinjection, solution.4 mg/2mLintramuscular; intravenousCardinal Health2011-10-25Not applicableUs
Glycopyrrolatetablet2 mg/1oralAmerican Health Packaging2015-03-312015-12-29Us
Glycopyrrolatetablet1 mg/1oralWest ward Pharmaceutical Corp2009-03-05Not applicableUs
Glycopyrrolateinjection, solution.2 mg/mLintramuscular; intravenousAmerican Regent, Inc.1990-09-30Not applicableUs
Glycopyrrolatetablet1 mg/1oralDr. Reddy's Laboratories Limited2008-07-14Not applicableUs
Glycopyrrolatetablet2 mg/1oralRising Pharmaceuticals, Inc.2008-12-29Not applicableUs
Glycopyrrolatetablet2 mg/1oralLeading Pharma, Llc2016-03-18Not applicableUs
Glycopyrrolateinjection.2 mg/mLintramuscular; intravenousWest ward Pharmaceutical Corp2015-06-01Not applicableUs
Glycopyrrolatetablet2 mg/1oralAv Kare, Inc.2015-05-14Not applicableUs
Glycopyrrolatetablet1 mg/1oralRanbaxy Pharmaceuticals Inc.2009-08-18Not applicableUs
Glycopyrrolateinjection.2 mg/mLintramuscular; intravenousWest ward Pharmaceutical Corp2011-09-21Not applicableUs
Glycopyrrolatetablet1 mg/1oralREMEDYREPACK INC.2013-10-04Not applicableUs
Glycopyrrolatetablet1 mg/1oralExcellium Pharmaceutical, Inc.2012-10-01Not applicableUs
Glycopyrrolatetablet2 mg/1oralWest ward Pharmaceutical Corp2009-03-05Not applicableUs
Glycopyrrolatetablet1.5 mg/1oralNexgen Pharma, Inc.2012-03-12Not applicableUs
Glycopyrrolateinjection.2 mg/mLintramuscular; intravenousCardinal Health2011-09-21Not applicableUs
Glycopyrrolatetablet1 mg/1oralCardinal Health2010-06-14Not applicableUs
Glycopyrrolatetablet1 mg/1oralCarilion Materials Management2008-07-14Not applicableUs
Glycopyrrolateinjection, solution.2 mg/mLintramuscular; intravenousAmerican Regent, Inc.1990-09-30Not applicableUs
Glycopyrrolatetablet1 mg/1oralDr. Reddy's Laboratories Limited2008-07-14Not applicableUs
Glycopyrrolatetablet2 mg/1oralRanbaxy Pharmaceuticals Inc.2009-08-18Not applicableUs
Glycopyrrolateinjection.2 mg/mLintramuscular; intravenousWest ward Pharmaceutical Corp2015-06-01Not applicableUs
Glycopyrrolatetablet1 mg/1oralPar Pharmaceutical Inc.2006-09-26Not applicableUs
Glycopyrrolateinjection.2 mg/mLintramuscular; intravenousWest ward Pharmaceutical Corp2011-09-21Not applicableUs
Glycopyrrolatetablet1 mg/1oralREMEDYREPACK INC.2013-10-04Not applicableUs
Glycopyrrolatetablet2 mg/1oralExcellium Pharmaceutical, Inc.2012-10-01Not applicableUs
Glycopyrrolatetablet1 mg/1oralAmerican Health Packaging2011-09-01Not applicableUs
Glycopyrrolateinjection.2 mg/mLintramuscular; intravenousWest ward Pharmaceutical Corp2015-06-01Not applicableUs
Glycopyrrolatetablet1 mg/1oralAurolife Pharma, LLC2013-04-15Not applicableUs
Glycopyrrolatetablet1 mg/1oralQuinn Pharmaceuticals, Llc2015-03-02Not applicableUs
Glycopyrrolateinjection, solution.2 mg/mLintramuscular; intravenousAmerican Regent, Inc.1990-09-30Not applicableUs
Glycopyrrolateinjection, solution.2 mg/mLintramuscular; intravenousCardinal Health2011-10-25Not applicableUs
Glycopyrrolatetablet2 mg/1oralPar Pharmaceutical Inc.2006-09-26Not applicableUs
Glycopyrrolatetablet1 mg/1oralbryant ranch prepack2008-12-29Not applicableUs
Glycopyrrolateinjection.2 mg/mLintramuscular; intravenousWest ward Pharmaceutical Corp2011-09-21Not applicableUs
Glycopyrrolateinjection, solution.2 mg/mLintramuscular; intravenousAmerican Regent, Inc.1990-09-30Not applicableUs
Glycopyrrolateinjection, solution.2 mg/mLintramuscular; intravenousGeneral Injectables & Vaccines, Inc2012-02-20Not applicableUs
Glycopyrrolatetablet1 mg/1oralRising Pharmaceuticals, Inc.2008-12-29Not applicableUs
Glycopyrrolatetablet1 mg/1oralLeading Pharma, Llc2016-03-18Not applicableUs
Glycopyrrolateinjection.2 mg/mLintramuscular; intravenousWest ward Pharmaceutical Corp2015-06-01Not applicableUs
Glycopyrrolatetablet1 mg/1oralAv Kare, Inc.2015-05-14Not applicableUs
Glycopyrrolatetablet2 mg/1oralAmerican Health Packaging2015-11-16Not applicableUs
Glycopyrrolateinjection, solution1 mg/5mLintramuscular; intravenousCardinal Health2011-10-25Not applicableUs
Glycopyrrolatetablet2 mg/1oralQuinn Pharmaceuticals, Llc2015-03-02Not applicableUs
Glycopyrrolatetablet1 mg/1oralQualitest Pharmaceuticals2008-12-29Not applicableUs
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Robinul Forte Tab 2mgtablet2 mgoralAyerst Laboratories1993-12-311997-08-15Canada
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Glycopyrrolateinjection, solution.2 mg/mLintravenousCantrell Drug Company2014-06-25Not applicableUs
International Brands
NameCompany
AcpanGray
NodaptonNot Available
RobanulNot Available
RobinalNot Available
TarodylLundbeck
Brand mixtures
NameLabellerIngredients
Ultibro BreezhalerNovartis Pharmaceuticals Canada Inc
Utibron NeohalerNovartis Pharmaceuticals Corporation
Salts
Name/CASStructureProperties
Glycopyrronium bromide
51186-83-5
Thumb
  • InChI Key: VPNYRYCIDCJBOM-QQTWVUFVSA-M
  • Monoisotopic Mass: 397.125257
  • Average Mass: 398.341
DBSALT001183
Categories
UNIIA14FB57V1D
CAS number740028-90-4
WeightAverage: 318.436
Monoisotopic: 318.206370186
Chemical FormulaC19H28NO3
InChI KeyANGKOCUUWGHLCE-HKUYNNGSSA-N
InChI
InChI=1S/C19H28NO3/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/q+1/t17-,19-/m0/s1
IUPAC Name
(3S)-3-{[(2R)-2-cyclopentyl-2-hydroxy-2-phenylacetyl]oxy}-1,1-dimethylpyrrolidin-1-ium
SMILES
[H][C@@]1(CC[N+](C)(C)C1)OC(=O)[C@@](O)(C1CCCC1)C1=CC=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Tertiary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Aromatic alcohol
  • Organic nitrogen compound
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor use as a preoperative antimuscarinic to reduce salivary, tracheobronchial, and pharyngeal secretions, to reduce the volume and free acidity of gastric secretions and to block cardiac vagal inhibitory reflexes during induction of anesthesia and intubation. Also used to treat chronic obstructive pulmonary disease (COPD).
PharmacodynamicsGlycopyrrolate decreases acid secretion in the stomach. Hence it can be used for treating ulcers in the stomach and small intestine, in combination with other medications. In anesthesia, glycopyrrolate injection serves as a preoperative antimuscarinic operation that reduces salivary, tracheobronchial, and pharyngeal secretions, as well as decreases the acidity of gastric secretions blocks cardiac vagal inhibitory reflexes during intubation
Mechanism of actionGlycopyrrolate binds competitively to the muscarinic acetylcholine receptor. Like other anticholinergic (antimuscarinic) agents, it inhibits the action of acetylcholine on structures innervated by postganglionic cholinergic nerves and on smooth muscles that respond to acetylcholine but lack cholinergic innervation. These peripheral cholinergic receptors are present in the autonomic effector cells of smooth muscle, cardiac muscle, the sinoatrial node, the atrioventricular node, exocrine glands and, to a limited degree, in the autonomic ganglia. Thus, it diminishes the volume and free acidity of gastric secretions and controls excessive pharyngeal, tracheal, and bronchial secretions.
Related Articles
AbsorptionRapidly absorbed (1-2 minutes) after intravenous injection
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half life0.6-1.2 hours
ClearanceNot Available
ToxicitySide effects include dry mouth, difficult urinating, heachaches, diarrhea and constipation. The medication also induces drowsiness or blurred vision. LD50=709 mg/kg (rat, oral).
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8406
Blood Brain Barrier+0.8436
Caco-2 permeable+0.5778
P-glycoprotein substrateSubstrate0.7928
P-glycoprotein inhibitor INon-inhibitor0.894
P-glycoprotein inhibitor IINon-inhibitor0.9731
Renal organic cation transporterNon-inhibitor0.5299
CYP450 2C9 substrateNon-substrate0.7812
CYP450 2D6 substrateNon-substrate0.7136
CYP450 3A4 substrateSubstrate0.662
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9133
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9243
CYP450 3A4 inhibitorNon-inhibitor0.8735
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.978
Ames testNon AMES toxic0.7888
CarcinogenicityNon-carcinogens0.9257
BiodegradationReady biodegradable0.8627
Rat acute toxicity2.5887 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9345
hERG inhibition (predictor II)Non-inhibitor0.7884
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Abraxis pharmaceutical products
  • Hospira inc
  • Luitpold pharmaceuticals inc
  • Teva parenteral medicines inc
  • Watson laboratories inc
  • Baxter healthcare corp anesthesia and critical care
  • Ah robins co
  • Shionogi pharma inc
  • Corepharma llc
  • Dr reddys laboratories ltd
  • Par pharmaceutical inc
  • Ranbaxy inc
  • Vintage pharmaceuticals llc
  • West ward pharmaceutical corp
Packagers
Dosage forms
FormRouteStrength
Liquidoral1 mg/5mL
Inhalation powder, hard capsuleInhalation use44 micrograms
Injectionintramuscular; intravenous.2 mg/mL
Injection, powder, for solutionintramuscular; intravenous.2 mg/mL
Injection, solutionintramuscular; intravenous.2 mg/mL
Injection, solutionintramuscular; intravenous.4 mg/2mL
Injection, solutionintramuscular; intravenous1 mg/5mL
Injection, solutionintravenous.2 mg/mL
Tabletoral1 mg/1
Tabletoral1.5 mg/1
Tabletoral2 mg/1
Liquidintramuscular; intravenous0.2 mg
Liquidintramuscular; intravenous.2 mg
Tabletoral2 mg
Tabletoral1 mg
Capsuleinhalation50 mcg
Capsulerespiratory (inhalation)15.6 ug/1
Kit; capsuleinhalation
Capsulerespiratory (inhalation)
Prices
Unit descriptionCostUnit
Glycopyrrolate powder278.46USD g
Robinul-Forte 2 mg tablet6.46USD tablet
Robinul forte 2 mg tablet6.21USD tablet
Robinul 1 mg tablet3.96USD tablet
Glycopyrrolate 0.2 mg/ml3.63USD ml
Glycopyrrolate 1 mg/5 ml syr2.91USD ml
Glycopyrrolate 2 mg tablet2.24USD tablet
Glycopyrrolate 1 mg tablet1.34USD tablet
Robinul 0.2 mg/ml vial1.26USD ml
Glycopyrrolate 0.2 mg/ml vial0.85USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6521260 No1996-01-312016-01-31Us
US6528678 No1998-04-242018-04-24Us
US6582678 No1998-04-242018-04-24Us
US6878721 No2000-10-102020-10-10Us
US7091236 No2004-04-242024-04-24Us
US7229607 No2001-04-092021-04-09Us
US7638552 No2003-08-202023-08-20Us
US7736670 No2001-06-272021-06-27Us
US7816396 No2003-08-202023-08-20Us
US7820694 No2000-06-022020-06-02Us
US8029768 No2001-04-092021-04-09Us
US8048451 No2001-06-272021-06-27Us
US8067437 No2000-06-022020-06-02Us
US8182838 No2008-10-202028-10-20Us
US8283362 No2000-06-022020-06-02Us
US8303991 No2001-06-272021-06-27Us
US8435567 No2001-06-272021-06-27Us
US8479730 No2008-10-112028-10-11Us
US8580306 No2001-06-272021-06-27Us
US8658673 No2000-06-022020-06-02Us
US8796307 No2000-06-022020-06-02Us
US8956661 No2001-06-272021-06-27Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point193-194.5U.S. Patent 2,956,062.
logP-0.99Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000944 mg/mLALOGPS
logP-1.2ALOGPS
logP-1.4ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)11.53ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity101.08 m3·mol-1ChemAxon
Polarizability35.99 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Michael Woehrmann, Lara Terstegen, Stefan Biel, Thomas Raschke, Svenja-Kathrin Cerv, Werner Zilz, Sven Untiedt, Thomas Nuebel, Uwe Schoenrock, Heiner Max, Helga Biergiesser, Yvonne Eckhard, Heike Miertsch, Heike Foelster, Cornelia Meier-Zimmerer, Bernd Traupe, Inge Kruse, “GLYCOPYRROLATE IN COSMETIC PREPARATIONS.” U.S. Patent US20090208437, issued August 20, 2009.

US20090208437
General References
  1. Ali-Melkkila T, Kanto J, Iisalo E: Pharmacokinetics and related pharmacodynamics of anticholinergic drugs. Acta Anaesthesiol Scand. 1993 Oct;37(7):633-42. [PubMed:8249551 ]
External Links
ATC CodesR03BB06R03AL04A03CA05A03AB02
AHFS Codes
  • 12:08.08
PDB EntriesNot Available
FDA labelDownload (193 KB)
MSDSDownload (73.7 KB)
Interactions
Drug Interactions
Drug
1,10-PhenanthrolineThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with 1,10-Phenanthroline.
AclidiniumThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Aclidinium.
AclidiniumAclidinium may increase the anticholinergic activities of Glycopyrronium.
AlfentanilThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Alfentanil.
AlphacetylmethadolThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Alphacetylmethadol.
AmantadineAmantadine may increase the anticholinergic activities of Glycopyrronium.
AmbenoniumThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Ambenonium.
Anisotropine MethylbromideThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Anisotropine Methylbromide.
Anisotropine MethylbromideAnisotropine Methylbromide may increase the anticholinergic activities of Glycopyrronium.
AtenololThe serum concentration of Atenolol can be increased when it is combined with Glycopyrronium.
Atracurium besylateThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Atracurium besylate.
Atracurium besylateAtracurium besylate may increase the anticholinergic activities of Glycopyrronium.
AtropineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Atropine.
AtropineAtropine may increase the anticholinergic activities of Glycopyrronium.
BenactyzineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Benactyzine.
BenactyzineBenactyzine may increase the anticholinergic activities of Glycopyrronium.
BendroflumethiazideThe serum concentration of Bendroflumethiazide can be increased when it is combined with Glycopyrronium.
BenzatropineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Benzatropine.
BenzatropineBenzatropine may increase the anticholinergic activities of Glycopyrronium.
BezitramideThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Bezitramide.
BiperidenThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Biperiden.
BiperidenBiperiden may increase the anticholinergic activities of Glycopyrronium.
Botulinum Toxin Type AGlycopyrronium may increase the anticholinergic activities of Botulinum Toxin Type A.
Botulinum Toxin Type BGlycopyrronium may increase the anticholinergic activities of Botulinum Toxin Type B.
BuprenorphineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Buprenorphine.
ButorphanolThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Butorphanol.
CarfentanilThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Carfentanil.
ChlorothiazideThe serum concentration of Chlorothiazide can be increased when it is combined with Glycopyrronium.
ChlorphenoxamineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Chlorphenoxamine.
ChlorphenoxamineChlorphenoxamine may increase the anticholinergic activities of Glycopyrronium.
ChlorthalidoneThe serum concentration of Chlorthalidone can be increased when it is combined with Glycopyrronium.
CimetropiumGlycopyrronium may increase the anticholinergic activities of Cimetropium.
CodeineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Codeine.
CoumaphosThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Coumaphos.
CyclopentolateThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Cyclopentolate.
CyclopentolateCyclopentolate may increase the anticholinergic activities of Glycopyrronium.
DarifenacinThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Darifenacin.
DarifenacinDarifenacin may increase the anticholinergic activities of Glycopyrronium.
DecamethoniumThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Decamethonium.
DemecariumThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Demecarium.
DesloratadineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Desloratadine.
DesloratadineDesloratadine may increase the anticholinergic activities of Glycopyrronium.
DexetimideThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Dexetimide.
DexetimideDexetimide may increase the anticholinergic activities of Glycopyrronium.
DextromoramideThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Dextromoramide.
DextropropoxypheneThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Dextropropoxyphene.
DezocineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Dezocine.
DichlorvosThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Dichlorvos.
DicyclomineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Dicyclomine.
DicyclomineDicyclomine may increase the anticholinergic activities of Glycopyrronium.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Glycopyrronium.
DihydrocodeineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Dihydrocodeine.
DihydroetorphineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Dihydroetorphine.
DihydromorphineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Dihydromorphine.
DiphenoxylateThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Diphenoxylate.
DonepezilThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Donepezil.
DPDPEThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with DPDPE.
DronabinolGlycopyrronium may increase the tachycardic activities of Dronabinol.
EchothiophateThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Echothiophate.
EdrophoniumThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Edrophonium.
EluxadolineGlycopyrronium may increase the constipating activities of Eluxadoline.
EthopropazineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Ethopropazine.
EthopropazineEthopropazine may increase the anticholinergic activities of Glycopyrronium.
EthylmorphineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Ethylmorphine.
EtorphineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Etorphine.
FentanylThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Fentanyl.
FenthionThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Fenthion.
FesoterodineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Fesoterodine.
FesoterodineFesoterodine may increase the anticholinergic activities of Glycopyrronium.
GalantamineThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Galantamine.
Gallamine TriethiodideThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Gallamine Triethiodide.
Gallamine TriethiodideGallamine Triethiodide may increase the anticholinergic activities of Glycopyrronium.
Ginkgo bilobaThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Ginkgo biloba.
Glucagon recombinantThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Glucagon recombinant.
HaloperidolThe serum concentration of Haloperidol can be decreased when it is combined with Glycopyrronium.
HeroinThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Heroin.
HexamethoniumThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Hexamethonium.
HexamethoniumHexamethonium may increase the anticholinergic activities of Glycopyrronium.
HomatropineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Homatropine.
HomatropineHomatropine may increase the anticholinergic activities of Glycopyrronium.
Huperzine AThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Huperzine A.
HydrochlorothiazideThe serum concentration of Hydrochlorothiazide can be increased when it is combined with Glycopyrronium.
HydrocodoneThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Hydrocodone.
HydroflumethiazideThe serum concentration of Hydroflumethiazide can be increased when it is combined with Glycopyrronium.
HydromorphoneThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Hydromorphone.
HyoscyamineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Hyoscyamine.
HyoscyamineHyoscyamine may increase the anticholinergic activities of Glycopyrronium.
IndapamideThe serum concentration of Indapamide can be increased when it is combined with Glycopyrronium.
Ipratropium bromideThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Ipratropium bromide.
Ipratropium bromideIpratropium bromide may increase the anticholinergic activities of Glycopyrronium.
IsoflurophateThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Isoflurophate.
ItoprideThe therapeutic efficacy of Itopride can be decreased when used in combination with Glycopyrronium.
KetobemidoneThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Ketobemidone.
LevodopaThe serum concentration of Levodopa can be decreased when it is combined with Glycopyrronium.
Levomethadyl AcetateThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Levomethadyl Acetate.
LevorphanolThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Levorphanol.
LofentanilThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Lofentanil.
MalathionThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Malathion.
MecamylamineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Mecamylamine.
MecamylamineMecamylamine may increase the anticholinergic activities of Glycopyrronium.
MefloquineThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Mefloquine.
MemantineThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Memantine.
MetforminThe serum concentration of Metformin can be increased when it is combined with Glycopyrronium.
MethadoneThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Methadone.
Methadyl AcetateThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Methadyl Acetate.
MethanthelineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Methantheline.
MethanthelineMethantheline may increase the anticholinergic activities of Glycopyrronium.
MethyclothiazideThe serum concentration of Methyclothiazide can be increased when it is combined with Glycopyrronium.
MetixeneThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Metixene.
MetixeneMetixene may increase the anticholinergic activities of Glycopyrronium.
MetolazoneThe serum concentration of Metolazone can be increased when it is combined with Glycopyrronium.
MianserinMianserin may increase the anticholinergic activities of Glycopyrronium.
MinaprineThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Minaprine.
MirabegronThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Mirabegron.
MorphineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Morphine.
N-butylscopolammonium bromideThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with N-butylscopolammonium bromide.
N-butylscopolammonium bromideN-butylscopolammonium bromide may increase the anticholinergic activities of Glycopyrronium.
NabiloneGlycopyrronium may increase the tachycardic activities of Nabilone.
NalbuphineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Nalbuphine.
NeostigmineThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Neostigmine.
NormethadoneThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Normethadone.
NVA237The risk or severity of adverse effects can be increased when Glycopyrronium is combined with NVA237.
NVA237NVA237 may increase the anticholinergic activities of Glycopyrronium.
OpiumThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Opium.
OrphenadrineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Orphenadrine.
OrphenadrineOrphenadrine may increase the anticholinergic activities of Glycopyrronium.
OxybutyninThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Oxybutynin.
OxybutyninOxybutynin may increase the anticholinergic activities of Glycopyrronium.
OxycodoneThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Oxycodone.
OxymorphoneThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Oxymorphone.
OxyphenoniumThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Oxyphenonium.
OxyphenoniumOxyphenonium may increase the anticholinergic activities of Glycopyrronium.
PancuroniumThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Pancuronium.
PancuroniumPancuronium may increase the anticholinergic activities of Glycopyrronium.
PentazocineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Pentazocine.
PentoliniumThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Pentolinium.
PentoliniumPentolinium may increase the anticholinergic activities of Glycopyrronium.
PethidineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Pethidine.
PhysostigmineThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Physostigmine.
PipecuroniumThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Pipecuronium.
PipecuroniumPipecuronium may increase the anticholinergic activities of Glycopyrronium.
PirenzepineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Pirenzepine.
PirenzepinePirenzepine may increase the anticholinergic activities of Glycopyrronium.
PolythiazideThe serum concentration of Polythiazide can be increased when it is combined with Glycopyrronium.
Potassium ChlorideGlycopyrronium may increase the ulcerogenic activities of Potassium Chloride.
PramlintidePramlintide may increase the anticholinergic activities of Glycopyrronium.
ProcyclidineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Procyclidine.
ProcyclidineProcyclidine may increase the anticholinergic activities of Glycopyrronium.
PropanthelineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Propantheline.
PropanthelinePropantheline may increase the anticholinergic activities of Glycopyrronium.
PyridostigmineThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Pyridostigmine.
QuinethazoneThe serum concentration of Quinethazone can be increased when it is combined with Glycopyrronium.
QuinidineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Quinidine.
QuinidineQuinidine may increase the anticholinergic activities of Glycopyrronium.
RamosetronGlycopyrronium may increase the constipating activities of Ramosetron.
RemifentanilThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Remifentanil.
RivastigmineThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Rivastigmine.
ScopolamineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Scopolamine.
ScopolamineScopolamine may increase the anticholinergic activities of Glycopyrronium.
Scopolamine butylbromideThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Scopolamine butylbromide.
Scopolamine butylbromideScopolamine butylbromide may increase the anticholinergic activities of Glycopyrronium.
SecretinThe therapeutic efficacy of Secretin can be decreased when used in combination with Glycopyrronium.
SolifenacinThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Solifenacin.
SolifenacinSolifenacin may increase the anticholinergic activities of Glycopyrronium.
SufentanilThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Sufentanil.
SulpirideThe therapeutic efficacy of Sulpiride can be decreased when used in combination with Glycopyrronium.
TacrineThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Tacrine.
TapentadolThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Tapentadol.
TiotropiumGlycopyrronium may increase the anticholinergic activities of Tiotropium.
TolterodineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Tolterodine.
TolterodineTolterodine may increase the anticholinergic activities of Glycopyrronium.
TopiramateThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Topiramate.
TramadolThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Tramadol.
TrichlorfonThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Trichlorfon.
TrichlormethiazideThe serum concentration of Trichlormethiazide can be increased when it is combined with Glycopyrronium.
TrihexyphenidylThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Trihexyphenidyl.
TrihexyphenidylTrihexyphenidyl may increase the anticholinergic activities of Glycopyrronium.
TrimethaphanThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Trimethaphan.
TrimethaphanTrimethaphan may increase the anticholinergic activities of Glycopyrronium.
TropicamideThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Tropicamide.
TropicamideTropicamide may increase the anticholinergic activities of Glycopyrronium.
TrospiumThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Trospium.
TrospiumTrospium may increase the anticholinergic activities of Glycopyrronium.
TubocurarineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Tubocurarine.
TubocurarineTubocurarine may increase the anticholinergic activities of Glycopyrronium.
UmeclidiniumThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Umeclidinium.
UmeclidiniumUmeclidinium may increase the anticholinergic activities of Glycopyrronium.
VecuroniumThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Vecuronium.
VecuroniumVecuronium may increase the anticholinergic activities of Glycopyrronium.
Food Interactions
  • Take without regard to meals.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Phosphatidylinositol phospholipase c activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM1
Uniprot ID:
P11229
Molecular Weight:
51420.375 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Ali-Melkkila T, Kanto J, Iisalo E: Pharmacokinetics and related pharmacodynamics of anticholinergic drugs. Acta Anaesthesiol Scand. 1993 Oct;37(7):633-42. [PubMed:8249551 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antagonist
General Function:
Receptor activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM3
Uniprot ID:
P20309
Molecular Weight:
66127.445 Da
References
  1. Haddad EB, Patel H, Keeling JE, Yacoub MH, Barnes PJ, Belvisi MG: Pharmacological characterization of the muscarinic receptor antagonist, glycopyrrolate, in human and guinea-pig airways. Br J Pharmacol. 1999 May;127(2):413-20. [PubMed:10385241 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
binder
General Function:
G-protein coupled acetylcholine receptor activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition. Signaling promotes phospholipase C activity, leading to the release of inositol trisphosphate (IP3); this then trigge...
Gene Name:
CHRM2
Uniprot ID:
P08172
Molecular Weight:
51714.605 Da
References
  1. Haddad EB, Patel H, Keeling JE, Yacoub MH, Barnes PJ, Belvisi MG: Pharmacological characterization of the muscarinic receptor antagonist, glycopyrrolate, in human and guinea-pig airways. Br J Pharmacol. 1999 May;127(2):413-20. [PubMed:10385241 ]
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Drug created on June 13, 2005 07:24 / Updated on September 28, 2016 02:28