Identification

Name
Glycopyrronium
Accession Number
DB00986  (APRD01000, DB06583)
Type
Small Molecule
Groups
Approved, Investigational, Vet Approved
Description

Glycopyrronium (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 IDs
DRM-04 / DRM04
Product Ingredients
IngredientUNIICASInChI Key
Glycopyrronium bromide68EL47CXSP51186-83-5VPNYRYCIDCJBOM-QQTWVUFVSA-M
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CuvposaSolution1 mgOralPediapharm IncNot applicableNot applicableCanada
CuvposaLiquid1 mg/5mLOralMerz Pharmaceuticals2013-01-01Not applicableUs
Enurev BreezhalerCapsule44 microgramsRespiratory (inhalation)Novartis Europharm Limited2012-09-28Not applicableEu
Enurev BreezhalerCapsule44 microgramsRespiratory (inhalation)Novartis Europharm Limited2012-09-28Not applicableEu
Enurev BreezhalerCapsule44 microgramsRespiratory (inhalation)Novartis Europharm Limited2012-09-28Not applicableEu
Enurev BreezhalerCapsule44 microgramsRespiratory (inhalation)Novartis Europharm Limited2012-09-28Not applicableEu
Enurev BreezhalerCapsule44 microgramsRespiratory (inhalation)Novartis Europharm Limited2012-09-28Not applicableEu
Enurev BreezhalerCapsule44 microgramsRespiratory (inhalation)Novartis Europharm Limited2012-09-28Not applicableEu
Enurev BreezhalerCapsule44 microgramsRespiratory (inhalation)Novartis Europharm Limited2012-09-28Not applicableEu
Enurev BreezhalerCapsule44 microgramsRespiratory (inhalation)Novartis Europharm Limited2012-09-28Not applicableEu
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
GlycateTablet1.5 mg/1OralNuro Pharma, Inc.2012-03-12Not applicableUs
GlycopyrrolateInjection.2 mg/mLIntramuscular; IntravenousWest Ward Pharmaceutical2011-09-21Not applicableUs
GlycopyrrolateTablet1 mg/1OralDr Reddy's Laboratories2008-07-14Not applicableUs
GlycopyrrolateInjection1 mg/5mLIntramuscular; IntravenousAmneal Biosciences2017-06-15Not applicableUs
GlycopyrrolateTablet2 mg/1OralAv Kare, Inc.2015-05-14Not applicableUs64125 0140 01 nlmimage10 a745d3ee
GlycopyrrolateTablet2 mg/1Oralbryant ranch prepack2006-09-26Not applicableUs
GlycopyrrolateInjection.2 mg/mLIntramuscular; IntravenousWest Ward Pharmaceutical2015-06-01Not applicableUs
GlycopyrrolateTablet1 mg/1OralMajor2012-10-01Not applicableUs
GlycopyrrolateInjection, solution1 mg/5mLIntramuscular; IntravenousCardinal Health2011-10-25Not applicableUs
GlycopyrrolateTablet2 mg/1OralAmerincan Health Packaging2015-03-312015-12-29Us
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
GlycopyrrolateInjection, solution.2 mg/mLIntramuscular; IntravenousFresenius Kabi2017-10-27Not applicableUs
Seebri NeohalerCapsule15.6 ug/1Respiratory (inhalation)Sunovion Pharmacueticals Inc.2017-10-03Not applicableUs
International/Other Brands
Acpan (Gray) / Nodapton / Robanul / Robinal / Tarodyl (Lundbeck)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Bevespi AerosphereGlycopyrronium bromide (9 ug/1) + Formoterol fumarate (4.8 ug/1)Aerosol, meteredRespiratory (inhalation)Astra Zeneca Lp2016-10-03Not applicableUs
Ultibro BreezhalerGlycopyrronium (50 mcg) + Indacaterol (110 mcg)Capsule; KitRespiratory (inhalation)Novartis2014-03-05Not applicableCanada
Utibron NeohalerGlycopyrronium bromide (15.6 ug/1) + Indacaterol Maleate (27.5 ug/1)CapsuleRespiratory (inhalation)Novartis2015-10-29Not applicableUs
Utibron NeohalerGlycopyrronium bromide (15.6 ug/1) + Indacaterol Maleate (27.5 ug/1)CapsuleRespiratory (inhalation)Sunovion2017-04-03Not applicableUs
Categories
UNII
HTB34557V4
CAS number
740028-90-4
Weight
Average: 318.436
Monoisotopic: 318.206370186
Chemical Formula
C19H28NO3
InChI Key
ANGKOCUUWGHLCE-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][[email protected]@]1(CC[N+](C)(C)C1)OC(=O)[[email protected]@](O)(C1CCCC1)C1=CC=CC=C1

Pharmacology

Indication

For 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).

Structured Indications
Pharmacodynamics

Glycopyrrolate 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 action

Glycopyrrolate 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.

TargetActionsOrganism
AMuscarinic acetylcholine receptor M1
antagonist
Human
UMuscarinic acetylcholine receptor M3
antagonist
Human
UMuscarinic acetylcholine receptor M2
binder
Human
Absorption

Rapidly absorbed (1-2 minutes) after intravenous injection

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life

0.6-1.2 hours

Clearance
Not Available
Toxicity

Side 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
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
1,10-PhenanthrolineThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with 1,10-Phenanthroline.Experimental
AclidiniumGlycopyrronium may increase the anticholinergic activities of Aclidinium.Approved
AlcuroniumAlcuronium may increase the anticholinergic activities of Glycopyrronium.Experimental
AlfentanilThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Alfentanil.Approved, Illicit
AlphacetylmethadolThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Alphacetylmethadol.Experimental, Illicit
AlphaprodineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Alphaprodine.Illicit
AmantadineAmantadine may increase the anticholinergic activities of Glycopyrronium.Approved
AmbenoniumThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Ambenonium.Approved
Anisotropine MethylbromideAnisotropine Methylbromide may increase the anticholinergic activities of Glycopyrronium.Approved
AtenololThe serum concentration of Atenolol can be increased when it is combined with Glycopyrronium.Approved
AtracuriumAtracurium may increase the anticholinergic activities of Glycopyrronium.Experimental, Investigational
Atracurium besylateAtracurium besylate may increase the anticholinergic activities of Glycopyrronium.Approved
AtropineAtropine may increase the anticholinergic activities of Glycopyrronium.Approved, Vet Approved
BenactyzineBenactyzine may increase the anticholinergic activities of Glycopyrronium.Withdrawn
BendroflumethiazideThe serum concentration of Bendroflumethiazide can be increased when it is combined with Glycopyrronium.Approved
BenzatropineBenzatropine may increase the anticholinergic activities of Glycopyrronium.Approved
BezitramideThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Bezitramide.Experimental, Illicit, Withdrawn
BiperidenBiperiden may increase the anticholinergic activities of Glycopyrronium.Approved, Investigational
BornaprineBornaprine may increase the anticholinergic activities of Glycopyrronium.Experimental
Botulinum Toxin Type AGlycopyrronium may increase the anticholinergic activities of Botulinum Toxin Type A.Approved, Investigational
Botulinum Toxin Type BGlycopyrronium may increase the anticholinergic activities of Botulinum Toxin Type B.Approved
BuprenorphineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Buprenorphine.Approved, Illicit, Investigational, Vet Approved
ButorphanolThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Butorphanol.Approved, Illicit, Vet Approved
ButylscopolamineScopolamine butylbromide may increase the anticholinergic activities of Glycopyrronium.Approved, Vet Approved
CarfentanilThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Carfentanil.Illicit, Investigational, Vet Approved
ChlorothiazideThe serum concentration of Chlorothiazide can be increased when it is combined with Glycopyrronium.Approved, Vet Approved
ChlorphenoxamineChlorphenoxamine may increase the anticholinergic activities of Glycopyrronium.Withdrawn
ChlorthalidoneThe serum concentration of Chlorthalidone can be increased when it is combined with Glycopyrronium.Approved
CimetropiumGlycopyrronium may increase the anticholinergic activities of Cimetropium.Experimental, Investigational
CodeineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Codeine.Approved, Illicit
CoumaphosThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Coumaphos.Vet Approved
CyclopenthiazideThe serum concentration of Cyclopenthiazide can be increased when it is combined with Glycopyrronium.Experimental
CyclopentolateCyclopentolate may increase the anticholinergic activities of Glycopyrronium.Approved
DarifenacinDarifenacin may increase the anticholinergic activities of Glycopyrronium.Approved, Investigational
DecamethoniumThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Decamethonium.Approved
DemecariumThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Demecarium.Approved
DesloratadineDesloratadine may increase the anticholinergic activities of Glycopyrronium.Approved, Investigational
DexetimideDexetimide may increase the anticholinergic activities of Glycopyrronium.Withdrawn
DextromoramideThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Dextromoramide.Experimental, Illicit
DextropropoxypheneThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Dextropropoxyphene.Approved, Illicit, Investigational, Withdrawn
DezocineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Dezocine.Approved, Investigational
DichlorvosThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Dichlorvos.Vet Approved
DicyclomineDicyclomine may increase the anticholinergic activities of Glycopyrronium.Approved
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Glycopyrronium.Approved
DihydrocodeineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Dihydrocodeine.Approved, Illicit
DihydroetorphineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Dihydroetorphine.Experimental, Illicit
DihydromorphineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Dihydromorphine.Experimental, Illicit
DiphenoxylateThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Diphenoxylate.Approved, Illicit
DistigmineThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Distigmine.Experimental
DonepezilThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Donepezil.Approved
DPDPEThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with DPDPE.Experimental
DronabinolGlycopyrronium may increase the tachycardic activities of Dronabinol.Approved, Illicit
EchothiophateThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Echothiophate.Approved
EdrophoniumThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Edrophonium.Approved
EluxadolineGlycopyrronium may increase the constipating activities of Eluxadoline.Approved
EmeproniumEmepronium may increase the anticholinergic activities of Glycopyrronium.Experimental
EtanautineEtanautine may increase the anticholinergic activities of Glycopyrronium.Experimental
EthopropazineEthopropazine may increase the anticholinergic activities of Glycopyrronium.Approved
EthylmorphineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Ethylmorphine.Approved, Illicit
EtorphineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Etorphine.Illicit, Vet Approved
EtybenzatropineEtybenzatropine may increase the anticholinergic activities of Glycopyrronium.Experimental
FentanylThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Fentanyl.Approved, Illicit, Investigational, Vet Approved
FenthionThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Fenthion.Vet Approved
FesoterodineFesoterodine may increase the anticholinergic activities of Glycopyrronium.Approved
GalantamineThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Galantamine.Approved
GallamineGallamine may increase the anticholinergic activities of Glycopyrronium.Experimental
Gallamine TriethiodideGallamine Triethiodide may increase the anticholinergic activities of Glycopyrronium.Approved
Glucagon recombinantThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Glucagon recombinant.Approved
HaloperidolThe serum concentration of Haloperidol can be decreased when it is combined with Glycopyrronium.Approved
HeroinThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Heroin.Approved, Illicit, Investigational
HexamethoniumHexamethonium may increase the anticholinergic activities of Glycopyrronium.Experimental
HomatropineHomatropine may increase the anticholinergic activities of Glycopyrronium.Approved
Huperzine AThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Huperzine A.Investigational
HydrochlorothiazideThe serum concentration of Hydrochlorothiazide can be increased when it is combined with Glycopyrronium.Approved, Vet Approved
HydrocodoneThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Hydrocodone.Approved, Illicit
HydroflumethiazideThe serum concentration of Hydroflumethiazide can be increased when it is combined with Glycopyrronium.Approved, Investigational
HydromorphoneThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Hydromorphone.Approved, Illicit
HyoscyamineHyoscyamine may increase the anticholinergic activities of Glycopyrronium.Approved
IndapamideThe serum concentration of Indapamide can be increased when it is combined with Glycopyrronium.Approved
IpidacrineThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Ipidacrine.Experimental
Ipratropium bromideIpratropium bromide may increase the anticholinergic activities of Glycopyrronium.Approved
IsoflurophateThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Isoflurophate.Approved, Investigational, Withdrawn
ItoprideThe therapeutic efficacy of Itopride can be decreased when used in combination with Glycopyrronium.Investigational
KetobemidoneThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Ketobemidone.Approved, Investigational
LevodopaThe serum concentration of Levodopa can be decreased when it is combined with Glycopyrronium.Approved
Levomethadyl AcetateThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Levomethadyl Acetate.Approved, Investigational
LevorphanolThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Levorphanol.Approved
LofentanilThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Lofentanil.Illicit
MalathionThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Malathion.Approved, Investigational
MazaticolMazaticol may increase the anticholinergic activities of Glycopyrronium.Experimental
MecamylamineMecamylamine may increase the anticholinergic activities of Glycopyrronium.Approved
MefloquineThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Mefloquine.Approved
MemantineThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Memantine.Approved, Investigational
MeptazinolThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Meptazinol.Experimental
MetforminThe serum concentration of Metformin can be increased when it is combined with Glycopyrronium.Approved
MethadoneThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Methadone.Approved
Methadyl AcetateThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Methadyl Acetate.Approved, Illicit
Methanesulfonyl FluorideThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Methanesulfonyl Fluoride.Investigational
MethanthelineMethantheline may increase the anticholinergic activities of Glycopyrronium.Approved, Investigational
MethyclothiazideThe serum concentration of Methyclothiazide can be increased when it is combined with Glycopyrronium.Approved
Methylscopolamine bromideMethylscopolamine bromide may increase the anticholinergic activities of Glycopyrronium.Approved
MetixeneMetixene may increase the anticholinergic activities of Glycopyrronium.Approved
MetoclopramideThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Metoclopramide.Approved, Investigational
MetolazoneThe serum concentration of Metolazone can be increased when it is combined with Glycopyrronium.Approved
MianserinMianserin may increase the anticholinergic activities of Glycopyrronium.Approved, Investigational
MinaprineThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Minaprine.Approved
MirabegronThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Mirabegron.Approved
MorphineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Morphine.Approved, Investigational
NabiloneGlycopyrronium may increase the tachycardic activities of Nabilone.Approved, Investigational
NalbuphineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Nalbuphine.Approved
NeostigmineThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Neostigmine.Approved, Vet Approved
NicomorphineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Nicomorphine.Experimental
NormethadoneThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Normethadone.Approved, Illicit
OpiumThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Opium.Approved, Illicit
OrphenadrineOrphenadrine may increase the anticholinergic activities of Glycopyrronium.Approved
OtiloniumOtilonium may increase the anticholinergic activities of Glycopyrronium.Experimental, Investigational
OxitropiumOxitropium may increase the anticholinergic activities of Glycopyrronium.Investigational
OxybutyninOxybutynin may increase the anticholinergic activities of Glycopyrronium.Approved, Investigational
OxycodoneThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Oxycodone.Approved, Illicit, Investigational
OxymorphoneThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Oxymorphone.Approved, Investigational, Vet Approved
OxyphenoniumOxyphenonium may increase the anticholinergic activities of Glycopyrronium.Approved
PancuroniumPancuronium may increase the anticholinergic activities of Glycopyrronium.Approved
ParaoxonThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Paraoxon.Experimental
PentazocineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Pentazocine.Approved, Vet Approved
PentoliniumPentolinium may increase the anticholinergic activities of Glycopyrronium.Approved
PethidineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Pethidine.Approved
PhenazocineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Phenazocine.Experimental
PhenglutarimidePhenglutarimide may increase the anticholinergic activities of Glycopyrronium.Experimental
PhenoperidineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Phenoperidine.Experimental
PhysostigmineThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Physostigmine.Approved
PipecuroniumPipecuronium may increase the anticholinergic activities of Glycopyrronium.Approved
PirenzepinePirenzepine may increase the anticholinergic activities of Glycopyrronium.Approved
PiritramideThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Piritramide.Investigational
PolythiazideThe serum concentration of Polythiazide can be increased when it is combined with Glycopyrronium.Approved
Potassium ChlorideThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Potassium Chloride.Approved, Withdrawn
PramlintidePramlintide may increase the anticholinergic activities of Glycopyrronium.Approved, Investigational
ProcyclidineProcyclidine may increase the anticholinergic activities of Glycopyrronium.Approved
PropanthelinePropantheline may increase the anticholinergic activities of Glycopyrronium.Approved
PropiverinePropiverine may increase the anticholinergic activities of Glycopyrronium.Approved, Investigational
PyridostigmineThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Pyridostigmine.Approved
QuinethazoneThe serum concentration of Quinethazone can be increased when it is combined with Glycopyrronium.Approved
QuinidineQuinidine may increase the anticholinergic activities of Glycopyrronium.Approved
RamosetronGlycopyrronium may increase the constipating activities of Ramosetron.Approved, Investigational
RemifentanilThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Remifentanil.Approved
RivastigmineThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Rivastigmine.Approved, Investigational
ScopolamineScopolamine may increase the anticholinergic activities of Glycopyrronium.Approved
SecretinThe therapeutic efficacy of Secretin can be decreased when used in combination with Glycopyrronium.Approved, Investigational
SolifenacinSolifenacin may increase the anticholinergic activities of Glycopyrronium.Approved
SufentanilThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Sufentanil.Approved, Investigational
SulpirideThe therapeutic efficacy of Sulpiride can be decreased when used in combination with Glycopyrronium.Approved, Investigational
TacrineThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Tacrine.Investigational, Withdrawn
TapentadolThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Tapentadol.Approved
TilidineThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Tilidine.Experimental
TiotropiumGlycopyrronium may increase the anticholinergic activities of Tiotropium.Approved
TolterodineTolterodine may increase the anticholinergic activities of Glycopyrronium.Approved, Investigational
TopiramateThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Topiramate.Approved
TramadolThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Tramadol.Approved, Investigational
TrichlorfonThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Trichlorfon.Vet Approved
TrichlormethiazideThe serum concentration of Trichlormethiazide can be increased when it is combined with Glycopyrronium.Approved, Vet Approved
TrihexyphenidylTrihexyphenidyl may increase the anticholinergic activities of Glycopyrronium.Approved
TrimethaphanTrimethaphan may increase the anticholinergic activities of Glycopyrronium.Approved, Investigational
TropatepineTropatepine may increase the anticholinergic activities of Glycopyrronium.Experimental
TropicamideTropicamide may increase the anticholinergic activities of Glycopyrronium.Approved
TrospiumTrospium may increase the anticholinergic activities of Glycopyrronium.Approved
TubocurarineTubocurarine may increase the anticholinergic activities of Glycopyrronium.Approved
UmeclidiniumGlycopyrronium may increase the anticholinergic activities of Umeclidinium.Approved
VecuroniumVecuronium may increase the anticholinergic activities of Glycopyrronium.Approved
Food Interactions
  • Take without regard to meals.

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
KEGG Drug
D00540
PubChem Compound
9933193
PubChem Substance
46509133
ChemSpider
8108821
ChEMBL
CHEMBL1201027
Therapeutic Targets Database
DAP001116
PharmGKB
PA164754882
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Glycopyrrolate
ATC Codes
R03BB06 — Glycopyrronium bromideR03AL04 — Indacaterol and glycopyrronium bromideA03CA05 — Glycopyrronium bromide and psycholepticsA03AB02 — Glycopyrronium bromide
AHFS Codes
  • 48:12.08 — Anticholinergic Agents
  • 12:08.08 — Antimuscarinics Antispasmodics
FDA label
Download (193 KB)
MSDS
Download (73.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentNeurogenic Bowel Dysfunction / Spinal Cord Injuries (SCI)1
1CompletedNot AvailableChronic Obstructive Pulmonary Disease (COPD)1
1CompletedNot AvailableImpaired Renal Function1
1CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)7
1CompletedTreatmentHealthy Volunteers2
1RecruitingNot AvailableGastrointestinal Dysfunction1
1RecruitingTreatmentNeurogenic Bowel Dysfunction / Spinal Cord Injuries (SCI)1
1TerminatedTreatmentDepression / Hyperhydrosis1
1, 2CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
1, 2Not Yet RecruitingTreatmentSialorrhea1
2CompletedTreatmentAsthma Bronchial1
2CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)10
2CompletedTreatmentPulmonary Disease, Chronic Obstructive1
2CompletedTreatmentUrological Surgery1
2RecruitingTreatmentParkinson's Disease (PD) / Sialorrhea1
2, 3Not Yet RecruitingDiagnosticChronic Obstructive Pulmonary Disease (COPD)1
3CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)26
3CompletedTreatmentChronic Obstructive Pulmonary Disease: COPD1
3CompletedTreatmentHyperhidrosis3
3CompletedTreatmentSurgical Procedures, Elective1
3RecruitingTreatmentCOPD (Chronic Obstructive Pulmonary Disease)1
3RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
3RecruitingTreatmentGeneral Surgery1
3WithdrawnTreatmentAsthma Bronchial1
3WithdrawnTreatmentChronic Obstructive Pulmonary Disease (COPD)1
3WithdrawnTreatmentPulmonary Disease, Chronic Obstructive1
4CompletedSupportive CareBMI >30 kg/m2 / Cerebral Tissue Oxygenation / Laparoscopic Gastric Bypass Surgery / Respiratory Function / Surgical Conditions1
4CompletedTreatmentAirway Reflexes, Protective / Anesthetic Recovery / Recovery After Neuromuscular Block1
4CompletedTreatmentAnaesthesia1
4CompletedTreatmentAsthma Bronchial2
4CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)7
4CompletedTreatmentGall Stone Disease1
4CompletedTreatmentPulmonary Disease, Chronic Obstructive1
4Enrolling by InvitationTreatmentNeuromuscular Blockade1
4Not Yet RecruitingNot AvailableChronic Obstructive Pulmonary Disease (COPD)1
4Not Yet RecruitingPreventionEmergence Delirium1
4Not Yet RecruitingPreventionPulmonary Complications1
4Not Yet RecruitingTreatmentAnaesthesia therapy / Neuromuscular Blockade1
4Not Yet RecruitingTreatmentNeuromuscular Blockade2
4Not Yet RecruitingTreatmentReversal of Neuromuscular Blockade1
4RecruitingSupportive CareBladder Cancers / Malignant Neoplasms of Urinary Tract1
4RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)3
4RecruitingTreatmentMicrolaryngoscopy / Rigid Bronchoscopy1
4RecruitingTreatmentNausea / Vomiting1
4RecruitingTreatmentNeuromuscular Blockade1
4RecruitingTreatmentPulmonary Disease, Chronic Obstructive1
4Unknown StatusSupportive CareAnesthesia Recovery Period1
4Unknown StatusTreatmentAnesthesia Recovery1
Not AvailableActive Not RecruitingPreventionSpinal Anaesthesia1
Not AvailableCompletedNot AvailableRhytidoplasty1
Not AvailableCompletedBasic ScienceHeart Failure, Unspecified1
Not AvailableCompletedPreventionFevers1
Not AvailableCompletedSupportive CareSialorrhea1
Not AvailableCompletedTreatmentSedation, Bronchoscopy1
Not AvailableRecruitingPreventionArterial Hypotension1
Not AvailableRecruitingPreventionSpinal Anaesthesia1
Not AvailableRecruitingSupportive CareCholecystitis, Acute1
Not AvailableUnknown StatusPreventionAnaesthesia therapy / Catheter Site Discomfort / Complications / Urinary Bladder Neoplasms1

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
Aerosol, meteredRespiratory (inhalation)
LiquidOral1 mg/5mL
SolutionOral1 mg
CapsuleRespiratory (inhalation)44 micrograms
TabletOral1.5 mg/1
InjectionIntramuscular; Intravenous.2 mg/mL
InjectionIntramuscular; Intravenous.4 mg/2mL
InjectionIntramuscular; Intravenous1 mg/5mL
InjectionIntramuscular; Intravenous4 mg/20mL
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
TabletOral2 mg/1
LiquidIntramuscular; Intravenous0.2 mg
LiquidIntramuscular; Intravenous.2 mg
TabletOral2 mg
TabletOral1 mg
CapsuleRespiratory (inhalation)50 mcg
CapsuleRespiratory (inhalation)15.6 ug/1
SolutionOral320 μg/ml
Capsule; kitRespiratory (inhalation)
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)
US7091236No2004-04-242024-04-24Us
US6878721No2000-10-102020-10-10Us
US6528678No1998-04-242018-04-24Us
US8067437No2000-06-022020-06-02Us
US8658673No2000-06-022020-06-02Us
US8796307No2000-06-022020-06-02Us
US8479730No2008-10-112028-10-11Us
US7638552No2003-08-202023-08-20Us
US7816396No2003-08-202023-08-20Us
US7229607No2001-04-092021-04-09Us
US7820694No2000-06-022020-06-02Us
US8029768No2001-04-092021-04-09Us
US8283362No2000-06-022020-06-02Us
US7736670No2001-06-272021-06-27Us
US8435567No2001-06-272021-06-27Us
US8303991No2001-06-272021-06-27Us
US8956661No2001-06-272021-06-27Us
US8580306No2001-06-272021-06-27Us
US6582678No1998-04-242018-04-24Us
US8182838No2008-10-202028-10-20Us
US6521260No1996-01-312016-01-31Us
US8048451No2001-06-272021-06-27Us
US9463161No2010-05-282030-05-28Us
US9415009No2010-05-282030-05-28Us
US8808713No2010-05-282030-05-28Us
US8324266No2010-05-282030-05-28Us
US8703806No2010-05-282030-05-28Us
US8815258No2011-03-172031-03-17Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)193-194.5U.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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Not Available
Direct Parent
Benzene and substituted derivatives
Alternative Parents
N-alkylpyrrolidines / Tetraalkylammonium salts / Tertiary alcohols / Carboxylic acid esters / Monocarboxylic acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organic salts / Organic oxides / Hydrocarbon derivatives
show 4 more
Substituents
Monocyclic benzene moiety / N-alkylpyrrolidine / Pyrrolidine / Quaternary ammonium salt / Tertiary alcohol / Tetraalkylammonium salt / Carboxylic acid ester / Organoheterocyclic compound / Azacycle / Carboxylic acid derivative
show 15 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

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...
Gene Name
CHRM1
Uniprot ID
P11229
Uniprot Name
Muscarinic acetylcholine receptor M1
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...
Gene Name
CHRM3
Uniprot ID
P20309
Uniprot Name
Muscarinic acetylcholine receptor M3
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...
Gene Name
CHRM2
Uniprot ID
P08172
Uniprot Name
Muscarinic acetylcholine receptor M2
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]

Drug created on June 13, 2005 07:24 / Updated on December 11, 2017 12:53