Identification

Name
Glycopyrronium
Accession Number
DB00986
Description

Glycopyrronium, also known as NVA237 or glycopyrrolate, is a racemic mixture of two enantiomers.15 They are both quaternary ammonium compounds and long acting muscarinic antagonists.15 It is one of the most commonly prescribed anticholinergic medications.2,3 Early research into glycopyrronium use was for its indication as an adjunct therapy in the treatment of peptic ulcers.9,10 Later research, taking advantage of the systemic distribution of muscarinic receptors through the body, found that glycopyrronium could also be used for reducing sweat gland,12 oral,18 airway, and gastric secretions;17 as well as reducing cardiac inhibitory reflexes;17 and reducing bronchoconstriction in COPD.13 Glycopyrronium is commonly prescribed as a first line treatment for a wide variety indications and is considered to have a wider therapeutic window than tiotropium.8

Glycopyrronium was originally granted FDA approval on 11 August 1961.10

Type
Small Molecule
Groups
Approved, Investigational, Vet approved
Structure
Thumb
Weight
Average: 318.4305
Monoisotopic: 318.206918767
Chemical Formula
C19H28NO3
Synonyms
  • Glicopirronio
  • Glycopyrrolate cation
  • Glycopyrrolate ion
  • Glycopyrronium
  • Glycopyrronium cation
  • Glycopyrronium ion
External IDs
  • DRM-04
  • DRM04

Pharmacology

Pharmacology
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Indication

Glycopyrronium formulated as a topical cloth is indicated to treat primary axillary hyperhidrosis in patients ≥9 years,12 and an inhalational solution is indicated for long term maintenance of airflow obstruction in COPD.13 A glycopyrronium intravenous and intramuscular injection is indicated in adults and pediatric patients to reduce the volume and acidity of gastric secretions, reduce airway secretions, and block cardiac inhibitory reflexes during the induction of anesthesia and intubation; to treat surgically-induced, drug-induced, or vagal reflex associated arrhythmias intraoperatively; and to prevent peripheral muscarinic effects of cholinergic drugs.17 The same injection is indicated in adults as an adjunct therapy in the treatment of peptic ulcers.17 An oral solution is indicated to treat excessive drooling associated with neurologic conditions in patients aged 3-16 years.18 Glycopyrronium and budesonide19 can be formulated with formoterol fumarate for the maintenance of COPD.20

Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
Contraindications & Blackbox Warnings
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Pharmacodynamics

Glycopyrronium is a quaternary ammonium compound that is one of the most commonly prescribed long acting muscarinic antagonists.2,3,15 Glycopyrronium slowly dissociated from muscarinic receptors, leading to a long duration of action.1 It has a wider therapeutic index than other anticholinergic medications, such as tiotropium.8 Patients should be counselled regarding the risk of worsening urinary retention, risk of overheating, and transient blurred vision.12

Mechanism of action

Glycopyrronium is a muscarinic antagonist with the highest affinity for M1 receptors, followed by M3, M2/M4, and M5.16

Muscarinic receptors M1 to M4 are found in the lung, although M3 is predominantly responsible for bronchoconstriction and airway secretions.1,19,16 Secretions from salivary4 and sweat5 glands, as well as gastric acid secretions,6 are also predominantly mediated by the M3 receptor. Salivary4 and gastric acid6 secretions are also partially mediated by the M1 receptor. Antagonism of these receptors decreases the volume of their respective secretions, and in the case of the gastrointestinal system, reduces the acidity of the stomach.7

In the cardiovascular system, muscarinic receptors M1 to M5 are all present, however the function of M5 has not been described in literature.7 Under normal circumstances, stimulation of the vagal nerve lowers the heart rate, potentially leading to intraoperative bradycardia.7 Studies in mice suggest that this stimulation is predominantly mediated by the M3 receptor, and mutant knockout mice are not susceptible to these effects.7

TargetActionsOrganism
AMuscarinic acetylcholine receptor M1
antagonist
Humans
AMuscarinic acetylcholine receptor M3
antagonist
Humans
AMuscarinic acetylcholine receptor M2
antagonist
Humans
AMuscarinic acetylcholine receptor M4
antagonist
Humans
UMuscarinic acetylcholine receptor M5
antagonist
Humans
Absorption

In adults, a 66 mg topical dose of glycopyrronium reaches a Cmax of 0.08 ± 0.04 ng/mL, with a Tmax of 1 hour, and an AUC0-24 of 0.88 ± 0.57 h*ng/mL.12

Inhaled glycopyrronium is approximately 40% bioavailable.15 A 25 µg inhaled solution reaches a Cmax of 34.5 pg/mL, with a Tmax of <20 minutes, and an AUC0-inf of 255 h*pg/mL.13

An 8 µg/kg intramuscular dose reaches a Cmax of 3.47 ± 1.48 µg/L, with a Tmax of 27.48 ± 6.12 minutes, and an AUC of 6.64 ± 2.33 h*g/L.17

Oral glycopyrronium has highly variable pharmacokinetics, reaching a mean Cmax of 0.318 ng/mL, a Tmax of 3.1 hours, and an AUC0-24 of 1.74 h*ng/mL.18

Volume of distribution

The mean volume of distribution in patients aged 1-14 years old is 1.3-1.8 L/kg, with a range of 0.7-3.9 L/kg.12 The volume of distribution in adults aged 60-75 years is 0.42 ± 0.22 L/kg.12

Protein binding

Glycopyrronium is 38-44% protein bound in plasma.15 It is bound to serum albumin, alpha-1-acid glycoprotein, as well as other plasma proteins that have not been identified in literature.16

Metabolism

Glycopyrronium is hydrolyzed to the inactive M9 metabolite.15,16 Metabolism was mainly mediated by CYP2D6, with minor contributions from CYP1A2, CYP2B6, CYP2C9, CYP2C18, CYP2C19, and CYP3A4.15,16

Hover over products below to view reaction partners

Route of elimination

85% of an intravenous dose was recovered in the urine, with <5% recovered in the bile.12 >80% of the recovered dose is the unchanged parent drug.12 The remainder is recovered as the inactive M9 metabolite.15,16

Half-life

The half life after inhalation is approximately 33-53 hours.15 The mean half life of a 6 µg/kg intravenous dose is 0.83 ± 0.27 hours.17 The mean half life of oral glycopyrronium is 3.0 hours.18

Clearance

A 6 µg/kg intravenous dose has a clearance of 0.54 ± 0.14 L/kg/h.17 An oral solution has a clearance of 5.28-38.95 L/h/kg in healthy adults and 8.07-25.65 L/h/kg in patients with cerebral palsy.18

Adverse Effects
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Toxicity

Patients presenting with an overdose typically present with flushing, hyperthermia, tachycardia, ileus, urinary retention, loss of ocular accommodation, light sensitivity, mydriasis, nausea, vomiting, dizziness, light headedness, and obstipation.12,13 Patients should be treated with symptomatic and supportive therapy, which may include the use of catheters for urinary retention, cardiovascular support, airway maintenance, ventilation, or neostigmine.12

The oral LD50 in mice is 570 mg/kg, and in rats is 709 mg/kg.14 The intraperitoneal LD50 in mice is 90 mg/kg, and in rats is 196 mg/kg.14

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcetazolamideAcetazolamide may increase the central nervous system depressant (CNS depressant) activities of Glycopyrronium.
AcetophenazineAcetophenazine may increase the central nervous system depressant (CNS depressant) activities of Glycopyrronium.
AclidiniumThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Aclidinium.
AdenosineThe risk or severity of Tachycardia can be increased when Adenosine is combined with Glycopyrronium.
AgomelatineAgomelatine may increase the central nervous system depressant (CNS depressant) activities of Glycopyrronium.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Glycopyrronium.
AlimemazineAlimemazine may increase the central nervous system depressant (CNS depressant) activities of Glycopyrronium.
AlloinThe therapeutic efficacy of Alloin can be decreased when used in combination with Glycopyrronium.
AlmotriptanAlmotriptan may increase the central nervous system depressant (CNS depressant) activities of Glycopyrronium.
AlosetronAlosetron may increase the central nervous system depressant (CNS depressant) activities of Glycopyrronium.
Interactions
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Food Interactions
  • Take with or without food. The absorption is unaffected by food.

Products

Products
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Product Ingredients
IngredientUNIICASInChI Key
Glycopyrronium bromideV92SO9WP2I51186-83-5VPNYRYCIDCJBOM-UHFFFAOYSA-M
Glycopyrronium tosylate1PVF6JLU7B1624259-25-1UOWOLENSDISMPG-UHFFFAOYSA-M
Product Images
International/Other Brands
Acpan (Gray) / Nodapton / Robanul / Robinal / Tarodyl (Lundbeck)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CuvposaLiquid1 mg/5mLOralMerz Pharmaceuticals, LLC2013-01-01Not applicableUS flag
CuvposaSolution1 mg/5mLOralShionogi Pharma, Inc.2010-07-282014-06-30US flag
CuvposaSolution1 mgOralMedexus Pharmaceuticals Inc2018-04-03Not applicableCanada flag
Enurev BreezhalerCapsule44 microgramsRespiratory (inhalation)Novartis Europharm Limited2016-09-08Not applicableEU flag
Enurev BreezhalerCapsule44 microgramsRespiratory (inhalation)Novartis Europharm Limited2016-09-08Not applicableEU flag
Enurev BreezhalerCapsule44 microgramsRespiratory (inhalation)Novartis Europharm Limited2016-09-08Not applicableEU flag
Enurev BreezhalerCapsule44 microgramsRespiratory (inhalation)Novartis Europharm Limited2016-09-08Not applicableEU flag
Enurev BreezhalerCapsule44 microgramsRespiratory (inhalation)Novartis Europharm Limited2016-09-08Not applicableEU flag
Enurev BreezhalerCapsule44 microgramsRespiratory (inhalation)Novartis Europharm Limited2016-09-08Not applicableEU flag
Enurev BreezhalerCapsule44 microgramsRespiratory (inhalation)Novartis Europharm Limited2016-09-08Not applicableEU flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
GlycateTablet1.5 mg/1OralCarWin Pharmaceutical Associates, LLC2018-06-10Not applicableUS flag
GlycateTablet1.5 mg/1OralNuro Pharma, Inc.2012-03-12Not applicableUS flag
GlycopyrrolateInjection, solution0.2 mg/1mLIntramuscular; IntravenousMedical Purchasing Solutions, Llc2019-07-11Not applicableUS flag
GlycopyrrolateInjection, solution0.2 mg/1mLIntramuscular; IntravenousAuroMedics Pharma LLC2018-11-28Not applicableUS flag
GlycopyrrolateInjection0.2 mg/1mLIntramuscular; IntravenousMedical Purchasing Solutions, Llc2020-09-09Not applicableUS flag
GlycopyrrolateTablet1 mg/1OralDr Reddy's Laboratories2008-07-14Not applicableUS flag
GlycopyrrolateInjection0.2 mg/1mLIntramuscular; IntravenousMeitheal Pharmaceuticals Inc.2019-05-15Not applicableUS flag
GlycopyrrolateInjection1 mg/5mLIntramuscular; IntravenousGeneral Injectables and Vaccines, Inc.2018-09-17Not applicableUS flag
GlycopyrrolateTablet1 mg/1OralMajor Pharmaceuticals2016-03-182019-03-31US flag
GlycopyrrolateTablet1 mg/1OralRemedy Repack2013-10-042014-10-04US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Bevespi AerosphereGlycopyrronium (7.2 mcg) + Formoterol fumarate (5.0 mcg)Respiratory (inhalation)Astra Zeneca Ab2020-12-16Not applicableEU flag
Bevespi AerosphereGlycopyrronium bromide (9 ug/1) + Formoterol fumarate (4.8 ug/1)Aerosol, meteredRespiratory (inhalation)AstraZeneca Pharmaceuticals LP2016-10-03Not applicableUS flag
Bevespi AerosphereGlycopyrronium bromide (8.3 mcg) + Formoterol fumarate (5.8 mcg)Aerosol, meteredRespiratory (inhalation)Astra ZenecaNot applicableNot applicableCanada flag
Bevespi AerosphereGlycopyrronium (7.2 mcg) + Formoterol fumarate (5.0 mcg)Respiratory (inhalation)Astra Zeneca Ab2020-12-16Not applicableEU flag
BEVESPİ AEROSPHERE® 7.2 MCG/5.0 MCG BASINÇLI İNHALASYON SÜSPANSİYONU ,120 DOZGlycopyrronium (7.2 mcg) + Formoterol fumarate (5 mcg)Aerosol, meteredRespiratory (inhalation)ASTRAZENECA İLAÇ SAN. VE TİC. LTD. ŞTİ.2020-08-14Not applicableTurkey flag
BİXBRİ NEOHALER 85 MCG/43 MCG İNHALER KAPSÜLGlycopyrronium bromide (43 mcg) + Indacaterol maleate (85 mcg)CapsuleRespiratory (inhalation)FARMANOVA SAĞLIK HİZMETLERİ LTD. ŞTİ.2020-08-14Not applicableTurkey flag
BreztriGlycopyrronium bromide (9 ug/1) + Budesonide (160 ug/1) + Formoterol (4.8 ug/1)Aerosol, meteredRespiratory (inhalation)AstraZeneca Pharmaceuticals LP2020-07-23Not applicableUS flag
Enerzair BreezhalerGlycopyrronium bromide (46 mcg) + Indacaterol (114 mcg) + Mometasone furoate (136 mcg)CapsuleRespiratory (inhalation)Novartis Europharm Limited2021-01-12Not applicableEU flag
Enerzair BreezhalerGlycopyrronium bromide (46 mcg) + Indacaterol (114 mcg) + Mometasone furoate (136 mcg)CapsuleRespiratory (inhalation)Novartis Europharm Limited2021-01-12Not applicableEU flag
Enerzair BreezhalerGlycopyrronium bromide (46 mcg) + Indacaterol (114 mcg) + Mometasone furoate (136 mcg)CapsuleRespiratory (inhalation)Novartis Europharm Limited2021-01-12Not applicableEU flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
GlycopyrrolateGlycopyrronium bromide (0.2 mg/1mL)Injection, solutionIntravenousCantrell Drug Company2014-08-052017-12-06US flag

Categories

ATC Codes
R03AL09 — Formoterol, glycopyrronium bromide and beclometasoneR03AL04 — Indacaterol and glycopyrronium bromideR03BB06 — Glycopyrronium bromideD11AA01 — GlycopyrroniumA03AB02 — Glycopyrronium bromideR03AL11 — Formoterol, glycopyrronium bromide and budesonideR03AL07 — Formoterol and glycopyrronium bromideA03CA05 — Glycopyrronium bromide and psycholepticsR03AL12 — Indacaterol, glycopyrronium bromide and mometasone
Drug Categories
Classification
Not classified

Chemical Identifiers

UNII
A14FB57V1D
CAS number
740028-90-4
InChI Key
ANGKOCUUWGHLCE-UHFFFAOYSA-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
IUPAC Name
3-[(2-cyclopentyl-2-hydroxy-2-phenylacetyl)oxy]-1,1-dimethylpyrrolidin-1-ium
SMILES
C[N+]1(C)CCC(C1)OC(=O)C(O)(C1CCCC1)C1=CC=CC=C1

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. 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]
  2. Reid SM, Westbury C, Guzys AT, Reddihough DS: Anticholinergic medications for reducing drooling in children with developmental disability. Dev Med Child Neurol. 2020 Mar;62(3):346-353. doi: 10.1111/dmcn.14350. Epub 2019 Sep 8. [PubMed:31495925]
  3. Kirchertz R, Hilbert T: A week of slow hearts: anaesthesia for eye surgery and shortage of glycopyrrolate. Minerva Anestesiol. 2019 Sep;85(9):1033-1034. doi: 10.23736/S0375-9393.19.13607-3. Epub 2019 Apr 16. [PubMed:30994316]
  4. Yamamura Y, Nonaka M: Sialorrhea Successfully Treated by the Combined Use of Selective M1 and M3 Muscarinic Acetylcholine Receptor Antagonists. J Nippon Med Sch. 2019;86(2):117-121. doi: 10.1272/jnms.JNMS.2019_86-207. [PubMed:31130562]
  5. Schiavone A, Brambilla A: Muscarinic M3 receptors mediate secretion from sweat glands in the rat. Pharmacol Res. 1991 Apr;23(3):233-9. doi: 10.1016/s1043-6618(05)80082-9. [PubMed:2068048]
  6. Aihara T, Nakamura Y, Taketo MM, Matsui M, Okabe S: Cholinergically stimulated gastric acid secretion is mediated by M(3) and M(5) but not M(1) muscarinic acetylcholine receptors in mice. Am J Physiol Gastrointest Liver Physiol. 2005 Jun;288(6):G1199-207. doi: 10.1152/ajpgi.00514.2004. Epub 2005 Feb 3. [PubMed:15691866]
  7. Saternos HC, Almarghalani DA, Gibson HM, Meqdad MA, Antypas RB, Lingireddy A, AbouAlaiwi WA: Distribution and function of the muscarinic receptor subtypes in the cardiovascular system. Physiol Genomics. 2018 Jan 1;50(1):1-9. doi: 10.1152/physiolgenomics.00062.2017. Epub 2017 Nov 1. [PubMed:29093194]
  8. Sykes DA, Dowling MR, Leighton-Davies J, Kent TC, Fawcett L, Renard E, Trifilieff A, Charlton SJ: The Influence of receptor kinetics on the onset and duration of action and the therapeutic index of NVA237 and tiotropium. J Pharmacol Exp Ther. 2012 Nov;343(2):520-8. doi: 10.1124/jpet.112.194456. Epub 2012 Aug 1. [PubMed:22854200]
  9. ABBOTT WE, SOURIAL AS, KRIEGER H, LEVEY S: Effect of glycopyrrolate (Robanul) on basal and histamine- or insulin-induced gastric secretion. Ann N Y Acad Sci. 1962 Feb 28;99:163-73. doi: 10.1111/j.1749-6632.1962.tb45300.x. [PubMed:13858833]
  10. FDA Approved Drug Products: Robinul (Glycopyrrolate) Oral Tablet (Discontinued) [Link]
  11. US Patent: US2956062A [Link]
  12. FDA Approved Drug Products: Qbrexza (Glycopyrronium Tosylate) Topical Cloth [Link]
  13. FDA Approved Drug Products: Lonhala Magnair (Glycopyrronium) Inhalation Solution [Link]
  14. Cayman Chemical: Glycopyrrolate MSDS [Link]
  15. FDA Assessment Report: Seebri Neohaler (Glycopyrronium) Inhalation Powder [Link]
  16. EMA Assessment Report: Seebri Breezhaler (Glycopyrronium) Inhalation Powder [Link]
  17. FDA Approved Drug Products: Glyrx-PF (Glycopyrronium) Intravenous or Intramuscular Injection [Link]
  18. FDA Approved Drug Products: Cuvposa (Glycopyrronium) Oral Solution [Link]
  19. FDA Approved Drug Products: Breztri Aerosphere (Budesonide, Glycopyrronium, and Formoterol Fumarate) Inhalation Aerosol [Link]
  20. FDA Approved Drug Products: Bevespi Aerosphere (Glycopyrronium and Formoterol Fumarate) Inhalation Aerosol [Link]
Human Metabolome Database
HMDB0015121
KEGG Drug
D00540
PubChem Compound
9933193
PubChem Substance
46509133
ChemSpider
3374
BindingDB
50417445
RxNav
1546438
ChEBI
94449
ChEMBL
CHEMBL1201335
Therapeutic Targets Database
DAP001116
PharmGKB
PA164754882
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
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
4CompletedBasic ScienceElectromyography / Respiratory Muscles1
4CompletedOtherChronic Obstructive Pulmonary Disease (COPD)1
4CompletedPreventionEffect of Drug / Glycopyrrolate / Hemodynamics Instability / Post-spinal Hypotension1
4CompletedPreventionEmergence Delirium1
4CompletedSupportive CareBMI >30 kg/m2 / Cerebral Tissue Oxygenation / Laparoscopic Gastric Bypass Surgery / Respiratory Function / Surgical Conditions1
4CompletedSupportive CareCancer, Bladder / Malignant Neoplasms of Urinary Tract1
4CompletedTreatmentAirway Reflexes, Protective / Anesthetic Recovery / Recovery After Neuromuscular Block1
4CompletedTreatmentAnaesthesia1
4CompletedTreatmentAnaesthesia therapy / Neuromuscular Blockade1
4CompletedTreatmentAnesthesia Recovery1

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
  • American Regent
  • Amerisource Health Services Corp.
  • Baxter International Inc.
  • Cardinal Health
  • Corepharma LLC
  • Dispensing Solutions
  • Doctor Reddys Laboratories Ltd.
  • General Injectables and Vaccines Inc.
  • Heartland Repack Services LLC
  • Kaiser Foundation Hospital
  • Kali Laboratories Inc.
  • Luitpold Pharmaceuticals Inc.
  • Medisca Inc.
  • Mikart Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Par Pharmaceuticals
  • Pharmaceutical Packaging Center
  • Pharmedium
  • Physicians Total Care Inc.
  • Qualitest
  • Ranbaxy Laboratories
  • Rising Pharmaceuticals
  • Sciele Pharma Inc.
  • Shionogi Pharma Inc.
  • Teva Pharmaceutical Industries Ltd.
  • UDL Laboratories
  • United Research Laboratories Inc.
  • Vangard Labs Inc.
  • West-Ward Pharmaceuticals
Dosage Forms
FormRouteStrength
SuspensionRespiratory (inhalation)
Aerosol, meteredRespiratory (inhalation)
Aerosol; suspensionRespiratory (inhalation)
SuspensionRespiratory (inhalation)
LiquidOral1 mg/5mL
SolutionOral1 mg
SolutionOral1 mg/5mL
CapsuleRespiratory (inhalation)44 micrograms
Injection, solution
TabletOral1.5 mg/1
Solution
InjectionIntramuscular; Intravenous0.2 mg/1mL
InjectionIntramuscular; Intravenous0.4 mg/2mL
InjectionIntramuscular; Intravenous1 mg/5mL
InjectionIntramuscular; Intravenous4 mg/20mL
Injection, solutionIntramuscular; Intravenous0.2 mg/1mL
Injection, solutionIntramuscular; Intravenous0.4 mg/2mL
Injection, solutionIntramuscular; Intravenous1 mg/5mL
Injection, solutionIntravenous0.2 mg/1mL
Injection, solutionIntravenous0.4 mg/2mL
Injection, solutionIntravenous1 mg/5mL
Injection, solutionIntravenous5 mg/20mL
PowderNot applicable1 g/1g
TabletOral1 mg/1
TabletOral2 mg/1
LiquidIntramuscular; Intravenous
SolutionIntramuscular; Intravenous
Injection, solutionParenteral
Injection, solutionIntramuscular; Intravitreal0.2 mg/1mL
SolutionRespiratory (inhalation)25 ug/1mL
CapsuleRespiratory (inhalation)
InjectionIntramuscular; Intravenous
ClothTopical2.4 g/100g
Injection, solutionIntramuscular; Intravenous
TabletOral
Capsule, coatedRespiratory (inhalation)
PowderRespiratory (inhalation)
Powder, meteredRespiratory (inhalation)
CapsuleRespiratory (inhalation)50 mcg
CapsuleRespiratory (inhalation)15.6 ug/1
SolutionOral
SolutionOral320 μg/ml
SolutionOral320 ?g/ml
SolutionRespiratory (inhalation)
AerosolRespiratory (inhalation)
CapsuleRespiratory (inhalation)
PowderRespiratory (inhalation)
Capsule, coatedRespiratory (inhalation)
Powder, meteredRespiratory (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)Region
US7091236No2006-08-152024-04-24US flag
US6878721No2005-04-122020-10-10US flag
US6528678No2003-03-042018-04-24US flag
US8067437No2011-11-292020-06-02US flag
US8658673No2014-02-252020-06-02US flag
US8796307No2014-08-052020-06-02US flag
US8479730No2013-07-092028-10-11US flag
US7638552No2009-12-292023-08-20US flag
US7816396No2010-10-192023-08-20US flag
US7229607No2007-06-122021-04-09US flag
US7820694No2010-10-262020-06-02US flag
US8029768No2011-10-042021-04-09US flag
US8283362No2012-10-092020-06-02US flag
US7736670No2010-06-152021-06-27US flag
US8435567No2013-05-072021-06-27US flag
US8303991No2012-11-062021-06-27US flag
US8956661No2015-02-172021-06-27US flag
US8580306No2013-11-122021-06-27US flag
US6582678No2003-06-242018-04-24US flag
US8182838No2012-05-222028-10-20US flag
US6521260No2003-02-182016-01-31US flag
US8048451No2011-11-012021-06-27US flag
US9463161No2016-10-112030-05-28US flag
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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)193-194.5U.S. Patent 2,956,062.
logP-1.52Glyrx-PF FDA Label
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
Polarizability35.88 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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets
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Kind
Protein
Organism
Humans
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]
  5. FDA Approved Drug Products: Breztri Aerosphere (Budesonide, Glycopyrronium, and Formoterol Fumarate) Inhalation Aerosol [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
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]
  2. FDA Approved Drug Products: Breztri Aerosphere (Budesonide, Glycopyrronium, and Formoterol Fumarate) Inhalation Aerosol [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
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]
  2. FDA Approved Drug Products: Breztri Aerosphere (Budesonide, Glycopyrronium, and Formoterol Fumarate) Inhalation Aerosol [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Guanyl-nucleotide exchange factor 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
CHRM4
Uniprot ID
P08173
Uniprot Name
Muscarinic acetylcholine receptor M4
Molecular Weight
53048.65 Da
References
  1. FDA Approved Drug Products: Breztri Aerosphere (Budesonide, Glycopyrronium, and Formoterol Fumarate) Inhalation Aerosol [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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
CHRM5
Uniprot ID
P08912
Uniprot Name
Muscarinic acetylcholine receptor M5
Molecular Weight
60073.205 Da
References
  1. FDA Approved Drug Products: Breztri Aerosphere (Budesonide, Glycopyrronium, and Formoterol Fumarate) Inhalation Aerosol [Link]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. FDA Assessment Report: Seebri Neohaler (Glycopyrronium) Inhalation Powder [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. FDA Assessment Report: Seebri Neohaler (Glycopyrronium) Inhalation Powder [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. FDA Assessment Report: Seebri Neohaler (Glycopyrronium) Inhalation Powder [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. FDA Assessment Report: Seebri Neohaler (Glycopyrronium) Inhalation Powder [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C18
Uniprot ID
P33260
Uniprot Name
Cytochrome P450 2C18
Molecular Weight
55710.075 Da
References
  1. FDA Assessment Report: Seebri Neohaler (Glycopyrronium) Inhalation Powder [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. FDA Assessment Report: Seebri Neohaler (Glycopyrronium) Inhalation Powder [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. FDA Assessment Report: Seebri Neohaler (Glycopyrronium) Inhalation Powder [Link]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. EMA Assessment Report: Seebri Breezhaler (Glycopyrronium) Inhalation Powder [Link]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Not Available
Specific Function
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...

Components:
References
  1. EMA Assessment Report: Seebri Breezhaler (Glycopyrronium) Inhalation Powder [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Quaternary ammonium group transmembrane transporter activity
Specific Function
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
References
  1. FDA Assessment Report: Seebri Neohaler (Glycopyrronium) Inhalation Powder [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Monovalent cation:proton antiporter activity
Specific Function
Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide (NMN), metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfat...
Gene Name
SLC47A1
Uniprot ID
Q96FL8
Uniprot Name
Multidrug and toxin extrusion protein 1
Molecular Weight
61921.585 Da
References
  1. FDA Assessment Report: Seebri Neohaler (Glycopyrronium) Inhalation Powder [Link]

Drug created on June 13, 2005 13:24 / Updated on April 17, 2021 10:37