Glycopyrronium

Identification

Summary

Glycopyrronium is an anticholinergic agent used to treat hyperhidrosis, severe drooling, COPD, used with other medications to treat ulcers, and used in anesthesia.

Brand Names

Bevespi, Breztri, Cuvposa, Enurev Breezhaler, Glycate, Glyrx, Lonhala, Qbrexza, Robinul, Robinul Forte, Seebri, Seebri Breezhaler, Sialanar, Tovanor Breezhaler, Ultibro

Generic Name

Glycopyrronium

DrugBank Accession Number

DB00986

Background

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

Similar Structures

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

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

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Associated Conditions

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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

Target	Actions	Organism
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 C_max of 0.08 ± 0.04 ng/mL, with a T_max of 1 hour, and an AUC_0-24 of 0.88 ± 0.57 h*ng/mL.¹²

Inhaled glycopyrronium is approximately 40% bioavailable.¹⁵ A 25 µg inhaled solution reaches a C_max of 34.5 pg/mL, with a T_max of <20 minutes, and an AUC_0-inf of 255 h*pg/mL.¹³

An 8 µg/kg intramuscular dose reaches a C_max of 3.47 ± 1.48 µg/L, with a T_max 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 C_max of 0.318 ng/mL, a T_max of 3.1 hours, and an AUC_0-24 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

Glycopyrronium
- Glycopyrronium M9 Metabolite

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

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.

Drug	Interaction
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1,2-Benzodiazepine	1,2-Benzodiazepine may increase the central nervous system depressant (CNS depressant) activities of Glycopyrronium.
Acetazolamide	Acetazolamide may increase the central nervous system depressant (CNS depressant) activities of Glycopyrronium.
Acetophenazine	Acetophenazine may increase the central nervous system depressant (CNS depressant) activities of Glycopyrronium.
Aclidinium	The risk or severity of adverse effects can be increased when Glycopyrronium is combined with Aclidinium.
Adenosine	The risk or severity of Tachycardia can be increased when Adenosine is combined with Glycopyrronium.
Agomelatine	Agomelatine may increase the central nervous system depressant (CNS depressant) activities of Glycopyrronium.
Alfentanil	The risk or severity of adverse effects can be increased when Alfentanil is combined with Glycopyrronium.
Alimemazine	Alimemazine may increase the central nervous system depressant (CNS depressant) activities of Glycopyrronium.
Alloin	The therapeutic efficacy of Alloin can be decreased when used in combination with Glycopyrronium.
Almotriptan	Almotriptan may increase the central nervous system depressant (CNS depressant) activities of Glycopyrronium.

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Food Interactions

Take with or without food. The absorption is unaffected by food.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Glycopyrronium bromide	V92SO9WP2I	51186-83-5	VPNYRYCIDCJBOM-UHFFFAOYSA-M
Glycopyrronium tosylate	1PVF6JLU7B	1624259-25-1	UOWOLENSDISMPG-UHFFFAOYSA-M

Product Images

International/Other Brands

Acpan (Gray) / Nodapton / Robanul / Robinal / Tarodyl (Lundbeck)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Cuvposa	Solution	1 mg / 5 mL	Oral	Medexus Pharmaceuticals Inc	2018-04-03	Not applicable
Cuvposa	Liquid	1 mg/5mL	Oral	Merz Pharmaceuticals, LLC	2013-01-01	Not applicable
Cuvposa	Solution	1 mg/5mL	Oral	Shionogi Pharma, Inc.	2010-07-28	2014-06-30
Enurev Breezhaler	Capsule	44 micrograms	Respiratory (inhalation)	Novartis Europharm Limited	2016-09-08	Not applicable
Enurev Breezhaler	Capsule	44 micrograms	Respiratory (inhalation)	Novartis Europharm Limited	2016-09-08	Not applicable
Enurev Breezhaler	Capsule	44 micrograms	Respiratory (inhalation)	Novartis Europharm Limited	2016-09-08	Not applicable
Enurev Breezhaler	Capsule	44 micrograms	Respiratory (inhalation)	Novartis Europharm Limited	2016-09-08	Not applicable
Enurev Breezhaler	Capsule	44 micrograms	Respiratory (inhalation)	Novartis Europharm Limited	2016-09-08	Not applicable
Enurev Breezhaler	Capsule	44 micrograms	Respiratory (inhalation)	Novartis Europharm Limited	2016-09-08	Not applicable
Enurev Breezhaler	Capsule	44 micrograms	Respiratory (inhalation)	Novartis Europharm Limited	2016-09-08	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Glycate	Tablet	1.5 mg/1	Oral	Nuro Pharma, Inc.	2012-03-12	Not applicable
Glycate	Tablet	1.5 mg/1	Oral	CarWin Pharmaceutical Associates, LLC	2018-06-10	Not applicable
Glycopyrrolate	Injection, solution	0.2 mg/1mL	Intramuscular; Intravenous	Cardinal Health	2011-10-25	Not applicable
Glycopyrrolate	Injection, solution	0.2 mg/1mL	Intramuscular; Intravenous	Fresenius Kabi USA, LLC	2020-10-30	Not applicable
Glycopyrrolate	Tablet	1 mg/1	Oral	Avera McKennan Hospital	2015-03-05	2017-05-24
Glycopyrrolate	Injection, solution	0.2 mg/1mL	Intramuscular; Intravenous	Piramal Critical Care Inc	2019-07-11	Not applicable
Glycopyrrolate	Tablet	2 mg/1	Oral	Par Formulations Private Limited	2006-09-26	Not applicable
Glycopyrrolate	Tablet	2 mg/1	Oral	HERITAGE PHARMACEUTICALS INC D/B/A AVET PHARMACEUTICALS INC	2017-02-27	Not applicable
Glycopyrrolate	Injection	0.2 mg/1mL	Intramuscular; Intravenous	Hikma Pharmaceuticals USA Inc.	2015-06-01	Not applicable
Glycopyrrolate	Injection	0.2 mg/1mL	Intramuscular; Intravenous	Medical Purchasing Solutions, Llc	2017-06-26	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Bevespi Aerosphere	Glycopyrronium bromide (9 ug/1) + Formoterol fumarate (4.8 ug/1)	Aerosol, metered	Respiratory (inhalation)	AstraZeneca Pharmaceuticals LP	2016-10-03	Not applicable
Bevespi Aerosphere	Glycopyrronium (7.2 mcg) + Formoterol fumarate (5.0 mcg)		Respiratory (inhalation)	Astra Zeneca Ab	2020-12-16	Not applicable
Bevespi Aerosphere	Glycopyrronium bromide (8.3 mcg / act) + Formoterol fumarate (5.8 mcg / act)	Aerosol, metered	Respiratory (inhalation)	Astra Zeneca	Not applicable	Not applicable
Bevespi Aerosphere	Glycopyrronium (7.2 mcg) + Formoterol fumarate (5.0 mcg)		Respiratory (inhalation)	Astra Zeneca Ab	2020-12-16	Not applicable
BEVESPİ AEROSPHERE® 7.2 MCG/5.0 MCG BASINÇLI İNHALASYON SÜSPANSİYONU ,120 DOZ	Glycopyrronium (7.2 mcg) + Formoterol fumarate (5 mcg)	Aerosol, metered	Respiratory (inhalation)	ASTRAZENECA İLAÇ SAN. VE TİC. LTD. ŞTİ.	2020-08-14	Not applicable
BİXBRİ NEOHALER 85 MCG/43 MCG İNHALER KAPSÜL	Glycopyrronium bromide (43 mcg) + Indacaterol maleate (85 mcg)	Capsule	Respiratory (inhalation)	FARMANOVA SAĞLIK HİZMETLERİ LTD. ŞTİ.	2020-08-14	Not applicable
Breztri	Glycopyrronium bromide (9 ug/1) + Budesonide (160 ug/1) + Formoterol (4.8 ug/1)	Aerosol, metered	Respiratory (inhalation)	AstraZeneca Pharmaceuticals LP	2020-07-23	Not applicable
Enerzair Breezhaler	Glycopyrronium bromide (46 mcg) + Indacaterol (114 mcg) + Mometasone furoate (136 mcg)	Capsule	Respiratory (inhalation)	Novartis Europharm Limited	2021-01-12	Not applicable
Enerzair Breezhaler	Glycopyrronium bromide (46 mcg) + Indacaterol (114 mcg) + Mometasone furoate (136 mcg)	Capsule	Respiratory (inhalation)	Novartis Europharm Limited	2021-01-12	Not applicable
Enerzair Breezhaler	Glycopyrronium bromide (46 mcg) + Indacaterol (114 mcg) + Mometasone furoate (136 mcg)	Capsule	Respiratory (inhalation)	Novartis Europharm Limited	2021-01-12	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Glycopyrrolate	Glycopyrronium bromide (0.2 mg/1mL)	Injection, solution	Intravenous	Cantrell Drug Company	2014-08-05	2017-12-06

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

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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
FDA Approved Drug Products: Robinul (Glycopyrrolate) Oral Tablet (Discontinued) [Link]
US Patent: US2956062A [Link]
FDA Approved Drug Products: Qbrexza (Glycopyrronium Tosylate) Topical Cloth [Link]
FDA Approved Drug Products: Lonhala Magnair (Glycopyrronium) Inhalation Solution [Link]
Cayman Chemical: Glycopyrrolate MSDS [Link]
FDA Assessment Report: Seebri Neohaler (Glycopyrronium) Inhalation Powder [Link]
EMA Assessment Report: Seebri Breezhaler (Glycopyrronium) Inhalation Powder [Link]
FDA Approved Drug Products: Glyrx-PF (Glycopyrronium) Intravenous or Intramuscular Injection [Link]
FDA Approved Drug Products: Cuvposa (Glycopyrronium) Oral Solution [Link]
FDA Approved Drug Products: Breztri Aerosphere (Budesonide, Glycopyrronium, and Formoterol Fumarate) Inhalation Aerosol [Link]
FDA Approved Drug Products: Bevespi Aerosphere (Glycopyrronium and Formoterol Fumarate) Inhalation Aerosol [Link]

External Links

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

FDA label

Download (193 KB)

MSDS

Download (73.7 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Completed	Basic Science	Electromyography / Respiratory Muscles	1
4	Completed	Other	Chronic Obstructive Pulmonary Disease (COPD)	1
4	Completed	Prevention	Effect of Drugs / Glycopyrrolate / Hemodynamics Instability / Post-spinal Hypotension	1
4	Completed	Prevention	Emergence Delirium	1
4	Completed	Supportive Care	Bladder Cancer, Cancer / Malignant Neoplasms of Urinary Tract	1
4	Completed	Supportive Care	BMI >30 kg/m2 / Cerebral Tissue Oxygenation / Laparoscopic Gastric Bypass Surgery / Respiratory Functions / Surgical Conditions	1
4	Completed	Treatment	Airway Reflexes, Protective / Anesthetic Recovery / Recovery After Neuromuscular Block	1
4	Completed	Treatment	Anaesthesia	1
4	Completed	Treatment	Anaesthesia therapy / Neuromuscular Blockade	1
4	Completed	Treatment	Anesthesia, Recovery	1

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

Form	Route	Strength
Suspension	Respiratory (inhalation)	7.2 mcg
Aerosol, metered	Respiratory (inhalation)
Aerosol; suspension	Respiratory (inhalation)
Suspension	Respiratory (inhalation)
Liquid	Oral	1 mg/5mL
Solution	Oral	1 mg / 5 mL
Solution	Oral	1 mg/5mL
Injection, solution
Tablet	Oral	1.5 mg/1
Solution		0.2 mg/1ml
Injection	Intramuscular; Intravenous	0.2 mg/1mL
Injection	Intramuscular; Intravenous	0.4 mg/2mL
Injection	Intramuscular; Intravenous	1 mg/5mL
Injection	Intramuscular; Intravenous	4 mg/20mL
Injection, solution	Intramuscular; Intravenous	0.2 mg/1mL
Injection, solution	Intramuscular; Intravenous	0.4 mg/2mL
Injection, solution	Intramuscular; Intravenous	1 mg/5mL
Injection, solution	Intravenous	0.2 mg/1mL
Injection, solution	Intravenous	0.4 mg/2mL
Injection, solution	Intravenous	1 mg/5mL
Injection, solution	Intravenous	5 mg/20mL
Powder	Not applicable	1 g/1g
Tablet	Oral	1 mg/1
Tablet	Oral	2 mg/1
Liquid	Intramuscular; Intravenous	0.2 mg / mL
Solution	Intramuscular; Intravenous	0.2 mg / 1 mL
Solution	Intramuscular; Intravenous	0.2 mg / mL
Solution	Intramuscular; Intravenous	0.4 mg / 2 mL
Solution	Intramuscular; Intravenous	4 mg / 20 mL
Injection, solution	Parenteral
Injection, solution	Intramuscular; Intravitreal	0.2 mg/1mL
Solution	Respiratory (inhalation)	25 ug/1mL
Capsule	Respiratory (inhalation)
Injection	Intramuscular; Intravenous
Cloth	Topical	2.4 g/100g
Injection, solution	Intramuscular; Intravenous
Liquid	Intramuscular; Intravenous	.2 mg / mL
Tablet	Oral	2 mg / tab
Tablet	Oral	1 mg
Tablet	Oral	2 mg
Capsule, coated	Respiratory (inhalation)
Powder	Respiratory (inhalation)
Powder, metered	Respiratory (inhalation)
Capsule	Respiratory (inhalation)	50 mcg
Capsule	Respiratory (inhalation)	15.6 ug/1
Solution	Oral
Solution	Oral	320 ?g/ml
Solution	Oral	320 μg/ml
Capsule	Respiratory (inhalation)	44 micrograms
Solution	Respiratory (inhalation)
Aerosol	Respiratory (inhalation)
Capsule	Respiratory (inhalation)
Powder	Respiratory (inhalation)
Capsule, coated	Respiratory (inhalation)
Powder, metered	Respiratory (inhalation)

Prices

Unit description	Cost	Unit
Glycopyrrolate powder	278.46USD	g
Robinul-Forte 2 mg tablet	6.46USD	tablet
Robinul forte 2 mg tablet	6.21USD	tablet
Robinul 1 mg tablet	3.96USD	tablet
Glycopyrrolate 0.2 mg/ml	3.63USD	ml
Glycopyrrolate 1 mg/5 ml syr	2.91USD	ml
Glycopyrrolate 2 mg tablet	2.24USD	tablet
Glycopyrrolate 1 mg tablet	1.34USD	tablet
Robinul 0.2 mg/ml vial	1.26USD	ml
Glycopyrrolate 0.2 mg/ml vial	0.85USD	ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US7091236	No	2006-08-15	2024-04-24
US6878721	No	2005-04-12	2020-10-10
US6528678	No	2003-03-04	2018-04-24
US8067437	No	2011-11-29	2020-06-02
US8658673	No	2014-02-25	2020-06-02
US8796307	No	2014-08-05	2020-06-02
US8479730	No	2013-07-09	2028-10-11
US7638552	No	2009-12-29	2023-08-20
US7816396	No	2010-10-19	2023-08-20
US7229607	No	2007-06-12	2021-04-09
US7820694	No	2010-10-26	2020-06-02
US8029768	No	2011-10-04	2021-04-09
US8283362	No	2012-10-09	2020-06-02
US7736670	No	2010-06-15	2021-06-27
US8435567	No	2013-05-07	2021-06-27
US8303991	No	2012-11-06	2021-06-27
US8956661	No	2015-02-17	2021-06-27
US8580306	No	2013-11-12	2021-06-27
US6582678	No	2003-06-24	2018-04-24
US8182838	No	2012-05-22	2028-10-20
US6521260	No	2003-02-18	2016-01-31
US8048451	No	2011-11-01	2021-06-27
US9463161	No	2016-10-11	2030-05-28
US9415009	No	2016-08-16	2030-05-28
US8808713	No	2014-08-19	2030-05-28
US8324266	No	2012-12-04	2030-05-28
US8703806	No	2014-04-22	2030-05-28
US8815258	No	2014-08-26	2031-03-17
US7458372	No	2008-12-02	2024-11-18
US9789270	No	2017-10-17	2030-10-30
US9168556	No	2015-10-27	2032-09-01
US9265900	No	2016-02-23	2028-12-07
US9604018	No	2017-03-28	2033-05-16
US7316067	No	2008-01-08	2022-09-06
US6962151	No	2005-11-08	2020-10-27
US7931212	No	2011-04-26	2025-11-25
US8511581	No	2013-08-20	2023-11-08
US9931304	No	2018-04-03	2021-06-27
US9962338	No	2018-05-08	2021-06-27
US10052267	No	2018-08-21	2028-10-17
US9259414	No	2016-02-16	2033-02-28
US9744105	No	2017-08-29	2030-07-18
US8618160	No	2013-12-31	2029-12-10
US6433003	No	2002-08-13	2020-04-10
US8859610	No	2014-10-14	2033-02-28
US10004717	No	2018-06-26	2033-02-28
US9006462	No	2015-04-14	2033-02-28
US10376661	No	2019-08-13	2035-09-14
US10543192	No	2013-02-28	2033-02-28
US10548875	No	2013-02-28	2033-02-28
US10688518	No	2016-11-12	2036-11-12
US10744277	No	2016-12-07	2036-12-07
US10716753	No	2010-05-28	2030-05-28
US10940110	No	2009-02-26	2029-02-26

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	193-194.5	U.S. Patent 2,956,062.
logP	-1.52	Glyrx-PF FDA Label

Predicted Properties

Property	Value	Source
Water Solubility	0.000944 mg/mL	ALOGPS
logP	-1.2	ALOGPS
logP	-1.4	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	11.53	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	101.08 m³·mol^-1	ChemAxon
Polarizability	35.88 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	-	0.8406
Blood Brain Barrier	+	0.8436
Caco-2 permeable	+	0.5778
P-glycoprotein substrate	Substrate	0.7928
P-glycoprotein inhibitor I	Non-inhibitor	0.894
P-glycoprotein inhibitor II	Non-inhibitor	0.9731
Renal organic cation transporter	Non-inhibitor	0.5299
CYP450 2C9 substrate	Non-substrate	0.7812
CYP450 2D6 substrate	Non-substrate	0.7136
CYP450 3A4 substrate	Substrate	0.662
CYP450 1A2 substrate	Non-inhibitor	0.9046
CYP450 2C9 inhibitor	Non-inhibitor	0.9133
CYP450 2D6 inhibitor	Non-inhibitor	0.9231
CYP450 2C19 inhibitor	Non-inhibitor	0.9243
CYP450 3A4 inhibitor	Non-inhibitor	0.8735
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.978
Ames test	Non AMES toxic	0.7888
Carcinogenicity	Non-carcinogens	0.9257
Biodegradation	Ready biodegradable	0.8627
Rat acute toxicity	2.5887 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9345
hERG inhibition (predictor II)	Non-inhibitor	0.7884

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available

Targets

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Details1. Muscarinic acetylcholine receptor M1

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
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. [Article]
Ali-Melkkila T, Kanto J, Iisalo E: Pharmacokinetics and related pharmacodynamics of anticholinergic drugs. Acta Anaesthesiol Scand. 1993 Oct;37(7):633-42. [Article]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
FDA Approved Drug Products: Breztri Aerosphere (Budesonide, Glycopyrronium, and Formoterol Fumarate) Inhalation Aerosol [Link]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	0.251	N/A	N/A	A29257

Details2. Muscarinic acetylcholine receptor M3

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

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. [Article]
FDA Approved Drug Products: Breztri Aerosphere (Budesonide, Glycopyrronium, and Formoterol Fumarate) Inhalation Aerosol [Link]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	0.158	N/A	N/A	A29257

Details3. Muscarinic acetylcholine receptor M2

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

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. [Article]
FDA Approved Drug Products: Breztri Aerosphere (Budesonide, Glycopyrronium, and Formoterol Fumarate) Inhalation Aerosol [Link]

Details4. Muscarinic acetylcholine receptor M4

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

FDA Approved Drug Products: Breztri Aerosphere (Budesonide, Glycopyrronium, and Formoterol Fumarate) Inhalation Aerosol [Link]

Details5. Muscarinic acetylcholine receptor M5

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

FDA Approved Drug Products: Breztri Aerosphere (Budesonide, Glycopyrronium, and Formoterol Fumarate) Inhalation Aerosol [Link]

Enzymes

Details1. Cytochrome P450 2D6

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

FDA Assessment Report: Seebri Neohaler (Glycopyrronium) Inhalation Powder [Link]

Details2. Cytochrome P450 1A2

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

FDA Assessment Report: Seebri Neohaler (Glycopyrronium) Inhalation Powder [Link]

Details3. Cytochrome P450 2B6

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

FDA Assessment Report: Seebri Neohaler (Glycopyrronium) Inhalation Powder [Link]

Details4. Cytochrome P450 2C9

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

FDA Assessment Report: Seebri Neohaler (Glycopyrronium) Inhalation Powder [Link]

Details5. Cytochrome P450 2C18

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

FDA Assessment Report: Seebri Neohaler (Glycopyrronium) Inhalation Powder [Link]

Details6. Cytochrome P450 2C19

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

FDA Assessment Report: Seebri Neohaler (Glycopyrronium) Inhalation Powder [Link]

Details7. Cytochrome P450 3A4

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

FDA Assessment Report: Seebri Neohaler (Glycopyrronium) Inhalation Powder [Link]

Carriers

Details1. Serum albumin

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

EMA Assessment Report: Seebri Breezhaler (Glycopyrronium) Inhalation Powder [Link]

Details2. alpha1-acid glycoprotein (Protein Group)

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:

Name	UniProt ID
Alpha-1-acid glycoprotein 1	P02763
Alpha-1-acid glycoprotein 2	P19652

References

EMA Assessment Report: Seebri Breezhaler (Glycopyrronium) Inhalation Powder [Link]

Transporters

Details1. Solute carrier family 22 member 2

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

FDA Assessment Report: Seebri Neohaler (Glycopyrronium) Inhalation Powder [Link]

Details2. Multidrug and toxin extrusion protein 1

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

FDA Assessment Report: Seebri Neohaler (Glycopyrronium) Inhalation Powder [Link]

Drug created on June 13, 2005 13:24 / Updated on July 29, 2021 06:27

Glycopyrronium

Identification

Structure for Glycopyrronium (DB00986)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Targets

References

References

References

References

References

Enzymes

References

References

References

References

References

References

References

Carriers

References

Components:

References

Transporters

References

References