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Glycopyrronium bromide

Anticholinergic

Summary

Anticholinergic

Field	Value
image	Glycopyrronium bromide.svg
image_class	skin-invert-image
Verifiedfields	changed
INN	Glycopyrronium
verifiedrevid	461122867
USAN	glycopyrrolate
tradename	Robinul, Cuvposa, Seebri, others
Drugs.com
MedlinePlus	a602014
DailyMedID	Glycopyrrolate
pregnancy_AU	B2
routes_of_administration	By mouth, intravenous, inhalation, topical, injection, subcutaneous
class	Antimuscarinic (peripherally-selective)
ATC_prefix	A03
ATC_suffix	AB02
ATC_supplemental
<!-- Legal status -->	legal_AU	S3 / S4
legal_BR
legal_CA	Rx-only
legal_CA_comment
legal_DE
legal_NZ
legal_UK	POM
legal_US	Rx-only
legal_US_comment
legal_EU	Rx-only
legal_EU_comment
legal_UN
legal_status	Rx-only
elimination_half-life	0.6–1.2 hours
excretion	85% Kidney, unknown amount in the bile
<!-- Identifiers -->	index2_label	as cation
CAS_number_Ref
CAS_number	51186-83-5
CAS_number2	596-51-0
PubChem	3494
PubChem2	11693
IUPHAR_ligand	7459
DrugBank_Ref
DrugBank	DBSALT001183
DrugBank2	DB00986
ChemSpiderID	11201
ChemSpiderID2	3374
UNII_Ref
UNII	V92SO9WP2I
UNII2	A14FB57V1D
KEGG_Ref
KEGG	D00540
KEGG2	D10938
ChEBI	90972
ChEMBL_Ref
ChEMBL	1201027
ChEMBL2	1201335
synonyms
IUPAC_name	3-[2-Cyclopentyl(hydroxy)phenylacetoxy]-1,1-dimethylpyrrolidinium bromide
C	19
H	28
Br	1
N	1
O	3
SMILES	C[N+]1(CCC(C1)OC(=O)C(C2CCCC2)(C3=CC=CC=C3)O)C.[Br-]
SMILES2	C[N+]1(CCC(C1)OC(=O)C(C2CCCC2)(C3=CC=CC=C3)O)C
StdInChI	1S/C19H28NO3.BrH/c1-20(2)13-12-17(14-20)23-18(21)19(22,16-10-6-7-11-16)15-8-4-3-5-9-15;/h3-5,8-9,16-17,22H,6-7,10-14H2,1-2H3;1H/q+1;/p-1
StdInChI2	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
StdInChIKey	VPNYRYCIDCJBOM-UHFFFAOYSA-M
StdInChIKey2	ANGKOCUUWGHLCE-UHFFFAOYSA-N

| Drugs.com =

| elimination_half-life = 0.6–1.2 hours

Glycopyrronium bromide is a medication of the muscarinic anticholinergic group. It does not cross the blood–brain barrier and consequently has few to no central effects. It is given by mouth, via intravenous injection, on the skin, and via inhalation. It is a synthetic quaternary ammonium compound. The cation, which is the active moiety, is called glycopyrronium (INN) or glycopyrrolate (USAN).

The most common side effects include irritability, flushing, nasal congestion, reduced secretions in the airways, dry mouth, constipation, diarrhea, nausea and vomiting, and urinary retention.

In September 2012, glycopyrronium was approved for medical use in the European Union. In June 2018, glycopyrronium was approved by the U.S. Food and Drug Administration (FDA) to treat excessive underarm sweating, becoming the first drug developed specifically to reduce excessive sweating. It is on the World Health Organization's List of Essential Medicines.

Medical uses

Glycopyrronium was first used in 1961 to treat peptic ulcers. Since 1975, intravenous glycopyrronium has been used before surgery to reduce salivary, tracheobronchial, and pharyngeal secretions. It can be administered to raise the heart rate in reflex bradycardia as a result of a vasovagal reaction, which often will also increase the blood pressure.

It is also used to reduce excessive saliva (sialorrhea), and to treat Ménière's disease.

It has been used topically and orally to treat hyperhidrosis, in particular, gustatory hyperhidrosis and generalized hyperhidrosis.

When inhaled, it is used to treat chronic obstructive pulmonary disease (COPD). Doses for inhalation are much lower than oral ones, so that swallowing a dose will not have an effect.

Side effects

Dry mouth, urinary retention, headaches, vomiting, diarrhea, constipation, and blurry vision are possible side effects of the medication.

Pharmacology

Mechanism of action

Glycopyrronium competitively blocks muscarinic receptors, thus inhibiting cholinergic transmission.

Pharmacokinetics

Glycopyrronium bromide affects the gastrointestinal tracts, liver and kidney but has a very limited effect on the brain and the central nervous system. In horse studies, after a single intravenous infusion, the observed tendencies of glycopyrronium followed a tri-exponential equation, by rapid disappearance from the blood followed by a prolonged terminal phase. Excretion was mainly in urine and in the form of an unchanged drug. Glycopyrronium has a relatively slow diffusion rate, and in a standard comparison to atropine, is more resistant to penetration through the blood-brain barrier and placenta.

Research

It has been studied in asthma.

References

(9 May 2018). "Neurological therapies".
(1 June 2021). "Robinul- glycopyrrolate tablet Robinul Forte- glycopyrrolate tablet".
(9 December 2021). "Dartisla ODT- glycopyrrolate orally disintegrating tablets tablet, orally disintegrating".
(17 September 2018). "Sialanar EPAR".
"Glycopyrrolate Oral Inhalation".
"Glycopyrronium Topical".
(July 2007). "Use of oral glycopyrronium bromide in hyperhidrosis". The British Journal of Dermatology.
"FDA OKs first drug made to reduce excessive sweating". AP News.
(2021). "World Health Organization model list of essential medicines: 22nd list (2021)". World Health Organization.
(February 2017). "Glycopyrrolate: It's time to review". Journal of Clinical Anesthesia.
(June 2023). "StatPearls [Internet]". StatPearls Publishing.
(December 2000). "Treatment of sialorrhea with glycopyrrolate: A double-blind, dose-ranging study". Archives of Pediatrics & Adolescent Medicine.
(October 2017). "Sialorrhea - therapeutic drug options". The Annals of Pharmacotherapy.
(October 1999). "Oral glycopyrrolate alleviates drooling in a patient with tongue cancer". Journal of Pain and Symptom Management.
(1 December 2012). "Medical therapy in Ménière's disease". Audiological Medicine.
(August 2003). "Treatment of compensatory gustatory hyperhidrosis with topical glycopyrrolate". Yonsei Medical Journal.
(May 2008). "Topical glycopyrrolate for patients with facial hyperhidrosis". The British Journal of Dermatology.
(17 September 2018). "Seebri Breezhaler EPAR".
(17 September 2018). "Tovanor Breezhaler EPAR".
(17 September 2018). "Enurev Breezhaler EPAR".
(28 September 2012). "EPAR – Product information for Seebri Breezhaler". [[European Medicines Agency]].
(January 1996). "Comparison of nebulized glycopyrrolate and metaproterenol in chronic obstructive pulmonary disease". The European Respiratory Journal.
(May 2019). "Pharmacology, toxicology and clinical safety of glycopyrrolate". Toxicology and Applied Pharmacology.
(May 1999). "Pharmacological characterization of the muscarinic receptor antagonist, glycopyrrolate, in human and guinea-pig airways". British Journal of Pharmacology.
(June 2014). "The pharmacokinetics of glycopyrrolate in Standardbred horses". Journal of Veterinary Pharmacology and Therapeutics.
(October 2005). "Glycopyrrolate causes prolonged bronchoprotection and bronchodilatation in patients with asthma". Chest.
(November 1990). "Comparison of aerosolized glycopyrrolate and metaproterenol in acute asthma". Chest.

Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

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