Glycopyrronium bromide

Glycopyrronium bromide
Clinical data
Trade names	Robinul, Cuvposa, Seebri, others
Other names	glycopyrrolate (USAN US)
AHFS/Drugs.com	Monograph
MedlinePlus	a602014
License data	EU EMA: by INN; US DailyMed: Glycopyrrolate;
Pregnancy; category	AU: B2;
Routes of; administration	By mouth, intravenous, inhalation, topical, injection, subcutaneous
Drug class	Antimuscarinic agent
ATC code	A03AB02 (WHO) D11AA01 (WHO) R03BB06 (WHO);
Legal status
Legal status	AU: S3 / S4; UK: POM (Prescription only); US: ℞-only; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Elimination half-life	0.6–1.2 hours
Excretion	85% Kidney, unknown amount in the bile
Identifiers
	IUPAC name 3-[2-Cyclopentyl(hydroxy)phenylacetoxy]-1,1-dimethylpyrrolidinium bromide;
CAS Number	51186-83-5 ; as cation: 596-51-0;
PubChem CID	3494; as cation: 11693;
IUPHAR/BPS	7459;
DrugBank	DBSALT001183 ; as cation: DB00986;
ChemSpider	11201; as cation: 3374;
UNII	V92SO9WP2I; as cation: A14FB57V1D;
KEGG	D00540 ; as cation: D10938;
ChEBI	CHEBI:90972;
ChEMBL	ChEMBL1201027 ; as cation: ChEMBL1201335;
CompTox Dashboard (EPA)	DTXSID6023109 ;
ECHA InfoCard	100.008.990
Chemical and physical data
Formula	C19H28BrNO3
Molar mass	398.341 g·mol−1
3D model (JSmol)	Interactive image; as cation: Interactive image;
	SMILES C[N+]1(CCC(C1)OC(=O)C(C2CCCC2)(C3=CC=CC=C3)O)C.[Br-]; ; as cation: C[N+]1(CCC(C1)OC(=O)C(C2CCCC2)(C3=CC=CC=C3)O)C;
	InChI InChI=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; Key:VPNYRYCIDCJBOM-UHFFFAOYSA-M; ; as cation: 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; Key:ANGKOCUUWGHLCE-UHFFFAOYSA-N;
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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, blocked nose, reduced secretions in the airways, dry mouth, constipation, diarrhea, vomiting and inability to completely empty the bladder (urinary retention).

In September 2012, glycopyrronium was approved for medical use in the European Union. In June 2018, glycopyrronium was approved by the US 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.

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