Glycopyrronium bromide

Glycopyrronium bromide

Systematic (IUPAC) name
3-[2-Cyclopentyl(hydroxy)phenylacetoxy]-1,1-dimethylpyrrolidinium bromide
Clinical data
Pregnancy category	US: B (No risk in non-human studies)
Legal status	US: ℞-only
Identifiers
ATC code	A03AB02 (WHO) R03BB06
PubChem	CID: 11693
ChemSpider	11201
Chemical data
Formula	C19H28BrNO3
Molecular mass	398.335 g/mol
SMILES C[N+]1(CCC(C1)OC(=O)C(C2CCCC2)(C3=CC=CC=C3)O)C.[Br-]
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

Glycopyrronium

Systematic (IUPAC) name
3-(2-Cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium
Clinical data
AHFS/Drugs.com	monograph
MedlinePlus	a602014
Pregnancy category	US: B (No risk in non-human studies)
Legal status	US: ℞-only
Routes of administration	oral, IV
Pharmacokinetic data
Biological half-life	0.6–1.2 hours
Excretion	85% renal, unknown amount in the bile
Identifiers
CAS Number	596-51-0 Y
ATC code	A03AB02 (WHO) R03BB06
PubChem	CID: 3494
IUPHAR/BPS	7459
DrugBank	DB00986 Y
ChemSpider	3374
UNII	V92SO9WP2I Y
KEGG	D00540 Y
ChEMBL	CHEMBL1201335 N
Chemical data
Formula	C19H28NO3+
Molecular mass	318.431 g/mol
SMILES C[N+]1(CCC(C1)OC(=O)C(C2CCCC2)(C3=CC=CC=C3)O)C
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 Key:ANGKOCUUWGHLCE-UHFFFAOYSA-N
NY (what is this?)  (verify)

Glycopyrronium bromide is a medication of the muscarinic anticholinergic group. It does not cross the blood–brain barrier and consequently has no to few central effects. A synthetic quaternary amine, it is available in oral and intravenous (i.v.) forms. It was developed by Sosei and licensed to Novartis in 2005. The cation, which is the active moiety, is also known as glycopyrrolate.

Medical uses

In anesthesia, glycopyrronium injection can be used as a preoperative medication in order to reduce salivary, tracheobronchial, and pharyngeal secretions, as well as decreasing the acidity of gastric secretion. It is also used in conjunction with neostigmine, a neuromuscular blocking reversal agent, to prevent neostigmine's muscarinic effects such as bradycardia.

It is also used to reduce excessive saliva (sialorrhea).

It decreases acid secretion in the stomach and so may be used for treating stomach ulcers, in combination with other medications.

Use in treating asthma and COPD has been described.

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

Side effects

Since glycopyrronium reduces the body's sweating ability, it can even cause fever and heat stroke in hot environments. Dry mouth, difficulty urinating, headaches, diarrhea and constipation are also observed side effects of the medication. The medication also induces drowsiness or blurred vision, an effect exacerbated by the consumption of alcohol.

Pharmacology

Glycopyrronium 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 tendency of glycopyrronium followed a tri-exponential equation, followed 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.