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SML0029

Sigma-Aldrich

Glycopyrrolate

≥98% (HPLC)

Synonym(s):

α-cyclopentylmandelic acid ester with 3-hydroxy-1,1-dimethylpyrrolidinium bromide, 1-methyl-3-pyrrolidyl α-cyclopentylmandelate methobromide, 1-methyl-3-pyrrolidyl α-phenyl-α-cyclopentylglycolate methobromide, 3-(2-phenyl-2-cyclopentylglycoloyloxy)-1,1-dimethylpyrrolidinium bromide, 3-hydroxy-1,1-dimethylpyrrolidinium bromide α-cyclopentylmandelate, AHR-504, Copyrrolate, Gastrodyn, NSC 250836, NSC 251251, NSC 251252, NVA-237, glycopyrronium bromide

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About This Item

Empirical Formula (Hill Notation):
C19H28NO3 · Br
CAS Number:
596-51-0
Molecular Weight:
398.33
EC Number:
209-887-0
MDL number:
MFCD00072137
UNSPSC Code:
12352200
PubChem Substance ID:
329825100
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to tan

solubility

H2O: ≥24 mg/mL

originator

Novartis

storage temp.

2-8°C

SMILES string

[Br-].C[N+]1(C)CCC(C1)OC(=O)C(O)(C2CCCC2)c3ccccc3

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

InChI key

VPNYRYCIDCJBOM-UHFFFAOYSA-M

Gene Information

human ... CHRM1(1128) , CHRM3(1131)

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General description

Glycopyrrolate is a quaternary ammonium compound and it shows structural similarity with atropine.

Biochem/physiol Actions

Glycopyrrolate is an anti-cholinergic drug. It is a potent controller of drooling, observed in children affected with cerebral palsy. Compared to other muscarinic antagonists, glycopyrrolate has lower CNS (central nervous system) penetration.
Glycopyrrolate is long-acting muscarinic antagonist (LAMA). It is kinetically selective muscarinic M3 receptor antagonist.

Features and Benefits

This compound was developed by Novartis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Pharmacokinetics of glycopyrrolate following intravenous administration in the horse.
Rumpler M J, et al.
Journal of Veterinary Pharmacology and Therapeutics, 34(6), 605-608 (2011)
Treatment of sialorrhea with glycopyrrolate: a double-blind, dose-ranging study.
Mier R J, et al.
Archives of Pediatrics & Adolescent Medicine, 154(12), 1214-1218 (2000)
J W Hamner et al.
The Journal of physiology, 590(24), 6343-6352 (2012-10-17)
Despite growing evidence of autonomic nervous system involvement in the regulation of cerebral blood flow, the specific contribution of cholinergic vasodilatation to cerebral autoregulation remains unknown. We examined cerebral and forearm blood flow responses to augmented arterial pressure oscillations with
Kai M Beeh et al.
International journal of chronic obstructive pulmonary disease, 7, 503-513 (2012-09-14)
Exercise limitation, dynamic hyperinflation, and exertional dyspnea are key features of symptomatic chronic obstructive pulmonary disease (COPD). We assessed the effects of glycopyrronium bromide (NVA237), a once-daily, long-acting muscarinic antagonist, on exercise tolerance in patients with moderate to severe COPD.
Edward Kerwin et al.
The European respiratory journal, 40(5), 1106-1114 (2012-10-13)
NVA237 (glycopyrronium bromide) is a once-daily long-acting muscarinic antagonist (LAMA) in development for chronic obstructive pulmonary disease (COPD). The GLycopyrronium bromide in COPD airWays clinical Study 2 (GLOW2) evaluated the efficacy and safety of NVA237 in moderate-to-severe COPD over 52
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