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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

Quality Level

100

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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David A Sykes et al.
The Journal of pharmacology and experimental therapeutics, 343(2), 520-528 (2012-08-03)
Studies under nonphysiological conditions suggest that long receptor residency time is responsible for the 24-h duration of action of the long-acting muscarinic antagonist (LAMA) tiotropium. Our aim was to determine how clinically relevant dissociation rates under more physiological conditions influence
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)
Kiril A Ahtarovski et al.
American journal of physiology. Heart and circulatory physiology, 303(12), H1469-H1473 (2012-10-23)
The aim of this study is to describe phasic volume changes of the left atrium (LA) in healthy young and elderly subjects at rest and during pharmacological stress (PS). LA maximum size is related to cardiovascular mortality. LA has passive
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
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