Glycopyrronium bromideProduct ingredient for Glycopyrronium

Name
Glycopyrronium bromide
Drug Entry
Glycopyrronium

Glycopyrronium, also known as NVA237 or glycopyrrolate, is a racemic mixture of two enantiomers.15 They are both quaternary ammonium compounds and long acting muscarinic antagonists.15 It is one of the most commonly prescribed anticholinergic medications.2,3 Early research into glycopyrronium use was for its indication as an adjunct therapy in the treatment of peptic ulcers.9,10 Later research, taking advantage of the systemic distribution of muscarinic receptors through the body, found that glycopyrronium could also be used for reducing sweat gland,12 oral,18 airway, and gastric secretions;17 as well as reducing cardiac inhibitory reflexes;17 and reducing bronchoconstriction in COPD.13 Glycopyrronium is commonly prescribed as a first line treatment for a wide variety indications and is considered to have a wider therapeutic window than tiotropium.8

Glycopyrronium was originally granted FDA approval on 11 August 1961.10

Accession Number
DBSALT001183
Structure
Synonyms
1-Methyl-3-pyrrolidyl alpha-phenylcyclopentaneglycolate methobromide / 1,1-Dimethyl-3-hydroxypyrrolidinium bromide alpha-cyclopentylmandelate / 3-Hydroxy-1,1-dimethylpyrrolidinium bromide alpha-cyclopentylmandelate / Glycopyrrolate / Glycopyrronium (as bromide)
External IDs
AD-237 / AHR-504 / CHF-5259 / CHF5259 / NVA237 / PT-001 / PT001 / QVA-149 component glycopyrronium bromide
UNII
V92SO9WP2I
CAS Number
51186-83-5
Weight
Average: 398.341
Monoisotopic: 397.125257
Chemical Formula
C19H28BrNO3
InChI Key
VPNYRYCIDCJBOM-UHFFFAOYSA-M
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
IUPAC Name
3-[(2-cyclopentyl-2-hydroxy-2-phenylacetyl)oxy]-1,1-dimethylpyrrolidin-1-ium bromide
SMILES
[Br-].C[N+]1(C)CCC(C1)OC(=O)C(O)(C1CCCC1)C1=CC=CC=C1
ChemSpider
11201
ChEBI
90972
ChEMBL
CHEMBL1201027
Wikipedia
Glycopyrronium_bromide
Predicted Properties
PropertyValueSource
Water Solubility0.000909 mg/mLALOGPS
logP-1ALOGPS
logP-1.4Chemaxon
logS-5.6ALOGPS
pKa (Strongest Acidic)11.53Chemaxon
pKa (Strongest Basic)-4.3Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area46.53 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity101.08 m3·mol-1Chemaxon
Polarizability36.26 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon