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Glycopyrronium

HCID 3494
NotesReactions
Basic informationOverviewNames & identifiersPropertiesChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
13283-82-4
Standard SMILES
C[N+]1(C)CCC(OC(=O)C(O)(c2ccccc2)C2CCCC2)C1
InChIKey
ANGKOCUUWGHLCE-UHFFFAOYSA-N
Molecular formula
C19H28NO3+
Average molar mass
318.4 g/mol
Monoisotopic mass
318.20691876

Overview

2-cyclopentyl-2-hydroxy-2-phenylacetic acid (1,1-dimethyl-3-pyrrolidin-1-iumyl) ester is a member of benzenes.

Names & identifiers

Preferred name
Glycopyrronium
IUPAC
(1,1-dimethylpyrrolidin-1-ium-3-yl) 2-cyclopentyl-2-hydroxy-2-phenylacetate

Names & synonyms

GlycopyrroniumGlycopyrrolate cationGlycopyrrolate ionGlycopyrronium ionGlycopyrronium cationGlycopyrronium, erythro-740028-90-4Pyrrolidinium, 3-((cyclopentylhydroxyphenylacetyl)oxy)-1,1-dimethyl-RefChem:922362Pyrrolidinium, 3-[(cyclopentylhydroxyphenylacetyl)oxy]-1,1-dimethyl-A14FB57V1D13283-82-4
Show more names
Robinal3-(2-Cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidin-1-iumNCGC00179456-02Tovanor Breezhaler.beta.-1-Methyl-3-pyrrolidyl-.alpha.-cyclopentylmandelate methobromidePrestwick0_000746Prestwick1_000746Prestwick2_000746

Database identifiers

CAS
13283-82-4、596-51-0、740028-90-4
PubChem CID
3494
DTXSID
DTXSID2048165
ChEMBL
CHEMBL1201335
ChEBI
CHEBI:94449
Nikkaji
J239.170H

Properties

Computed structural properties

XLogP
3.1
Topological polar surface area
46.5 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
5
Heavy atoms
23
Formal charge
1
Complexity
424

Experimental & physicochemical properties

LogP-0.99
Solubility9.44e-04 g/L
Human Drugs · 2 items

Pharmaceuticals

Antiasthmatic and medicines for chronic obstructive pulmonary disease

Melting Point · 2 items

193-194.5

192.5 °C

Physical DescriptionSolid

Chemistry & industry

Pharmacology

ATC Code · 3 items

D - Dermatologicals

QA - Alimentary tract and metabolism

QD - Dermatologicals

Protein BindingGlycopyrronium is 38-44% protein bound in plasma. It is bound to serum albumin, alpha-1-acid glycoprotein, as well as other plasma proteins that have not been identified in literature.
Pharmacodynamics · 1 item

Glycopyrronium is a quaternary ammonium compound that is one of the most commonly prescribed long acting muscarinic antagonists. Glycopyrronium slowly dissociated from muscarinic receptors, leading to a long duration of action. It has a wider therapeutic index than other anticholinergic medications, such as [tiotropium]. Patients should be counselled regarding the risk of worsening urinary retention, risk of overheating, and transient blurred vision.

Mechanism of Action · 1 item

Glycopyrronium is a muscarinic antagonist with the highest affinity for M1 receptors, followed by M3, M2/M4, and M5. Muscarinic receptors M1 to M4 are found in the lung, although M3 is predominantly responsible for bronchoconstriction and airway secretions. Secretions from salivary and sweat glands, as well as gastric acid secretions, are also predominantly mediated by the M3 receptor. Salivary and gastric acid secretions are also partially mediated by the M1 receptor. Antagonism of these receptors decreases the volume of their respective secretions, and in the case of the gastrointestinal system, reduces the acidity of the stomach. In the cardiovascular system, muscarinic receptors M1 to M5 are all present, however the function of M5 has not been described in literature. Under normal circumstances, stimulation of the vagal nerve lowers the heart rate, potentially leading to intraoperative bradycardia. Studies in mice suggest that this stimulation is predominantly mediated by the M3 receptor, and mutant knockout mice are not susceptible to these effects.

Biological Half-LifeThe half life after inhalation is approximately 33-53 hours. The mean half life of a 6 µg/kg intravenous dose is 0.83 ± 0.27 hours. The mean half life of oral glycopyrronium is 3.0 hours.

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesChemistry & industryRelated reactionsCompound notes
Metabolism/Metabolites
Glycopyrronium is hydrolyzed to the inactive M9 metabolite. Metabolism was mainly mediated by CYP2D6, with minor contributions from CYP1A2, CYP2B6, CYP2C9, CYP2C18, CYP2C19, and CYP3A4.
FDA Pharmacological Classification · 6 items

A14FB57V1D

GLYCOPYRRONIUM

Established Pharmacologic Class [EPC] - Anticholinergic

Mechanisms of Action [MoA] - Cholinergic Antagonists

Established Pharmacologic Class [EPC] - Cholinergic Muscarinic Antagonist

Mechanisms of Action [MoA] - Cholinergic Muscarinic Antagonists

MeSH Pharmacological Classification · 2 items

Agents that are administered in association with anesthetics to increase effectiveness, improve delivery, or decrease required dosage.

Drugs that bind to but do not activate MUSCARINIC RECEPTORS, thereby blocking the actions of endogenous ACETYLCHOLINE or exogenous agonists. Muscarinic antagonists have widespread effects including actions on the iris and ciliary muscle of the eye, the heart and blood vessels, secretions of the respiratory tract, GI system, and salivary glands, GI motility, urinary bladder tone, and the central nervous system.

Absorption, Distribution and Excretion · 4 items

In adults, a 66 mg topical dose of glycopyrronium reaches a Cmax of 0.08 ± 0.04 ng/mL, with a Tmax of 1 hour, and an AUC0-24 of 0.88 ± 0.57 h\*ng/mL. Inhaled glycopyrronium is approximately 40% bioavailable. A 25 µg inhaled solution reaches a Cmax of 34.5 pg/mL, with a Tmax of <20 minutes, and an AUC0-inf of 255 h\*pg/mL. An 8 µg/kg intramuscular dose reaches a Cmax of 3.47 ± 1.48 µg/L, with a Tmax of 27.48 ± 6.12 minutes, and an AUC of 6.64 ± 2.33 h\*g/L. Oral glycopyrronium has highly variable pharmacokinetics, reaching a mean Cmax of 0.318 ng/mL, a Tmax of 3.1 hours, and an AUC0-24 of 1.74 h\*ng/mL.

85% of an intravenous dose was recovered in the urine, with <5% recovered in the bile. >80% of the recovered dose is the unchanged parent drug. The remainder is recovered as the inactive M9 metabolite.

The mean volume of distribution in patients aged 1-14 years old is 1.3-1.8 L/kg, with a range of 0.7-3.9 L/kg. The volume of distribution in adults aged 60-75 years is 0.42 ± 0.22 L/kg.

A 6 µg/kg intravenous dose has a clearance of 0.54 ± 0.14 L/kg/h. An oral solution has a clearance of 5.28-38.95 L/h/kg in healthy adults and 8.07-25.65 L/h/kg in patients with cerebral palsy.

Cellular LocationsMembrane

Uses & manufacturing

Use ClassificationPharmaceuticals