glycopyrrolate   Click here for help

GtoPdb Ligand ID: 7459

Synonyms: AHR-504 | Qbrexza® (glycopyrronium cloth) | Robinul® | Seebri Neohaler® | Tovanor Breezhaler®
Approved drug Immunopharmacology Ligand
glycopyrrolate is an approved drug (FDA (1961), EMA (2012))
Compound class: Synthetic organic
Comment: Glycopyrrolate is the active moiety of the approved drug glycopyrronium bromide. It is an anticholinergic drug.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: glycopyrronium

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 46.53
Molecular weight 318.21
XLogP 2.59
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES O=C(C(c1ccccc1)(C1CCCC1)O)OC1CC[N+](C1)(C)C
Isomeric SMILES O=C(C(c1ccccc1)(C1CCCC1)O)OC1CC[N+](C1)(C)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
InChI Key ANGKOCUUWGHLCE-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Approved as an anticholinergic bronchodilator to relieve the symptoms of chronic obstructive pulmonary disease (COPD) [4] and asthma [1]. This drug may also be used pre-operatively to reduce salivary tracheobronchial and pharyngeal secretions and to reduce the acidity of gastric contents.
An inhalation formuation containing glycopyrrolate and indacaterol (Utibron Neohaler®) was approved by the US FDA in November 2015 for the treatment of COPD.
In April 2016, the US FDA approved another fixed-dose inhalation aerosol formulation, glycopyrrolate plus the long-acting β agonist (LABA) formoterol (Bevespi Aerosphere®) for long-term, maintenance treatment of airflow obstruction in patients with COPD, including chronic bronchitis and/or emphysema.
In June 2018 the FDA approved glycopyrronium for the topical treatment (administered using a medicated cloth/wipe called Qbrexza®) of primary axillary hyperhidrosis.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Glycopyrrolate is an antagonist of muscarinic acetylcholine receptors. Peripherally, muscarinic receptors are present in the autonomic effector cells of smooth muscle, cardiac muscle, the sinoatrial node, the atrioventricular node, exocrine glands and, minimally, in the autonomic ganglia. Glycopyrrolate antagonism of these peripheral receptors reduces gastric acid secretions and controls excessive pharyngeal, tracheal, and bronchial secretions.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com
European Medicines Agency (EMA)