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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2D Structure
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Physico-chemical Properties
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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
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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
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.
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