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Details

Stereochemistry RACEMIC
Molecular Formula C19H28NO3.Br
Molecular Weight 398.335
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GLYCOPYRROLATE

SMILES

[Br-].C[N+]1(C)CC[C@@H](C1)OC(=O)[C@@](O)(C2CCCC2)C3=CC=CC=C3

InChI

InChIKey=VPNYRYCIDCJBOM-QQTWVUFVSA-M
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/t17-,19-;/m0./s1

HIDE SMILES / InChI

Description

Glycopyrrolate is a synthetic anticholinergic agent with a quaternary ammonium structure. Glycopyrrolate is a muscarinic competitive antagonist used as an antispasmodic, in some disorders of the gastrointestinal tract, and to reduce salivation with some anesthetics. Glycopyrrolate binds competitively to the muscarinic acetylcholine receptor. Like other anticholinergic (antimuscarinic) agents, it inhibits the action of acetylcholine on structures innervated by postganglionic cholinergic nerves and on smooth muscles that respond to acetylcholine but lack cholinergic innervation. These peripheral cholinergic receptors are present in the autonomic effector cells of smooth muscle, cardiac muscle, the sinoatrial node, the atrioventricular node, exocrine glands and, to a limited degree, in the autonomic ganglia. Thus, it diminishes the volume and free acidity of gastric secretions and controls excessive pharyngeal, tracheal, and bronchial secretions. Glycopyrrolate antagonizes muscarinic symptoms (e.g., bronchorrhea, bronchospasm, bradycardia, and intestinal hypermotility) induced by cholinergic drugs such as the anticholinesterases. The highly polar quaternary ammonium group of glycopyrrolate limits its passage across lipid membranes, such as the blood-brain barrier, in contrast to atropine sulfate and scopolamine hydrobromide, which are highly non-polar tertiary amines which penetrate lipid barriers easily. Glycopyrrolate is marketed under the brand names Robinul, Robinul Forte, Cuvposa. In October 2015, glycopyrrolate was approved by the FDA for use as a standalone treatment for Chronic obstructive pulmonary disease (COPD), as Seebri Neohaler.

CNS Activity

Originator

Approval Year

PMID

PMID

TitleDatePMID
Comparative study of atropine and glycopyrrolate on suxamethonium-induced changes in cardiac rate and rhythm.
1980 Mar
Comparison of some postanaesthetic effects of atropine and glycopyrrolate with particular emphasis on urinary problems.
1984 Feb
Excess tachycardia: heart rate after antimuscarinic agents in conscious dogs.
1984 Feb
Effect of halogenated anaesthetics on heart rate changes during reversal of neuromuscular block with glycopyrrolate and neostigmine.
1984 Nov
Comparison of i.v. glycopyrrolate and atropine in the prevention of bradycardia and arrhythmias following repeated doses of suxamethonium in children.
1984 Sep
Effects of oral potassium supplements on upper gastrointestinal mucosa: multicenter clinical comparison of three formulations and placebo.
1986
Refractory bradycardia after reversal of muscle relaxant in a diabetic with vagal neuropathy.
1986 Nov
Twelve-hour bronchodilation in asthma with a single aerosol dose of the anticholinergic compound glycopyrrolate.
1988 Jul
A glycopyrrolate-ritodrine drug-drug interaction.
1988 Mar
Glycopyrronium requirements for antagonism of the muscarinic side effects of edrophonium.
1989 Jan
Complete heart block following glycopyrronium/neostigmine mixture.
1989 May
Correlation of brain levels of 9-amino-1,2,3,4-tetrahydroacridine (THA) with neurochemical and behavioral changes.
1989 Nov 28
Sensitivity to both vecuronium and neostigmine in a sero-negative myasthenic patient.
1989 Oct
Effects of anticholinergic treatment on the cardiac and respiratory systems in dogs sedated with medetomidine.
1991 Oct 5
[A comparison of the two anticholinergic agents atropine and glycopyrrolate during antagonism of a muscle relaxation with pyridostigmine].
1993
Attenuation of vagal reflexes during tracheal intubation following vagotonic anesthetic agents.
1994 Oct
Asystole associated with iohexol myelography in a dog.
1997 Jul-Aug
Postoperative reparalysis after rocuronium following nebulized epinephrine.
1997 Mar
Neuromuscular blockade after clindamycin administration: a case report.
1999 May
Vagal cardiac function and arterial blood pressure stability.
2001 Nov
Treatment of compensatory gustatory hyperhidrosis with topical glycopyrrolate.
2003 Aug 30
Acute hypertensive crisis resulting in pulmonary edema and myocardial ischemia during orthognathic surgery.
2004 Feb
Masseter muscle spasm following atracurium.
2004 May
Pharmacokinetic and pharmacodynamic evaluations of the zwitterionic metabolite of a new series of N-substituted soft anticholinergics.
2005 Dec
Urinary retention caused by topical glycopyrrolate for hyperhidrosis.
2006 Sep
An exaggerated hypertensive response to glycopyrrolate therapy for bradycardia associated with high-dose dexmedetomidine.
2009 Mar
Inhalation by design: novel tertiary amine muscarinic M₃ receptor antagonists with slow off-rate binding kinetics for inhaled once-daily treatment of chronic obstructive pulmonary disease.
2011 Oct 13
Comparing the cardiovascular therapeutic indices of glycopyrronium and tiotropium in an integrated rat pharmacokinetic, pharmacodynamic and safety model.
2015 Aug 15
Patent

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Anesthesia Preanesthetic (reduction of secretions): 0.004 mg (0.02 mL)/kg IM 30 to 60 minutes prior to the anticipated time of induction of anesthesia or at the time the preanesthetic narcotic and/or sedative are administered. Intraoperative: 0.1 mg (0.5 mL) IV repeated as needed every 2 to 3 minutes. Reversal of neuromuscular blockade: 0.2 mg (1.0 mL) IV for each 1.0 mg of neostigmine or 5 mg of pyridostigmine. Reversal of bradycardia, vagal reflexes (intraoperative): 0.1 mg IV repeated as needed at 2 to 3 minute intervals. Usual Adult Dose for Peptic Ulcer Parenteral: 0.1 mg (0.5 mL) IV or IM every 4 hours, 3 to 4 times daily. If a more profound effect is required the dose may be increased to 0.2 mg (1 mL). 1 mg oral tablet: Initial dose: 1 mg orally 3 times daily or 1 mg in the morning, 1 mg in the early afternoon, and 2 mg at bedtime. Maintenance dose: 1 mg orally twice daily to a maximum of 8 mg per day. 2 mg oral tablet: 2 mg orally 2 to 3 times daily to a maximum of 8 mg per day. 1.5 mg oral tablet: Used to provide intermediate titration doses based on patient response. Usual Pediatric Dose for Anesthesia Preanesthetic: 0.004 mg (0.02 mL)/kg IM 30 to 60 minutes prior to the anticipated time of induction of anesthesia or at the time the preanesthetic narcotic and/or sedative are administered. Children under 2 years of age may require up to 0.009 mg (0.45 mL)/kg. Intraoperative: 0.004 mg (0.02 mL)/kg IV not to exceed 0.1 mg (0.5 mL) in a single dose, repeated as needed every 2 to 3 minutes. Reversal of neuromuscular blockade: 0.4 mg (2 mL)/kg IV for each 1 mg of neostigmine or 5 mg of pyridostigmine. Reversal of bradycardia, vagal reflexes (intraoperative): 4 mcg/kg/dose IV (maximum dose: 100 mcg/dose) at 2 to 3 minute intervals. Usual Pediatric Dose for Excessive Salivation 3 years to 16 years with neurologic conditions associated with problem drooling: Initiate dosing at 0.02 mg/kg orally three times daily and titrate in increments of 0.02 mg/kg every 5 to 7 days, based on therapeutic response and adverse reactions. Maximum recommended dose is 0.1 mg/kg three times daily, not to exceed 1.5 to 3 mg per dose based upon weight. Administer at least one hour before or two hours after meals.
Route of Administration: Parenteral: IV or IM; oral
In Vitro Use Guide
Glycopyrrolate inhibited contraction induced by EFS (40 V, 0.5 ms, 4 Hz for 15 s every 4 min) in guinea-pig trachea in a concentration-dependent manner (IC50=0.15 nM, n=5 ± 12). Glycopyrrolate inhibited contraction induced by EFS (40 V, 0.5 ms, 8 Hz for 15 s every 4 min) in human trachea in a concentration-dependent manner (IC50=0.44 nM, n=3 ± 8).
Name Type Language
GLYCOPYRROLATE
GREEN BOOK   MI   ORANGE BOOK   USAN   USP   VANDF  
USAN  
Official Name English
GLYCOPYRROLATE [VANDF]
Common Name English
GLYCOPYRROLATE [USP]
Common Name English
TARODYL
Brand Name English
NVA-237
Code English
CHF5259
Code English
PYRROLIDINIUM, 3-((CYCLOPENTYLHYDROXYPHENYLACETYL)OXY)-1,1-DIMETHYL-, BROMIDE
Systematic Name English
GLYCOPYRRONIUM BROMIDE [WHO-DD]
Common Name English
GLYCOPYRRONIUM BROMIDE [EP]
Common Name English
GLYCOPYRROLATE [ORANGE BOOK]
Common Name English
GLYCOPYRROLATE COMPONENT OF UTIBRON
Common Name English
PYRROLIDINIUM, 3-((2-CYCLOPENTYL-2-HYDROXY-2-PHENYLACETYL)OXY)-1,1-DIMETHYL-, BROMIDE (1:1)
Systematic Name English
PYRROLIDINIUM, 3-(((2R)-2-CYCLOPENTYL-2-HYDROXY-2-PHENYLACETYL)OXY)-1,1-DIMETHYL-, BROMIDE (1:1), (3S)-REL-
Systematic Name English
GLYCOPYRROLATE [USAN]
Common Name English
NSC-250836
Code English
SEEBRI
Brand Name English
NODAPTON
Brand Name English
PT-001
Code English
ROBINUL
Brand Name English
TARODYN
Brand Name English
NSC-251252
Code English
LONHALA MAGNAIR KIT
Brand Name English
GLYCOPYRROLATE COMPONENT OF BEVESPI AEROSPHERE
Common Name English
GLYCOPYRRONIUM BROMIDE [JAN]
Common Name English
GLYCOPYRRONIUM BROMIDE [INN]
Common Name English
GLYCOPYRRONIUM BROMIDE
EP   INN   JAN   MART.   WHO-DD  
INN  
Official Name English
CHF-5259
Code English
GLYCOPYRRONIUM BROMIDE [MART.]
Common Name English
ROBANUL
Brand Name English
NVA237
Code English
NSC-251251
Code English
GLYCOPYRROLATE, ERYTHRO-
Common Name English
BEVESPI AEROSPHERE COMPONENT GLYCOPYRROLATE
Brand Name English
PT001
Code English
3-HYDROXY-1,1-DIMETHYLPYRROLIDINIUM BROMIDE .ALPHA.-CYCLOPENTYLMANDELATE
Common Name English
GLYCOPYRRONIUM (AS BROMIDE)
Common Name English
AD-237
Code English
ORG-NC-45
Code English
BEVESPI AEROSPHERE COMPONENT OF GLYCOPYRROLATE
Common Name English
GLYCOPYRROLATE [GREEN BOOK]
Common Name English
AHR-504
Code English
GLYCOPYRROLATE [MI]
Common Name English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS SEEBRI BREEZHALER (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Tue Mar 06 10:25:42 UTC 2018 , Edited by admin on Tue Mar 06 10:25:42 UTC 2018
WHO-ATC R03AL04
Created by admin on Tue Mar 06 10:25:42 UTC 2018 , Edited by admin on Tue Mar 06 10:25:42 UTC 2018
EMA ASSESSMENT REPORTS ULUNAR BREEZHALER (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Tue Mar 06 10:25:42 UTC 2018 , Edited by admin on Tue Mar 06 10:25:42 UTC 2018
EMA ASSESSMENT REPORTS ULTIBRO BREEZHALER (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Tue Mar 06 10:25:42 UTC 2018 , Edited by admin on Tue Mar 06 10:25:42 UTC 2018
CFR 21 CFR 522.1066
Created by admin on Tue Mar 06 10:25:42 UTC 2018 , Edited by admin on Tue Mar 06 10:25:42 UTC 2018
WHO-ATC A03AB02
Created by admin on Tue Mar 06 10:25:42 UTC 2018 , Edited by admin on Tue Mar 06 10:25:42 UTC 2018
EMA ASSESSMENT REPORTS ENUREV BREEZHALER (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Tue Mar 06 10:25:42 UTC 2018 , Edited by admin on Tue Mar 06 10:25:42 UTC 2018
WHO-ATC A03CA05
Created by admin on Tue Mar 06 10:25:42 UTC 2018 , Edited by admin on Tue Mar 06 10:25:42 UTC 2018
WHO-VATC QR03AL04
Created by admin on Tue Mar 06 10:25:42 UTC 2018 , Edited by admin on Tue Mar 06 10:25:42 UTC 2018
LIVERTOX 464
Created by admin on Tue Mar 06 10:25:42 UTC 2018 , Edited by admin on Tue Mar 06 10:25:42 UTC 2018
WHO-ATC R03BB06
Created by admin on Tue Mar 06 10:25:42 UTC 2018 , Edited by admin on Tue Mar 06 10:25:42 UTC 2018
EMA ASSESSMENT REPORTS XOTERNA BREEZHALER (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Tue Mar 06 10:25:42 UTC 2018 , Edited by admin on Tue Mar 06 10:25:42 UTC 2018
EMA ASSESSMENT REPORTS TOVANOR BREEZHALER (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Tue Mar 06 10:25:42 UTC 2018 , Edited by admin on Tue Mar 06 10:25:42 UTC 2018
WHO-VATC QR03BB06
Created by admin on Tue Mar 06 10:25:42 UTC 2018 , Edited by admin on Tue Mar 06 10:25:42 UTC 2018
Code System Code Type Description
MESH
D006024
Created by admin on Tue Mar 06 10:25:42 UTC 2018 , Edited by admin on Tue Mar 06 10:25:42 UTC 2018
PRIMARY
IUPHAR
7459
Created by admin on Tue Mar 06 10:25:42 UTC 2018 , Edited by admin on Tue Mar 06 10:25:42 UTC 2018
PRIMARY
NCI_THESAURUS
C29078
Created by admin on Tue Mar 06 10:25:42 UTC 2018 , Edited by admin on Tue Mar 06 10:25:42 UTC 2018
PRIMARY
CAS
596-51-0
Created by admin on Tue Mar 06 10:25:42 UTC 2018 , Edited by admin on Tue Mar 06 10:25:42 UTC 2018
NON-SPECIFIC STEREOCHEMISTRY
ECHA (EC/EINECS)
209-887-0
Created by admin on Tue Mar 06 10:25:42 UTC 2018 , Edited by admin on Tue Mar 06 10:25:42 UTC 2018
PRIMARY
MERCK INDEX
M5807
Created by admin on Tue Mar 06 10:25:42 UTC 2018 , Edited by admin on Tue Mar 06 10:25:42 UTC 2018
PRIMARY Merck Index
LactMed
596-51-0
Created by admin on Tue Mar 06 10:25:42 UTC 2018 , Edited by admin on Tue Mar 06 10:25:42 UTC 2018
PRIMARY
RXCUI
4955
Created by admin on Tue Mar 06 10:25:42 UTC 2018 , Edited by admin on Tue Mar 06 10:25:42 UTC 2018
PRIMARY RxNorm
INN
1038
Created by admin on Tue Mar 06 10:25:42 UTC 2018 , Edited by admin on Tue Mar 06 10:25:42 UTC 2018
PRIMARY
PUBCHEM
67204829
Created by admin on Tue Mar 06 10:25:42 UTC 2018 , Edited by admin on Tue Mar 06 10:25:42 UTC 2018
PRIMARY SWITZERF
EPA CompTox
51186-83-5
Created by admin on Tue Mar 06 10:25:42 UTC 2018 , Edited by admin on Tue Mar 06 10:25:42 UTC 2018
PRIMARY
ChEMBL
CHEMBL1201335
Created by admin on Tue Mar 06 10:25:42 UTC 2018 , Edited by admin on Tue Mar 06 10:25:42 UTC 2018
PRIMARY
CAS
59677-71-3
Created by admin on Tue Mar 06 10:25:42 UTC 2018 , Edited by admin on Tue Mar 06 10:25:42 UTC 2018
SUPERCEDED
EVMPD
SUB07951MIG
Created by admin on Tue Mar 06 10:25:42 UTC 2018 , Edited by admin on Tue Mar 06 10:25:42 UTC 2018
PRIMARY
CAS
51186-83-5
Created by admin on Tue Mar 06 10:25:42 UTC 2018 , Edited by admin on Tue Mar 06 10:25:42 UTC 2018
PRIMARY