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Glycopyrrolate

CAS# 596-51-0

Glycopyrrolate

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Chemical structure

Glycopyrrolate

3D structure

Chemical Properties of Glycopyrrolate

Cas No. 596-51-0 SDF Download SDF
PubChem ID 11693 Appearance Powder
Formula C19H28BrNO3 M.Wt 398.33
Type of Compound N/A Storage Desiccate at -20°C
Synonyms Glycopyrrolate bromide; Glycopyrronium bromide
Solubility H2O : ≥ 45 mg/mL (112.97 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name (1,1-dimethylpyrrolidin-1-ium-3-yl) 2-cyclopentyl-2-hydroxy-2-phenylacetate;bromide
SMILES C[N+]1(CCC(C1)OC(=O)C(C2CCCC2)(C3=CC=CC=C3)O)C.[Br-]
Standard InChIKey VPNYRYCIDCJBOM-UHFFFAOYSA-M
Standard 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Glycopyrrolate

DescriptionGlycopyrrolate(Glycopyrronium Br) is a muscarinic competitive antagonist used as an antispasmodic. IC50 Value: Target: mAChR (Muscarinic acetylcholine receptor M1) in vitro: Glycopyrrolate showed no selectivity in its binding to the M1-M3 receptors. Kinetics studies, however, showed that glycopyrrolate dissociates slowly from HASM muscarinic receptors (60% protection against [3H]-NMS binding at 30 nM) compared to ipratropium bromide [1]. in vivo: Glycopyrrolate (1 mg) tablets were then administered, starting with one tablet daily the third week and increasing the daily dose by one tablet per week until a maximum of four tablets during week six and 4 days of week seven when the daily dose was reduced to two tablets for 3 days. glycopyrrolate can be given in controlled doses provided that an adequate medical assessment has been undertaken [2]. Glycopyrrolate has a slow and erratic absorption from the gastrointestinal system, but even low plasma levels are associated with a distinct and long-lasting antisialogic effect [3]. Oral glycopyrrolate is emerging as a potential second-line treatment option, but experience with safety, efficacy, and dosing is especially limited in children [4]. phase III study, 52.3% of glycopyrrolate oral solution recipients (aged 3-18 years; n = 137) had an mTDS response (primary endpoint); the response rate was consistently above 50% at all 4-weekly timepoints, aside from the first assessment at week 4 (40.3%). In general, glycopyrrolate oral solution was well tolerated in clinical trials. The majority of adverse events were within expectations as characteristic anticholinergic outcomes [5]. Toxicity: Side effects include dry mouth, difficult urinating, heachaches, diarrhea and constipation. The medication also induces drowsiness or blurred vision. LD50=709 mg/kg (rat, oral).

References:
[1]. Haddad, E.B., et al., Pharmacological characterization of the muscarinic receptor antagonist, glycopyrrolate, in human and guinea-pig airways. Br J Pharmacol, 1999. 127(2): p. 413-20. [2]. Neverlien, P.O., et al., Glycopyrrolate treatment of drooling in an adult male patient with cerebral palsy. Clin Exp Pharmacol Physiol, 2000. 27(4): p. 320-2. [3]. Olsen, A.K. and P. Sjogren, Oral glycopyrrolate alleviates drooling in a patient with tongue cancer. J Pain Symptom Manage, 1999. 18(4): p. 300-2. [4]. Kumar, M.G., et al., Oral Glycopyrrolate for Refractory Pediatric and Adolescent Hyperhidrosis. Pediatr Dermatol, 2013. [5]. Garnock-Jones, K.P., Glycopyrrolate oral solution: for chronic, severe drooling in pediatric patients with neurologic conditions. Paediatr Drugs, 2012. 14(4): p. 263-9.

Glycopyrrolate Dilution Calculator

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Glycopyrrolate Molarity Calculator

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Preparing Stock Solutions of Glycopyrrolate

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.5105 mL 12.5524 mL 25.1048 mL 50.2096 mL 62.762 mL
5 mM 0.5021 mL 2.5105 mL 5.021 mL 10.0419 mL 12.5524 mL
10 mM 0.251 mL 1.2552 mL 2.5105 mL 5.021 mL 6.2762 mL
50 mM 0.0502 mL 0.251 mL 0.5021 mL 1.0042 mL 1.2552 mL
100 mM 0.0251 mL 0.1255 mL 0.251 mL 0.5021 mL 0.6276 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Glycopyrrolate

Glycopyrrolate is a muscarinic competitive antagonist used as an antispasmodic.

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References on Glycopyrrolate

The Effect of Glycopyrrolate on Nocturnal Sialorrhea in Patients Using Clozapine: A Randomized, Crossover, Double-Blind, Placebo-Controlled Trial.[Pubmed:28129312]

J Clin Psychopharmacol. 2017 Apr;37(2):155-161.

BACKGROUND: Nocturnal sialorrhea is one of the most frequent adverse events in clozapine treatment. Symptomatic management of sialorrhea usually consists of off-label treatment with anticholinergic agents. The aim of the current study is to evaluate the efficacy and safety of Glycopyrrolate in patients using clozapine that experience sialorrhea. METHODS: In a double-blind randomized crossover trial, patients with nocturnal sialorrhea (n = 32) were randomized to treatment with Glycopyrrolate 1 mg or placebo. This double-blinded phase was followed by an optional open label extension phase with Glycopyrrolate 2 mg. Exposure periods consisted of 6 consecutive days and were separated with 1 washout week. The primary outcome was clinical improvement of nocturnal sialorrhea assessed by the Patient Global Impression of Improvement (PGI-I). RESULTS: The proportion of patients with a clinical improvement according to PGI-I did not significantly differ between 1 mg and placebo (18.8% vs 6.3%, P = 0.289); however, in patients using Glycopyrrolate 2 mg once daily versus placebo, it did (43.5% vs 6.3%, P = 0.039). Glycopyrrolate was not associated with severe adverse events or worsening of cognitive adverse events. CONCLUSIONS: Glycopyrrolate 1 mg was not superior to placebo, whereas 2 mg showed a significant clinical improvement of nocturnal sialorrhea compared with placebo. Glycopyrrolate seemed to be a tolerable anticholinergic agent in the treatment of clozapine-associated sialorrhea.

The Effect of Nebulized Glycopyrrolate on Posterior Drooling in Patients with Brain Injury: Two Cases of Different Brain Lesions.[Pubmed:28081026]

Am J Phys Med Rehabil. 2017 Aug;96(8):e155-e158.

Posterior drooling, which can lead to substantial respiratory morbidity, including unexplained lung diseases and recurrent pneumonia, is an important issue in the rehabilitation unit. There are various treatment options for posterior drooling, including pharmacologic therapy, oral motor or behavioral therapy, biofeedback, local glandular injection of botulinum toxin, irradiation, and surgery. Among them, nebulized Glycopyrrolate has the following advantages: It is noninvasive and is relatively free of central adverse effects because it does not cross the blood-brain barrier unlike other anticholinergics. Although there has been one case report regarding the effectiveness of nebulized Glycopyrrolate for drooling in a motor neuron patient, there have not been any reports on its effectiveness for posterior drooling. Herein, we report two cases (an 82-year-old male bilateral hemiplegic stroke patient and a 1-year-old female cerebral palsy infant with bilaterally spastic hemiplegia of posterior drooling treated with nebulized Glycopyrrolate) and identify salivary aspiration and the effect of nebulized Glycopyrrolate using radionuclide salivagram. Considering its advantages and effectiveness, nebulized Glycopyrrolate should be considered as one of the reliable methods to manage posterior drooling in patients with impaired cognition or swallowing difficulties, such as severe brain injury.

Glycopyrrolate: It's time to review.[Pubmed:28183573]

J Clin Anesth. 2017 Feb;36:51-53.

Medication shortages have become an all-too-common inconvenience that has forced anesthesia providers to examine our administering practices. Because of these shortages, commonly used medications are at the greatest risk. Glycopyrrolate (Robinul), which has been in short supply in recent years, is one of the most widely used anticholinergic agents, especially in conjunction with the anticholinesterase neostigmine, for reversal of neuromuscular blockade (NMB) drugs. Here we review multiple studies from 1972 through 1986 that used varying methods of patient selection and dosage and drug combination criteria, and which noted that Glycopyrrolate had a superior efficacy and adverse effect profile when compared with atropine in NMB reversal. Meta-analysis from these studies indicated that the dosage of 0.2 mg of Glycopyrrolate for every 1 mg of neostigmine, given concomitantly (maximum 1 mg Glycopyrrolate and 5 mg neostigmine), demonstrated the greatest efficacy with the lowest incidence of unwanted adverse effects. It has now become common practice to use a dosage ratio of 0.2 mg Glycopyrrolate to 1.0 mg neostigmine for NMB reversal. Yet since 1986, there have been no studies on reversal with Glycopyrrolate and neostigmine. Frequent medication shortages and good medical practice should be an impetus for clinicians to reevaluate dosing practices of critical medications and revisit these drugs, such as Glycopyrrolate, with more current studies.

Description

Glycopyrrolate (Glycopyrronium bromide) is a muscarinic competitive antagonist used as an antispasmodic.

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