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Home > Encyclopedia > (1,1-dimethylpyrrolidin-1-ium-3-yl) 2-cyclopentyl-2-hydroxy-2-phenylacetate

(1,1-dimethylpyrrolidin-1-ium-3-yl) 2-cyclopentyl-2-hydroxy-2-phenylacetate

(1,1-dimethylpyrrolidin-1-ium-3-yl) 2-cyclopentyl-2-hydroxy-2-phenylacetate structure

(1,1-dimethylpyrrolidin-1-ium-3-yl) 2-cyclopentyl-2-hydroxy-2-phenylacetate 

structure
  • CAS No:

    13283-82-4

  • Formula:

    C19H28NO3+

  • Chemical Name:

    (1,1-dimethylpyrrolidin-1-ium-3-yl) 2-cyclopentyl-2-hydroxy-2-phenylacetate

  • Synonyms:

    Bromide, Glycopyrronium;Glycopyrrolate;Glycopyrronium;Glycopyrronium Bromide;NVA 237;NVA-237;NVA237;Pyrrolidinium, 3-((cyclopentylhydroxyphenylacetyl)oxy)-1,1-dimethyl-, bromide;Glycopyrronium;glycopyrronium bromide;Robanul;Robinal;13283-82-4;Glycopyrrolate cation;Seebri Neohaler;(1,1-dimethylpyrrolidin-1-ium-3-yl) 2-cyclopentyl-2-hydroxy-2-phenylacetate;3-[(2-cyclopentyl-2-hydroxy-2-phenylacetyl)oxy]-1,1-dimethylpyrrolidin-1-ium;Glycopyrronium (USAN);NSC250836;NSC251251;NSC251252;NCGC00179456-02;Glycopyrrolate ion;Glycopyrronium ion;Tovanor Breezhaler;zlchem 10;Glycopyrronium cation;.beta.-1-Methyl-3-pyrrolidyl-.alpha.-cyclopentylmandelate methobromide;G00010-Watson-Int;Prestwick0_000746;Prestwick1_000746;Prestwick2_000746;Prestwick3_000746;BSPBio_000732;SCHEMBL133002;SPBio_002671;BPBio1_000806;GTPL7459;CHEMBL1201335;DTXSID2048165;CHEBI:94449;ZLA0012;Qbrexza® (glycopyrronium cloth);740028-90-4;BDBM50417445;Pyrrolidinium, 3-hydroxy-1,1-dimethyl-, bromide, .alpha.-cyclopentylmandelate;DB00986;MRF-0000310;NCGC00179456-01;SBI-0206947.P001;AB00513912;D10938;AB00513912-08;AB00513912_10;L001045;Q411917;BRD-A81233518-004-07-0;(1,1-dimethylpyrrolidin-1-ium-3-yl) 2-cyclopentyl-2-hydroxy-2-phenyl-acetate;2-cyclopentyl-2-hydroxy-2-phenylacetic acid (1,1-dimethyl-3-pyrrolidin-1-iumyl) ester;(1,1-Dimethyl-2,3,4,5-tetrahydropyrrol-3-yl) 2-cyclopentyl-2-hydroxy-2-phenyl-acetate bromide;(1,1-Dimethyl-2,3,4,5-tetrahydropyrrol-3-yl) 2-cyclopentyl-2-hydroxy-2-phenyl-acetate bromide Glycopyrronium bromide

Description

Solid


2-cyclopentyl-2-hydroxy-2-phenylacetic acid (1,1-dimethyl-3-pyrrolidin-1-iumyl) ester is a member of benzenes.|Glycopyrronium (as the bromide salt glycopyrrolate) is a synthetic anticholinergic agent with a quaternary ammonium structure. A muscarinic competitive antagonist used as an antispasmodic, in some disorders of the gastrointestinal tract, and to reduce salivation with some anesthetics. In October 2015, glycopyrrolate was approved by the FDA for use as a standalone treatment for Chronic obstructive pulmonary disease (COPD), as Seebri Neohaler.|A muscarinic antagonist used as an antispasmodic, in some disorders of the gastrointestinal tract, and to reduce salivation with some anesthetics.

(1,1-dimethylpyrrolidin-1-ium-3-yl) 2-cyclopentyl-2-hydroxy-2-phenylacetate Basic Attributes

318.4 g/mol

318.20691876 g/mol

209-887-0

DTXSID2048165

R03AL09|R03BB06|R03AL04|R03AL07|A03AB02|R03AL|A - Alimentary tract and metabolism|D - Dermatologicals|R - Respiratory system

Characteristics

46.5 Ų

-0.99

193-194.5|192.5°C

9.44e-04 g/L

Safety Information

|Warning|H302 (22%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 50 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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).

Drug Information

For use as a preoperative antimuscarinic to reduce salivary, tracheobronchial, and pharyngeal secretions, to reduce the volume and free acidity of gastric secretions and to block cardiac vagal inhibitory reflexes during induction of anesthesia and intubation. Also used to treat chronic obstructive pulmonary disease (COPD).|FDA Label|Maintenance treatment of asthma, in adults not adequately controlled with a maintenance combination of a long-acting beta2-agonist and high dose of inhaled corticosteroid, and who experienced one or more asthma exacerbations in the previous year.COPDMaintenance treatment in adult patients with moderate to severe chronic obstructive pulmonary disease (COPD) who are not adequately treated by a combination of an inhaled corticosteroid and a long-acting beta2-agonist or a combination of a long-acting beta2-agonist and a long-acting muscarinic antagonist (for effects on symptoms control and prevention of exacerbations see section 5.1).AsthmaMaintenance treatment of asthma, in adults not adequately controlled with a maintenance combination of a long-acting beta2-agonist and medium dose of inhaled corticosteroid, and who experienced one or more asthma exacerbations in the previous year. |Tovanor Breezhaler is indicated as a maintenance bronchodilator treatment to relieve symptoms in adult patients with chronic obstructive pulmonary disease (COPD).|Seebri Breezhaler is indicated as a maintenance bronchodilator treatment to relieve symptoms in adult patients with chronic obstructive pulmonary disease (COPD).|Xoterna Breezhaler is indicated as a maintenance bronchodilator treatment to relieve symptoms in adult patients with chronic obstructive pulmonary disease (COPD).|Ulunar Breezhaler is indicated as a maintenance bronchodilator treatment to relieve symptoms in adult patients with chronic obstructive pulmonary disease (COPD).|Enurev Breezhaler is indicated as a maintenance bronchodilator treatment to relieve symptoms in adult patients with chronic obstructive pulmonary disease (COPD).|Ultibro Breezhaler is indicated as a maintenance bronchodilator treatment to relieve symptoms in adult patients with chronic obstructive pulmonary disease (COPD).|Bevespi Aerosphere is indicated as a maintenance bronchodilator treatment to relieve symptoms in adult patients with chronic obstructive pulmonary disease (COPD).|Symptomatic treatment of severe sialorrhoea (chronic pathological drooling) in children and adolescents aged 3 years and older with chronic neurological disorders.|Maintenance treatment in adult patients with moderate to severe chronic obstructive pulmonary disease (COPD) who are not adequately treated by a combination of an inhaled corticosteroid and a long-acting beta2-agonist (for effects on symptoms control and prevention of exacerbations see section 5.1).|Treatment of sialorrhoea|Chronic obstructive pulmonary disease|Enerzair Breezhaler is indicated as a maintenance treatment of asthma in adult patients not adequately controlled with a maintenance combination of a long acting beta2 agonist and a high dose of an inhaled corticosteroid who experienced one or more asthma exacerbations in the previous year.|Maintenance treatment of asthma in adults whose disease is not adequately controlled.|Trixeo Aerosphere is indicated as a maintenance treatment in adult patients with moderate to severe chronic obstructive pulmonary disease (COPD) who are not adequately treated by a combination of an inhaled corticosteroid and a long acting beta2 agonist or combination of a long-acting beta2 agonist and a long acting muscarinic antagonist.|Treatment of asthma|Treatment of hyperhidrosis

Glycopyrrolate decreases acid secretion in the stomach. Hence it can be used for treating ulcers in the stomach and small intestine, in combination with other medications. In anesthesia, glycopyrrolate injection serves as a preoperative antimuscarinic operation that reduces salivary, tracheobronchial, and pharyngeal secretions, as well as decreases the acidity of gastric secretions blocks cardiac vagal inhibitory reflexes during intubation

Agents that are administered in association with anesthetics to increase effectiveness, improve delivery, or decrease required dosage. (See all compounds classified as Adjuvants, Anesthesia.)|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. (See all compounds classified as Muscarinic Antagonists.)

Rapidly absorbed (1-2 minutes) after intravenous injection

0.6-1.2 hours

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.

Bromide, Glycopyrronium

(1,1-dimethylpyrrolidin-1-ium-3-yl) 2-cyclopentyl-2-hydroxy-2-phenylacetate Use and Manufacturing

Human drugs -> Trimbow -> EMA Drug Category|Drugs for obstructive airway diseases -> Human pharmacotherapeutic group|Human drugs -> Tovanor Breezhaler -> EMA Drug Category|Human drugs -> Seebri Breezhaler -> EMA Drug Category|Human drugs -> Xoterna Breezhaler -> EMA Drug Category|Adrenergics in combinations with anticholinergics incl. triple combinations with corticosteroids -> Human pharmacotherapeutic group|Human drugs -> Ulunar Breezhaler -> EMA Drug Category|Human drugs -> Enurev Breezhaler -> EMA Drug Category|Human drugs -> Ultibro Breezhaler -> EMA Drug Category|Drugs for obstructive airway diseases, Adrenergics in combinations with anticholinergics incl. triple combinations with corticosteroids -> Human pharmacotherapeutic group|Human drugs -> Bevespi Aerosphere -> EMA Drug Category|formoterol and glycopyrronium bromide -> Human pharmacotherapeutic group|Human drugs -> Sialanar -> EMA Drug Category|Drugs for functional gastrointestinal disorders -> Human pharmacotherapeutic group|Human drugs -> Trydonis -> EMA Drug Category|Human drugs -> Riarify (previously CHF 5993 Chiesi Farmaceutici S.p.A.) -> EMA Drug Category|Human Drugs -> EU pediatric investigation plans|Human drugs -> Enerzair Breezhaler -> EMA Drug Category|Human drugs -> Zimbus Breezhaler -> EMA Drug Category|Human drugs -> Trixeo Aerosphere -> EMA Drug Category|Pharmaceuticals

Computed Properties

Molecular Weight:318.4
XLogP3:3.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:5
Exact Mass:318.20691876
Monoisotopic Mass:318.20691876
Topological Polar Surface Area:46.5
Heavy Atom Count:23
Formal Charge:1
Complexity:424
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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