Glycopyrrolate

HCID 11693
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Basic information

CAS
596-51-0
Standard SMILES
C[N+]1(C)CCC(OC(=O)C(O)(c2ccccc2)C2CCCC2)C1.[Br-]
InChIKey
VPNYRYCIDCJBOM-UHFFFAOYSA-M
Molecular formula
C19H28BrNO3
Average molar mass
398.3 g/mol

Overview

Glycopyrronium bromide is a quaternary ammonium salt composed of 3-{[cyclopentyl(hydroxy)phenylacetyl]oxy}-1,1-dimethylpyrrolidin-1-ium and bromide ions in a 1:1 ratio. It is a quaternary ammonium salt and an organic bromide salt.

Names & identifiers

Preferred name
Glycopyrrolate
IUPAC
(1,1-dimethylpyrrolidin-1-ium-3-yl) 2-cyclopentyl-2-hydroxy-2-phenylacetate bromide
English name
Glycopyrrolate
Molecular formula
C19H28BrNO3-
Molecular weight
398.33

Names & synonyms

GLYCOPYRROLATE596-51-0glycopyrronium bromideRobinulNodaptonTarodylTarodynCuvposaRobanulGlycopyrronii bromidumBromuro de glicopirronioBromure de glycopyrronium
Show more names
GLYCOPYRRONIUMGLYCOPYROLATEGlycopyrronium impurity NGlycopyrrone bromideGlycopyrronium for peak identificationGlycopyrronium for peak identification CRSPyrrolidinium, 3-(cyclopentylhydroxyphenylacetyl)oxy-1,1-dimethyl-, bromideahr504NVA237
SeebriROBINUL FORTESeebri NeohalerAHR-5041,1-Dimethyl-3-hydroxypyrrolidinium bromide alpha-cyclopentylmandelateNVA 237NVA-237Glycopyrrolate, erythro-

Database identifiers

CAS
596-51-0
PubChem CID
11693
DTXSID
DTXSID6023109
ChEMBL
CHEMBL1201027
ChEBI
CHEBI:90972
EC Number
209-887-0

Properties

Computed structural properties

Topological polar surface area
46.5 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
5
Heavy atoms
24

Experimental & physicochemical properties

Human Drugs · 6 items

Breast Feeding; Lactation; Milk, Human; Adjuvants, Anesthesia; Bronchodilator Agents; Muscarinic Antagonists; Parasympatholytics

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

Animal DrugsActive Ingredients (Glycopyrrolate) -> FDA Greenbook
Collision Cross Section203.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
192 · 192-195°C
Density
1.3222 · 1.3222 (rough estimate)
refractive index
1.62 · 1.6200 (estimate)
storage temp.
2 · 2-8°C
solubility
2 O: · H2O: ≥24mg/mL
form
powder

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (23.5%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 51 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationGlycopyrronium bromide: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Other Safety InformationIMAP assessments - Pyrrolidinium, 3-[(cyclopentylhydroxyphenylacetyl)oxy]-1,1-dimethyl-, bromide: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (23.5%)

Toxicology

HepatotoxicityLike other anticholinergic agents, glycopyrrolate has not been linked to episodes of liver enzyme elevations or clinically apparent liver injury. A major reason for its safety may relate to the low daily dose.
Adverse Effects · 1 item

Potential adverse reactions associated with glycopyrrolate administration include anticholinergic symptoms such as mydriasis, hyperthermia, tachycardia, and cardiac arrhythmia. They may also include blurred vision, constipation, cycloplegia, dry mouth, dry skin, flushing, photophobia, urinary retention, and xerophthalmia.

Toxicity Summary · 1 item

Acute toxicity with glycopyrrolate is secondary to an extension of the pharmacologic effects on the muscarinic cholinergic receptors. Muscarinic receptor sites are located in the brain's cerebral cortex, thalamus, hippocampus, and reticular activating system. They are also present in the postganglionic parasympathetic nervous system and other sites like sweat glands. Anticholinergic agents block the effects of acetylcholine by competitively binding and blocking muscarinic receptors.

Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Glycopyrrolate

vNo-DILI-concern

0

No match

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Safety data

wgk
3
rtecs
UY4337630
hs_code
29339900
Toxicity
LD50 (72 hr.) in female mice, female rats (mg/kg): 107, 196 i.p.; in male rats (mg/kg): 1150 orally (Franko)
risk_code
36/37/38
Signal word
Warning

Chemistry & industry

Pharmacology

ATC Code · 4 items

A03AB02

R - Respiratory system

A - Alimentary tract and metabolism

QR - Respiratory system

FDA Pharmacological Classification · 4 items

GLYCOPYRROLATE

Cholinergic Muscarinic Antagonist [EPC]; Cholinergic Muscarinic Antagonists [MoA]; Cholinergic Antagonists [MoA]; Anticholinergic [EPC]

GLYCOPYRROLATE ORAL SOLUTION

Cholinergic Muscarinic Antagonists [MoA]; Cholinergic Muscarinic Antagonist [EPC]; Cholinergic Antagonists [MoA]; Anticholinergic [EPC]

MeSH Pharmacological Classification · 2 items

Agents that are administered in association with anesthetics to increase effectiveness, improve delivery, or decrease required dosage.

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.

Uses & manufacturing

Use ClassificationAnimal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients
Applications · 7 items

DescriptionGlycopyrrolate is an antagonist of muscarinic acetylcholine receptors (mAChRs; Kis = 0.42, 1.77, 0.52, 0.78, and 1.29 nM for the M1-M5 receptors, respectively). It induces relaxation of precontracted isolated human bronchi when used at concentrations of 0.01, 0.1, or 1 μM. Glycopyrrolate reduces post-prandial gastric antral motility in dogs when administered at a dose of 0.01 mg/kg. It inhibits salivation in a rat model of sialorrhea induced by pilocarpine with an ED50 value of 0.74 μg/kg. Formulations containing glycopyrrolate have been used in the treatment of sialorrhea, peptic ulcers, and chronic obstructive pulmonary disease (COPD).

Usessunscreen

UsesFor 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 intubat

UsesInhaled glycopyrrolate of is used to treat air flow blockage and prevent worsening of chronic obstructive pulmonary disease (COPD), including chronic bronchitis and emphysema. COPD is a long-term lung disease that causes bronchospasm (difficulty with breathing).

UsesGlycopyrrolate inhibits secretion of digestive juices and restores normal stomach function. It is used for treating stomach ulcers, inflamed intestine, and also as a pre-operational drug for inhibiting excess stomach secretion.

UsesA synthetic, quaternary ammonium anticholinergic. Antispasmodic; preanesthetic medicant.

General DescriptionGlycopyrrolate, 3-hydroxy-1,1-dimethylpyrrolidinium bromide -cyclopentylmandelate(Robinul), occurs as a white, crystalline powder that is solublein water or alcohol but practically insoluble in chloroformor ether.Glycopyrrolate is a typical anticholinergic and possesses,at adequate dosage levels, the atropine-like effectscharacteristic of this class of drugs. It has a spasmolyticeffect on the musculature of the GI tract as well as the genitourinarytract. It diminishes gastric and pancreatic secretionsand the quantity of perspiration and saliva. Its sideeffects are also typically atropine-like (i.e., dryness of themouth, urinary retention, blurred vision, constipation).Glycopyrrolate is a more potent antagonist on M1 than onM2 and M3 receptors. The low affinity of M2 receptorsmay, in part, explain the low incidence of tachycardiaduring use of this drug as an antispasmodic.77 Because ofits quaternary ammonium character, glycopyrrolate rarelycauses CNS disturbances, although in sufficiently highdosage, it can bring about ganglionic and myoneural junctionblock.

Upstream & downstream products

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]
山东雨禾医药科技有限公司15263077727

Additional notes

DefinitionChEBI: A quaternary ammonium salt composed of 3-{[cyclopentyl(hydroxy)phenylacetyl]oxy}-1,1-dimethylpyrrolidin-1-ium and bromide ions in a 1:1 ratio.

Related reactions

5 records
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Compound notes

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