Grundinformationen
- Standard-SMILES
C[N+]1(C)CCC(OC(=O)C(O)(c2ccccc2)C2CCCC2)C1.[Br-]- InChIKey
VPNYRYCIDCJBOM-UHFFFAOYSA-M- Summenformel
- C19H28BrNO3
- Durchschnittliche Molmasse
- 398,3 g/mol
Überblick
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.
Namen und Bezeichner
- Bevorzugter Name
- Glycopyrrolate
- IUPAC
- (1,1-dimethylpyrrolidin-1-ium-3-yl) 2-cyclopentyl-2-hydroxy-2-phenylacetate bromide
- Lokaler Name
- Glycopyrroniumbromid
- Englischer Name
- Glycopyrrolate
- Summenformel
- C19H28BrNO3-
- Molmasse
- 398.33
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
596-51-0- PubChem CID
- 11693
- DTXSID
DTXSID6023109- ChEMBL
CHEMBL1201027- ChEBI
CHEBI:90972- EC Number
- 209-887-0
Eigenschaften
Berechnete Struktureigenschaften
- Polarare Oberfläche (TPSA)
- 46,5 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 5
- Schwere Atome
- 24
- Formalladung
- 0
- Komplexität
- 424
Experimentelle und physikochemische Eigenschaften
Human Drugs
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
Physikochemische Eigenschaften
- Schmelzpunkt
- 192 · 192-195°C
- Dichte
- 1.3222 · 1.3222 (rough estimate)
- Brechungsindex
- 1.62 · 1.6200 (estimate)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- 2 O: · H2O: ≥24mg/mL
- Aggregatzustand
- powder
- Farbe
- white to tan
- Wasserlöslichkeit
- 2 O: · H2O: ≥24mg/mL
- Merck
- 14 · 14,4501
- Stabilität
- Hygroscopic
- 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
- InChIKey
- VPNYRYCIDCJBOM-UHFFFAOYSA-M
- SMILES
- C(O)(C(=O)OC1CC[N+](C)(C)C1)(C1=CC=CC=C1)C1CCCC1.[Br-]
- CAS Datenbank
- 596 · 596-51-0(CAS DataBase Reference)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
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.
Gefahrenhinweise
Toxikologische Informationen
Adverse Effects
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
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
Drug Induced Liver Injury Rank (DILIrank 2.0)
Glycopyrrolate
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
Sicherheitsdaten
- wgk
- 3
- hs_code
- 29339900
- RTECS-Nr.
- UY4337630
- risk_code
- 36/37/38
- Toxizität
- LD50 (72 hr.) in female mice, female rats (mg/kg): 107, 196 i.p.; in male rats (mg/kg): 1150 orally (Franko)
- hazard_code
- Xi
- safety_code
- 26
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Chemie und Industrie
Pharmakologische Informationen
ATC Code
A03AB02
R - Respiratory system
A - Alimentary tract and metabolism
QR - Respiratory system
FDA Pharmacological Classification
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
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.
Verwendung und Herstellung
Anwendungen
BeschreibungGlycopyrrolate 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).
VerwendenGlycopyrrolate 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.
VerwendenA synthetic, quaternary ammonium anticholinergic. Antispasmodic; preanesthetic medicant.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Anbieter50 Anbieter
Ergänzende Hinweise
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.
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