Glycopyrroniumbromid
Glycopyrrolate
Daten werden ergänzt – lade die Seite später neu, um den aktuellen Stand zu sehen
Grundinformationen
- CAS
596-51-0- 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
GLYCOPYRROLATE596-51-0glycopyrronium bromideRobinulNodaptonTarodylTarodynCuvposaRobanulGlycopyrronii bromidumBromuro de glicopirronioBromure de glycopyrronium
Weitere Namen anzeigen
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-
Datenbank-Bezeichner
- CAS
596-51-0- PubChem CID
- 11693
- DTXSID
DTXSID6023109- ChEMBL
CHEMBL1201027- ChEBI
CHEBI:90972- EC Number
- 209-887-0
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- 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
Animal DrugsActive Ingredients (Glycopyrrolate) -> FDA Greenbook
Collision Cross Section203.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
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
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
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
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%)
Toxikologische Informationen
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
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
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
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
Use ClassificationAnimal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients
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
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.
Zugehörige Reaktionen
5
Notizen zur Verbindung
Wird geladen…