Glycopyrroniumbromid

Glycopyrrolate

HCID 11693CAS 596-51-0

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

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 Struktureigenschaften

Polarare Oberfläche (TPSA)
46,5 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
5
Schwere Atome
24

Experimentelle und physikochemische Eigenschaften

Human Drugs · 6 Einträge

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

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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 · 1 Eintrag

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 Eintrag

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 Einträge

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

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 4 Einträge

A03AB02

R - Respiratory system

A - Alimentary tract and metabolism

QR - Respiratory system

FDA Pharmacological Classification · 4 Einträge

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 Einträge

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 · 3 Einträge

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

Anbieter50 Anbieter

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

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

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