Glycopyrrolate (HCID 11693)

概要

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.

名称と識別子

優先名称: Glycopyrrolate
IUPAC: (1,1-dimethylpyrrolidin-1-ium-3-yl) 2-cyclopentyl-2-hydroxy-2-phenylacetate bromide
現地名: グリコピロニウム臭化物
英語名: Glycopyrrolate
分子式: C19H28BrNO3-
分子量: 398.33

名称と別名

GLYCOPYRROLATE596-51-0glycopyrronium bromideRobinulNodaptonTarodylTarodynCuvposaRobanulGlycopyrronii bromidumBromuro de glicopirronioBromure de glycopyrronium

名称をさらに表示

3-(フェニルシクロペンチルヒドロキシアセトキシ)-1,1-ジメチルピロリジニウム·ブロミドタロジルタロジングリコピロニウムブロミドグリコピロニウム3-(ヒドロキシシクロペンチルフェニルアセトキシ)-1,1-ジメチルピロリジニウム3-(フェニルシクロペンチルヒドロキシアセトキシ)-1,1-ジメチルピロリジニウムロバヌル1,1-ジメチル-3-[(2-シクロペンチル-2-フェニル-2-ヒドロキシアセチル)オキシ]ピロリジン-1-イウムノダプトングリコピロラート臭化グリコピロニウムロビナール【副交感神経作用薬】3-(2-シクロペンチル-2-ヒドロキシ-2-フェニルアセトキシ)-1,1-ジメチルピロリジニウムブロミド臭化グリコピロラートグリコピロニウム臭化物グリコピロニウム臭化物 (JAN)3-(フェニルシクロペンチルヒドロキシアセトキシ)-1,1-ジメチルピロリジニウム・ブロミドシーブリ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-

データベース識別子

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

物性

構造計算による物性

極性表面積: 46.5 Å²
水素結合供与体数: 1
水素結合受容体数: 4
回転可能結合数: 5
重原子数: 24
形式電荷: 0
複雑度: 424

実験および物理化学的性質

Human Drugs · 6 件

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

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine

Animal DrugsActive Ingredients (Glycopyrrolate) -> FDA Greenbook

Collision Cross Section203.8 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

物理化学的性質

融点: 192 · 192-195°C
比重(密度): 1.3222 · 1.3222 (rough estimate)
屈折率: 1.62 · 1.6200 (estimate)
貯蔵温度: 2 · 2-8°C
溶解性: 2 O: · H2O: ≥24mg/mL
外見: 粉
色: 白から黄褐色
水溶解度: 2 O: · H2O: ≥24mg/mL
Merck: 14 · 14,4501
安定性: 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 データベース: 596 · 596-51-0(CAS DataBase Reference)

化学的性質

化学的特性White Solid

安全と法規制

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

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%)

毒性情報

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 件

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 件

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 件

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

安全データ

wgk: 3
rtecs: UY4337630
毒性: LD50 (72 hr.) in female mice, female rats (mg/kg): 107, 196 i.p.; in male rats (mg/kg): 1150 orally (Franko)
hs_code: 29339900
risk_code: 36/37/38
hazard_code: Xi
safety_code: 26
Hazard Classifications: Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
ストレージクラス: 11 - Combustible Solids

化学と産業

薬理情報

ATC Code · 4 件

A03AB02

R - Respiratory system

A - Alimentary tract and metabolism

QR - Respiratory system

FDA Pharmacological Classification · 4 件

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 件

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.

用途と製造

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

応用分野 · 4 件

説明Glycopyrrolate 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).

使用Glycopyrrolate 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.

使用A synthetic, quaternary ammonium anticholinergic. Antispasmodic; preanesthetic medicant.

一般的な説明Glycopyrrolate, 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.

上流・下流製品情報

上流原料

1-メチルピロリジン-3-オールブロモメタン塩酸ナトリウム

サプライヤー50 社

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

補足説明

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

グリコピロニウム臭化物

基本情報

概要