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N-エチル-N,N-ジメチル-2-ブロモベンゼンメタンアミニウム

Bretylium

HCID 2431
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
59-41-6
標準SMILES
CC[N+](C)(C)Cc1ccccc1Br
InChIKey
AAQOQKQBGPPFNS-UHFFFAOYSA-N
分子式
C11H17BrN+
平均分子量
243.16 g/mol
単同位体質量
242.05444

概要

Bretylium is a quaternary ammonium cation having 2-bromobenzyl, ethyl and two methyl groups attached to the nitrogen. It blocks noradrenaline release from the peripheral sympathetic nervous system, and is used in emergency medicine, cardiology, and other specialties for the acute management of ventricular tachycardia and ventricular fibrillation. It has a role as an antihypertensive agent, an adrenergic antagonist and an anti-arrhythmia drug.

名称と識別子

優先名称
Bretylium
IUPAC
(2-bromophenyl)methyl-ethyl-dimethylazanium
現地名
N-エチル-N,N-ジメチル-2-ブロモベンゼンメタンアミニウム
英語名
Bretylium
分子式
C11H17BrN
分子量
0

名称と別名

Bretylium59-41-6Bretylium ionBretylium cation(2-bromobenzyl)ethyldimethylaminium2-bromo-N-ethyl-N,N-dimethylbenzenemethanaminiumN-ethyl-N,N-dimethyl-2-bromobenzenemethanaminiumRZR75EQ2KJBenzenemethanaminium, 2-bromo-N-ethyl-N,N-dimethyl-CHEBI:3172DTXSID3046958[(2-bromophenyl)methyl](ethyl)dimethylazanium
名称をさらに表示
(2-ブロモベンジル)エチルジメチルアミニウム2-ブロモ-N-エチル-N,N-ジメチルベンゼンメタンアミニウムブレチリウムN-エチル-N,N-ジメチル-2-ブロモベンゼンメタンアミニウム[(2-ブロモフェニル)メチル](エチル)ジメチルアザニウムUnii-rzr75eq2kj(2-bromophenyl)methyl-ethyl-dimethylazanium bromide
((2-bromophenyl)methyl)(ethyl)dimethylazaniumRefChem:570223DTXCID1026958BretylumBretylium tolsylate(2-bromophenyl)methyl-ethyl-dimethylazaniumBretylanBretylium tosylate(USAN)

データベース識別子

CAS
59-41-6

物性

構造計算による物性

XLogP
2.8
極性表面積
0 Ų
水素結合供与体数
0
水素結合受容体数
0
回転可能結合数
3
重原子数
13
形式電荷
1
複雑度
156

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15
Solubility · 2 件

Freely soluble

1.54e-04 g/L

Human Drugs · 2 件

Breast Feeding; Lactation; Antiarrhythmics;

Pharmaceuticals

Physical DescriptionSolid

物理化学的性質

InChI
InChI=1S/C11H17BrN/c1-4-13(2,3)9-10-7-5-6-8-11(10)12/h5-8H,4,9H2,1-3H3/q+1
InChIKey
AAQOQKQBGPPFNS-UHFFFAOYSA-N
SMILES
CC[N+](C)(CC1C=CC=CC=1Br)C

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

毒性情報

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

化学と産業

薬理情報

Pharmacodynamics · 1 件

Bretylium is a bromobenzyl quaternary ammonium compound which selectively accumulates in sympathetic ganglia and their postganglionic adrenergic neurons where it inhibits norepinephrine release by depressing adrenergic nerve terminal excitability. Bretylium also suppresses ventricular fibrillation and ventricular arrhythmias.

Mechanism of Action · 1 件

Bretylium inhibits norepinephrine release by depressing adrenergic nerve terminal excitability. The mechanisms of the antifibrillatory and antiarrhythmic actions of bretylium are not established. In efforts to define these mechanisms, the following electrophysiologic actions of bretylium have been demonstrated in animal experiments: increase in ventricular fibrillation threshold, increase in action potential duration and effective refractory period without changes in heart rate, little effect on the rate of rise or amplitude of the cardiac action potential (Phase 0) or in resting membrane potential (Phase 4) in normal myocardium, decrease in the disparity in action potential duration between normal and infarcted regions, and increase in impulse formation and spontaneous firing rate of pacemaker tissue as well as increase ventricular conduction velocity.

Biological Half-LifeThe terminal half-life in four normal volunteers averaged 7.8±0.6 hours (range 6.9-8.1). During hemodialysis, this patient's arterial and venous bretylium concentrations declined rapidly, resulting in a half-life of 13 hours.
Metabolism/MetabolitesNo metabolites have been identified following administration in man and laboratory animals.
MeSH Pharmacological Classification · 1 件

Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade.

関連反応

1 件
反応記録を作成
HRID 1816205 の反応式
HRID 1816205反応物としてuspto-grants-2005_04

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
PubChem CID
2431
DTXSID
DTXSID3046958
ChEMBL
CHEMBL1199080
ChEBI
CHEBI:3172
UNII
RZR75EQ2KJ
Nikkaji
J4.602G
Cellular Locations
Membrane

用途と製造

Use ClassificationPharmaceuticals
応用分野 · 1 件

使用Bretylium possesses sympatholytic action, which is associated with blockage of norepinephrine (noradrenaline) from presynaptic nerve endings. It also has a direct effect on ischemic myocytes. Bretylium is an urgent treatment that is used in situations of ventricular tachycardia and ventricular fibrillation, primarily in the severe phase of a myocardial infarction, during which use of other medications or procedures have proven unsuccessful. It requires great caution and should be used only in urgent situations.

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補足説明 · 1 件

定義ChEBI: A quaternary ammonium cation having 2-bromobenzyl, ethyl and two methyl groups attached to the nitrogen. It blocks noradrenaline release from the peripheral sympathetic nervous system, and is used in emergency medicine, cardiology, and other specialties fo the acute management of ventricular tachycardia and ventricular fibrillation.