基本情報
- CAS
66778-36-7- 標準SMILES
COc1ccc(C(=O)Nc2ccccc2CCC2CCCCN2C)cc1- InChIKey
PJWPNDMDCLXCOM-UHFFFAOYSA-N- 分子式
- C22H28N2O2
- 平均分子量
- 352.5 g/mol
- 単同位体質量
- 352.21507814
概要
Encainide is 4-Methoxy-N-phenylbenzamide in which the hydrogen at the 2 position of the phenyl group is substituted by a 2-(1-methylpiperidin-2-yl)ethyl group. A class Ic antiarrhythmic, the hydrochloride was used for the treatment of severe or life-threatening ventricular arrhythmias, but it was associated with increased death rates in patients who had asymptomatic heart rhythm abnormalities after a recent heart attack and was withdrawn from the market. It has a role as an anti-arrhythmia drug and a sodium channel blocker. It is a member of benzamides and a member of piperidines.
名称と識別子
- 優先名称
- Encainide
- IUPAC
- 4-methoxy-N-[2-[2-(1-methylpiperidin-2-yl)ethyl]phenyl]benzamide
- 現地名
- 4-メトキシ-2'-[2-(1-メチル-3-ピペリジル)エチル]ベンズアニリド
- 英語名
- Benzamide, 4-methoxy-N-[2-[2-(1-methyl-2-piperidinyl)ethyl]phenyl]-
- 分子式
- C22H28N2O2
- 分子量
- 352.47
名称と別名
Encainide66778-36-7EncainidaEncainidum4-Methoxy-N-(2-(2-(1-methylpiperidin-2-yl)ethyl)phenyl)benzamideMJ 90674-methoxy-N-{2-[2-(1-methylpiperidin-2-yl)ethyl]phenyl}benzamideSY3J0147NB(+-)-4-Methoxy-N-(2-(2-(1-methyl-2-piperidinyl)ethyl)phenyl)benzamide4-methoxy-N-[2-[2-(1-methylpiperidin-2-yl)ethyl]phenyl]benzamideBENZAMIDE, 4-METHOXY-N-(2-(2-(1-METHYL-2-PIPERIDINYL)ETHYL)PHENYL)-, (+-)-CHEBI:4788
名称をさらに表示
4-メトキシ-2'-[2-(1-メチル-3-ピペリジル)エチル]ベンズアニリドエンカイドrac-4-メトキシ-N-[2-[2-[(2R*)-1-メチル-2-ピペリジニル]エチル]フェニル]ベンズアミドエンカイニド4-メトキシ-2′-[2-(1-メチル-3-ピペリジル)エチル]ベンズアニリド4-メトキシ-N-{2-[2-(1-メチルピペリジン-3-イル)エチル]フェニル}ベンズアミドEnkaidEnkadeMJ-9067M-9067-1Brn 0497572MJ-9067[AS BASE]Encainide [french]Encainida [spanish]
DTXSID0022983(+-)-2'-[2-(1-methyl-2-piperidyl)ethyl]-p-anisanilide4-methoxy-2'-[2-(1-methyl-2-piperidyl)ethyl]benzanilide4-Methoxy-N-{2-[2-(1-methyl-piperidin-2-yl)-ethyl]-phenyl}-benzamide(+-)-2'-(2-(1-Methyl-2-piperidyl)ethyl)-P-anisanilide4-Methoxy-2'-(2-(1-methyl-2-piperidyl)ethyl)benzanilide4-Methoxy-N-(2-(2-(1-methyl-piperidin-2-yl)-ethyl)-phenyl)-benzamideRefChem:136750
物性
構造計算による物性
- XLogP
- 4.3
- 極性表面積
- 41.6 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 3
- 回転可能結合数
- 6
- 重原子数
- 26
- 形式電荷
- 0
- 複雑度
- 434
実験および物理化学的性質
LogP4
Solubility4.01e-03 g/L
Physical DescriptionSolid
物理化学的性質
- 貯蔵温度
- -20 °C · Store at -20°C
- 外見
- Solid
- 色
- White to off-white
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。
GHS分類
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
危険有害性情報
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
毒性情報
Toxicity Summary
Encainide is a sodium channel blocker, binding to voltage gated sodium channels. It stabilizes the neuronal membrane by inhibiting the ionic fluxes required for the initiation and conduction of impulses. Ventricular excitability is depressed and the stimulation threshold of the ventricle is increased during diastole.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
安全データ
- 注意喚起語
- 警告
- 危険有害性情報
- コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード H315
化学と産業
薬理情報
ATC Code
C - Cardiovascular system
QC - Cardiovascular system
Pharmacodynamics
Used to treat irregular heartbeats, encainide decreases excitability, conduction velocity, and automaticity as a result of slowed atrial, atrioventricular (AV) nodal, His-Purkinje, and intraventricular conduction. It causes a slight but significant prolongation of refractory periods in these tissues. The greatest effect is on the His-Purkinje system. Encainide decreases the rate of rise of the action potential without markedly affecting its duration.
Mechanism of Action
Encainide is a sodium channel blocker, binding to voltage gated sodium channels. It stabilizes the neuronal membrane by inhibiting the ionic fluxes required for the initiation and conduction of impulses. Ventricular excitability is depressed and the stimulation threshold of the ventricle is increased during diastole.
Biological Half-Life1-2 hours
Metabolism/Metabolites
Encainide has known human metabolites that include O-demethylencainide and N-demethylencainide.
Route of Elimination: A radiolabeled dose of encainide is excreted in approximately equal amounts in the urine and feces. Half Life: 1-2 hours
MeSH Pharmacological Classification
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.
A class of drugs that inhibit the activation of VOLTAGE-GATED SODIUM CHANNELS.
Absorption, Distribution and ExcretionA radiolabeled dose of encainide is excreted in approximately equal amounts in the urine and feces.
関連反応
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化合物ノート
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