基本情報
- CAS
41708-72-9- 標準SMILES
Cc1cccc(C)c1NC(=O)C(C)N- InChIKey
BUJAGSGYPOAWEI-UHFFFAOYSA-N- 分子式
- C11H16N2O
- 平均分子量
- 192.26 g/mol
- 単同位体質量
- 192.12626314
概要
Tocainide is a monocarboxylic acid amide in which 2,6-dimethylphenylaniline and isobutyric acid have combined to form the amide bond; used as a local anaesthetic. It has a role as a local anaesthetic, an anti-arrhythmia drug and a sodium channel blocker.
名称と識別子
- 優先名称
- Tocainide
- IUPAC
- 2-amino-N-(2,6-dimethylphenyl)propanamide
- 現地名
- [R,(-)]-N-(2,6-ジメチルフェニル)-2-アミノプロパンアミド
- 英語名
- (2R)-N-(2,6-Dimethylphenyl)-2-aminopropanamide
- 分子式
- C11H16N2O
- 分子量
- 192.26
名称と別名
tocainide41708-72-92-AMINO-N-(2,6-DIMETHYLPHENYL)PROPANAMIDETocainidaTocainidumAlanyl-2,6-xylidide2-Amino-2',6'-propionoxylidideAstra W 36095W-360952-Amino-N-(2,6-dimethylphenyl)propionamid27DXO59SANCHEBI:9611
名称をさらに表示
[R,(-)]-N-(2,6-ジメチルフェニル)-2-アミノプロパンアミド(-)-トカイニド(2R)-N-(2,6-ジメチルフェニル)-2-アミノプロパンアミド(R)-2-アミノ-N-(2,6-ジメチルフェニル)プロパンアミドR(-)-トカイニドR(-)-TocainideTocainide Hydrochloride Impurity 1(R)-2-Amino-N-(2,6-dimethylphenyl)propanamide(2R)-N-(2,6-Dimethylphenyl)-2-aminopropanamide[R,(-)]-N-(2,6-Dimethylphenyl)-2-aminopropanamidePropanamide, 2-amino-N-(2,6-dimethylphenyl)-, (2R)-
DTXSID90407662-amino-N-(2,6-dimethylphenyl)propanimidic acidW 36095RefChem:898536DTXCID7020766C01BB03W36095255-505-0
データベース識別子
物性
構造計算による物性
- XLogP
- 0.8
- 極性表面積
- 55.1 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 2
- 回転可能結合数
- 2
- 重原子数
- 14
- 形式電荷
- 0
- 複雑度
- 195
実験および物理化学的性質
LogP
1.1
0.76
Solubility1.60e+00 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antiarrhythmics
Pharmaceuticals
Melting Point
246-266 °C
246 - 266 °C
Physical DescriptionSolid
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
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Tocainide
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
化学と産業
薬理情報
ATC Code
C - Cardiovascular system
QC - Cardiovascular system
Protein BindingApproximately 10 percent bound to plasma protein.
Pharmacodynamics
Tocainide is a primary amine analog of lidocaine with antiarrhythmic properties useful in the treatment of ventricular arrhythmias. Tocainide, like lidocaine, produces dose dependent decreases in sodium and potassium conductance, thereby decreasing the excitability of myocardial cells. In experimental animal models, the dose-related depression of sodium current is more pronounced in ischemic tissue than in normal tissue. Tocainide is a Class I antiarrhythmic compound with electrophysiologic properties in man similar to those of lidocaine, but dissimilar from quinidine, procainamide, and disopyramide.
Mechanism of Action
Tocainide acts on sodium channels on the neuronal cell membrane, limiting the spread of seizure activity and reducing seizure propagation. Tocainide binds preferentially to the inactive state of the sodium channels.The antiarrhythmic actions are mediated through effects on sodium channels in Purkinje fibers.
Biological Half-LifeThe average plasma half-life in patients is approximately 15 hours. May be prolonged up to 35 hours in patients with severe renal function impairment (creatinine clearance less than 30 mL per min per 1.73 square meters of body surface area.
Metabolism/MetabolitesNegligible first pass hepatic degradation. No active metabolites have been found.
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.
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