Tocainide
Basic information
- CAS
41708-72-9- Standard SMILES
Cc1cccc(C)c1NC(=O)C(C)N- InChIKey
BUJAGSGYPOAWEI-UHFFFAOYSA-N- Molecular formula
- C11H16N2O
- Average molar mass
- 192.26 g/mol
- Monoisotopic mass
- 192.12626314
Overview
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.
Names & identifiers
- Preferred name
- Tocainide
- IUPAC
- 2-amino-N-(2,6-dimethylphenyl)propanamide
- English name
- (2R)-N-(2,6-Dimethylphenyl)-2-aminopropanamide
- Molecular formula
- C11H16N2O
- Molecular weight
- 192.26
Names & synonyms
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
Show more names
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
Database identifiers
- CAS
41708-72-9、53984-26-2、76213-25-7- PubChem CID
- 38945
- DTXSID
DTXSID9040766- ChEMBL
CHEMBL1762- ChEBI
CHEBI:9611
Properties
Computed structural properties
- XLogP
- 0.8
- Topological polar surface area
- 55.1 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 195
Experimental & physicochemical properties
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
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
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
Chemistry & industry
Pharmacology
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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