2-amino-N-(2,6-dimethylphenyl)propanamide

• ChemBase ID: 927
• Molecular Formular: C11H16N2O
• Molecular Mass: 192.25754
• Monoisotopic Mass: 192.12626314
• SMILES: O=C(Nc1c(cccc1C)C)C(N)C
• Canonical SMILES: CC(C(=O)Nc1c(C)cccc1C)N
• InChI: InChI=1S/C11H16N2O/c1-7-5-4-6-8(2)10(7)13-11(14)9(3)12/h4-6,9H,12H2,1-3H3,(H,13,14)
• InChIKey: BUJAGSGYPOAWEI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-N-(2,6-dimethylphenyl)propanamide
• IUPAC Traditional name: tocainide
• Brand Name: Tonocard
• Synonyms: Tocainida [INN-Spanish]; Tocainidum [INN-Latin]; Tocainide

Database IDs

• CAS Number: 41708-72-9
• PubChem SID: 160964390; 46505385
• PubChem CID: 38945

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.653854
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.6713139
• LogD (pH = 7.4): 0.9973883
• Log P: 1.8824334
• Molar Refractivity: 58.857 cm^3
• Polarizability: 22.107647 Å^3
• Polar Surface Area: 55.12 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.55
• LOG S: -2.08
• Solubility (Water): 1.60e+00 g/l

PROPERTIES

Physical Property

• Solubility: 1.07E+004 mg/L
• Hydrophobicity(logP): 1.1

DETAILS

DrugBank - DB01056

• Drug Groups: approved
• Description: An antiarrhythmic agent which exerts a potential- and frequency-dependent block of sodium channels. [PubChem]
• Indication: For the treatment of documented ventricular arrhythmias, such as sustained ventricular tachycardia, that, in the judgment of the physician, are life-threatening.
• Pharmacology: 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.
• Toxicity: The oral LD₅₀ of tocainide was calculated to be about 800 mg/kg in mice, 1000 mg/kg in rats, and 230 mg/kg in guinea pigs; deaths were usually preceded by convulsions.
• Affected Organisms: Humans and other mammals
• Biotransformation: Negligible first pass hepatic degradation. No active metabolites have been found.
• Absorption: Following oral administration, the bioavailability approaches 100 percent, and is unaffected by food.
• Half Life: The 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.
• Protein Binding: Approximately 10 percent bound to plasma protein.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com