| Stereochemistry | RACEMIC |
| Molecular Formula | C11H16N2O |
| Molecular Weight | 192.2575 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(N)C(=O)NC1=C(C)C=CC=C1C
InChI
InChIKey=BUJAGSGYPOAWEI-UHFFFAOYSA-N
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)
| Molecular Formula | C11H16N2O |
| Molecular Weight | 192.2575 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
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. The recommended initial dosage is 400 mg every 8 hours. The usual adult dosage is between 1200 and 1800 mg/day in a three-dose daily divided regimen. Doses beyond 2400 mg per day have been administered infrequently. Patients who tolerate the t.i.d. the regimen may be tried on a twice-daily regimen with careful monitoring. Tocainide commonly produces minor, transient, nervous system and gastrointestinal adverse reactions, but is otherwise generally well tolerated.
CNS Activity
Originator
Approval Year
Doses
AEs
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
Sourcing
PubMed
Sample Use Guides
Initial dose: 400 mg orally every 8 hours.
Maintenance dose: 1200-1800 mg/day in 3 divided doses.
Route of Administration:
Oral
Cardiac myocytes were isolated from adult male Sprague-Dawley rats. Myocytes (6 x 10^5) in 50 mkl of incubation buffer were incubated with 1.3 mkM sea anemone toxin II, 13 nM [3H] BTXB (50 Ci/mmol), and 0.13 mM tetrodotoxin for 45-60 mm at 37C. Tetrodotoxin was added to prevent depolarization induced by sodium influx; without tetrodotoxin, no specific binding is observed. Various concentrations of tocainide enantiomers were included in the incubations. Assays were done in parallel with tubes containing 0.2 mM aconitine to define nonspecific binding. Concentration-response curves for both stereoisomers were performed on common preparations of cells and toxins. Reactions were terminated by adding 10 ml of KHS buffer (Krebs-Henseleit-BSA; 127 mM NaCl, 2.33 mM KC1, 1.30 mM KH2PO4, 1.23 mM MgSO4, 25 mM NaHCO3, 10 mM glucose, 50 mkM CaCl2, 1% BSA) equilibrated with 95% 02/5% CO2 and incubated at 3C for 1 min, then filtered through a Whatman GF-C 24-mm filter and washed five times with 5 ml of rinse buffer (25 mM Tris-Cl, pH 7.4, 130 mM NaCl, 5.5 mM KC1, 0.8 mM MgSO4, 5.5 mM glucose, 50 mkM CaCl2.) The filters were then dried and counted in Econofluor scintillation fluid. The retained radioactivity represents [3H]BTXB bound to the myocyte.
