Details
| 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)
DescriptionCurator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB01056 | https://www.ncbi.nlm.nih.gov/pubmed/2499645 | https://www.ncbi.nlm.nih.gov/pubmed/3107988 | https://www.ncbi.nlm.nih.gov/pubmed/2108835 | https://www.ncbi.nlm.nih.gov/pubmed/3161487
Curator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB01056 | https://www.ncbi.nlm.nih.gov/pubmed/2499645 | https://www.ncbi.nlm.nih.gov/pubmed/3107988 | https://www.ncbi.nlm.nih.gov/pubmed/2108835 | https://www.ncbi.nlm.nih.gov/pubmed/3161487
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
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3.2 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3116834 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
TOCAINIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
7.8 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2127569 |
200 mg single, intravenous dose: 200 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
R(-)-TOCAINIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
11.7 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2127569 |
200 mg single, intravenous dose: 200 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
(S)-TOCAINIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
84 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3116834 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
TOCAINIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
11.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2127569 |
200 mg single, intravenous dose: 200 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
R(-)-TOCAINIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
17.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2127569 |
200 mg single, intravenous dose: 200 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
(S)-TOCAINIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
15 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3116834 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
TOCAINIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
250 mg 2 times / day single, intravenous (starting) Dose: 250 mg, 2 times / day Route: intravenous Route: single Dose: 250 mg, 2 times / day Sources: |
unhealthy, 34 - 75 years n = 50 Health Status: unhealthy Condition: Acute Ventricular Arrhythmias Age Group: 34 - 75 years Sex: M+F Population Size: 50 Sources: |
Disc. AE: Hypotension... Other AEs: Nausea, Vomiting... AEs leading to discontinuation/dose reduction: Hypotension (3 patients) Other AEs:Nausea (1 patient) Sources: Vomiting (1 patient) Junctional rhythm (1 patient) |
600 mg 2 times / day multiple, oral Dose: 600 mg, 2 times / day Route: oral Route: multiple Dose: 600 mg, 2 times / day Sources: |
unhealthy, 59 years (range: 28-83 years) n = 67 Health Status: unhealthy Condition: benign and potentially lethal ventricular arrhythmias Age Group: 59 years (range: 28-83 years) Sex: M+F Population Size: 67 Sources: |
Disc. AE: Ataxia, Tremor... AEs leading to discontinuation/dose reduction: Ataxia (8 patients) Sources: Tremor (8 patients) Dizzy (8 patients) Rash (4 patients) Diarrhea (1 patient) Nausea (1 patient) Vomiting (1 patient) Anorexia (1 patient) Congestive heart failure (1 patient) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Junctional rhythm | 1 patient | 250 mg 2 times / day single, intravenous (starting) Dose: 250 mg, 2 times / day Route: intravenous Route: single Dose: 250 mg, 2 times / day Sources: |
unhealthy, 34 - 75 years n = 50 Health Status: unhealthy Condition: Acute Ventricular Arrhythmias Age Group: 34 - 75 years Sex: M+F Population Size: 50 Sources: |
| Nausea | 1 patient | 250 mg 2 times / day single, intravenous (starting) Dose: 250 mg, 2 times / day Route: intravenous Route: single Dose: 250 mg, 2 times / day Sources: |
unhealthy, 34 - 75 years n = 50 Health Status: unhealthy Condition: Acute Ventricular Arrhythmias Age Group: 34 - 75 years Sex: M+F Population Size: 50 Sources: |
| Vomiting | 1 patient | 250 mg 2 times / day single, intravenous (starting) Dose: 250 mg, 2 times / day Route: intravenous Route: single Dose: 250 mg, 2 times / day Sources: |
unhealthy, 34 - 75 years n = 50 Health Status: unhealthy Condition: Acute Ventricular Arrhythmias Age Group: 34 - 75 years Sex: M+F Population Size: 50 Sources: |
| Hypotension | 3 patients Disc. AE |
250 mg 2 times / day single, intravenous (starting) Dose: 250 mg, 2 times / day Route: intravenous Route: single Dose: 250 mg, 2 times / day Sources: |
unhealthy, 34 - 75 years n = 50 Health Status: unhealthy Condition: Acute Ventricular Arrhythmias Age Group: 34 - 75 years Sex: M+F Population Size: 50 Sources: |
| Anorexia | 1 patient Disc. AE |
600 mg 2 times / day multiple, oral Dose: 600 mg, 2 times / day Route: oral Route: multiple Dose: 600 mg, 2 times / day Sources: |
unhealthy, 59 years (range: 28-83 years) n = 67 Health Status: unhealthy Condition: benign and potentially lethal ventricular arrhythmias Age Group: 59 years (range: 28-83 years) Sex: M+F Population Size: 67 Sources: |
| Congestive heart failure | 1 patient Disc. AE |
600 mg 2 times / day multiple, oral Dose: 600 mg, 2 times / day Route: oral Route: multiple Dose: 600 mg, 2 times / day Sources: |
unhealthy, 59 years (range: 28-83 years) n = 67 Health Status: unhealthy Condition: benign and potentially lethal ventricular arrhythmias Age Group: 59 years (range: 28-83 years) Sex: M+F Population Size: 67 Sources: |
| Diarrhea | 1 patient Disc. AE |
600 mg 2 times / day multiple, oral Dose: 600 mg, 2 times / day Route: oral Route: multiple Dose: 600 mg, 2 times / day Sources: |
unhealthy, 59 years (range: 28-83 years) n = 67 Health Status: unhealthy Condition: benign and potentially lethal ventricular arrhythmias Age Group: 59 years (range: 28-83 years) Sex: M+F Population Size: 67 Sources: |
| Nausea | 1 patient Disc. AE |
600 mg 2 times / day multiple, oral Dose: 600 mg, 2 times / day Route: oral Route: multiple Dose: 600 mg, 2 times / day Sources: |
unhealthy, 59 years (range: 28-83 years) n = 67 Health Status: unhealthy Condition: benign and potentially lethal ventricular arrhythmias Age Group: 59 years (range: 28-83 years) Sex: M+F Population Size: 67 Sources: |
| Vomiting | 1 patient Disc. AE |
600 mg 2 times / day multiple, oral Dose: 600 mg, 2 times / day Route: oral Route: multiple Dose: 600 mg, 2 times / day Sources: |
unhealthy, 59 years (range: 28-83 years) n = 67 Health Status: unhealthy Condition: benign and potentially lethal ventricular arrhythmias Age Group: 59 years (range: 28-83 years) Sex: M+F Population Size: 67 Sources: |
| Rash | 4 patients Disc. AE |
600 mg 2 times / day multiple, oral Dose: 600 mg, 2 times / day Route: oral Route: multiple Dose: 600 mg, 2 times / day Sources: |
unhealthy, 59 years (range: 28-83 years) n = 67 Health Status: unhealthy Condition: benign and potentially lethal ventricular arrhythmias Age Group: 59 years (range: 28-83 years) Sex: M+F Population Size: 67 Sources: |
| Ataxia | 8 patients Disc. AE |
600 mg 2 times / day multiple, oral Dose: 600 mg, 2 times / day Route: oral Route: multiple Dose: 600 mg, 2 times / day Sources: |
unhealthy, 59 years (range: 28-83 years) n = 67 Health Status: unhealthy Condition: benign and potentially lethal ventricular arrhythmias Age Group: 59 years (range: 28-83 years) Sex: M+F Population Size: 67 Sources: |
| Dizzy | 8 patients Disc. AE |
600 mg 2 times / day multiple, oral Dose: 600 mg, 2 times / day Route: oral Route: multiple Dose: 600 mg, 2 times / day Sources: |
unhealthy, 59 years (range: 28-83 years) n = 67 Health Status: unhealthy Condition: benign and potentially lethal ventricular arrhythmias Age Group: 59 years (range: 28-83 years) Sex: M+F Population Size: 67 Sources: |
| Tremor | 8 patients Disc. AE |
600 mg 2 times / day multiple, oral Dose: 600 mg, 2 times / day Route: oral Route: multiple Dose: 600 mg, 2 times / day Sources: |
unhealthy, 59 years (range: 28-83 years) n = 67 Health Status: unhealthy Condition: benign and potentially lethal ventricular arrhythmias Age Group: 59 years (range: 28-83 years) Sex: M+F Population Size: 67 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Open clinical studies at a referral center: chronic maintenance tocainide therapy in patients with recurrent sustained ventricular tachycardia refractory to conventional antiarrhythmic agents. | 1980 Dec |
|
| Tocainide-induced ventricular fibrillation. | 1981 Apr |
|
| New drugs for treating cardiac arrhythmias. | 1981 Jan |
|
| Severe paranoia with concomitant tocainide and propranolol therapy. | 1982 Mar-Apr |
|
| Antiarrhythmic effects of tocainide and lidocaine in dogs. | 1983 Aug |
|
| Tocainide. A review of its pharmacological properties and therapeutic efficacy. | 1983 Aug |
|
| Paranoid psychosis induced by tocainide. | 1984 Feb 25 |
|
| Heart failure and hepatitis in a patient taking tocainide. | 1984 Jan |
|
| Exacerbation of ventricular tachycardia by tocainide. | 1985 Jan |
|
| Aplastic anemia due to tocainide. | 1986 Feb 27 |
|
| A seizure induced by concurrent lidocaine-tocainide therapy--is it just a case of additive toxicity? | 1986 Jan |
|
| Tocainide-induced granulomatous hepatitis. | 1986 Jun 27 |
|
| Successful treatment with tocainide of recessive generalized congenital myotonia. | 1986 May |
|
| Tocainide-induced reversible agranulocytosis and anemia. | 1987 Mar |
|
| Possible proarrhythmic effects of tocainide in dilated cardiomyopathy. | 1988 Jul |
|
| Tocainide-induced aplastic anemia. | 1989 Jan |
|
| Congestive heart failure induced by six of the newer antiarrhythmic drugs. | 1989 Nov 1 |
|
| Pulmonary fibrosis associated with tocainide: report of a case with literature review. | 1990 Feb |
|
| [Na channel myotonia]. | 2001 |
|
| Effect of acidity on the enantiomeric resolution of thyroxine and tocainide by HPLC on a (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid column. | 2002 Dec 31 |
|
| A comparison of the antinociceptive effects of voltage-activated Na+ channel blockers in two rat models of neuropathic pain. | 2003 Jan 5 |
|
| Enantiomeric separation of tocainide and its analogues on an optically active crown ether-based stationary phase by liquid chromatography. | 2003 May 9 |
|
| Optimal requirements for high affinity and use-dependent block of skeletal muscle sodium channel by N-benzyl analogs of tocainide-like compounds. | 2003 Oct |
|
| High-speed chiral separations on a microchip with UV detection. | 2003 Sep |
|
| Chiral separations on multichannel microfluidic chips. | 2005 Dec |
|
| Systemic administration of local anesthetic agents to relieve neuropathic pain. | 2005 Oct 19 |
|
| Robust randomised control trials needed for drug treatments for trigeminal neuralgia. | 2006 |
|
| Quantitative structure-pharmacokinetic relationships for drug clearance by using statistical learning methods. | 2006 Mar |
|
| Synthesis and biological evaluation of chiral alpha-aminoanilides with central antinociceptive activity. | 2007 Apr 19 |
|
| [Eulenburg's paramyotonia congenita]. | 2007 Nov |
|
| Cyclic metabolites: chemical and biological considerations. | 2008 Feb |
|
| Preparation of two new liquid chromatographic chiral stationary phases based on diastereomeric chiral crown ethers incorporating two different chiral units and their applications. | 2008 May 16 |
|
| Liquid chromatographic direct resolution of tocainide and its analogs on a (3,3'-diphenyl-1,1'-binaphthyl)-20-crown-6-based chiral stationary phase containing residual silanol protecting n-octyl groups. | 2009 Jan |
|
| Update on methodologies available for ciguatoxin determination: perspectives to confront the onset of ciguatera fish poisoning in Europe. | 2010 Jun 14 |
|
| Tocainide analogues binding to human serum albumin: a HPLAC and circular dichroism study. | 2010 Oct 10 |
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.
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C47793
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NCI_THESAURUS |
C93038
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WHO-ATC |
C01BB03
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WHO-VATC |
QC01BB03
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| Code System | Code | Type | Description | ||
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42359
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PRIMARY | RxNorm | ||
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Tocainide
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9611
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7309
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38945
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C66607
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m10918
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DB01056
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TOCAINIDE
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SUB11136MIG
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DTXSID9040766
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100000077726
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D016677
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255-505-0
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27DXO59SAN
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4056
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CHEMBL1762
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41708-72-9
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2686
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
