Identification
- Summary
Tocainide is an orally active class 1b antiarrhythmic agent that interferes with cardiac sodium channels and typically used to treat ventricular arrhythmias.
- Generic Name
- Tocainide
- DrugBank Accession Number
- DB01056
- Background
An antiarrhythmic agent which exerts a potential- and frequency-dependent block of sodium channels.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Tocainide (DB01056)
- Weight
- Average: 192.2575
Monoisotopic: 192.126263144 - Chemical Formula
- C11H16N2O
- Synonyms
- 2-Amino-2',6'-propionoxylidide
- 2-amino-N-(2,6-dimethylphenyl)propanamide
- 2-Amino-N-(2,6-dimethylphenyl)propionamid
- Alanyl-2,6-xylidide
- Tocainida
- Tocainide
- Tocainidum
- External IDs
- W-36095
Pharmacology
- Indication
For the treatment of documented ventricular arrhythmias, such as sustained ventricular tachycardia, that, in the judgment of the physician, are life-threatening.
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism ASodium channel protein type 5 subunit alpha inhibitorHumans - Absorption
Following oral administration, the bioavailability approaches 100 percent, and is unaffected by food.
- Volume of distribution
Not Available
- Protein binding
Approximately 10 percent bound to plasma protein.
- Metabolism
Negligible first pass hepatic degradation. No active metabolites have been found.
- Route of elimination
Not Available
- 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.
- Clearance
Not Available
- Adverse Effects
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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.
- Pathways
Pathway Category Tocainide Action Pathway Drug action - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Tocainide can be increased when it is combined with Abametapir. Abatacept The metabolism of Tocainide can be increased when combined with Abatacept. Abiraterone The serum concentration of Tocainide can be increased when it is combined with Abiraterone. Acebutolol Tocainide may increase the arrhythmogenic activities of Acebutolol. Acenocoumarol The metabolism of Acenocoumarol can be decreased when combined with Tocainide. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Tocainide hydrochloride 2K7I38CKN5 71395-14-7 AMZACPWEJDQXGW-UHFFFAOYSA-N - International/Other Brands
- Tonocard
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Tonocard Tab 400 mg Tablet 400 mg Oral Astra Zeneca 1985-12-31 2003-07-24 Canada 
Categories
- ATC Codes
- C01BB03 — Tocainide
- Drug Categories
- Amides
- Amines
- Anilides
- Aniline Compounds
- Antiarrhythmic agents
- Antiarrhythmics, Class I
- Antiarrhythmics, Class Ib
- Cardiac Therapy
- Cardiovascular Agents
- Cytochrome P-450 CYP1A2 Inhibitors
- Cytochrome P-450 CYP1A2 Inhibitors (weak)
- Cytochrome P-450 CYP1A2 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Membrane Transport Modulators
- Sodium Channel Blockers
- Voltage-Gated Sodium Channel Blockers
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as m-xylenes. These are aromatic compounds that contain a m-xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 3-positions.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Xylenes
- Direct Parent
- m-Xylenes
- Alternative Parents
- Propargyl-type 1,3-dipolar organic compounds / Carboximidic acids / Organopnictogen compounds / Organooxygen compounds / Monoalkylamines / Hydrocarbon derivatives
- Substituents
- Amine / Aromatic homomonocyclic compound / Carboximidic acid / Carboximidic acid derivative / Hydrocarbon derivative / M-xylene / Organic 1,3-dipolar compound / Organic nitrogen compound / Organic oxygen compound / Organonitrogen compound
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- monocarboxylic acid amide (CHEBI:9611)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 27DXO59SAN
- CAS number
- 41708-72-9
- InChI Key
- BUJAGSGYPOAWEI-UHFFFAOYSA-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)
- IUPAC Name
- 2-amino-N-(2,6-dimethylphenyl)propanamide
- SMILES
- CC(N)C(=O)NC1=C(C)C=CC=C1C
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015189
- KEGG Drug
- D06172
- KEGG Compound
- C07142
- PubChem Compound
- 38945
- PubChem Substance
- 46505385
- ChemSpider
- 35632
- BindingDB
- 50092595
- 42359
- ChEBI
- 9611
- ChEMBL
- CHEMBL1762
- Therapeutic Targets Database
- DAP000517
- PharmGKB
- PA451706
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Tocainide
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral 400 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 246-266 °C PhysProp water solubility 1.07E+004 mg/L Not Available logP 0.76 SANGSTER (1993) - Predicted Properties
Property Value Source Water Solubility 1.6 mg/mL ALOGPS logP 0.55 ALOGPS logP 1.88 Chemaxon logS -2.1 ALOGPS pKa (Strongest Acidic) 13.65 Chemaxon pKa (Strongest Basic) 8.23 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 55.12 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 58.86 m3·mol-1 Chemaxon Polarizability 21.59 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9157 Blood Brain Barrier + 0.9154 Caco-2 permeable + 0.7383 P-glycoprotein substrate Non-substrate 0.6763 P-glycoprotein inhibitor I Non-inhibitor 0.9482 P-glycoprotein inhibitor II Non-inhibitor 0.9932 Renal organic cation transporter Non-inhibitor 0.962 CYP450 2C9 substrate Non-substrate 0.8363 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.6629 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5113 Ames test AMES toxic 0.5064 Carcinogenicity Non-carcinogens 0.5713 Biodegradation Not ready biodegradable 0.9784 Rat acute toxicity 2.4615 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9919 hERG inhibition (predictor II) Non-inhibitor 0.9537
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 149.9440971 predictedDarkChem Lite v0.1.0 [M-H]- 144.80768 predictedDeepCCS 1.0 (2019) [M+H]+ 151.7227971 predictedDarkChem Lite v0.1.0 [M+H]+ 147.1657 predictedDeepCCS 1.0 (2019) [M+Na]+ 149.7180971 predictedDarkChem Lite v0.1.0 [M+Na]+ 153.9796 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Voltage-gated sodium channel activity involved in sa node cell action potential
- Specific Function
- This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the pr...
- Gene Name
- SCN5A
- Uniprot ID
- Q14524
- Uniprot Name
- Sodium channel protein type 5 subunit alpha
- Molecular Weight
- 226937.475 Da
References
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInhibitor
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- Loi CM, Wei X, Parker BM, Korrapati MR, Vestal RE: The effect of tocainide on theophylline metabolism. Br J Clin Pharmacol. 1993 Apr;35(4):437-40. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Other/unknown
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Pistolozzi M, Franchini C, Corbo F, Muraglia M, De Giorgi M, Felix G, Bertucci C: Tocainide analogues binding to human serum albumin: a HPLAC and circular dichroism study. J Pharm Biomed Anal. 2010 Oct 10;53(2):179-85. doi: 10.1016/j.jpba.2010.03.005. Epub 2010 Mar 7. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 02, 2024 22:48