Tocainide

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Tocainide

Systematic (IUPAC) name
N-(2,6-dimethylphenyl)alaninamide
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a601248
Legal status	?
Pharmacokinetic data
Bioavailability	0.9-1 (oral)
Protein binding	10-20%
Metabolism	glucuronidation (primary)
Half-life	9-14 R, 13-20 S
Excretion	30-50% urine (unchanged)
Identifiers
CAS number	41708-72-9^Y
ATC code	C01BB03
PubChem	CID 38945
DrugBank	DB01056
ChemSpider	35632^Y
UNII	27DXO59SAN^Y
KEGG	D06172^Y
ChEBI	CHEBI:9611^Y
ChEMBL	CHEMBL1762^Y
Chemical data
Formula	C₁₁H₁₆N₂O
Mol. mass	192.258 g/mol
SMILES O=C(Nc1c(cccc1C)C)C(N)C
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)^Y Key:BUJAGSGYPOAWEI-UHFFFAOYSA-N^Y
Y (what is this?) (verify)

Tocainide (Tonocard) is a class Ib antiarrhythmic agent. It is no longer sold in the United States.

Quick look at the Pharmacokinetics

Tocainide is a lidocaine analog, that does not have significant 1st pass metabolism. It is found in two enantiomers. The R isomer is 4x as potent as the S. Oral bioavailability is 0.9-1.0. In the blood tocainide is 10-20% protein bound. The Volume of distribution is 2.5-3.5 L/kg. 30-50% is excreted unchanged in the urine. The more active R-isomer is cleared faster in anephric patients or those with severe renal dysfunction. The main metabolite is the glucuronidated tocainide carbamic acid. The glucuronosyl transferase is apparently induced by rifampin. Weak inhibition of Cyp1A2 leads to a mild theophylline interaction. (Not verbatim)

External links

MedlinePlus DrugInfo medmaster-a685030

Burton ME. Applied Pharmacokinetics & Pharmacodynamics: Principles of Therapeutic Drug Monitoring. 4th ed. Philadelphia: Lippincott Williams & Wilkins; 2006.

v t e Channel blockers

Calcium (Ca²⁺)	Amlodipine Amrinone Anandamide Anipamil Aranidipine Azelnidipine Azimilide Barnidipine Bencyclane Benidipine Bepridil Berbamine Bevantolol Canadine Carboxyamidotriazole Caroverine Cilnidipine Cinnarizine Clentiazem Clevidipine Conotoxins Darodipine Dauricine Devapamil Diltiazem Dimeditiapramine Dotarizine Dronedarone Efonidipine Emopamil Enpiperate Eperisone Ethosuximide Falipamil Fantofarone Fasudil Felodipine Fenamic acid Fendiline Flunarizine Fostedil Gallopamil Isradipine Lacidipine Lamotrigine Lercanidipine Lidoflazine Magnesium sulfate Manidipine Manoalide Mepirodipine Mesuximide Mibefradil Monatepil Naftopidil Nicardipine Nifedipine Niguldipine Niludipin Nilvadipine Nimodipine Nisoldipine Nitrendipine Norverapamil Ochratoxin A Osthol Otilonium bromide Oxodipine Perhexiline Phensuximide Pinaverium Piperidine Pranidipine Prenylamine Risedronic acid Ryodipine Sesamodil Sodium valproate Stepholidine TROX-1 Terodiline Tetrahydropalmatine Tetrandrine Tolfenamic acid Tranilast Valnoctamide Valperinol Valproate pivoxil Valproate semisodium Valproic acid Valpromide Verapamil Ziconotide Selective VDCC ligands: 4-Methylpregabalin Atagabalin Gabapentin Gabapentin enacarbil Imagabalin PD-200,347 PD-217,014 PD-299,685 Pregabalin

Potassium (K⁺)	3,4-Diaminopyridine 4-Aminopyridine Amiodarone Bretylium Bunaftine Charybdotoxin Conotoxins Dofetilide Dronedarone E-4031 Ibutilide Linopirdine Maurotoxin Nifekalant Paxilline Sotalol Tedisamil Tetraethylammonium Vernakalant

Sodium (Na⁺)	Antiarrhythmics: Ajmaline Aprindine Disopyramide Dronedarone Encainide Flecainide Lidocaine Lorajmine Lorcainide Mexiletine Moricizine Phenytoin Pilsicainide Prajmaline Procainamide Propafenone Quinidine Sparteine Tocainide Anticonvulsants: Carbamazepine Eslicarbazepine acetate Ethotoin Fosphenytoin Licarbazepine Mephenytoin Oxcarbazepine Oxitriptyline Phenytoin Rufinamide Topiramate Sodium valproate Valnoctamide Valproate pivoxil Valproate semisodium Valproic acid Valpromide Diuretics: Amiloride Benzamil Triamterene Local anesthetics: pFBT Amylocaine Articaine Benzocaine Bupivacaine (Levobupivacaine, Ropivacaine) Butacaine Butamben Chloroprocaine Cinchocaine Cocaine Cyclomethycaine Dimethocaine Etidocaine Hexylcaine Iontocaine Lidocaine Mepivacaine Meprylcaine Metabutoxycaine Orthocaine Piperocaine Prilocaine Procaine Propoxycaine Proxymetacaine Risocaine Tetracaine Trimecaine Toxins: Conotoxins Neosaxitoxin Saxitoxin Tetrodotoxin Others: Menthol

Other	Uncategorized: Ethadione Paramethadione Phenacemide Pheneturide Trimethadione

Antiarrhythmic agents (C01B)

Channel blockers

class I
(Na⁺ channel blockers)

class Ia (Phase 0→ and Phase 3→)	Ajmaline Disopyramide Lorajmine Prajmaline Procainamide^# Quinidine^# Sparteine

class Ib (Phase 3←)	IV (Lidocaine^#) enteral (Aprindine Mexiletine Tocainide)

class Ic (Phase 0→)	Encainide^‡ Ethacizine Flecainide Indecainide^‡ Lorcainide Moracizine^‡ Propafenone

class III
(Phase 3→, K⁺ channel blockers)

class IV
(Phase 4→, Ca²⁺ channel blockers)

Diltiazem
Verapamil^#

Receptor agonists
and antagonists

class II (Phase 4→, β blockers)	Nadolol Pindolol Propranolol cardioselective (Acebutolol Atenolol Esmolol Metoprolol)

A₁ agonist	Adenosine Benzodiazepines Barbiturates

M₂	muscarinic antagonist: Atropine Disopyramide Quinidine muscarinic agonist: Digoxin

α receptors	Amiodarone Bretylium Quinidine Verapamil

Ion transporters

Na⁺ / K⁺-ATPase	Digoxin

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

M: HRT

anat/phys/devp

noco/cong/tumr, sysi/epon, injr

proc, drug (C1A/1B/1C/1D), blte

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