Tocainide

Tocainide
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a601248
ATC code	C01BB03 (WHO) ;
Pharmacokinetic data
Bioavailability	0.9-1 (oral)
Protein binding	10-20%
Metabolism	glucuronidation (primary)
Elimination half-life	9-14 R, 13-20 S
Excretion	30-50% urine (unchanged)
Identifiers
	IUPAC name N-(2,6-dimethylphenyl)alaninamide;
CAS Number	41708-72-9 ;
PubChem CID	38945;
IUPHAR/BPS	7309;
DrugBank	DB01056 ;
ChemSpider	35632 ;
UNII	27DXO59SAN;
KEGG	D06172 ;
ChEBI	CHEBI:9611 ;
ChEMBL	ChEMBL1762 ;
CompTox Dashboard (EPA)	DTXSID9040766 ;
ECHA InfoCard	100.050.441
Chemical and physical data
Formula	C11H16N2O
Molar mass	192.262 g·mol−1
3D model (JSmol)	Interactive image;
	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) ; Key:BUJAGSGYPOAWEI-UHFFFAOYSA-N ;
	(verify)

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

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)

Synthesis

References

^ R.N. Boyes, E.W. Byrnes, DE 2235745 (1972).
^ Astra Pharmaceutical Products Inc., GB 1461602 (1974).
^ R.N. Boyes, B.R. Duce, E.M. Smith, E.W. Byrnes, DE2400540 (1974).
^ Byrnes, Eugene W. (1979). "New antiarrhythmic agents. 1. Primary .alpha.-amino anilides". Journal of Medicinal Chemistry. 22 (10): 1171–1176. doi:10.1021/jm00196a005.

External links

MedlinePlus DrugInfo medmaster-a685030

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

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[1] R.N. Boyes, E.W. Byrnes, DE 2235745 (1972).

[2] Astra Pharmaceutical Products Inc., GB 1461602 (1974).

[3] R.N. Boyes, B.R. Duce, E.M. Smith, E.W. Byrnes, DE2400540 (1974).

[4] Byrnes, Eugene W. (1979). "New antiarrhythmic agents. 1. Primary .alpha.-amino anilides". Journal of Medicinal Chemistry. 22 (10): 1171–1176. doi:10.1021/jm00196a005.

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