Tocainide

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Tocainide
Tocainide.svg
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)
Biological half-life 9-14 R, 13-20 S
Excretion 30-50% urine (unchanged)
Identifiers
CAS Number 41708-72-9 YesY
PubChem (CID) 38945
IUPHAR/BPS 7309
DrugBank DB01056 YesY
ChemSpider 35632 YesY
UNII 27DXO59SAN YesY
KEGG D06172 YesY
ChEBI CHEBI:9611 YesY
ChEMBL CHEMBL1762 YesY
ECHA InfoCard 100.050.441
Chemical and physical data
Formula C11H16N2O
Molar mass 192.258 g/mol
3D model (Jmol) Interactive image
  (verify)

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

Pharmacokinetics[edit]

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[edit]

Tocainide synthesis:[1][2][3][4]

References[edit]

  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. 

External links[edit]

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