WordNet

antiarrhythmic drug (trade name Tonocard) used to treat ventricular arrhythmias when less dangerous drugs have failed (同)Tonocard
a complex consisting of an organic base in association with hydrogen chloride

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/05/12 19:14:31」(JST)

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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

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

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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UpToDate Contents

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English Journal

Searching for novel anti-myotonic agents: pharmacophore requirement for use-dependent block of skeletal muscle sodium channels by N-benzylated cyclic derivatives of tocainide.

De Luca A, De Bellis M, Corbo F, Franchini C, Muraglia M, Catalano A, Carocci A, Camerino DC.SourceUnit of Pharmacology, Department of Pharmacobiology, Faculty of Pharmacy, University of Bari Aldo Moro, Italy.
Neuromuscular disorders : NMD.Neuromuscul Disord.2012 Jan;22(1):56-65. doi: 10.1016/j.nmd.2011.07.001. Epub 2011 Jul 29.
Drug screening on sodium currents of native myofibers by means of voltage-clamp recordings is predictive of pre-clinical anti-myotonic activity in vivo and ex vivo. By this approach we identified the N-benzylated beta-proline derivative of tocainide (To10) as the most potent use-dependent blocker of
PMID 21802953

The efficacy of anticonvulsants on orofacial pain: a systematic review.

Martin WJ, Forouzanfar T.SourceDepartment of Oral and Maxillofacial Surgery/Oral Pathology, Vrije Universiteit Medical Center/Academic Center for Dentistry Amsterdam, Amsterdam, The Netherlands.
Oral surgery, oral medicine, oral pathology, oral radiology, and endodontics.Oral Surg Oral Med Oral Pathol Oral Radiol Endod.2011 May;111(5):627-33. doi: 10.1016/j.tripleo.2011.01.033.
OBJECTIVE: Controversy exists about the effectiveness of anticonvulsants for the management of orofacial pain disorders. To ascertain appropriate therapies, a systematic review was conducted of existing randomized controlled trials.STUDY DESIGN: Trials were identified from PubMed, Cochrane, and Ovid
PMID 21497736

Non-antiepileptic drugs for trigeminal neuralgia.

Yang M, Zhou M, He L, Chen N, Zakrzewska JM.SourceDepartment of Neurology, West China Hospital, Sichuan University, No. 37, Guo Xue Xiang, Chengdu, Sichuan, China, 610041.
Cochrane database of systematic reviews (Online).Cochrane Database Syst Rev.2011 Jan 19;(1):CD004029. doi: 10.1002/14651858.CD004029.pub3.
BACKGROUND: Non-antiepileptic drugs have been used in the management of trigeminal neuralgia since the 1970s.OBJECTIVES: The objective was to systematically review the efficacy and tolerability of non-antiepileptic drugs for trigeminal neuralgia.SEARCH STRATEGY: For this updated review we searched t
PMID 21249658

「トカイニド」

Tocainide
Systematic (IUPAC) name
	N-(2,6-dimethylphenyl)alaninamide
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a601248
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
ATC code	C01BB03 (WHO)
PubChem	CID 38945
IUPHAR/BPS	7309
DrugBank	DB01056
ChemSpider	35632
UNII	27DXO59SAN
KEGG	D06172
ChEBI	CHEBI:9611
ChEMBL	CHEMBL1762
Chemical data
Formula	C11H16N2O
Molar 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) ; Key:BUJAGSGYPOAWEI-UHFFFAOYSA-N ;
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