関: tocainide hydrochloride

WordNet

antiarrhythmic drug (trade name Tonocard) used to treat ventricular arrhythmias when less dangerous drugs have failed (同)Tonocard

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/03/04 09:50:54」(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

N-aryl-2,6-dimethylbenzamides, a new generation of tocainide analogues as blockers of skeletal muscle voltage-gated sodium channels.

Muraglia M1, De Bellis M, Catalano A, Carocci A, Franchini C, Carrieri A, Fortugno C, Bertucci C, Desaphy JF, De Luca A, Conte Camerino D, Corbo F.
Journal of medicinal chemistry.J Med Chem.2014 Mar 27;57(6):2589-600. doi: 10.1021/jm401864b. Epub 2014 Mar 7.
On the basis of a 3D-QSAR study, a new generation of tocainide analogues were designed and synthesized as voltage-gated skeletal muscle sodium channel blockers. Data obtained by screening new compounds by means of Hille-Campbell Vaseline gap voltage-clamp recordings showed that the elongation of the
PMID 24568674

Species-dependent binding of tocainide analogues to albumin: Affinity chromatography and circular dichroism study.

Pistolozzi M1, Fortugno C2, Franchini C3, Corbo F3, Muraglia M3, Roy M4, Félix G4, Bertucci C5.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.J Chromatogr B Analyt Technol Biomed Life Sci.2014 Jan 10. pii: S1570-0232(14)00009-9. doi: 10.1016/j.jchromb.2014.01.007. [Epub ahead of print]
A series of novel tocainide analogues were characterized for their HSA and RSA binding, by using high-performance liquid affinity chromatography (HPLAC) and circular dichroism (CD). In this HPLAC study, HSA and RSA were covalently immobilized to the silica matrix of HPLC columns, with a procedure th
PMID 24472243

Non-antiepileptic drugs for trigeminal neuralgia.

Zhang J1, Yang M, Zhou M, He L, Chen N, Zakrzewska JM.
The Cochrane database of systematic reviews.Cochrane Database Syst Rev.2013 Dec 3;12:CD004029. doi: 10.1002/14651858.CD004029.pub4.
BACKGROUND: Trigeminal neuralgia was defined by the International Association for the Study of Pain as a sudden, usually unilateral, severe, brief, stabbing recurrent pain in the distribution of one or more branches of the fifth cranial nerve. Standard treatment is with anti-epileptic drugs. Non-ant
PMID 24297506

Japanese Journal

67) 犬急性心筋梗塞巣に対するTocainideの効果 : 電気生理学的検討から(日本循環器学会第81回北陸地方会)

Japanese circulation journal 59(SupplementIV), 1030, 1996-02-20
NAID 110002622001

Assay of tocainide enantiomers in plasma by solid-phase extraction and indirect chiral high-performance liquid chromatography after derivatization with (-)-menthyl chloroformate

Journal of chromatography. B, Biomedical applications 670(2), 243-249, 1995-08-18
NAID 10024549252

TocainideのNa電流抑制作用 : 日本循環器学会第59回中国・四国地方会

Japanese circulation journal 57(SupplementIII), 1068-1069, 1993-08-20
NAID 110002635022

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リンク元	「トカイニド」
拡張検索	「tocainide hydrochloride」

「トカイニド」

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)
Biological 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 ;
ECHA InfoCard	100.050.441
Chemical and physical data
Formula	C11H16N2O
Molar mass	192.258 g/mol
3D model (Jmol)	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 ;
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