Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C19H27N5O5 |
| Molecular Weight | 405.4482 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1C(=O)C=C(NCCN(CCO)CCCC2=CC=C(C=C2)[N+]([O-])=O)N(C)C1=O
InChI
InChIKey=OEBPANQZQGQPHF-UHFFFAOYSA-N
InChI=1S/C19H27N5O5/c1-21-17(14-18(26)22(2)19(21)27)20-9-11-23(12-13-25)10-3-4-15-5-7-16(8-6-15)24(28)29/h5-8,14,20,25H,3-4,9-13H2,1-2H3
DescriptionCurator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/16157956
Curator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/16157956
Nifekalant is a class III antiarrhythmic agent approved in Japan for the treatment of arrhythmias and ventricular tachycardia. It has the brand name Shinbit. It is a nonselective K+ channel blocker without any β-blocking actions. Administration of nifekalant suppressed sustained ventricular tachyarrhythmias in acute coronary syndrome patients, and in cardiac arrest victims as well as during or after cardiac surgery. The major adverse effect of nifekalant is QT interval prolongation and occurrence of torsades de pointes which requires frequent monitoring of the QT interval during nifekalant infusion with adequate dose adjustment.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Reverse use-dependent QT prolongation during infusion of nifekalant in a case of recurrent ventricular tachycardia with old myocardial infarction. | 2001 Jan |
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| [Synthesis and vasorelaxant activities of benzopyran-4-one hydrazone derivatives]. | 2002 Aug |
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| Pretreatments with a novel pure potassium channel blocker, Nifekalant, were effective in the electrical atrial defibrillation: a report of two cases. | 2002 Dec |
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| Inhibitory effect of the class III antiarrhythmic drug nifekalant on HERG channels: mode of action. | 2002 Dec 13 |
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| [Pharmacological and clinical profile of nifekalant (shinbit injection), a class III antiarrhythmic drug]. | 2002 Feb |
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| Antiarrhythmic effect of nifekalant on atrial tachyarrhythmia in four patients with severe heart failure. | 2002 Mar |
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| [Recent findings on the dromotropic actions of the class III antiarrhythmic agents]. | 2002 Nov |
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| Anti-arrhythmic efficacy of nifekalant hydrochloride, a pure class III anti-arrhythmic agent, in patients with healed myocardial infarction and inducible sustained ventricular tachycardia. | 2002 Nov |
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| [Successful hybrid therapy combined with oral bepridil and ICD in a patient with amiodarone refractory life-threatening ventricular tachyarrhythmia associated with ischemic cardiomyopathy]. | 2002 Sep 1 |
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| [Effects of clinically available drugs on the repolarization process of the heart assessed by the in vivo canine models]. | 2003 Jun |
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| IKr channel blockers: novel antiarrhythmic agents. | 2003 Oct |
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| Effects of intravenous nifekalant, a class III antiarrhythmic drug, on atrial vulnerability parameters in patients with paroxysmal atrial fibrillation. | 2004 Feb |
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| Development of a halothane-adrenaline arrhythmia model using in vivo Guinea pigs. | 2004 Jun |
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| Electropharmacological and proarrhythmic effects of a class III antiarrhythmic drug nifekalant hydrochloride assessed using the in vivo canine models. | 2004 May |
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| Sotalol-induced coronary spasm in a patient with dilated cardiomyopathy associated with sustained ventricular tachycardia. | 2004 Nov |
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| Defibrillation effects of intravenous nifekalant in patients with out-of-hospital ventricular fibrillation. | 2005 Jan |
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| Efficacy of nifekalant hydrochloride in the treatment of fatal ventricular arrhythmia in patients with ischemic heart disease. | 2005 Jul |
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| Enhancing electrical cardioversion and preventing immediate reinitiation of hemodynamically deleterious atrial fibrillation with class III drug pretreatment. | 2005 Jul |
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| Effect of nifekalant, a class III anti-arrhythmic agent, on Ca2+ waves in rat intact trabeculae. | 2005 Jun |
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| Effect of IKr blocker nifekalant on atrial action potential duration after successful internal cardioversion of chronic atrial fibrillation. | 2005 May |
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| Combined effects of nifekalant and lidocaine on the spiral-type re-entry in a perfused 2-dimensional layer of rabbit ventricular myocardium. | 2005 May |
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| Optical imaging of spiral waves: pharmacological modification of spiral-type excitations in a 2-dimensional layer of ventricular myocardium. | 2005 Oct |
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| Emergency treatment with nifekalant, a novel class III anti-arrhythmic agent, for life-threatening refractory ventricular tachyarrhythmias: post-marketing special investigation. | 2005 Oct |
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| [Strategy for cardiac arrhythmias in acute coronary syndrome]. | 2006 Apr |
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| Comparison of nifekalant and lidocaine for the treatment of shock-refractory ventricular fibrillation. | 2006 Apr |
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| Effects of antiarrhythmic drugs on apoptotic pathways in H9c2 cardiac cells. | 2006 Aug |
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| Effect of nifekalant on acute electrical remodelling in rapid atrial pacing canine model. | 2006 Dec 20 |
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| Fatal case of amiodarone-induced acute respiratory distress syndrome in a patient with severe left ventricular dysfunction due to extensive anterior acute myocardial infarction. | 2006 Feb |
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| Destabilization and early termination of spiral-wave reentry by a class III antiarrhythmic agent, nifekalant, in a perfused two-dimensional layer of rabbit ventricular myocardium. | 2006 Feb 17 |
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| Can nifekalant hydrochloride be used as a first-line drug for cardiopulmonary arrest (CPA)? : comparative study of out-of-hospital CPA with acidosis and in-hospital CPA without acidosis. | 2006 Jan |
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| Comparison of efficacy of sotalol and nifekalant for ventricular tachyarrhythmias. | 2006 May |
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| Molecular determinants of HERG channel block. | 2006 May |
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| Reduced inotropic effect of nifekalant in failing hearts in rats. | 2006 Sep |
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| Drug therapy for ventricular tachyarrhythmia in heart failure. | 2007 |
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| Analysis of arrhythmogenic profile in a canine model of chronic atrioventricular block by comparing in vitro effects of the class III antiarrhythmic drug nifekalant on the ventricular action potential indices between normal heart and atrioventricular block heart. | 2007 Feb |
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| Mechanisms of destabilization and early termination of spiral wave reentry in the ventricle by a class III antiarrhythmic agent, nifekalant. | 2007 Jan |
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| Mutational analysis of block and facilitation of HERG current by a class III anti-arrhythmic agent, nifekalant. | 2007 May-Jun |
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| [Despite medication, overdrive pacing is required to stabilize the electrical storm associated with acute coronary syndrome: a case report]. | 2007 Oct |
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| Effect of nifekalant for acute conversion of atrial flutter: the possible termination mechanism of typical atrial flutter. | 2007 Oct |
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| Characterization of transient atrial rhythm occurring between typical atrial flutter and its termination with class III drugs. | 2008 Aug |
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| Clinical study of the acute effects of intravenous nifekalant on the defibrillation threshold in patients with persistent and paroxysmal atrial fibrillation. | 2008 Jan |
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| Human atrial natriuretic peptide suppresses torsades de pointes in rabbits. | 2008 May |
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| Nifekalant and disopyramide in a patient with short QT syndrome: evaluation of pharmacological effects and electrophysiological properties. | 2008 Sep |
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| Effects of intravenous nifekalant as a lifesaving drug for severe ventricular tachyarrhythmias complicating acute coronary syndrome. | 2009 Nov |
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| Comparative study of nifekalant versus amiodarone for shock-resistant ventricular fibrillation in out-of-hospital cardiopulmonary arrest patients. | 2010 Apr |
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| Comparison of the efficacy of nifekalant and amiodarone in a porcine model of cardiac arrest. | 2010 Aug |
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| Nifekalant versus lidocaine for in-hospital shock-resistant ventricular fibrillation or tachycardia. | 2010 Jan |
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| Junctional ectopic tachycardia. | 2010 Jul 20 |
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| Effects of landiolol, an ultra-short-acting beta1-selective blocker, on electrical storm refractory to class III antiarrhythmic drugs. | 2010 May |
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| [Successful use of intravenous amiodarone for refractory ventricular fibrillation just after releasing aortic cross-clamp]. | 2010 Oct |
Sample Use Guides
For acute coronary syndrome treatment the mean dose level of nifekalant was 0.19 ± 0.14 mg/kg body weight per hour;
For peri-operative Ventricular tachyarrhythmia treatment - intravenous administration of nifekalant in a dose of 0.3 mg/kg;
For cardiopulmonary resuscitation treatment - 0.15-0.3 mg/kg followed by intravenous infusion of 0.3-0.4 mg/kg per hour as antiarrhythmic therapy
Route of Administration:
Intravenous
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NCI_THESAURUS |
C47793
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NCI_THESAURUS |
C93038
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DTXSID9046495
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7478
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m7884
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100000084421
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NIFEKALANT
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CHEMBL360861
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C75132
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130636-43-0
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C076259
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SUB09254MIG
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5VZ7GZM43E
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1923
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4486
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
