U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C19H27N5O5.ClH
Molecular Weight 441.909
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NIFEKALANT HYDROCHLORIDE

SMILES

Cl.CN1C(=O)C=C(NCCN(CCO)CCCC2=CC=C(C=C2)[N+]([O-])=O)N(C)C1=O

InChI

InChIKey=YPVGGQKNWAKOPX-UHFFFAOYSA-N
InChI=1S/C19H27N5O5.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C19H27N5O5
Molecular Weight 405.4482
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
2.7 µM [IC50]
7.9 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Shinbit

Approved Use

For the treatment of arrhythmia

Launch Date

1999
PubMed

PubMed

TitleDatePubMed
Pretreatments with a novel pure potassium channel blocker, Nifekalant, were effective in the electrical atrial defibrillation: a report of two cases.
2002 Dec
Inhibitory effect of the class III antiarrhythmic drug nifekalant on HERG channels: mode of action.
2002 Dec 13
Sotalol-induced coronary spasm in a patient with dilated cardiomyopathy associated with sustained ventricular tachycardia.
2004 Nov
Effect of nifekalant, a class III anti-arrhythmic agent, on Ca2+ waves in rat intact trabeculae.
2005 Jun
Emergency treatment with nifekalant, a novel class III anti-arrhythmic agent, for life-threatening refractory ventricular tachyarrhythmias: post-marketing special investigation.
2005 Oct
[Strategy for cardiac arrhythmias in acute coronary syndrome].
2006 Apr
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
Reduced inotropic effect of nifekalant in failing hearts in rats.
2006 Sep
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
[Successful use of intravenous amiodarone for refractory ventricular fibrillation just after releasing aortic cross-clamp].
2010 Oct
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Patents

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
In Vitro Use Guide
Nifekalant in concentrations of 1 and 10 uM prolonged the action potential durations of Purkinje fiber and the free wall in a concentration-dependent manner in dogs.
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:37:35 GMT 2023
Edited
by admin
on Sat Dec 16 01:37:35 GMT 2023
Record UNII
TPP5R0MDQS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NIFEKALANT HYDROCHLORIDE
MI   WHO-DD  
Common Name English
NIFEKALANT HYDROCHLORIDE [MI]
Common Name English
Nifekalant hydrochloride [WHO-DD]
Common Name English
Code System Code Type Description
SMS_ID
100000086472
Created by admin on Sat Dec 16 01:37:35 GMT 2023 , Edited by admin on Sat Dec 16 01:37:35 GMT 2023
PRIMARY
PUBCHEM
122188
Created by admin on Sat Dec 16 01:37:35 GMT 2023 , Edited by admin on Sat Dec 16 01:37:35 GMT 2023
PRIMARY
FDA UNII
TPP5R0MDQS
Created by admin on Sat Dec 16 01:37:35 GMT 2023 , Edited by admin on Sat Dec 16 01:37:35 GMT 2023
PRIMARY
MESH
C076259
Created by admin on Sat Dec 16 01:37:35 GMT 2023 , Edited by admin on Sat Dec 16 01:37:35 GMT 2023
PRIMARY
EPA CompTox
DTXSID7048374
Created by admin on Sat Dec 16 01:37:35 GMT 2023 , Edited by admin on Sat Dec 16 01:37:35 GMT 2023
PRIMARY
MERCK INDEX
m7884
Created by admin on Sat Dec 16 01:37:35 GMT 2023 , Edited by admin on Sat Dec 16 01:37:35 GMT 2023
PRIMARY Merck Index
CAS
130656-51-8
Created by admin on Sat Dec 16 01:37:35 GMT 2023 , Edited by admin on Sat Dec 16 01:37:35 GMT 2023
PRIMARY
EVMPD
SUB20699
Created by admin on Sat Dec 16 01:37:35 GMT 2023 , Edited by admin on Sat Dec 16 01:37:35 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE