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

Details

Stereochemistry RACEMIC
Molecular Formula C18H18N2
Molecular Weight 262.3496
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CIFENLINE

SMILES

c1ccc(cc1)C2(CC2C3=NCCN3)c4ccccc4

InChI

InChIKey=IPOBOOXFSRWSHL-UHFFFAOYSA-N
InChI=1S/C18H18N2/c1-3-7-14(8-4-1)18(15-9-5-2-6-10-15)13-16(18)17-19-11-12-20-17/h1-10,16H,11-13H2,(H,19,20)

HIDE SMILES / InChI

Molecular Formula C18H18N2
Molecular Weight 262.3496
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Cibenzoline is a class I sodium channel blocker antiarrhythmic drug available in a limited number of countries. Cibenzoline also has moderate calcium channel blocking (class IV) effects and prolongs the action potential duration through its potassium channel blocking (class III) effect. It is used for the treatment of supraventricular and ventricular arrhythmias, and in obstructive hypertrophic cardiomyopathy.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Antiarrhythmic plasma concentrations of cibenzoline on canine ventricular arrhythmias.
1987 Feb
Antiarrhythmic effects of optical isomers of cibenzoline on canine ventricular arrhythmias.
1990 Sep
Frequency analysis of atrial fibrillation from the surface electrocardiogram.
2004 Jul 1
Fractionation of electrograms and linking of activation during pharmacologic cardioversion of persistent atrial fibrillation in the goat.
2004 May
[Cibenzoline-succinate-induced hypoglycemia].
2004 Oct 10
Antiarrhythmic drug cibenzoline attenuates left ventricular pressure gradient and improves transmitral Doppler flow pattern in patients with hypertrophic obstructive cardiomyopathy caused by midventricular obstruction.
2005 Aug
A novel mutation in the PTPN11 gene in a patient with Noonan syndrome and rapidly progressive hypertrophic cardiomyopathy.
2005 Aug
[Coronary vasospasm induced by cibenzoline succinate in a patient with brugada-type electrocardiogram].
2005 Dec
Appropriate dosing of antiarrhythmic drugs in Japan requires therapeutic drug monitoring.
2005 Feb
Oral cibenzoline reduces postoperative atrial fibrillation in coronary artery bypass grafting.
2005 Jan
Cibenzoline attenuates upregulation of Kv1.5 channel gene expression by experimental paroxysmal atrial fibrillation.
2005 Mar
Cibenzoline induced Brugada ECG pattern.
2005 Nov
Atrial fibrillation and pacing algorithms.
2006 Jul 1
[Cibenzoline succinate induced pneumonitis].
2006 Jul 10
Too little, too late: chasing atrial fibrillation with sodium channel antagonists.
2006 Jun
Serial cardioversion by class IC Drugs during 4 months of persistent atrial fibrillation in the goat.
2006 Jun
Randomized crossover study of the long-term effects of pilsicainide and cibenzoline in preventing recurrence of symptomatic paroxysmal atrial fibrillation: influence of the duration of arrhythmia before therapy.
2006 Jun
Relief of left ventricular outflow obstruction by cibenzoline in a patient with Fabry's disease--a case report.
2006 Mar-Apr
Heart failure elevates serum levels of cibenzoline in arrhythmic patients.
2006 May
Cibenzoline improves coronary flow velocity reserve in patients with hypertrophic obstructive cardiomyopathy.
2006 Nov
Cibenzoline attenuates coronary systolic reversal flow in a patient with hypertrophic obstructive cardiomyopathy: a case report.
2006 Oct
Topics on the Na+/Ca2+ exchanger: pharmacological characterization of Na+/Ca2+ exchanger inhibitors.
2006 Sep
Symptomatic hypoglycemia in a patient with chronic hemodialysis.
2006 Sep-Oct
Clinical review: aggressive management and extracorporeal support for drug-induced cardiotoxicity.
2007
A novel and lethal de novo LQT-3 mutation in a newborn with distinct molecular pharmacology and therapeutic response.
2007 Dec 5
Quantification of cibenzoline by enzyme-linked immunosorbent assay.
2007 Jun
Effect of intravenous administration of cibenzoline on left ventricular diastolic pressures in patients with hypertrophic cardiomyopathy: its relationship to transmitral Doppler flow profiles.
2007 Oct
Na+/Ca2+ exchange inhibitors: a new class of calcium regulators.
2007 Sep
[Myasthenia-like syndrome induced by cibenzoline overdose in a patient with chronic kidney disease].
2008
Recommendations for performing acetylcholine tests safely: STOP dangerous complications induced by acetylcholine tests (STOP DCIAT).
2008 Apr
Cibenzoline intoxication: effect of combined hemoperfusion-hemodialysis on plasma clearance.
2008 Apr
Effect of cibenzoline and atenolol administration on dynamic left ventricular obstruction due to sigmoid-shaped septum.
2008 Dec
Clinical and electrophysiological characteristics of patients having atrial flutter with 1:1 atrioventricular conduction.
2008 Mar
Use of bepridil in combination with Ic antiarrhythmic agent in converting persistent atrial fibrillation to sinus rhythm.
2008 May
Cibenzoline attenuates systolic anterior motion of the mitral valve after mitral valvoplasty.
2009
Dobutamine stress echocardiography unmasks acute worsening of mitral regurgitation with latent left ventricular outflow tract obstruction behind diastolic heart failure in hypertensive heart disease.
2009
Quantitative assessment of cibenzoline administration for vagally mediated paroxysmal atrial fibrillation using frequency-domain heart rate variability analysis.
2009 Aug
A randomized study on the efficacy of intravenous cibenzoline and pilsicainide administered prior to electrical cardioversion in patients with lone paroxysmal and persistent atrial fibrillation.
2009 Feb
Effects of antiarrhythmic drugs on the hyperpolarization-activated cyclic nucleotide-gated channel current.
2009 Jun
A danger of induction of Brugada syndrome during pill-in-the-pocket therapy for paroxysmal atrial fibrillation.
2010
Hypertrophic obstructive cardiomyopathy causing severe right and left ventricular outflow tract obstruction.
2010 Apr
Hemolytic anemia in a patient with hypertrophic obstructive cardiomyopathy.
2010 Jan
Cibenzoline intoxication necessitating implantation of a biventricular assist system in a patient with severe cardiomyopathy.
2010 Jul
Effect of cibenzoline on biventricular pressure gradients in a pediatric patient with hypertrophic obstructive cardiomyopathy.
2010 Jul
Pilsicainide.
2010 Mar 5
Pharmacogenetic interactions between Angiotensin-converting enzyme insertion/deletion polymorphism and response to cibenzoline in patients with hypertrophic obstructive cardiomyopathy.
2010 May
Comparison of acute reduction in left ventricular outflow tract pressure gradient in obstructive hypertrophic cardiomyopathy by disopyramide versus pilsicainide versus cibenzoline.
2010 Nov 1
Prospective comparative study of intravenous cibenzoline and disopyramide therapy in the treatment of paroxysmal atrial fibrillation after cardiovascular surgery.
2010 Sep
Amiodarone sensitizes human glioma cells but not astrocytes to TRAIL-induced apoptosis via CHOP-mediated DR5 upregulation.
2011 Mar
Refining the human iPSC-cardiomyocyte arrhythmic risk assessment model.
2013 Dec

Sample Use Guides

In Vivo Use Guide
130 to 160 mg bid
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Jun 26 11:00:00 UTC 2021
Edited
by admin
on Sat Jun 26 11:00:00 UTC 2021
Record UNII
Z7489237QT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CIFENLINE
MI   USAN  
USAN  
Official Name English
CIBENZOLINE [INN]
Common Name English
CIBENZOLINE
INN   MART.   WHO-DD  
INN  
Official Name English
RO-22-7796
Code English
CIBENZOLINE [WHO-DD]
Common Name English
1H-IMIDAZOLE, 2-(2,2-DIPHENYLCYCLOPROPYL)-4,5-DIHYDRO-, (+/-)-
Systematic Name English
CIFENLINE [MI]
Common Name English
RO 22-7796
Code English
CIFENLINE [USAN]
Common Name English
(+/-)-2-(2,2-DIPHENYLCYCLOPROPYL)-2-IMIDAZOLINE
Systematic Name English
CIBENZOLINE [MART.]
Common Name English
Classification Tree Code System Code
WHO-ATC C01BG07
Created by admin on Sat Jun 26 11:00:01 UTC 2021 , Edited by admin on Sat Jun 26 11:00:01 UTC 2021
WHO-VATC QC01BG07
Created by admin on Sat Jun 26 11:00:01 UTC 2021 , Edited by admin on Sat Jun 26 11:00:01 UTC 2021
Code System Code Type Description
FDA UNII
Z7489237QT
Created by admin on Sat Jun 26 11:00:01 UTC 2021 , Edited by admin on Sat Jun 26 11:00:01 UTC 2021
PRIMARY
EVMPD
SUB06229MIG
Created by admin on Sat Jun 26 11:00:01 UTC 2021 , Edited by admin on Sat Jun 26 11:00:01 UTC 2021
PRIMARY
ChEMBL
CHEMBL87045
Created by admin on Sat Jun 26 11:00:01 UTC 2021 , Edited by admin on Sat Jun 26 11:00:01 UTC 2021
PRIMARY
INN
4568
Created by admin on Sat Jun 26 11:00:01 UTC 2021 , Edited by admin on Sat Jun 26 11:00:01 UTC 2021
PRIMARY
EPA CompTox
53267-01-9
Created by admin on Sat Jun 26 11:00:01 UTC 2021 , Edited by admin on Sat Jun 26 11:00:01 UTC 2021
PRIMARY
MERCK INDEX
M3542
Created by admin on Sat Jun 26 11:00:01 UTC 2021 , Edited by admin on Sat Jun 26 11:00:01 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB13358
Created by admin on Sat Jun 26 11:00:01 UTC 2021 , Edited by admin on Sat Jun 26 11:00:01 UTC 2021
PRIMARY
RXCUI
21099
Created by admin on Sat Jun 26 11:00:01 UTC 2021 , Edited by admin on Sat Jun 26 11:00:01 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C171690
Created by admin on Sat Jun 26 11:00:01 UTC 2021 , Edited by admin on Sat Jun 26 11:00:01 UTC 2021
PRIMARY
MESH
C032151
Created by admin on Sat Jun 26 11:00:01 UTC 2021 , Edited by admin on Sat Jun 26 11:00:01 UTC 2021
PRIMARY
CAS
53267-01-9
Created by admin on Sat Jun 26 11:00:01 UTC 2021 , Edited by admin on Sat Jun 26 11:00:01 UTC 2021
PRIMARY
DRUG CENTRAL
630
Created by admin on Sat Jun 26 11:00:01 UTC 2021 , Edited by admin on Sat Jun 26 11:00:01 UTC 2021
PRIMARY
ECHA (EC/EINECS)
258-453-7
Created by admin on Sat Jun 26 11:00:01 UTC 2021 , Edited by admin on Sat Jun 26 11:00:01 UTC 2021
PRIMARY
PUBCHEM
2747
Created by admin on Sat Jun 26 11:00:01 UTC 2021 , Edited by admin on Sat Jun 26 11:00:01 UTC 2021
PRIMARY
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