CIFENLINE SUCCINATE

Details

Stereochemistry	RACEMIC
Molecular Formula	C18H18N2.C4H6O4
Molecular Weight	380.437
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)CCC(O)=O.C1C(C2=NCCN2)C1(C3=CC=CC=C3)C4=CC=CC=C4

InChI

InChIKey=XFUIOIWYMHEPIE-UHFFFAOYSA-N

InChI=1S/C18H18N2.C4H6O4/c1-3-7-14(8-4-1)18(15-9-5-2-6-10-15)13-16(18)17-19-11-12-20-17;5-3(6)1-2-4(7)8/h1-10,16H,11-13H2,(H,19,20);1-2H2,(H,5,6)(H,7,8)

HIDE SMILES / InChI

Molecular Formula	C4H6O4
Molecular Weight	118.088
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C18H18N2
Molecular Weight	262.3489
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/16216754

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

Targets

Primary Target	Pharmacology	Condition	Potency
Voltage-gated calcium channel 37 Target ID: CHEMBL2363032 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16216754	Blocker 537
Sulfonylurea receptors; K-ATP channels 11 Target ID: CHEMBL2095152 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16216754	Blocker 537
Voltage-sensitive sodium channel 7 Target ID: CHEMBL2362985 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16216754	Blocker 537

Conditions

Condition	Modality	Highest Phase	Product
Paroxysmal atrial arrhythmias 2 Sources: http://www.ncbi.nlm.nih.gov/pubmed/7657846	Preventing	Phase I 428	Unknown Approved Use Unknown
Symptomatic ventricular arrhythmias 2 Sources: http://www.ncbi.nlm.nih.gov/pubmed/2477130	Preventing	Phase II 1132	Unknown Approved Use Unknown
Hypertrophic obstructive cardiomyopathy 2 Sources: http://www.ncbi.nlm.nih.gov/pubmed/9315541	Preventing	Phase I 428	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Antiarrhythmic effects of optical isomers of cibenzoline on canine ventricular arrhythmias.	1990 Sep	1700207
[Sudden cardiac arrest after induction of general anesthesia: a case report].	2000 Jan	10689846
Spectral characteristics of human atrial fibrillation waves of the right atrial free wall with respect to the duration of atrial fibrillation and effect of class I antiarrhythmic drugs.	2001 Dec	11767996
Blurred vision, left bundle-branch block and cardiac failure.	2001 Feb	11315123
[Efficacy of cibenzoline in the termination and long-term prevention of paroxysmal atrial fibrillation: analysis based on the time of onset].	2001 Feb	11255698
Effects of cibenzoline on cardiac function and metabolism in the rat heart--lung preparation.	2001 Mar	11298178
Idiopathic left ventricular aneurysm associated with pleomorphic ventricular tachycardia: a case report.	2002 Dec	12528649
MDR1-mediated interaction of digoxin with antiarrhythmic or antianginal drugs.	2002 Dec	12499648
Percutaneous cardiopulmonary support aids resuscitation from sustained ventricular tachycardia.	2003 Dec	14639025
[Beneficial effect of cibenzoline in a patient with hypertrophic obstructive cardiomyopathy complicated with idiopathic interstitial pneumonia].	2003 Jan	12649850
Decrease in the spatial dispersion at the termination of atrial fibrillation by intravenous cibenzoline.	2003 Oct	14578610
Mitral regurgitation disappearance after cibenzoline treatment in a patient with hypertrophic obstructive cardiomyopathy.	2004 Jan	14964580
Fractionation of electrograms and linking of activation during pharmacologic cardioversion of persistent atrial fibrillation in the goat.	2004 May	15149428
A novel mutation in the PTPN11 gene in a patient with Noonan syndrome and rapidly progressive hypertrophic cardiomyopathy.	2005 Aug	15889278
Appropriate dosing of antiarrhythmic drugs in Japan requires therapeutic drug monitoring.	2005 Feb	15658999
Cibenzoline induced Brugada ECG pattern.	2005 Nov	16216754
Atrial fibrillation and pacing algorithms.	2006 Jul 1	16943966
[Cibenzoline succinate induced pneumonitis].	2006 Jul 10	16893032
Too little, too late: chasing atrial fibrillation with sodium channel antagonists.	2006 Jun	16836717
Serial cardioversion by class IC Drugs during 4 months of persistent atrial fibrillation in the goat.	2006 Jun	16836716
Heart failure elevates serum levels of cibenzoline in arrhythmic patients.	2006 May	16636495
Cibenzoline improves coronary flow velocity reserve in patients with hypertrophic obstructive cardiomyopathy.	2006 Nov	17143709
Symptomatic hypoglycemia in a patient with chronic hemodialysis.	2006 Sep-Oct	17240739
Clinical review: aggressive management and extracorporeal support for drug-induced cardiotoxicity.	2007	17367544
Quantification of cibenzoline by enzyme-linked immunosorbent assay.	2007 Jun	17541252
[Myasthenia-like syndrome induced by cibenzoline overdose in a patient with chronic kidney disease].	2008	19069153
Recommendations for performing acetylcholine tests safely: STOP dangerous complications induced by acetylcholine tests (STOP DCIAT).	2008 Apr	18522786
Effects of antiarrhythmic drugs on the hyperpolarization-activated cyclic nucleotide-gated channel current.	2009 Jun	19498275
Hypertrophic obstructive cardiomyopathy causing severe right and left ventricular outflow tract obstruction.	2010 Apr	20676000
Cibenzoline intoxication necessitating implantation of a biventricular assist system in a patient with severe cardiomyopathy.	2010 Jul	20421279
Comparison of acute reduction in left ventricular outflow tract pressure gradient in obstructive hypertrophic cardiomyopathy by disopyramide versus pilsicainide versus cibenzoline.	2010 Nov 1	21029829
Prospective comparative study of intravenous cibenzoline and disopyramide therapy in the treatment of paroxysmal atrial fibrillation after cardiovascular surgery.	2010 Sep	20631453
Amiodarone sensitizes human glioma cells but not astrocytes to TRAIL-induced apoptosis via CHOP-mediated DR5 upregulation.	2011 Mar	21292685

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 `Fri Dec 15 15:37:13 GMT 2023` Edited by `admin` on `Fri Dec 15 15:37:13 GMT 2023`
Record UNII	38G16RWJ37
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CIFENLINE SUCCINATE

Official Name

English

RO 22-7796/001

Code

English

RO-22-7796/001

Code

English

CIPRALAN

Brand Name

English

CIBENOL

Brand Name

English

1H-IMIDAZOLE, 2-(2,2-DIPHENYLCYCLOPROPYL)-4,5-DIHYDRO-, (±)-, BUTANEDIOATE (1:1)

Systematic Name

English

CIBENZOLINE SUCCINATE [JAN]

Common Name

English

RO-227796001

Code

English

CIFENLINE SUCCINATE [MI]

Common Name

English

(±)-2-(2,2-DIPHENYLCYCLOPROPYL)-2-IMIDAZOLINE SUCCINATE (1:1)

Systematic Name

English

CIBENZOLINE SUCCINATE

Common Name

English

Cibenzoline succinate [WHO-DD]

Common Name

English

CIFENLINE SUCCINATE [USAN]

Common Name

English

Code System Code Type Description

EVMPD

SUB01290MIG