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
Cibenzoline has an inhibitory effect on vasorelaxation mediated by adenosine triphosphate-sensitive K(+) channels in the rat carotid artery.	2001 Aug	11473844
Prevalence of asymptomatic ST segment elevation in right precordial leads with right bundle branch block (Brugada-type ST shift) among the general Japanese population.	2001 Aug	11454832
Cibenzoline, an ATP-sensitive K(+) channel blocker, binds to the K(+)-binding site from the cytoplasmic side of gastric H(+),K(+)-ATPase.	2001 Dec	11739241
Idiopathic left ventricular aneurysm associated with pleomorphic ventricular tachycardia: a case report.	2002 Dec	12528649
[Relationship between long-term preventive efficacy of cibenzoline and atrial natriuretic peptide in patients with paroxysmal atrial fibrillation].	2002 Feb	11873440
Percutaneous cardiopulmonary support aids resuscitation from sustained ventricular tachycardia.	2003 Dec	14639025
Decrease in the spatial dispersion at the termination of atrial fibrillation by intravenous cibenzoline.	2003 Oct	14578610
Cibenzoline therapy for mitral regurgitation in patients with HOCM.	2004 Jan	14964571
Frequency analysis of atrial fibrillation from the surface electrocardiogram.	2004 Jul 1	16943980
[Cibenzoline-succinate-induced hypoglycemia].	2004 Oct 10	15552920
[Coronary vasospasm induced by cibenzoline succinate in a patient with brugada-type electrocardiogram].	2005 Dec	16389745
Appropriate dosing of antiarrhythmic drugs in Japan requires therapeutic drug monitoring.	2005 Feb	15658999
Oral cibenzoline reduces postoperative atrial fibrillation in coronary artery bypass grafting.	2005 Jan	15724496
Cibenzoline induced Brugada ECG pattern.	2005 Nov	16216754
Too little, too late: chasing atrial fibrillation with sodium channel antagonists.	2006 Jun	16836717
Topics on the Na+/Ca2+ exchanger: pharmacological characterization of Na+/Ca2+ exchanger inhibitors.	2006 Sep	16990699
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
Cibenzoline intoxication: effect of combined hemoperfusion-hemodialysis on plasma clearance.	2008 Apr	18363124
Use of bepridil in combination with Ic antiarrhythmic agent in converting persistent atrial fibrillation to sinus rhythm.	2008 May	18441448
Hemolytic anemia in a patient with hypertrophic obstructive cardiomyopathy.	2010 Jan	20122559
Pharmacogenetic interactions between Angiotensin-converting enzyme insertion/deletion polymorphism and response to cibenzoline in patients with hypertrophic obstructive cardiomyopathy.	2010 May	20179607
Amiodarone sensitizes human glioma cells but not astrocytes to TRAIL-induced apoptosis via CHOP-mediated DR5 upregulation.	2011 Mar	21292685
Refining the human iPSC-cardiomyocyte arrhythmic risk assessment model.	2013 Dec	24052561

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

Download

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