CIFENLINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C18H18N2
Molecular Weight	262.3489
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C1C(C2=NCCN2)C1(C3=CC=CC=C3)C4=CC=CC=C4

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	262.3489
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
[Fatal poisoning by cibenzoline].	2001 Mar-Apr	11471373
Effect of cibenzoline, a class ia antiarrhythmic agent, on left ventricular diastolic function in hypertrophic cardiomyopathy.	2001 Sep	11855665
Idiopathic left ventricular aneurysm associated with pleomorphic ventricular tachycardia: a case report.	2002 Dec	12528649
Atrial fibrillation threshold predicted long-term efficacy of pharmacological treatment of patients without structural heart disease.	2002 Oct	12408258
[Comparison of the efficacies of disopyramide, cibenzoline and aprindine for the termination of paroxysmal and persistent atrial fibrillation in elderly and non-elderly patients].	2003 Apr	12728540
[Beneficial effect of cibenzoline in a patient with hypertrophic obstructive cardiomyopathy complicated with idiopathic interstitial pneumonia].	2003 Jan	12649850
[A case of acute cibenzoline intoxication in a hemodialysis patient].	2003 Jul	14582357
Role of fibrillation cycle length in spontaneous and drug-induced termination of human atrial fibrillation.	2003 May	12736475
Decrease in the spatial dispersion at the termination of atrial fibrillation by intravenous cibenzoline.	2003 Oct	14578610
Frequency analysis of atrial fibrillation from the surface electrocardiogram.	2004 Jul 1	16943980
[Cibenzoline-succinate-induced hypoglycemia].	2004 Oct 10	15552920
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	16041163
Relief of left ventricular outflow obstruction by cibenzoline in a patient with Fabry's disease--a case report.	2006 Mar-Apr	16518535
A novel and lethal de novo LQT-3 mutation in a newborn with distinct molecular pharmacology and therapeutic response.	2007 Dec 5	18060054
[Myasthenia-like syndrome induced by cibenzoline overdose in a patient with chronic kidney disease].	2008	19069153
Cibenzoline intoxication: effect of combined hemoperfusion-hemodialysis on plasma clearance.	2008 Apr	18363124
Clinical and electrophysiological characteristics of patients having atrial flutter with 1:1 atrioventricular conduction.	2008 Mar	18258806
Use of bepridil in combination with Ic antiarrhythmic agent in converting persistent atrial fibrillation to sinus rhythm.	2008 May	18441448
Quantitative assessment of cibenzoline administration for vagally mediated paroxysmal atrial fibrillation using frequency-domain heart rate variability analysis.	2009 Aug	19632526
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 15:26:08 GMT 2023` Edited by `admin` on `Fri Dec 15 15:26:08 GMT 2023`
Record UNII	Z7489237QT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CIFENLINE

Official Name

English

cibenzoline [INN]

Common Name

English

CIBENZOLINE

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