U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

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 of CIFENLINE

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

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

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Blocker
555
Blocker
555
Blocker
555
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Phase I
438
Unknown

Approved Use

Unknown
Preventing
Phase II
1147
Unknown

Approved Use

Unknown
Preventing
Phase I
438
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
419 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3783460/
160 mg single, oral
dose: 160 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CIFENLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1150 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3783460/
160 mg single, intravenous
dose: 160 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CIFENLINE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
3278 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3783460/
160 mg single, oral
dose: 160 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CIFENLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
3929 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3783460/
160 mg single, intravenous
dose: 160 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CIFENLINE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
7.8 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3783460/
160 mg single, oral
dose: 160 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CIFENLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
7.5 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3783460/
160 mg single, intravenous
dose: 160 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CIFENLINE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
80 mg 4 times / day multiple, oral
Highest studied dose
Dose: 80 mg, 4 times / day
Route: oral
Route: multiple
Dose: 80 mg, 4 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/3693585/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/3693585/
Disc. AE: Hypoglycemia...
AEs leading to
discontinuation/dose reduction:
Hypoglycemia (severe, 1 pt)
Sources:
https://pubmed.ncbi.nlm.nih.gov/3693585/
81.25 mg 4 times / day multiple, oral
Highest studied dose
Dose: 81.25 mg, 4 times / day
Route: oral
Route: multiple
Dose: 81.25 mg, 4 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/3680596/
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/3680596/
Other AEs: Dry mouth...
Other AEs:
Dry mouth (1 pt)
Sources:
https://pubmed.ncbi.nlm.nih.gov/3680596/
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/19069153/
unhealthy
Health Status: unhealthy
Sex: F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/19069153/
Disc. AE: Myasthenia...
AEs leading to
discontinuation/dose reduction:
Myasthenia (1 pt)
Sources:
https://pubmed.ncbi.nlm.nih.gov/19069153/
32.5 mg 4 times / day multiple, oral
Studied dose
Dose: 32.5 mg, 4 times / day
Route: oral
Route: multiple
Dose: 32.5 mg, 4 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/3680596/
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/3680596/
Disc. AE: Dry mouth, Cardiac pain...
AEs leading to
discontinuation/dose reduction:
Dry mouth (1 pt)
Cardiac pain (1 pt)
Sources:
https://pubmed.ncbi.nlm.nih.gov/3680596/
65 mg 4 times / day multiple, oral
Studied dose
Dose: 65 mg, 4 times / day
Route: oral
Route: multiple
Dose: 65 mg, 4 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/3680596/
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/3680596/
Disc. AE: Cardiac pain, Vision abnormal...
AEs leading to
discontinuation/dose reduction:
Cardiac pain (1 pt)
Vision abnormal (1 pt)
Dizziness (1 pt)
Sources:
https://pubmed.ncbi.nlm.nih.gov/3680596/
70 mg single, intravenous
Studied dose
Dose: 70 mg
Route: intravenous
Route: single
Dose: 70 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/20631453/
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/20631453/
Sources:
https://pubmed.ncbi.nlm.nih.gov/20631453/
AEs

AEs

AESignificanceDosePopulation
Hypoglycemia severe, 1 pt
Disc. AE
80 mg 4 times / day multiple, oral
Highest studied dose
Dose: 80 mg, 4 times / day
Route: oral
Route: multiple
Dose: 80 mg, 4 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/3693585/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/3693585/
Dry mouth 1 pt
81.25 mg 4 times / day multiple, oral
Highest studied dose
Dose: 81.25 mg, 4 times / day
Route: oral
Route: multiple
Dose: 81.25 mg, 4 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/3680596/
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/3680596/
Myasthenia 1 pt
Disc. AE
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/19069153/
unhealthy
Health Status: unhealthy
Sex: F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/19069153/
Cardiac pain 1 pt
Disc. AE
32.5 mg 4 times / day multiple, oral
Studied dose
Dose: 32.5 mg, 4 times / day
Route: oral
Route: multiple
Dose: 32.5 mg, 4 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/3680596/
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/3680596/
Dry mouth 1 pt
Disc. AE
32.5 mg 4 times / day multiple, oral
Studied dose
Dose: 32.5 mg, 4 times / day
Route: oral
Route: multiple
Dose: 32.5 mg, 4 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/3680596/
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/3680596/
Cardiac pain 1 pt
Disc. AE
65 mg 4 times / day multiple, oral
Studied dose
Dose: 65 mg, 4 times / day
Route: oral
Route: multiple
Dose: 65 mg, 4 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/3680596/
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/3680596/
Dizziness 1 pt
Disc. AE
65 mg 4 times / day multiple, oral
Studied dose
Dose: 65 mg, 4 times / day
Route: oral
Route: multiple
Dose: 65 mg, 4 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/3680596/
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/3680596/
Vision abnormal 1 pt
Disc. AE
65 mg 4 times / day multiple, oral
Studied dose
Dose: 65 mg, 4 times / day
Route: oral
Route: multiple
Dose: 65 mg, 4 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/3680596/
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/3680596/
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
Mitral regurgitation disappearance after cibenzoline treatment in a patient with hypertrophic obstructive cardiomyopathy.
2004 Jan
Frequency analysis of atrial fibrillation from the surface electrocardiogram.
2004 Jul 1
Block of HERG current expressed in HEK293 cells by the Na+-channel blocker cibenzoline.
2004 May
Fractionation of electrograms and linking of activation during pharmacologic cardioversion of persistent atrial fibrillation in the goat.
2004 May
Beneficial effect of cibenzoline on left ventricular pressure gradient with sigmoid septum.
2004 Oct
[Cibenzoline-succinate-induced hypoglycemia].
2004 Oct 10
Human organic cation transporter 3 mediates the transport of antiarrhythmic drugs.
2004 Sep 19
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
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
Clinical and electrophysiological characteristics of patients having atrial flutter with 1:1 atrioventricular conduction.
2008 Mar
Cibenzoline attenuates systolic anterior motion of the mitral valve after mitral valvoplasty.
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 Mon Mar 31 17:57:37 GMT 2025
Edited
by admin
on Mon Mar 31 17:57:37 GMT 2025
Record UNII
Z7489237QT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CIBENZOLINE
INN   MART.   WHO-DD  
INN  
Preferred Name English
CIFENLINE
MI   USAN  
USAN  
Official Name English
cibenzoline [INN]
Common 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 Mon Mar 31 17:57:37 GMT 2025 , Edited by admin on Mon Mar 31 17:57:37 GMT 2025
WHO-VATC QC01BG07
Created by admin on Mon Mar 31 17:57:37 GMT 2025 , Edited by admin on Mon Mar 31 17:57:37 GMT 2025
Code System Code Type Description
FDA UNII
Z7489237QT
Created by admin on Mon Mar 31 17:57:38 GMT 2025 , Edited by admin on Mon Mar 31 17:57:38 GMT 2025
PRIMARY
EVMPD
SUB06229MIG
Created by admin on Mon Mar 31 17:57:37 GMT 2025 , Edited by admin on Mon Mar 31 17:57:37 GMT 2025
PRIMARY
SMS_ID
100000092561
Created by admin on Mon Mar 31 17:57:38 GMT 2025 , Edited by admin on Mon Mar 31 17:57:38 GMT 2025
PRIMARY
ChEMBL
CHEMBL87045
Created by admin on Mon Mar 31 17:57:37 GMT 2025 , Edited by admin on Mon Mar 31 17:57:37 GMT 2025
PRIMARY
INN
4568
Created by admin on Mon Mar 31 17:57:37 GMT 2025 , Edited by admin on Mon Mar 31 17:57:37 GMT 2025
PRIMARY
EPA CompTox
DTXSID9022819
Created by admin on Mon Mar 31 17:57:38 GMT 2025 , Edited by admin on Mon Mar 31 17:57:38 GMT 2025
PRIMARY
MERCK INDEX
m3542
Created by admin on Mon Mar 31 17:57:37 GMT 2025 , Edited by admin on Mon Mar 31 17:57:37 GMT 2025
PRIMARY Merck Index
DRUG BANK
DB13358
Created by admin on Mon Mar 31 17:57:38 GMT 2025 , Edited by admin on Mon Mar 31 17:57:38 GMT 2025
PRIMARY
RXCUI
21099
Created by admin on Mon Mar 31 17:57:37 GMT 2025 , Edited by admin on Mon Mar 31 17:57:37 GMT 2025
PRIMARY RxNorm
NCI_THESAURUS
C171690
Created by admin on Mon Mar 31 17:57:38 GMT 2025 , Edited by admin on Mon Mar 31 17:57:38 GMT 2025
PRIMARY
MESH
C032151
Created by admin on Mon Mar 31 17:57:37 GMT 2025 , Edited by admin on Mon Mar 31 17:57:37 GMT 2025
PRIMARY
WIKIPEDIA
Cibenzoline
Created by admin on Mon Mar 31 17:57:38 GMT 2025 , Edited by admin on Mon Mar 31 17:57:38 GMT 2025
PRIMARY
CAS
53267-01-9
Created by admin on Mon Mar 31 17:57:37 GMT 2025 , Edited by admin on Mon Mar 31 17:57:37 GMT 2025
PRIMARY
DRUG CENTRAL
630
Created by admin on Mon Mar 31 17:57:38 GMT 2025 , Edited by admin on Mon Mar 31 17:57:38 GMT 2025
PRIMARY
ECHA (EC/EINECS)
258-453-7
Created by admin on Mon Mar 31 17:57:37 GMT 2025 , Edited by admin on Mon Mar 31 17:57:37 GMT 2025
PRIMARY
PUBCHEM
2747
Created by admin on Mon Mar 31 17:57:37 GMT 2025 , Edited by admin on Mon Mar 31 17:57:37 GMT 2025
PRIMARY
USAN
S-110
Created by admin on Mon Mar 31 17:57:38 GMT 2025 , Edited by admin on Mon Mar 31 17:57:38 GMT 2025
PRIMARY
Related Record Type Details
POTASSIUM VOLTAGE-GATED CHANNEL SUBFAMILY H MEMBER 2
TARGET -> INHIBITOR
IC50
CYTOCHROME P450 2D6
METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
Structure of CIFENLINE, (R)-
ENANTIOMER -> RACEMATE
Structure of CIFENLINE SUCCINATE
SALT/SOLVATE -> PARENT
Structure of ESCIBENZOLINE
ENANTIOMER -> RACEMATE
Related Record Type Details
Structure of 4-(2-(4,5-DIHYDRO-1H-IMIDAZOL-2-YL)-1-PHENYLCYCLOPROPYL)PHENOL
METABOLITE -> PARENT
IN VITRO; R-ISOMER IS METABOLIZED AT 23 TIMES THE RATE OF THE S-ISOMER
Structure of 2-(2,2-DIPHENYLCYCLOPROPYL)-1H-IMIDAZOLE
METABOLITE -> PARENT
IN VITRO
Related Record Type Details
Structure of CIFENLINE
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966