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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 of CIFENLINE SUCCINATE

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

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
Refining the human iPSC-cardiomyocyte arrhythmic risk assessment model.
2013-12
Amiodarone sensitizes human glioma cells but not astrocytes to TRAIL-induced apoptosis via CHOP-mediated DR5 upregulation.
2011-03
Comparison of acute reduction in left ventricular outflow tract pressure gradient in obstructive hypertrophic cardiomyopathy by disopyramide versus pilsicainide versus cibenzoline.
2010-11-01
Prospective comparative study of intravenous cibenzoline and disopyramide therapy in the treatment of paroxysmal atrial fibrillation after cardiovascular surgery.
2010-09
Cibenzoline intoxication necessitating implantation of a biventricular assist system in a patient with severe cardiomyopathy.
2010-07
Effect of cibenzoline on biventricular pressure gradients in a pediatric patient with hypertrophic obstructive cardiomyopathy.
2010-07
Pharmacogenetic interactions between Angiotensin-converting enzyme insertion/deletion polymorphism and response to cibenzoline in patients with hypertrophic obstructive cardiomyopathy.
2010-05
Hypertrophic obstructive cardiomyopathy causing severe right and left ventricular outflow tract obstruction.
2010-04
Pilsicainide.
2010-03-05
Hemolytic anemia in a patient with hypertrophic obstructive cardiomyopathy.
2010-01
A danger of induction of Brugada syndrome during pill-in-the-pocket therapy for paroxysmal atrial fibrillation.
2010
Quantitative assessment of cibenzoline administration for vagally mediated paroxysmal atrial fibrillation using frequency-domain heart rate variability analysis.
2009-08
Effects of antiarrhythmic drugs on the hyperpolarization-activated cyclic nucleotide-gated channel current.
2009-06
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.
2009-02
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
Effect of cibenzoline and atenolol administration on dynamic left ventricular obstruction due to sigmoid-shaped septum.
2008-12
Use of bepridil in combination with Ic antiarrhythmic agent in converting persistent atrial fibrillation to sinus rhythm.
2008-05
Recommendations for performing acetylcholine tests safely: STOP dangerous complications induced by acetylcholine tests (STOP DCIAT).
2008-04
Cibenzoline intoxication: effect of combined hemoperfusion-hemodialysis on plasma clearance.
2008-04
Clinical and electrophysiological characteristics of patients having atrial flutter with 1:1 atrioventricular conduction.
2008-03
[Myasthenia-like syndrome induced by cibenzoline overdose in a patient with chronic kidney disease].
2008
A novel and lethal de novo LQT-3 mutation in a newborn with distinct molecular pharmacology and therapeutic response.
2007-12-05
Effect of intravenous administration of cibenzoline on left ventricular diastolic pressures in patients with hypertrophic cardiomyopathy: its relationship to transmitral Doppler flow profiles.
2007-10
Na+/Ca2+ exchange inhibitors: a new class of calcium regulators.
2007-09
Quantification of cibenzoline by enzyme-linked immunosorbent assay.
2007-06
Symptomatic hypoglycemia in a patient with chronic hemodialysis.
2007-01-24
Clinical review: aggressive management and extracorporeal support for drug-induced cardiotoxicity.
2007
Cibenzoline improves coronary flow velocity reserve in patients with hypertrophic obstructive cardiomyopathy.
2006-11
Cibenzoline attenuates coronary systolic reversal flow in a patient with hypertrophic obstructive cardiomyopathy: a case report.
2006-10
Topics on the Na+/Ca2+ exchanger: pharmacological characterization of Na+/Ca2+ exchanger inhibitors.
2006-09
[Cibenzoline succinate induced pneumonitis].
2006-07-10
Atrial fibrillation and pacing algorithms.
2006-07-01
Too little, too late: chasing atrial fibrillation with sodium channel antagonists.
2006-06
Serial cardioversion by class IC Drugs during 4 months of persistent atrial fibrillation in the goat.
2006-06
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.
2006-06
Heart failure elevates serum levels of cibenzoline in arrhythmic patients.
2006-05
Relief of left ventricular outflow obstruction by cibenzoline in a patient with Fabry's disease--a case report.
2006-03-07
[Coronary vasospasm induced by cibenzoline succinate in a patient with brugada-type electrocardiogram].
2005-12
Cibenzoline induced Brugada ECG pattern.
2005-11
Antiarrhythmic drug cibenzoline attenuates left ventricular pressure gradient and improves transmitral Doppler flow pattern in patients with hypertrophic obstructive cardiomyopathy caused by midventricular obstruction.
2005-08
A novel mutation in the PTPN11 gene in a patient with Noonan syndrome and rapidly progressive hypertrophic cardiomyopathy.
2005-08
Cibenzoline attenuates upregulation of Kv1.5 channel gene expression by experimental paroxysmal atrial fibrillation.
2005-03
Appropriate dosing of antiarrhythmic drugs in Japan requires therapeutic drug monitoring.
2005-02
Oral cibenzoline reduces postoperative atrial fibrillation in coronary artery bypass grafting.
2005-01
[Cibenzoline-succinate-induced hypoglycemia].
2004-10-10
Beneficial effect of cibenzoline on left ventricular pressure gradient with sigmoid septum.
2004-10
Frequency analysis of atrial fibrillation from the surface electrocardiogram.
2004-07-01
Antiarrhythmic effects of optical isomers of cibenzoline on canine ventricular arrhythmias.
1990-09
Antiarrhythmic plasma concentrations of cibenzoline on canine ventricular arrhythmias.
1987-02

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 18:03:14 GMT 2025
Edited
by admin
on Mon Mar 31 18:03:14 GMT 2025
Record UNII
38G16RWJ37
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CIFENLINE SUCCINATE
MI   USAN  
USAN  
Official Name English
CIBENZOLINE SUCCINATE
JAN   WHO-DD  
Preferred 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 [WHO-DD]
Common Name English
CIFENLINE SUCCINATE [USAN]
Common Name English
Code System Code Type Description
EVMPD
SUB01290MIG
Created by admin on Mon Mar 31 18:03:14 GMT 2025 , Edited by admin on Mon Mar 31 18:03:14 GMT 2025
PRIMARY
CAS
100678-32-8
Created by admin on Mon Mar 31 18:03:14 GMT 2025 , Edited by admin on Mon Mar 31 18:03:14 GMT 2025
PRIMARY
USAN
Y-47
Created by admin on Mon Mar 31 18:03:14 GMT 2025 , Edited by admin on Mon Mar 31 18:03:14 GMT 2025
PRIMARY
FDA UNII
38G16RWJ37
Created by admin on Mon Mar 31 18:03:14 GMT 2025 , Edited by admin on Mon Mar 31 18:03:14 GMT 2025
PRIMARY
MERCK INDEX
m3542
Created by admin on Mon Mar 31 18:03:14 GMT 2025 , Edited by admin on Mon Mar 31 18:03:14 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C166655
Created by admin on Mon Mar 31 18:03:14 GMT 2025 , Edited by admin on Mon Mar 31 18:03:14 GMT 2025
PRIMARY
WIKIPEDIA
Cifenline succinate
Created by admin on Mon Mar 31 18:03:14 GMT 2025 , Edited by admin on Mon Mar 31 18:03:14 GMT 2025
PRIMARY
ChEMBL
CHEMBL87045
Created by admin on Mon Mar 31 18:03:14 GMT 2025 , Edited by admin on Mon Mar 31 18:03:14 GMT 2025
PRIMARY
EPA CompTox
DTXSID0047820
Created by admin on Mon Mar 31 18:03:14 GMT 2025 , Edited by admin on Mon Mar 31 18:03:14 GMT 2025
PRIMARY
PUBCHEM
57952
Created by admin on Mon Mar 31 18:03:14 GMT 2025 , Edited by admin on Mon Mar 31 18:03:14 GMT 2025
PRIMARY
SMS_ID
100000084909
Created by admin on Mon Mar 31 18:03:14 GMT 2025 , Edited by admin on Mon Mar 31 18:03:14 GMT 2025
PRIMARY
Related Record Type Details
Structure of CIFENLINE
PARENT -> SALT/SOLVATE
Structure of CIFENLINE SUCCINATE, (S)-
ENANTIOMER -> RACEMATE
Structure of CIFENLINE SUCCINATE, (R)-
ENANTIOMER -> RACEMATE
Related Record Type Details
Structure of CIFENLINE
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