CIFENLINE

Possibly Marketed Outside US

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

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

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

Targets

Primary Target	Pharmacology	Condition	Potency
Voltage-gated calcium channel 37	Blocker 555
Sulfonylurea receptors; K-ATP channels 11	Blocker 555
Voltage-sensitive sodium channel 7	Blocker 555

Conditions

Condition	Modality	Highest Phase	Product
Paroxysmal atrial arrhythmias 2	Preventing	Phase I 438	Unknown
Symptomatic ventricular arrhythmias 2	Preventing	Phase II 1,147	Unknown
Hypertrophic obstructive cardiomyopathy 2	Preventing	Phase I 438	Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
419 ng/mL	160 mg single, oral		CIFENLINE plasma	Homo sapiens
1150 ng/mL	160 mg single, intravenous		CIFENLINE serum	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
3278 ng × h/mL	160 mg single, oral		CIFENLINE plasma	Homo sapiens
3929 ng × h/mL	160 mg single, intravenous		CIFENLINE serum	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
7.8 h	160 mg single, oral		CIFENLINE plasma	Homo sapiens
7.5 h	160 mg single, intravenous		CIFENLINE serum	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
80 mg 4 times / day multiple, oral Highest studied dose	unhealthy, ADULT	Disc. AE: Hypoglycemia...
81.25 mg 4 times / day multiple, oral Highest studied dose	unhealthy	Other AEs: Dry mouth...
300 mg 1 times / day multiple, oral Recommended	unhealthy	Disc. AE: Myasthenia...
32.5 mg 4 times / day multiple, oral Studied dose	unhealthy	Disc. AE: Dry mouth, Cardiac pain...
65 mg 4 times / day multiple, oral Studied dose	unhealthy	Disc. AE: Cardiac pain, Vision abnormal...

Showing 1 to 5 of 6 entries

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AEs

Show entries

AE	Significance	Dose	Population
Hypoglycemia	severe, 1 pt Disc. AE	80 mg 4 times / day multiple, oral Highest studied dose	unhealthy, ADULT
Dry mouth	1 pt	81.25 mg 4 times / day multiple, oral Highest studied dose	unhealthy
Myasthenia	1 pt Disc. AE	300 mg 1 times / day multiple, oral Recommended	unhealthy
Cardiac pain	1 pt Disc. AE	32.5 mg 4 times / day multiple, oral Studied dose	unhealthy
Dry mouth	1 pt Disc. AE	32.5 mg 4 times / day multiple, oral Studied dose	unhealthy

Showing 1 to 5 of 8 entries

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PubMed

PubMed

Show entries

Title	Date	PubMed
Antiarrhythmic plasma concentrations of cibenzoline on canine ventricular arrhythmias.	1987 Feb	2435991
Choreic movements induced by cibenzoline: an Ic class antiarrhythmic effect?	2000 Sep	11009224
Cibenzoline has an inhibitory effect on vasorelaxation mediated by adenosine triphosphate-sensitive K(+) channels in the rat carotid artery.	2001 Aug	11473844
Efficacy of therapeutic drug monitoring in prevention of hypoglycemia caused by cibenzoline.	2001 Dec	11829197
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

Showing 1 to 5 of 31 entries

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Sample Use Guides

In Vivo Use Guide

130 to 160 mg bid

Route of Administration: Oral

In Vitro Use Guide

Unknown

Show entries

Name

Type

Language

CIBENZOLINE

Preferred Name

English

CIFENLINE

Official Name

English

cibenzoline [INN]

Common Name

English

RO-22-7796

Code

English

Cibenzoline [WHO-DD]

Common Name

English

Showing 1 to 5 of 11 entries

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Show entries

Classification Tree

Code System

Code

Other antiarrhythmics, class I and III

WHO-ATC

C01BG07

Other antiarrhythmics, class I and III

WHO-VATC

QC01BG07

Showing 1 to 2 of 2 entries

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Show entries

Code System

Code

Type

Description

FDA UNII

Z7489237QT

PRIMARY

EVMPD

SUB06229MIG

PRIMARY

SMS_ID

100000092561

PRIMARY

ChEMBL

CHEMBL87045

PRIMARY

INN

4568

PRIMARY

Showing 1 to 5 of 17 entries

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ACTIVE MOIETY


					Z7489237QT

CIFENLINE

METABOLITE (PARENT)


					Q8XZO8PG0V

4-(2-(4,5-DIHYDRO-1H-IMIDAZOL-2-YL)-1-PHENYLCYCLOPROPYL)PHENOL

METABOLITE (PARENT)


					KWS2KJ794X

2-(2,2-DIPHENYLCYCLOPROPYL)-1H-IMIDAZOLE

SMILES

InChI

Description<div class="info-popup-container"><div><span class="pop-sub-key ">Sources:&nbsp;</span><span class="pop-sub-val"><span class="ext-link"><a target="_self" href="http://www.ncbi.nlm.nih.gov/pubmed/16216754">http://www.ncbi.nlm.nih.gov/pubmed/16216754</a></span></span></div></div>

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

AEs

PubMed

Sample Use Guides

Description

C_max

T_1/2