U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C34H47NO4.C4H4O4
Molecular Weight 649.8134
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CELIVARONE FUMARATE

SMILES

OC(=O)\C=C\C(O)=O.CCCCN(CCCC)CCCC1=CC=C(C=C1)C(=O)C2=C(CCCC)OC3=C2C=C(C=C3)C(=O)OC(C)C

InChI

InChIKey=OJGUHVXJDZPQSK-WLHGVMLRSA-N
InChI=1S/C34H47NO4.C4H4O4/c1-6-9-14-31-32(29-24-28(19-20-30(29)39-31)34(37)38-25(4)5)33(36)27-17-15-26(16-18-27)13-12-23-35(21-10-7-2)22-11-8-3;5-3(6)1-2-4(7)8/h15-20,24-25H,6-14,21-23H2,1-5H3;1-2H,(H,5,6)(H,7,8)/b;2-1+

HIDE SMILES / InChI

Molecular Formula C34H47NO4
Molecular Weight 533.7413
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Celivarone is a benzofuran derivative with a multifactorial mode of action including class IV Vaughan Williams’ electrophysiological as well as anti-adrenergic properties. It has no iodine and has a limited tissue accumulation compared with amiodarone. Celivarone exhibits effective anti-arrhythmic properties in several ventricular ischemia- or reperfusioninduced arrhythmia models as well as in in vitro and in vivo atrial fibrillation (AF) models. Its electrophysiological properties are similar to amiodarone (multifactorial mode of action) but with different relative effects on the ion channels. At the ventricular level, celivarone shows anti-arrhythmic activities by suppressing reperfusion-induced arrhythmias (i.v. and oral routes) and reducing the early mortality due to myocardial infarction (oral route) in rats models. At the atrial level, celivarone is effective in atrial fibrillation models with restoration of sinus rhythm or prevention of AF induction and AF recurrence.

Approval Year

PubMed

PubMed

TitleDatePubMed
In vivo and in vitro characterization of the novel antiarrhythmic agent SSR149744C: electrophysiological, anti-adrenergic, and anti-angiotensin II effects.
2004 Aug
Patents

Patents

Sample Use Guides

100 or 300 mg once daily for 6 months
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:41:24 GMT 2023
Edited
by admin
on Fri Dec 15 15:41:24 GMT 2023
Record UNII
GA9K2RD7NJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CELIVARONE FUMARATE
Common Name English
5-BENZOFURANCARBOXYLIC ACID, 2-BUTYL-3-(4-(3-(DIBUTYLAMINO)PROPYL)BENZOYL)-, 1-METHYLETHYL ESTER, (2E)-2-BUTENEDIOATE (1:1)
Systematic Name English
SSR-149744C
Code English
Code System Code Type Description
FDA UNII
GA9K2RD7NJ
Created by admin on Fri Dec 15 15:41:25 GMT 2023 , Edited by admin on Fri Dec 15 15:41:25 GMT 2023
PRIMARY
CAS
401925-44-8
Created by admin on Fri Dec 15 15:41:25 GMT 2023 , Edited by admin on Fri Dec 15 15:41:25 GMT 2023
NON-SPECIFIC STOICHIOMETRY
CAS
752253-75-1
Created by admin on Fri Dec 15 15:41:25 GMT 2023 , Edited by admin on Fri Dec 15 15:41:25 GMT 2023
PRIMARY
PUBCHEM
9852525
Created by admin on Fri Dec 15 15:41:25 GMT 2023 , Edited by admin on Fri Dec 15 15:41:25 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY