Celivarone free base

For research use only. Not for therapeutic Use.

  • CAT Number: I024356
  • CAS Number: 401925-43-7
  • Molecular Formula: C34H47NO4
  • Molecular Weight: 533.753
  • Purity: 98%
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Celivarone , also known as SSR149744, is a benzofuran derivative with a multifactorial mode of action including class IV Vaughan Williams’ electrophysiological as well as anti-adrenergic properties. 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. 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.


Catalog Number I024356
CAS Number 401925-43-7
Synonyms

SSR149744C; SSR-149744C SSR 149744C; Celivarone

Molecular Formula C34H47NO4
Purity 98%
Solubility Soluble in DMSO
Appearance Solid powder
Storage Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
IUPAC Name 5-Benzofurancarboxylic acid, 2-butyl-3-(4-(3-(dibutylamino)propyl)benzoyl)-, 1-methylethyl ester
InChI InChI=1S/C34H47NO4/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/h15-20,24-25H,6-14,21-23H2,1-5H3
InChIKey ZCENNVQCOZQSGH-UHFFFAOYSA-N
SMILES O=C(C1=CC=C(OC(CCCC)=C2C(C3=CC=C(CCCN(CCCC)CCCC)C=C3)=O)C2=C1)OC(C)C
Reference

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2: Gojkovic O, Aliot EM, Capucci A, Connolly SJ, Crijns H, Hohnloser SH, Kulakowski P, Roy D, Radzik D, Singh BN, Kowey PR. Celivarone in patients with an implantable cardioverter-defibrillator: adjunctive therapy for the reduction of ventricular arrhythmia-triggered implantable cardioverter-defibrillator interventions. Heart Rhythm. 2012 Feb;9(2):217-224.e2. doi: 10.1016/j.hrthm.2011.09.073. Epub 2011 Oct 4. PubMed PMID: 21978965.
3: Whitehead DM, Hartmann S, Ilyas T, Taylor KR, Kohler AD, Ellames GJ. A convenient method to produce [(14) C]carbon monoxide and its application to the radiosynthesis of [carboxyl-(14) C]celivarone, [carboxyl-(14) C]SSR149744. J Labelled Comp Radiopharm. 2013 Feb;56(2):36-41. doi: 10.1002/jlcr.3009. Epub 2013 Jan 22. PubMed PMID: 24285280.
4: Kowey PR, Crijns HJ, Aliot EM, Capucci A, Kulakowski P, Radzik D, Roy D, Connolly SJ, Hohnloser SH; ALPHEE Study Investigators. Efficacy and safety of celivarone, with amiodarone as calibrator, in patients with an implantable cardioverter-defibrillator for prevention of implantable cardioverter-defibrillator interventions or death: the ALPHEE study. Circulation. 2011 Dec 13;124(24):2649-60. doi: 10.1161/CIRCULATIONAHA.111.072561. Epub 2011 Nov 14. PubMed PMID: 22082672.
5: Bunch TJ, Anderson JL. Adjuvant antiarrhythmic therapy in patients with implantable cardioverter defibrillators. Am J Cardiovasc Drugs. 2014 Apr;14(2):89-100. doi: 10.1007/s40256-013-0056-x. Review. PubMed PMID: 24288157.
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11: Verma A. Alternatives to amiodarone: search for the Holy Grail. Europace. 2009 Apr;11(4):402-4. doi: 10.1093/europace/eup042. Epub 2009 Feb 17. PubMed PMID: 19223364.
12: Arya A, Silberbauer J, Teichman SL, Milner P, Sulke N, Camm AJ. A preliminary assessment of the effects of ATI-2042 in subjects with paroxysmal atrial fibrillation using implanted pacemaker methodology. Europace. 2009 Apr;11(4):458-64. doi: 10.1093/europace/eun384. Epub 2009 Jan 26. PubMed PMID: 19174378; PubMed Central PMCID: PMC2659603.
13: Gautier P, Serre M, Cosnier-Pucheu S, Djandjighian L, Roccon A, Herbert JM, Nisato D. In vivo and in vitro antiarrhythmic effects of SSR149744C in animal models of atrial fibrillation and ventricular arrhythmias. J Cardiovasc Pharmacol. 2005 Feb;45(2):125-35. PubMed PMID: 15654261.
14: Gautier P, Guillemare E, Djandjighian L, Marion A, Planchenault J, Bernhart C, Herbert JM, Nisato D. In vivo and in vitro characterization of the novel antiarrhythmic agent SSR149744C: electrophysiological, anti-adrenergic, and anti-angiotensin II effects. J Cardiovasc Pharmacol. 2004 Aug;44(2):244-57. PubMed PMID: 15243307.

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