Progress toward the development of a safe and effective agent for treating reentrant cardiac arrhythmias: Synthesis and evaluation of ibutilide analogues with enhanced metabolic stability and diminished proarrhythmic potential

Journal of Medicinal Chemistry

Volumn 44, Issue 7, 2001, Pages 1099-1115

  Hester, J B ^a   Gibson, J K ^a   Buchanan, L V ^a   Cimini, M G ^a   Clark, M A ^a   Emmert, D E ^a   Glavanovich, M A ^a   Imbordino, R J ^a   LeMay, R J ^a   McMillan, M W ^a   Perricone, S C ^a   Squires, D M ^a   Walters, R R ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIARRHYTHMIC AGENT; IBUTILIDE FUMARATE; TRECETILIDE FUMARATE; UNCLASSIFIED DRUG;

ANIMAL MODEL; ARTICLE; CHIRALITY; CONTROLLED STUDY; DRUG EFFICACY; DRUG MECHANISM; DRUG METABOLISM; DRUG SAFETY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; HEART ARRHYTHMIA; HEART MUSCLE REFRACTORY PERIOD; NONHUMAN; QT INTERVAL; RABBIT;

ANIMALS; ANTI-ARRHYTHMIA AGENTS; ARRHYTHMIA; ATRIAL FLUTTER; DOGS; HUMANS; MALE; MICROSOMES, LIVER; RABBITS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES; TACHYCARDIA, VENTRICULAR;

EID: 0035966868     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0004289     Document Type: Article

References (68)

1. Prevalence, age distribution and gender of patients with atrial fibrillation: Analysis and implications
2. The use of drugs for cardioversion of recent onset atrial fibrillation and flutter
3. Impact of atrial fibrillation on the risk of death. The Framingham heart study
4. The natural history of atrial fibrillation: Incidence, risk factors, and prognosis in the Manitoba follow-up study
5. Pathogenesis of atrial flutter
6. Sudden cardiac death
7. Mechanisms of cardiac arrhythmias
8. Arrhythmias and antiarrhythmic drugs: Mechanism of action and structure-activity relationship I
9. Antiarrhythmic drugs: A reorientation in light of recent developments in the control of disorders of rhythm
10. Classification of antiarrhythmic drugs
11. Preliminary report: Effect of encainide and flecainide on mortality in a randomized trial of arrhythmia suppression after mycardial infarction
12. Effect of the antiarrhythmic agent moricizine on survival after myocardial infarction
13. Experimental evidence for proarrhythmic mechanisms of antiarrhythmic drugs
14. What should we expect from the next generation of antiarrhythmic drugs?
15. A third class of anti-arrhythmic action. Effects on atrial and ventricular intracellular potentials, and other pharmacological actions on cardiac muscle, of MJ 1999 and AH 3474
16. The effect of amiodarone, a new anti-anginal drug, on cardiac muscle
17. Potassium channel blockers as antiarrhythmic drugs
18. Current antiarrhythmic drugs: An overview of mechanisms of action and potential clinical utility
19. Effects of class III drugs on atrial fibrillation
20. Antiarrhythmic drugs and torsade de pointes
21. Arrhythmia control by prolonging repolarization: The concept and its potential therapeutic impact
22. The long QT syndrome: Ion channel diseases of the heart
23. KVLQT1 C-terminal missence mutation causes a form fruste long QT syndrome
24. Homozygous deletion in KVLQT1 associated with Jervell and Lange-Nielsen syndrome
25. Low penetrance in the long QT syndrome clinical impact
26. Genetic and molecular basis of cardiac arrhythmias: Impact on clinical management. Parts I and II
27. Genetic and molecular basis of cardiac arrhythmias: Impact on clinical management. PART III
28. Mechanisms and management of proarrhythmia
29. Ibutilide a review of its pharmacological properties and clinical potential in the acute management of atrial flutter and fibrillation
30. The case for inpatient initiation of antiarrhythmic therapy
31. Predicting antiarrhythmic performance
32. N-[(ω-Amino-1-hydroxyalkyl)phenyl]methanesulfonamide derivatives with class III antiarrhythmic activity
33. Ibutilide fumarate: A new class III agent for termination of atrial fibrillation and atrial flutter
34. Suppression of inducible ventricular tachycardia by ibutilide in patients with coronary artery disease
35. 14C]ibutilide fumarate in rat, dog, and human
36. Synthesis of (R)-N-[4-[4-(Dibutylamino)-1-hydroxybutyl] phenyl] methane-sulfonamide, (E)-2-Butenedioate (2:1) Salt (Artilide Fumarate) and the Enantiomers of N-[4-[4-(Ethylheptylamino)-1-hydroxy-butyl]phenyl]methanesulfonamide, (E)-2-Butenedioate (2:1) Salt (Ibutilide Fumarate)
37. No. 463 - Préparation d'alcools à fonctions complexes et d'alcényltétrahydro furannes
38. Vicinal bromofluoroalkanes. Their regioselective formation and their conversion to fluoroolefins
39. Gem-difluoro compounds: A convenient preparation from ketones and aldehydes by hydrogen fluoride treatment of 1,3-dithiolanes
40. Effects of ibutilide fumarate. A novel antiarrhythmic agent, and its enantiomers on isolated rabbit myocardium
41. QTU-prolongation and torsades de pointes induced by putative class III antiarrhythmic agents in the rabbit: Etiology and interventions
42. Comparative assessment of ibutilide, d-sotalol, clofilium, E-4031 and UK 68798 in a rabbit model of proarrhythmia
43. Some influences of fluorine in bioorganic chemistry
44. Effects of fluorine substitution on drug metabolism: Pharmacological and toxicological implications
45. Development of class III antiarrhythmic agents
46. Which cardiac potessium channel subtype is the preferable target for suppression of ventricular arrhythmias?
47. The cardiac ion channels: Relevance to management of arrhythmias
48. Kr, and effects on myocardial refractoriness for class III antiarrhythmic agents
49. + current in guinea pig ventricular cells
50. Ionic mechanism of ibutilide in human atrium: Evidence for a drug induced Na current through a nifedipine inhibited inward channel
51. Membrane activity of class III antiarrhthmic compounds; a comparison between ibutilide, d-Sotalol, E-4031, sematilide and dofetilide
52. Kr) in AT-1 cells
53. + current in rabbit sinoatrial and atrioventricular node cells
54. + current activated by pinacidil
55. Atrial reentry around an anatomic barrier with a partially refractory excitable gap. A canine model of atrial flutter
56. Circus movement in the canine atrium around the tricuspid ring during experimental atrial flutter and during reentry in vitro
57. Antiarrhythmic and electrophysiologic effects of ibutilide in a chronic canine model of atrial flutter
58. Acute intravenous conversion of canine atrial flutter: Comparison of antiarrhythmic agents
59. Effects of ibutilide on spontaneous and induced ventricular arrhythmias in 24-hour canine myocardial infaraction: A comparative study with sotalol and encainide
60. Cyclohexanone oxygenase: Stereochemistry, enantioselectivity, and regioselectivity of an enzyme-catalyzed Baeyer-Villiger reaction
61. The reactions of dianions of carboxylic acids and ester enolates
62. Partial purification of cytochrome P-450 and cytochrome P-448 from rat liver microscomes
63. Delayed development of ventricular ectopic rhythm following experimental coronary occlusion
64. Effects of artilide on spontaneous and induced ventricular arrhythmias in 24-hour canine myocardial infarction