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122647-32-9 | Methanesulfonamide, N-[4-[4-(ethylheptylamino)-1-hydroxybutyl]phenyl]-, (2E)-2-butenedioate (2:1)
CAS No: 122647-32-9 Catalog No: AG0017L2 MDL No:MFCD01715410
Product Description
Catalog Number:
AG0017L2
Chemical Name:
Methanesulfonamide, N-[4-[4-(ethylheptylamino)-1-hydroxybutyl]phenyl]-, (2E)-2-butenedioate (2:1)
CAS Number:
122647-32-9
Molecular Formula:
C44H76N4O10S2
Molecular Weight:
885.2250
MDL Number:
MFCD01715410
IUPAC Name:
(E)-but-2-enedioic acid;N-[4-[4-[ethyl(heptyl)amino]-1-hydroxybutyl]phenyl]methanesulfonamide
InChI:
InChI=1S/2C20H36N2O3S.C4H4O4/c2*1-4-6-7-8-9-16-22(5-2)17-10-11-20(23)18-12-14-19(15-13-18)21-26(3,24)25;5-3(6)1-2-4(7)8/h2*12-15,20-21,23H,4-11,16-17H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;;2-1+
InChI Key:
PCIOHQNIRPWFMV-WXXKFALUSA-N
SMILES:
OC(=O)/C=C/C(=O)O.CCCCCCCN(CCCC(c1ccc(cc1)NS(=O)(=O)C)O)CC.CCCCCCCN(CCCC(c1ccc(cc1)NS(=O)(=O)C)O)CC
Properties
Complexity:
561
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
3
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
1
Exact Mass:
884.5g/mol
Formal Charge:
0
Heavy Atom Count:
60
Hydrogen Bond Acceptor Count:
14
Hydrogen Bond Donor Count:
6
Isotope Atom Count:
0
Molecular Weight:
885.23g/mol
Monoisotopic Mass:
884.5g/mol
Rotatable Bond Count:
30
Topological Polar Surface Area:
231A^2
Undefined Atom Stereocenter Count:
2
Undefined Bond Stereocenter Count:
0
Literature
| Title | Journal |
|---|---|
| Effect of ibutilide on the canine cardiac conduction system. | Cell biochemistry and biophysics 20121101 |
| Enhanced sensitivity to drug-induced QT interval lengthening in patients with heart failure due to left ventricular systolic dysfunction. | Journal of clinical pharmacology 20120901 |
| Ibutilide decreases defibrillation threshold by the reduction of activation pattern complexity during ventricular fibrillation in canine hearts. | Chinese medical journal 20120801 |
| The Modified Ablation Guided by Ibutilide Use in Chronic Atrial Fibrillation (MAGIC-AF) Study: clinical background and study design. | Journal of cardiovascular electrophysiology 20120401 |
| Brugada syndrome masked by ibutilide treatment in a patient with atrial flutter. | Cardiology 20120101 |
| [Efficacy of ibutilide for cardioversion of persistent atrial fibrillation during radiofrequency ablation]. | Zhonghua xin xue guan bing za zhi 20111101 |
| Factors affecting the degree of QT prolongation with drug challenge in a large cohort of normal volunteers. | Heart rhythm 20111001 |
| Predicting the degree of drug-induced QT prolongation and the risk for torsades de pointes. | Heart rhythm 20111001 |
| Drug-induced torsade de pointes arrhythmias in the chronic AV block dog are perpetuated by focal activity. | Circulation. Arrhythmia and electrophysiology 20110801 |
| A 2-year survey of treatment of acute atrial fibrillation in an ED. | The American journal of emergency medicine 20110601 |
| Effects of ibutilide on inhibiting heart rate and rapidly terminating atrial flutter in canine. | Cell biochemistry and biophysics 20110401 |
| Atrial fibrillation: AVRO--were the results a surprise? | Nature reviews. Cardiology 20110401 |
| Single dose of ibutilide for conversion of persistent atrial fibrillation after radiofrequency ablation. | Chinese medical journal 20110301 |
| Safety and efficacy of ibutilide in cardioversion of atrial flutter and fibrillation. | Journal of the American Board of Family Medicine : JABFM 20110101 |
| Effect of high doses of magnesium on converting ibutilide to a safe and more effective agent. | The American journal of cardiology 20100901 |
| Pre-injection of magnesium sulfate enhances the efficacy of ibutilide for the conversion of typical but not of atypical persistent atrial flutter. | International journal of cardiology 20100611 |
| Intraprocedural use of ibutilide to organize and guide ablation of complex fractionated atrial electrograms: preliminary assessment of a modified step-wise approach to ablation of persistent atrial fibrillation. | Journal of cardiovascular electrophysiology 20100601 |
| 2:1 left to right interatrial block and other effects of ibutilide during non-isthmus-dependent atrial flutter. | Pacing and clinical electrophysiology : PACE 20091001 |
| [The study of inhibiting heart rate and rapidly terminating atrial flutter of ibutilide on canine]. | Zhonghua xin xue guan bing za zhi 20091001 |
| Ibutilide-induced changes in the temporal lability of ventricular repolarization in patients with and without structural heart disease. | Journal of cardiovascular electrophysiology 20090801 |
| The organic cation transporter, OCTN1, expressed in the human heart, potentiates antagonism of the HERG potassium channel. | Journal of cardiovascular pharmacology 20090701 |
| Influence of the G2677T/C3435T haplotype of MDR1 on P-glycoprotein trafficking and ibutilide-induced block of HERG. | The pharmacogenomics journal 20090601 |
| Safety and efficacy of ibutilide in heart transplant recipients. | The Journal of heart and lung transplantation : the official publication of the International Society for Heart Transplantation 20090501 |
| Acute beta-adrenoceptor blockade improves efficacy of ibutilide in conversion of atrial fibrillation with a rapid ventricular rate. | Europace : European pacing, arrhythmias, and cardiac electrophysiology : journal of the working groups on cardiac pacing, arrhythmias, and cardiac cellular electrophysiology of the European Society of Cardiology 20090101 |
| Ibutilide revisited: stronger and safer than ever. | Europace : European pacing, arrhythmias, and cardiac electrophysiology : journal of the working groups on cardiac pacing, arrhythmias, and cardiac cellular electrophysiology of the European Society of Cardiology 20090101 |
| Pharmacokinetics of ibutilide in patients with heart failure due to left ventricular systolic dysfunction. | Pharmacotherapy 20081201 |
| Extracellular acidification and hyperkalemia induce changes in HERG inhibition by ibutilide. | Cardiology 20080101 |
| Rapid ventricular response. | American journal of critical care : an official publication, American Association of Critical-Care Nurses 20080101 |
| Ibutilide therapy for atrial fibrillation: 5-year experience in a community hospital. | The Journal of cardiovascular nursing 20080101 |
| Intravenous magnesium sulfate enhances the ability of intravenous ibutilide to successfully convert atrial fibrillation or flutter. | Pacing and clinical electrophysiology : PACE 20071101 |
| Autonomic tone attenuates drug-induced QT prolongation. | Journal of cardiovascular electrophysiology 20070901 |
| Monotherapy versus combination therapy with class III antiarrhythmic agents to attenuate transmural dispersion of repolarization: a potential risk factor for torsade de pointes. | Pharmacotherapy 20070901 |
| Pharmacokinetic and pharmacodynamic properties of a single intravenous dose of ibutilide fumarate: a phase I, randomized, open-label, increasing-dose study in healthy Chinese men. | Clinical therapeutics 20070901 |
| The safety and efficacy of ibutilide in children and in patients with congenital heart disease. | Pacing and clinical electrophysiology : PACE 20070801 |
| Enhancement of bupivacaine local anesthesia with the potassium channel blocker ibutilide. | European journal of pain (London, England) 20070701 |
| Cardioversion of persistent atrial fibrillation by a combination of atrial specific and non-specific class III drugs in the goat. | Cardiovascular research 20070701 |
| Conversion efficacy of intravenous ibutilide compared with intravenous amiodarone in patients with recent-onset atrial fibrillation and atrial flutter. | International journal of cardiology 20070612 |
| Ibutilide and sinus arrest. | Herz 20070601 |
| Ibutilide-induced cardioversion of atrial fibrillation during pregnancy. | Journal of cardiovascular electrophysiology 20070501 |
| Successful termination of atrial flutter by ibutilide during pregnancy. | Pacing and clinical electrophysiology : PACE 20070201 |
| The role of amiodarone in recent-onset atrial fibrillation after ibutilide has failed to restore sinus rhythm. | Cardiology 20070101 |
| The mechanisms of atrial fibrillation. | Journal of cardiovascular electrophysiology 20061201 |
| Bazett and Fridericia QT correction formulas interfere with measurement of drug-induced changes in QT interval. | Heart rhythm 20060901 |
| Ibutilide to expedite ED therapy for recent-onset atrial fibrillation flutter. | The American journal of emergency medicine 20060701 |
| Propafenone added to ibutilide increases conversion rates of persistent atrial fibrillation. | Heart (British Cardiac Society) 20060501 |
| Efficacy and safety of ibutilide for the conversion of monomorphic atrial tachycardia. | Pacing and clinical electrophysiology : PACE 20060401 |
| Drug binding interactions in the inner cavity of HERG channels: molecular insights from structure-activity relationships of clofilium and ibutilide analogs. | Molecular pharmacology 20060201 |
| Ibutilide for treatment of atrial fibrillation in the emergency department. | Emergency medicine journal : EMJ 20060201 |
| Is pretreatment with ibutilide useful for atrial fibrillation cardioversion when combined with biphasic shock? | Journal of cardiovascular medicine (Hagerstown, Md.) 20060201 |
| High-density mapping of pulmonary veins and left atrium during ibutilide administration in a canine model of sustained atrial fibrillation. | American journal of physiology. Heart and circulatory physiology 20051201 |
| In vivo antiarrhythmic and cardiac electrophysiologic effects of a novel diphenylphosphine oxide IKur blocker (2-isopropyl-5-methylcyclohexyl) diphenylphosphine oxide. | The Journal of pharmacology and experimental therapeutics 20051201 |
| Comparison of intravenous ibutilide vs. propafenone for rapid termination of recent onset atrial fibrillation. | International journal of clinical practice 20051201 |
| [Inhibition of the muscarinic potassium current by KB130015, a new antiarrhythmic agent to treat atrial fibrillation]. | Medizinische Klinik (Munich, Germany : 1983) 20051115 |
| [Atrial flutter and fibrillation]. | Praxis 20051109 |
| Synthesis of biologically active amines via rhodium-bisphosphite-catalyzed hydroaminomethylation. | Organic letters 20051027 |
| Efficacy and safety of ibutilide for cardioversion of atrial flutter and fibrillation in patients receiving amiodarone or propafenone. | Pacing and clinical electrophysiology : PACE 20050901 |
| Rapid cardioversion of new onset atrial fibrillation with ibutilide in the emergency department. | Irish medical journal 20050901 |
| The combined use of ibutilide as an active control with intensive electrocardiographic sampling and signal averaging as a sensitive method to assess the effects of tadalafil on the human QT interval. | Journal of the American College of Cardiology 20050816 |
| Making a silk purse out of a sow's ear. | Journal of the American College of Cardiology 20050816 |
| Consequences of atrial electrical remodeling for the anti-arrhythmic action of class IC and class III drugs. | Cardiovascular research 20050701 |
| Conversion of recent-onset atrial fibrillation or flutter with amiodarone after ibutilide has failed: a rapid, efficient, and safe algorithm. | Annals of noninvasive electrocardiology : the official journal of the International Society for Holter and Noninvasive Electrocardiology, Inc 20050701 |
| Ibutilide--recent molecular insights and accumulating evidence for use in atrial flutter and fibrillation. | Expert opinion on investigational drugs 20050501 |
| [Immediate cardioversion of atrial fibrillation and atrial flutter lasting less than 90 days by ibutilide versus propafenone: a multicenter study]. | Zhonghua yi xue za zhi 20050330 |
| Ibutilide in persistent atrial fibrillation refractory to conventional cardioversion methods. | International journal of cardiology 20050318 |
| Sensitive method for the determination of ibutilide in human plasma by liquid chromatography-tandem mass spectrometry. | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20050225 |
| Ibutilide for rapid conversion of atrial fibrillation or flutter in a mixed critically ill patient population. | Wiener klinische Wochenschrift 20050201 |
| Comparative efficacy of monophasic and biphasic waveforms for transthoracic cardioversion of atrial fibrillation and atrial flutter. | American heart journal 20050201 |
| Clinical comparison of ibutilide and propafenone for converting atrial flutter. | Cardiovascular drugs and therapy 20050101 |
| A benefit-risk assessment of class III antiarrhythmic agents. | Expert opinion on drug safety 20041101 |
| Ibutilide (Corvert): suspected association with torsades de pointes. | CMAJ : Canadian Medical Association journal = journal de l'Association medicale canadienne 20041012 |
| Electrophysiological and proarrhythmic parameters in transmural canine left-ventricular needle biopsies. | Pflugers Archiv : European journal of physiology 20041001 |
| 'Early' class III drugs for the treatment of atrial fibrillation: efficacy and atrial selectivity of AVE0118 in remodeled atria of the goat. | Circulation 20040928 |
| Ibutilide added to propafenone for the conversion of atrial fibrillation and atrial flutter. | Journal of the American College of Cardiology 20040818 |
| Use of ibutilide in cardioversion of patients with atrial fibrillation or atrial flutter treated with class IC agents. | Journal of the American College of Cardiology 20040818 |
| Structural determinants of HERG channel block by clofilium and ibutilide. | Molecular pharmacology 20040801 |
| Pharmacological cardioversion of recent onset atrial fibrillation. | European heart journal 20040801 |
| Flecainide versus ibutilide for immediate cardioversion of atrial fibrillation of recent onset. | European heart journal 20040801 |
| [Perspectives and limitations in the treatment of vagus-induced atrial fibrillation. Insights from cellular pharmacology]. | Medizinische Klinik (Munich, Germany : 1983) 20040715 |
| Efficacy and safety of ibutilide vs. transoesophageal atrial pacing for the termination of type I atrial flutter. | Europace : European pacing, arrhythmias, and cardiac electrophysiology : journal of the working groups on cardiac pacing, arrhythmias, and cardiac cellular electrophysiology of the European Society of Cardiology 20040701 |
| Atrial-selective antiarrhythmic actions of novel Ikur vs. Ikr, Iks, and IKAch class Ic drugs and beta blockers in pigs. | Medical science monitor : international medical journal of experimental and clinical research 20040701 |
| Intrapericardial ibutilide administration fails to terminate pacing-induced sustained atrial fibrillation in dogs. | Cardiovascular drugs and therapy 20040701 |
| Facilitating internal cardioversion of chronic atrial fibrillation with ibutilide--predictors of atrial defibrillation-threshold decrease. | Medical science monitor : international medical journal of experimental and clinical research 20040601 |
| Female preponderance in ibutilide-induced torsade de pointes. | International journal of cardiology 20040601 |
| Ibutilide-induced alterations in electrocardiographic and spatial vectorcardiographic descriptors of ventricular repolarization. | Clinical cardiology 20040601 |
| Comparing methods of measurement for detecting drug-induced changes in the QT interval: implications for thoroughly conducted ECG studies. | Annals of noninvasive electrocardiology : the official journal of the International Society for Holter and Noninvasive Electrocardiology, Inc 20040401 |
| Model of effect of magnesium prophylaxis on frequency of torsades de pointes in ibutilide-treated patients. | American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists 20040401 |
| Ibutilide for cardioversion of atrial flutter: efficacy of a single dose in recent-onset arrhythmias. | Minerva cardioangiologica 20040201 |
| Oral class III antiarrhythmics: what is new? | Current opinion in cardiology 20040101 |
| Use of ibutilide for cardioversion of recent-onset atrial fibrillation and flutter in elderly. | American journal of therapeutics 20040101 |
| Genetic basis of drug-induced arrhythmias. | Annals of medicine 20040101 |
| Recent developments in cardiovascular drug therapy: treatment of atrial arrhythmias with new class III drugs and beyond. | Current medicinal chemistry. Cardiovascular and hematological agents 20040101 |
| Cost effectiveness of ibutilide with prophylactic magnesium in the treatment of atrial fibrillation. | PharmacoEconomics 20040101 |
| Adjunctive intravenous magnesium to reduce toxicity and enhance efficacy of class III antiarrhythmic agents. | Connecticut medicine 20040101 |
| Impact of prophylactic i.v. magnesium on the efficacy of ibutilide for conversion of atrial fibrillation or flutter. | American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists 20031115 |
| [Progress in the clinical use of anti-arrhythmic drugs (I)]. | Zhonghua er ke za zhi = Chinese journal of pediatrics 20031001 |
| An update on electrical cardioversion of atrial fibrillation. | Cardiac electrophysiology review 20030901 |
| Effectiveness of ibutilide in cardioversion of persistent atrial fibrillation in patients with dual chamber stimulation. | Journal of interventional cardiac electrophysiology : an international journal of arrhythmias and pacing 20030801 |
| Ibutilide versus amiodarone in atrial fibrillation: a double-blinded, randomized study. | Critical care medicine 20030401 |
| Pharmacologic and nonpharmacologic options to maintain sinus rhythm: guideline-based and new approaches. | The American journal of cardiology 20030320 |
| Effects of intravenous magnesium sulfate on the QT interval in patients receiving ibutilide. | Pharmacotherapy 20030301 |
| Propafenone versus ibutilide for post operative atrial fibrillation following cardiac surgery: neither strategy improves outcomes compared to rate control alone (the PIPAF study). | Medical science monitor : international medical journal of experimental and clinical research 20030301 |
| Atrial fibrillation in the elderly. | The American journal of geriatric cardiology 20030101 |
| Potentially significant drug interactions of class III antiarrhythmic drugs. | Drug safety 20030101 |
| Ibutilide for pharmacological cardioversion of atrial fibrillation and flutter: impact of race on efficacy and safety. | American journal of therapeutics 20030101 |
| [Development of original Russian antiarrhythmic drugs of the 3rd class]. | Vestnik Rossiiskoi akademii meditsinskikh nauk 20030101 |
| Electrophysiological and antiarrhythmic effects of the novel I(Kur) channel blockers, S9947 and S20951, on left vs. right pig atrium in vivo in comparison with the I(Kr) blockers dofetilide, azimilide, d,l-sotalol and ibutilide. | Naunyn-Schmiedeberg's archives of pharmacology 20021101 |
| Hybrid therapy of atrial fibrillation. | Italian heart journal : official journal of the Italian Federation of Cardiology 20021001 |
| Comparison of amiodarone versus ibutilide for the prevention of immediate recurrences of atrial fibrillation during pulmonary vein isolation. | The American journal of cardiology 20020901 |
| Cardioversion of atrial fibrillation with ibutilide: when is it most effective? | Clinical cardiology 20020901 |
| Electrophysiological response of the right atrium to ibutilide during typical atrial flutter. | Circulation 20020813 |
| Conversion of recent-onset atrial fibrillation or flutter with ibutilide after amiodarone has failed. | Intensive care medicine 20020701 |
| [Current strategies of pharmacological and non-pharmacological treatment in atrial fibrillation and atrial flutter]. | Nihon rinsho. Japanese journal of clinical medicine 20020701 |
| [Ventricular fibrillation/tachycardia]. | Nihon rinsho. Japanese journal of clinical medicine 20020701 |
| Comparison of verapamil and ibutilide for the suppression of immediate recurrences of atrial fibrillation after transthoracic cardioversion. | Journal of cardiovascular pharmacology and therapeutics 20020701 |
| The JT-area indicates dispersion of repolarization in dogs with atrioventricular block. | Journal of interventional cardiac electrophysiology : an international journal of arrhythmias and pacing 20020601 |
| Effects of verapamil and ibutilide on atrial fibrillation and postfibrillation atrial refractoriness. | Journal of cardiovascular electrophysiology 20020201 |
| New antiarrhythmic drugs for the treatment of atrial fibrillation. | Pacing and clinical electrophysiology : PACE 20020201 |
| Clinical and electrophysiologic effects of calcium channel blockers in patients receiving ibutilide. | American heart journal 20020101 |
| Ibutilide in rapid conversion of atrial flutter in octogenarians. | Drugs & aging 20020101 |
| Ibutilide-induced long QT syndrome and torsade de pointes. | American journal of therapeutics 20020101 |
| Electrophysiological effects of ibutilide in patients with accessory pathways. | Circulation 20011016 |
| [Severe ibutilide-induced arrhythmia in patients with heart failure]. | Tidsskrift for den Norske laegeforening : tidsskrift for praktisk medicin, ny raekke 20011010 |
| Cardiovascular effects of the R- and S-enantiomers of ibutilide in conscious beagle dogs. | Methods and findings in experimental and clinical pharmacology 20011001 |
| Ibutilide induced intraatrial Wenckebach periodicity in the neonatal canine heart. | Pacing and clinical electrophysiology : PACE 20010901 |
| Ibutilide: efficacy and safety in atrial fibrillation and atrial flutter in a general cardiology practice. | Clinical cardiology 20010701 |
| Female gender does not influence the magnitude of ibutilide-induced repolarization delay and incidence of torsades de pointes in an in vivo rabbit model of the acquired long QT syndrome. | Journal of cardiovascular pharmacology and therapeutics 20010701 |
| Comparison of the rate dependent effects of dofetilide and ibutilide in the newborn heart. | Pacing and clinical electrophysiology : PACE 20010501 |
| Safety and effectiveness of ibutilide in a community hospital. | Pharmacotherapy 20010401 |
| 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 20010329 |
| Usefulness of handgrip to improve ibutilide efficacy in organizing atrial electrical activity during atrial fibrillation. | The American journal of cardiology 20010315 |
| Drug-induced QT prolongation in women during the menstrual cycle. | JAMA 20010314 |
| Frequency-dependent electrophysiological effect of ibutilide on human atrium and ventricle. | Journal of interventional cardiac electrophysiology : an international journal of arrhythmias and pacing 20010301 |
| Comparison of the effects on drug concentrations, electrophysiologic parameters, and termination of atrial fibrillation in dogs when procainamide and ibutilide are delivered into the right atrium versus intravenously. | Journal of cardiovascular electrophysiology 20010301 |
| Myocardial repolarization and drugs. Impossibility to predict the dominance of anti-arrhythmic over pro-arrhythmic effects of drugs due to differential and ventricular electrical remodeling. | Anadolu kardiyoloji dergisi : AKD = the Anatolian journal of cardiology 20010301 |
| Potassium and calcium current blocking properties of the novel antiarrhythmic agent H 345/52: implications for proarrhythmic potential. | Cardiovascular research 20010201 |
| Chemical cardioversion of atrial fibrillation or flutter with ibutilide in patients receiving amiodarone therapy. | Circulation 20010116 |
| Altered response to ibutilide in a heart failure model. | Cardiovascular research 20010101 |
| Ibutilide: a class III rapidly acting antidysrhythmic for atrial fibrillation or atrial flutter. | The Journal of emergency medicine 20010101 |
| Multifocal atrial tachycardia and Ibutilide. | The American journal of geriatric cardiology 20010101 |
| Newer antiarrhythmic drugs. | Indian heart journal 20010101 |
| New antiarrhythmic agents for atrial fibrillation. | Current opinion in investigational drugs (London, England : 2000) 20010101 |
| Pharmacologic conversion of atrial fibrillation: a systematic review of available evidence. | Progress in cardiovascular diseases 20010101 |
| Termination of recent-onset atrial fibrillation/flutter in the emergency department: a sequential approach with intravenous ibutilide and external electrical cardioversion. | Resuscitation 20000801 |
| Usefulness of ibutilide in facilitating successful external cardioversion of refractory atrial fibrillation. | The American journal of cardiology 19991101 |
| Acute renal failure after ibutilide. | Lancet (London, England) 19990206 |
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