Home Imidazoles 100678-32-8
100678-32-8,MFCD00941423
Catalog No.:AA0002JB
100678-32-8 | Butanedioic acid, compd. with 2-(2,2-diphenylcyclopropyl)-4,5-dihydro-1H-imidazole (1:1)
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Technical Information
Catalog Number:
AA0002JB
Chemical Name:
Butanedioic acid, compd. with 2-(2,2-diphenylcyclopropyl)-4,5-dihydro-1H-imidazole (1:1)
CAS Number:
100678-32-8
Molecular Formula:
C22H24N2O4
Molecular Weight:
380.4370
MDL Number:
MFCD00941423
IUPAC Name:
butanedioic acid;2-(2,2-diphenylcyclopropyl)-4,5-dihydro-1H-imidazole
InChI:
InChI=1S/C18H18N2.C4H6O4/c1-3-7-14(8-4-1)18(15-9-5-2-6-10-15)13-16(18)17-19-11-12-20-17;5-3(6)1-2-4(7)8/h1-10,16H,11-13H2,(H,19,20);1-2H2,(H,5,6)(H,7,8)
InChI Key:
XFUIOIWYMHEPIE-UHFFFAOYSA-N
SMILES:
c1ccc(cc1)C1(CC1C1=NCCN1)c1ccccc1.OC(=O)CCC(=O)O
Properties
Computed Properties
 
Complexity:
450  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
2  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
380.174g/mol
Formal Charge:
0
Heavy Atom Count:
28  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
380.444g/mol
Monoisotopic Mass:
380.174g/mol
Rotatable Bond Count:
6  
Topological Polar Surface Area:
99A^2
Undefined Atom Stereocenter Count:
1  
Undefined Bond Stereocenter Count:
0

Synonyms
 
2-(2,2-diphenylcyclopropyl)-2-imidazoline 
cibenzoline 
CIFENLINE SUCCINATE 
100678-32-8 
Cibenol 
Ritmalan 
Exacor 
Cifenline succinate [USAN] 
Cibenzoline succinate (1:1) 
Ro 22-7796/001 
2-(2,2-diphenylcyclopropyl)-4,5-dihydro-1H-imidazole succinate 
(+-)-2-(2,2-Diphenylcyclopropyl)-2-imidazoline succinate (1:1) 
cibenzoline succinate 
4,5-Dihydro-2-(2,2-diphenylcyclopropyl)-1H-imidazole succinate 
1H-Imidazole, 4,5-dihydro-2-(2,2-diphenylcyclopropyl)-, succinate 
Cifenline succinate (USAN) 
1H-Imidazole, 2-(2,2-diphenylcyclopropyl)-4,5-dihydro-, (+-)-, butanedioate (1:1) 
Butanedioic acid, compd. with 2-(2,2-diphenylcyclopropyl)-4,5-dihydro-1H-imidazole 
Butanedioic acid, compd. with 2-(2,2-diphenylcyclopropyl)-4,5-dihydro-1H-imidazole (1:1) 
85589-37-3 
Ro-227796 
NCGC00162222-01 
Cibenzoline succinate [JAN] 
cifenline 
C18H18N2.C4H6O4 
Cipralan (TN) 
Cibenol (TN) 
butanedioic acid; 2-(2,2-diphenylcyclopropyl)-4,5-dihydro-1H-imidazole 
AC1L1O0B 
DSSTox_CID_27797 
DSSTox_RID_82569 
DSSTox_GSID_47820 
SCHEMBL121044 
Cibenzoline succinate (JP17) 
cifenline succinate 
CHEMBL3189111 
DTXSID0047820 
CHEBI:31396 
CTK3E8730 
KS-00002WVJ 
HMS3262I07 
Tox21_112004 
Tox21_500683 
MFCD00941423 
AKOS016339647 
cifenline, (S)-isomer 
API0002004 
CCG-221987 
KS-1343 
LP00683 
NCGC00261368-01 
AN-34360 
LS-45740 
U041 
UP-33901 
CAS-100678-32-8 
Cipralan 
FT-0623817 
Cibenzoline succinate, >=97% (NMR), solid 
D01455 
678C328 
J-000196 
2-(2,2-diphenylcyclopropyl)-4,5-dihydro-1H-imidazole; succinic acid 
UNII-38G16RWJ37 
C18H18N2.xC4H6O4 
38G16RWJ37 
C22H24N2O4 
Exacor 
CID57952 
C18-H18-N2.C4-H6-O4 
C18-H18-N2.x-C4-H6-O4 
cibenzoline succinate 
Cipralan 
Literature

Title: Andersen-Tawil syndrome associated with aborted sudden cardiac death: atrial pacing was effective for ventricular arrhythmias.

Journal: The American journal of the medical sciences 20120901

Title: Agranulocytosis immediately after oral administration of cibenzoline and dabigatran in a patient with paroxysmal atrial fibrillation.

Journal: Internal medicine (Tokyo, Japan) 20120101

Title: Inhibitory effect of cibenzoline on Na+/Ca2+ exchange current in guinea-pig cardiac ventricular myocytes.

Journal: Journal of pharmacological sciences 20120101

Title: Pharmacodynamics of cibenzoline-induced hypoglycemia in rats.

Journal: Drug metabolism and pharmacokinetics 20110601

Title: Antiarrhythmic agent cibenzoline attenuates latent obstruction in the left ventricular outflow tract of hypertrophic cardiomyopathy.

Journal: International journal of cardiology 20110505

Title: Myocardial fibrosis attenuates the effect of cibenzoline on left ventricular diastolic function in patients with hypertrophic cardiomyopathy.

Journal: Journal of cardiovascular pharmacology 20110201

Title: Comparison of acute reduction in left ventricular outflow tract pressure gradient in obstructive hypertrophic cardiomyopathy by disopyramide versus pilsicainide versus cibenzoline.

Journal: The American journal of cardiology 20101101

Title: Prospective comparative study of intravenous cibenzoline and disopyramide therapy in the treatment of paroxysmal atrial fibrillation after cardiovascular surgery.

Journal: Circulation journal : official journal of the Japanese Circulation Society 20100901

Title: Effect of cibenzoline on biventricular pressure gradients in a pediatric patient with hypertrophic obstructive cardiomyopathy.

Journal: Pediatric cardiology 20100701

Title: Cibenzoline intoxication necessitating implantation of a biventricular assist system in a patient with severe cardiomyopathy.

Journal: Interactive cardiovascular and thoracic surgery 20100701

Title: Pharmacogenetic interactions between Angiotensin-converting enzyme insertion/deletion polymorphism and response to cibenzoline in patients with hypertrophic obstructive cardiomyopathy.

Journal: Journal of cardiovascular pharmacology 20100501

Title: Hemolytic anemia in a patient with hypertrophic obstructive cardiomyopathy.

Journal: Journal of cardiology 20100101

Title: Quantitative assessment of cibenzoline administration for vagally mediated paroxysmal atrial fibrillation using frequency-domain heart rate variability analysis.

Journal: Journal of cardiology 20090801

Title: A randomized study on the efficacy of intravenous cibenzoline and pilsicainide administered prior to electrical cardioversion in patients with lone paroxysmal and persistent atrial fibrillation.

Journal: Journal of cardiology 20090201

Title: Dobutamine stress echocardiography unmasks acute worsening of mitral regurgitation with latent left ventricular outflow tract obstruction behind diastolic heart failure in hypertensive heart disease.

Journal: Internal medicine (Tokyo, Japan) 20090101

Title: Cibenzoline attenuates systolic anterior motion of the mitral valve after mitral valvoplasty.

Journal: Journal of anesthesia 20090101

Title: Effect of cibenzoline and atenolol administration on dynamic left ventricular obstruction due to sigmoid-shaped septum.

Journal: Circulation journal : official journal of the Japanese Circulation Society 20081201

Title: Use of bepridil in combination with Ic antiarrhythmic agent in converting persistent atrial fibrillation to sinus rhythm.

Journal: Circulation journal : official journal of the Japanese Circulation Society 20080501

Title: Cibenzoline intoxication: effect of combined hemoperfusion-hemodialysis on plasma clearance.

Journal: Clinical toxicology (Philadelphia, Pa.) 20080401

Title: Clinical and electrophysiological characteristics of patients having atrial flutter with 1:1 atrioventricular conduction.

Journal: 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 20080301

Title: [Myasthenia-like syndrome induced by cibenzoline overdose in a patient with chronic kidney disease].

Journal: Nihon Jinzo Gakkai shi 20080101

Title: Effect of intravenous administration of cibenzoline on left ventricular diastolic pressures in patients with hypertrophic cardiomyopathy: its relationship to transmitral Doppler flow profiles.

Journal: Circulation journal : official journal of the Japanese Circulation Society 20071001

Title: Quantification of cibenzoline by enzyme-linked immunosorbent assay.

Journal: Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan 20070601

Title: Cibenzoline improves coronary flow velocity reserve in patients with hypertrophic obstructive cardiomyopathy.

Journal: Heart and vessels 20061101

Title: Cibenzoline attenuates coronary systolic reversal flow in a patient with hypertrophic obstructive cardiomyopathy: a case report.

Journal: Journal of cardiology 20061001

Title: [Cibenzoline succinate induced pneumonitis].

Journal: Nihon Naika Gakkai zasshi. The Journal of the Japanese Society of Internal Medicine 20060710

Title: Randomized crossover study of the long-term effects of pilsicainide and cibenzoline in preventing recurrence of symptomatic paroxysmal atrial fibrillation: influence of the duration of arrhythmia before therapy.

Journal: Circulation journal : official journal of the Japanese Circulation Society 20060601

Title: Serial cardioversion by class IC Drugs during 4 months of persistent atrial fibrillation in the goat.

Journal: Journal of cardiovascular electrophysiology 20060601

Title: Too little, too late: chasing atrial fibrillation with sodium channel antagonists.

Journal: Journal of cardiovascular electrophysiology 20060601

Title: Heart failure elevates serum levels of cibenzoline in arrhythmic patients.

Journal: Circulation journal : official journal of the Japanese Circulation Society 20060501

Title: Relief of left ventricular outflow obstruction by cibenzoline in a patient with Fabry's disease--a case report.

Journal: Angiology 20060101

Title: Symptomatic hypoglycemia in a patient with chronic hemodialysis.

Journal: Acta clinica Belgica 20060101

Title: [Coronary vasospasm induced by cibenzoline succinate in a patient with brugada-type electrocardiogram].

Journal: Journal of cardiology 20051201

Title: Cibenzoline induced Brugada ECG pattern.

Journal: 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 20051101

Title: A novel mutation in the PTPN11 gene in a patient with Noonan syndrome and rapidly progressive hypertrophic cardiomyopathy.

Journal: European journal of pediatrics 20050801

Title: Antiarrhythmic drug cibenzoline attenuates left ventricular pressure gradient and improves transmitral Doppler flow pattern in patients with hypertrophic obstructive cardiomyopathy caused by midventricular obstruction.

Journal: Circulation journal : official journal of the Japanese Circulation Society 20050801

Title: Cibenzoline attenuates upregulation of Kv1.5 channel gene expression by experimental paroxysmal atrial fibrillation.

Journal: International heart journal 20050301

Title: Oral cibenzoline reduces postoperative atrial fibrillation in coronary artery bypass grafting.

Journal: The Japanese journal of thoracic and cardiovascular surgery : official publication of the Japanese Association for Thoracic Surgery = Nihon Kyobu Geka Gakkai zasshi 20050101

Title: [Cibenzoline-succinate-induced hypoglycemia].

Journal: Nihon Naika Gakkai zasshi. The Journal of the Japanese Society of Internal Medicine 20041010

Title: Beneficial effect of cibenzoline on left ventricular pressure gradient with sigmoid septum.

Journal: Circulation journal : official journal of the Japanese Circulation Society 20041001

Title: Fractionation of electrograms and linking of activation during pharmacologic cardioversion of persistent atrial fibrillation in the goat.

Journal: Journal of cardiovascular electrophysiology 20040501

Title: Block of HERG current expressed in HEK293 cells by the Na+-channel blocker cibenzoline.

Journal: Heart and vessels 20040501

Title: Cibenzoline therapy for mitral regurgitation in patients with HOCM.

Journal: Internal medicine (Tokyo, Japan) 20040101

Title: Mitral regurgitation disappearance after cibenzoline treatment in a patient with hypertrophic obstructive cardiomyopathy.

Journal: Internal medicine (Tokyo, Japan) 20040101

Title: Percutaneous cardiopulmonary support aids resuscitation from sustained ventricular tachycardia.

Journal: Circulation journal : official journal of the Japanese Circulation Society 20031201

Title: Decrease in the spatial dispersion at the termination of atrial fibrillation by intravenous cibenzoline.

Journal: Circulation journal : official journal of the Japanese Circulation Society 20031001

Title: [A case of acute cibenzoline intoxication in a hemodialysis patient].

Journal: Chudoku kenkyu : Chudoku Kenkyukai jun kikanshi = The Japanese journal of toxicology 20030701

Title: Role of fibrillation cycle length in spontaneous and drug-induced termination of human atrial fibrillation.

Journal: Circulation journal : official journal of the Japanese Circulation Society 20030501

Title: [Comparison of the efficacies of disopyramide, cibenzoline and aprindine for the termination of paroxysmal and persistent atrial fibrillation in elderly and non-elderly patients].

Journal: Journal of cardiology 20030401

Title: [Beneficial effect of cibenzoline in a patient with hypertrophic obstructive cardiomyopathy complicated with idiopathic interstitial pneumonia].

Journal: Nihon Ronen Igakkai zasshi. Japanese journal of geriatrics 20030101

Title: Attenuation of biventricular pressure gradients by cibenzo-line in an 18-year-old patient with hypertrophic obstructive cardiomyopathy.

Journal: Circulation journal : official journal of the Japanese Circulation Society 20021201

Title: Idiopathic left ventricular aneurysm associated with pleomorphic ventricular tachycardia: a case report.

Journal: Journal of cardiology 20021201

Title: Atrial fibrillation threshold predicted long-term efficacy of pharmacological treatment of patients without structural heart disease.

Journal: 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 20021001

Title: Extremely prolonged elimination of cibenzoline at toxic plasma concentrations in patients with renal impairments.

Journal: Therapeutic drug monitoring 20020801

Title: A case of severe respiratory depression due to cibenzoline overdosage induced by a transient renal dysfunction.

Journal: International journal of cardiology 20020201

Title: [Relationship between long-term preventive efficacy of cibenzoline and atrial natriuretic peptide in patients with paroxysmal atrial fibrillation].

Journal: Journal of cardiology 20020201

Title: Cibenzoline, an ATP-sensitive K(+) channel blocker, binds to the K(+)-binding site from the cytoplasmic side of gastric H(+),K(+)-ATPase.

Journal: British journal of pharmacology 20011201

Title: Efficacy of therapeutic drug monitoring in prevention of hypoglycemia caused by cibenzoline.

Journal: European journal of clinical pharmacology 20011201

Title: Effect of cibenzoline, a class ia antiarrhythmic agent, on left ventricular diastolic function in hypertrophic cardiomyopathy.

Journal: Cardiovascular drugs and therapy 20010901

Title: Cibenzoline has an inhibitory effect on vasorelaxation mediated by adenosine triphosphate-sensitive K(+) channels in the rat carotid artery.

Journal: Anesthesia and analgesia 20010801

Title: Antiarrhythmic drug, cibenzoline, can directly improve the left ventricular diastolic function in patients with hypertrophic cardiomyopathy.

Journal: Japanese circulation journal 20010601

Title: Dual action of ZD6169, a novel K(+) channel opener, on ATP-sensitive K(+) channels in pig urethral myocytes.

Journal: British journal of pharmacology 20010501

Title: Effects of cibenzoline on cardiac function and metabolism in the rat heart--lung preparation.

Journal: European journal of anaesthesiology 20010301

Title: Hypoglycemic syncope induced by a combination of cibenzoline and angiotensin converting enzyme inhibitor.

Journal: Japanese heart journal 20010301

Title: [Efficacy of cibenzoline in the termination and long-term prevention of paroxysmal atrial fibrillation: analysis based on the time of onset].

Journal: Journal of cardiology 20010201

Title: Blurred vision, left bundle-branch block and cardiac failure.

Journal: Acta cardiologica 20010201

Title: [Fatal poisoning by cibenzoline].

Journal: Therapie 20010101

Title: Choreic movements induced by cibenzoline: an Ic class antiarrhythmic effect?

Journal: Movement disorders : official journal of the Movement Disorder Society 20000901

Title: [Sudden cardiac arrest after induction of general anesthesia: a case report].

Journal: Masui. The Japanese journal of anesthesiology 20000101

Title: Antiarrhythmic effects of optical isomers of cibenzoline on canine ventricular arrhythmias.

Journal: Journal of cardiovascular pharmacology 19900901

Title: Antiarrhythmic plasma concentrations of cibenzoline on canine ventricular arrhythmias.

Journal: Journal of cardiovascular pharmacology 19870201

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