Details
Stereochemistry | ACHIRAL |
Molecular Formula | C22H30N2 |
Molecular Weight | 322.487 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCN(CC)CCCN(C1CC2=C(C1)C=CC=C2)C3=CC=CC=C3
InChI
InChIKey=NZLBHDRPUJLHCE-UHFFFAOYSA-N
InChI=1S/C22H30N2/c1-3-23(4-2)15-10-16-24(21-13-6-5-7-14-21)22-17-19-11-8-9-12-20(19)18-22/h5-9,11-14,22H,3-4,10,15-18H2,1-2H3
DescriptionSources: http://www.ndrugs.com/?s=aprindineCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/6186851
Sources: http://www.ndrugs.com/?s=aprindine
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/6186851
Aprindine is a class Ib antiarrhythmic agent. It is not approved in USA, but is available in European countries, where it is used to treat supraventricular and ventricular arrhythmias. Aprindine acts by blocking sodium voltage channels and disrupting interactions between calmodulin and prosphodiesterase.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2331043 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1660104 |
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Target ID: CHEMBL6093 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6186851 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Preventing | Unknown Approved UseUnknown |
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Primary | FIBORAN Approved UseAprindine is indicated for treatment of therapy-resistant ventricular tachycardias and ventricular extrasystoles. |
PubMed
Title | Date | PubMed |
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Antiarrhythmic and antifibrillatory properties of aprindine. | 1975 Aug |
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[Accident during local anesthesia in a patient with antiarrhythmic therapy]. | 1975 Jul |
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New drugs for treating cardiac arrhythmias. | 1981 Jan |
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Effect of sotalol, aprindine and their combination on maximum upstroke velocity of action potential in guinea-pig papillary muscle. | 1986 Nov 19 |
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Broad sensitivity of rodent arrhythmia models to class I, II, III, and IV antiarrhythmic agents. | 1989 Jun |
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Complex frequency-dependent interaction of class-I antiarrhythmic drugs as they affect intraventricular conduction. | 1995 Jun |
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Effects of aprindine on ischemia/reperfusion-induced cardiac contractile dysfunction of perfused rat heart. | 1996 Mar |
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Prediction of catalepsies induced by amiodarone, aprindine and procaine: similarity in conformation of diethylaminoethyl side chain. | 1998 Nov |
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Inhibitory effects of aprindine on the delayed rectifier K+ current and the muscarinic acetylcholine receptor-operated K+ current in guinea-pig atrial cells. | 1999 Feb |
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Double-blind placebo-controlled trial of aprindine and digoxin for the prevention of symptomatic atrial fibrillation. | 2002 Jun |
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Inhibitory effect of aprindine on Na+/Ca2+ exchange current in guinea-pig cardiac ventricular myocytes. | 2002 Jun |
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Atrial fibrillation threshold predicted long-term efficacy of pharmacological treatment of patients without structural heart disease. | 2002 Oct |
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[Comparison of the efficacies of disopyramide, cibenzoline and aprindine for the termination of paroxysmal and persistent atrial fibrillation in elderly and non-elderly patients]. | 2003 Apr |
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Usefulness and safety of bepridil in converting persistent atrial fibrillation to sinus rhythm. | 2003 Aug 15 |
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Role of atrial fibrillation threshold evaluation on guiding treatment. | 2003 Oct 1 |
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Additional gene variants reduce effectiveness of beta-blockers in the LQT1 form of long QT syndrome. | 2004 Feb |
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Theoretical possibilities for the development of novel antiarrhythmic drugs. | 2004 Jan |
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Appropriate dosing of antiarrhythmic drugs in Japan requires therapeutic drug monitoring. | 2005 Feb |
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Proteasomal degradation of Kir6.2 channel protein and its inhibition by a Na+ channel blocker aprindine. | 2005 Jun 17 |
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Effect of antiarrhythmic agents on heart rate variability indices after myocardial infarction: comparative experimental study of aprindine and procainamide. | 2005 Oct |
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[Strategy for cardiac arrhythmias in acute coronary syndrome]. | 2006 Apr |
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Nonlinear mixed effects model analysis of the pharmacokinetics of routinely administered bepridil in Japanese patients with arrhythmias. | 2006 Mar |
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Topics on the Na+/Ca2+ exchanger: pharmacological characterization of Na+/Ca2+ exchanger inhibitors. | 2006 Sep |
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Pharmacological cardioversion of persistent atrial fibrillation with and without a history of drug-resistant paroxysmal atrial fibrillation. | 2006 Sep |
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Na+/Ca2+ exchange inhibitors: a new class of calcium regulators. | 2007 Sep |
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Relation of interleukin-6 and C-reactive protein levels to sinus maintenance after pharmacological cardioversion in persistent atrial fibrillation. | 2007 Sep |
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Relationship between serum aprindine concentration and neurologic side effects in Japanese. | 2009 Apr |
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Inflammatory cytokines and atrial fibrillation: current and prospective views. | 2010 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: http://www.ndrugs.com/?s=aprindine
150-200 mg daily in divided doses, up to 300 mg/day may be used under strict observation for the first 2-3 days if needed.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1660104
Effects of aprindine (3 umol/l) on the Na+ current using whole cell voltage clamp was studied in guinea-pig ventricular myocytesd. Aprindine revealed tonic block (Kdrest = 37.7 umol/l, Kdi = 0.74 umol/l) and shifted inactivation curve to hyperpolarizing direction by 11.4+3.5 mV (n = 4) without changes in slope factor.
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C47793
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C01BB04
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D001073
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231
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5Y48085P9Q
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CHEMBL1213033
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C77975
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37640-71-4
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1054
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APRINDINE
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SUB05542MIG
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3179
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DTXSID3022615
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m2013
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DB01429
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)