Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C15H23N3O2 |
| Molecular Weight | 277.362 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCN(CC)CCNC(=O)C1=CC=C(NC(C)=O)C=C1
InChI
InChIKey=KEECCEWTUVWFCV-UHFFFAOYSA-N
InChI=1S/C15H23N3O2/c1-4-18(5-2)11-10-16-15(20)13-6-8-14(9-7-13)17-12(3)19/h6-9H,4-5,10-11H2,1-3H3,(H,16,20)(H,17,19)
Acecainide (N-acetylprocainamide), the N-acetylated metabolite of procainamide, is a Class III antiarrhythmic agent. Acecainide exerts cardiac anticholinergic effect. It elicits smooth muscle relaxation mainly through the activation of plasma membrane K+ channels. Acecainide markedly reduced premature ventricular beats and prevented induction of ventricular tachycardia. Acecainide appears to offer advantages over procainamide, particularly with respect to the reduced formation of antinuclear antibodies. Acecainide development has been discontinued.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Pharmacologically active drug metabolites: therapeutic and toxic activities, plasma and urine data in man, accumulation in renal failure. | 1976 Nov-Dec |
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| Cumulation of N-acetylprocainamide, an active metabolite of procainamide, in patients with impaired renal function. | 1977 Jul |
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| Torsade de pointes associated with elevated N-acetylprocainamide levels. | 1985 Feb |
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| Polymorphic ventricular tachycardia and ventricular fibrillation due to N-acetyl procainamide. | 1985 Jan 1 |
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| Torsades de pointes due to n-acetylprocainamide. | 1985 Jul |
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| Study of procainamide hapten-specific antibodies in rabbits and humans. | 1993 Nov |
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| N-substituted benzamides inhibit nuclear factor-kappaB and nuclear factor of activated T cells activity while inducing activator protein 1 activity in T lymphocytes. | 2001 Aug |
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| Quantitative estimation of renal clearance of N-acetylprocainamide in rats with various experimental acute renal failure. | 2001 Jun |
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| Role of K+ channels in N-acetylprocainamide-induced relaxation of bovine tracheal smooth muscle. | 2001 Mar 9 |
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| cDNA cloning, functional characterization, and tissue distribution of an alternatively spliced variant of organic cation transporter hOCT2 predominantly expressed in the human kidney. | 2002 Jul |
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| Massive cell vacuolization induced by organic amines such as procainamide. | 2004 Jul |
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| Class I antiarrhythmics inhibit Na+ absorption and Cl- secretion in rabbit descending colon epithelium. | 2005 Jun |
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| High-throughput solution-based medicinal library screening against human serum albumin. | 2005 Mar 1 |
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| St. John's wort does not interfere with therapeutic drug monitoring of 12 commonly monitored drugs using immunoassays. | 2006 |
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| Therapeutic levels of intravenous procainamide in neonates: a retrospective assessment. | 2006 Dec |
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| Application of a generic physiologically based pharmacokinetic model to the estimation of xenobiotic levels in human plasma. | 2006 Jan |
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| Drug-herb interaction: effect of St John's wort on bioavailability and metabolism of procainamide in mice. | 2007 Jul |
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| Simultaneous determination of procaine and para-aminobenzoic acid by LC-MS/MS method. | 2007 Mar 1 |
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| Clinical review: Drug metabolism and nonrenal clearance in acute kidney injury. | 2008 |
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| Effect of drugs on defibrillation capacity. | 2008 |
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| Drug therapy considerations in arrhythmias in children. | 2008 Aug 1 |
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| Procainamide, but not N-acetylprocainamide, induces protein free radical formation on myeloperoxidase: a potential mechanism of agranulocytosis. | 2008 May |
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| The prince and the pauper. A tale of anticancer targeted agents. | 2008 Oct 23 |
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| Overview of therapeutic drug monitoring. | 2009 Mar |
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| Development of multifocal atrial tachycardia in a patient using aminophylline -A case report-. | 2010 Dec |
Patents
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| Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
35989
Created by
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NCI_THESAURUS |
C47793
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FDA ORPHAN DRUG |
99196
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NCI_THESAURUS |
C93038
Created by
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m1291
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100000081770
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D000120
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60728
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N-ACETYLPROCAINAMIDE
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4342
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CHEMBL1097
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C75125
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SUB07372MIG
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DTXSID6048414
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ACTIVE MOIETY
PARENT (METABOLITE ACTIVE)
SALT/SOLVATE (PARENT)
