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acecainide

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Also known as N-Acetyloprokainamid, Acekainid, 4'-((2-(Diethylamino)ethyl)carbamoyl)acetanilide, NAPA, N-acetyl procainamide, N-acetylprocainamide, acetylprocainamide

Acecainide ('''N-acetylprocainamide, NAPA') is an antiarrhythmic drug. Chemically, it is the N''-acetylated metabolite of procainamide. It is a Class III antiarrhythmic agent, whereas procainamide is a Class Ia antiarrhythmic drug. It is only partially as active as procainamide; when checking levels, both must be included in the final calculation.

Wikidata facts

Mass
277.179
Show 4 more facts
chemical formula
C₁₅H₂₃N₃O₂
canonical SMILES
CCN(CC)CCNC(=O)C1=CC=C(C=C1)NC(=O)C
World Health Organisation international non-proprietary name
acecainide
Commons category
Acecainide
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~14 min read

Article

20 sections
Contents
  • History
  • Synthesis
  • Activity
  • Mechanism
  • Medical uses
  • Toxicokinetics
  • Absorption and plasma concentrations
  • Distribution
  • Metabolism and elimination
  • Influence on clearance and concentration rate
  • Administration
  • Intravenous administration
  • Oral administration
  • Drug interaction
  • Toxicity
  • Effects on humans
  • Effects on animals
  • Detoxification
  • References
  • External links

Acecainide ('''N-acetylprocainamide, NAPA') is an antiarrhythmic drug. Chemically, it is the N-acetylated metabolite of procainamide. It is a Class III antiarrhythmic agent, whereas procainamide is a Class Ia antiarrhythmic drug. It is only partially as active as procainamide; when checking levels, both must be included in the final calculation.

==History== In the early 1930s, Claude Beck was undertaking pioneer cardiac surgery at the Lakeside Hospital in Cleveland, Ohio. During and after his surgery he was facing problems with arrhythmias. These problems were investigated by Frederick R. Mautz. In these experiments he used drugs similar to cocaine, because these drugs were readily absorbed from mucous membranes and were also known to have some effect on the myocardium. Mautz tried procaine, but its action was short-lived owing to digestion by esterases. From procaine Mautz synthesized procainamide, which is not a substrate for esterases. Procainamide has the additional advantage of being active by mouth. Procainamide was approved by the US FDA on June 2, 1950 under the brand name Pronestyl. In 1951 Pronestyl was launched by Bristol-Myers Squibb, a pharmaceutical company in the US. Along with the discovery of procainamide came the discovery of its metabolite acecainide.

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