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Disopyramide phosphate

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Structure

  • Disopyramide phosphate is a class IA antiarrhythmic agent with a quinuclidine core structure. It features a dibenzodioxepin ring system linked to a quinuclidine moiety and a diethylamino group.

  • Chemical Formula: C₂₀H₂₉N₃O₄S·H₃PO₄

    Chemical Formula Disopyramide phosphate

Structure of Disopyramide phosphate
Structure of Disopyramide phosphate

Mode of Action

  • Class IA Antiarrhythmic: Inhibits fast sodium channels, prolongs action potential duration and refractory period.

  • Potassium Channel Blockade: Extends repolarization by blocking potassium efflux.

  • Anticholinergic Effects: Exhibits antimuscarinic activity, which can lead to side effects like dry mouth and blurred vision.

  • Effect on Heart Rate: Converts atrial fibrillation to sinus rhythm and prevents reentrant arrhythmias.

Uses

  • Ventricular Arrhythmias: Treats ventricular tachycardia and ventricular fibrillation.

  • Atrial Arrhythmias: Manages atrial fibrillation and atrial flutter.

  • Reentrant Arrhythmias Prevention: Effective in preventing recurrence post-cardiac events.

  • Antiarrhythmic Prophylaxis: Used after myocardial infarction to prevent arrhythmias.

Structure-Activity Relationship (SAR)

  • Quinuclidine Core: Essential for blocking fast sodium channels and prolonging the action potential.

  • Dibenzodioxepin Ring System: Enhances lipophilicity, improving membrane permeability and binding affinity to cardiac ion channels.

  • Diethylamino Group: Increases affinity for sodium channels and contributes to antimuscarinic side effects.

  • Substituents: Modifications on the aromatic rings can influence potency and selectivity for ion channels.

Synthesis of Disopyramide phosphate

  • Disopyramide phosphate can be synthesized through the following steps:

  • Starting Material: Quinuclidine.

  • Alkylation: Introduction of diethylamino groups through nucleophilic substitution with appropriate diethylating agents.

  • Coupling with Dibenzodioxepin: React quinuclidine derivative with dibenzodioxepin to form the linked structure.

  • Phosphorylation: Addition of phosphate groups to form the phosphate salt.

  • Purification: Isolation and recrystallization to obtain pure disopyramide phosphate.

Synthetic Route Overview:

  • Quinuclidine → Diethylaminoalkylation → Coupling with Dibenzodioxepin → Phosphorylation → Disopyramide Phosphate


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