Moracizine

ATC codePharmacokinetic dataBioavailability34–38%Protein binding95%Elimination half-life3–4 hours (healthy volunteers), 6–13 hours (cardiac disease)IdentifiersCAS NumberPubChem CIDIUPHAR/BPSDrugBankChemSpiderUNIIKEGGChEBIChEMBLCompTox Dashboard (EPA)ECHA InfoCard100.046.216 Chemical and physical dataFormulaC₂₂H₂₅N₃O₄SMolar mass427.52 g·mol⁻¹3D model (JSmol) ^NY (what is this?)  (verify)

Moracizine^[1] or moricizine, sold under the trade name Ethmozine, is an antiarrhythmic of class IC.^[2] It was used for the prophylaxis and treatment of serious and life-threatening ventricular arrhythmias,^[3] but was withdrawn in 2007 for commercial reasons.^[4]

Pharmacology

Moracizine, a phenothiazine derivative, undergoes extensive first-pass metabolism and is also extensively metabolized after it has entered the circulation. It may have pharmacologically active metabolites. A clinical study has shown that moracizine is slightly less effective than encainide or flecainide in suppressing ventricular premature depolarizations.^{[citation needed]} Compared with disopyramide and quinidine, moracizine was equally or more effective in suppressing premature ventricular contractions, couplets, and nonsustained ventricular tachycardia.^{[citation needed]}

In the Cardiac Arrhythmia Suppression Trial (CAST), a large study testing the influence of antiarrhythmics on mortality, showed a statistically non-significant increase of mortality from 5.4 to 7.2% under moracizine. This is in line with other class IC antiarrhythmics.^[5]

Synthesis

Note: The carbamate structure reminds the reader of Gastrophenzine or particularly Ethacizine.

The amide formation between Phenothiazine-2-ethylcarbamate [37711-29-8] (1) and 3-Chloropropionyl chloride [625-36-5] (2) gives ethyl N-[10-(3-chloropropanoyl)phenothiazin-2-yl]carbamate [119407-03-3] [34749-22-9] (3). Displacement of the remaining ω-halogen by morpholine (4) then completes the synthesis of Moricizine (5).

References