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 It was used for the prophylaxis and treatment of serious and life-threatening ventricular arrhythmias, but was withdrawn in 2007 for commercial reasons.

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. Compared with disopyramide and quinidine, moracizine was equally or more effective in suppressing premature ventricular contractions, couplets, and nonsustained ventricular tachycardia. In the Cardiac Arrhythmia Suppression Trial (CAST), a large study testing the influence of antiarrhythmics on

mortality Mortality is the state of being mortal, or susceptible to death; the opposite of immortality. Mortality may also refer to: * Fish mortality, a parameter used in fisheries population dynamics to account for the loss of fish in a fish stock throug ...

, 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.

Synthesis

Note: The carbamate structure reminds the reader o
Gastrophenzine
or particularly Ethacizine. Moracizine synthesis

The amide formation between Phenothiazine-2-ethylcarbamate 7711-29-8(1) and 3-Chloropropionyl chloride 25-36-5(2) gives ethyl N-

0-(3-chloropropanoyl)phenothiazin-2-yl Theta (, ; uppercase: Θ or ; lowercase: θ or ; grc, ''thē̂ta'' ; Modern: ''thī́ta'' ) is the eighth letter of the Greek alphabet, derived from the Phoenician letter Teth . In the system of Greek numerals, it has a value of 9. ...

arbamate

19407-03-3 Year 194 ( CXCIV) was a common year starting on Tuesday (link will display the full calendar) of the Julian calendar. At the time, it was known as the Year of the Consulship of Septimius and Septimius (or, less frequently, year 947 ''Ab urbe c ...

4749-22-9(3). Displacement of the remaining ω-halogen by

morpholine Morpholine is an organic chemical compound having the chemical formula O( C H2CH2)2 NH. This heterocycle features both amine and ether functional groups. Because of the amine, morpholine is a base; its conjugate acid is called morpholinium. Fo ...

(4) then completes the synthesis of Moricizine (5).

References

Antiarrhythmic agents Sodium channel blockers Phenothiazines 4-Morpholinyl compunds Carbamates Abandoned drugs Drugs in the Soviet Union {{cardiovascular-drug-stub