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| Clinical data | |
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| Trade names | Ethmozine |
| Other names | Moricizine (USANUS) |
| AHFS/Drugs.com | Consumer Drug Information |
| MedlinePlus | a601214 |
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| ATC code | |
| Pharmacokinetic data | |
| Bioavailability | 34–38% |
| Protein binding | 95% |
| Eliminationhalf-life | 3–4 hours (healthy volunteers), 6–13 hours (cardiac disease) |
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| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.046.216 |
| Chemical and physical data | |
| Formula | C22H25N3O4S |
| Molar mass | 427.52 g·mol−1 |
| 3D model (JSmol) | |
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Moracizine[1] ormoricizine, sold under the trade nameEthmozine, is anantiarrhythmic 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It was used for the prophylaxis and treatment of serious and life-threatening ventricular arrhythmias,[3] but was withdrawn in 2007 for commercial reasons.[4]
Moracizine, aphenothiazine derivative, undergoes extensivefirst-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 thanencainide orflecainide in suppressing ventricular premature depolarizations.[citation needed] Compared withdisopyramide andquinidine, moracizine was equally or more effective in suppressingpremature ventricular contractions, couplets, and nonsustainedventricular tachycardia.[citation needed]
In theCardiac Arrhythmia Suppression Trial (CAST), a large study testing the influence of antiarrhythmics onmortality, 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]
The reaction between N-phenyl-1,3-benzenediamine (1) andethyl chloroformate (2) gives thecarbamate (3). Treatment with sulfur and iodine forms the phenothiazine derivative (4).Amide formation with 3-chloropropionyl chloride (5) gives the penultimate intermediate (6).Alkylation ofmorpholine bynucleophilic substitution at the sidechain chlorine yields moricizine.[6][7]
