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Chemical compound From Wikipedia, the free encyclopedia
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It was used for the prophylaxis and treatment of serious and life-threatening ventricular arrhythmias,[3] but was withdrawn in 2007 for commercial reasons.[4]
Clinical data | |
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Trade names | Ethmozine |
Other names | Moricizine (USAN US) |
AHFS/Drugs.com | Consumer Drug Information |
MedlinePlus | a601214 |
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ATC code | |
Pharmacokinetic data | |
Bioavailability | 34–38% |
Protein binding | 95% |
Elimination half-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, 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]
The reaction between N-phenyl-1,3-benzenediamine (1) and ethyl chloroformate (2) gives the carbamate (3). Treatment with sulfur and iodine forms the phenothiazine derivative (4). Amide formation with 3-chloropropionyl chloride (5) gives the penultimate intermediate (6). Alkylation of morpholine by nucleophilic substitution at the sidechain chlorine yields moricizine.[6][7]
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