Mesoridazine (Serentil) is a phenothiazine class drug that is used in the treatment of schizophrenia.[2] It is one of the active metabolites of thioridazine. The drug's name is derived from the methylsulfoxy and piperidine functional groups in its chemical structure.
It has central antiadrenergic, antidopaminergic, antiserotonergic and weak muscarinic anticholinergic effects.
Mesoridazine was withdrawn from the United States market in 2004 due to dangerous side effects, namely irregular heart beat and QT-prolongation of the electrocardiogram.[3]
Mesoridazine is on the FDA's Discontinued Drug Product List.[4]
2-Methylthiophenothiazine [7643-08-5] (1) is treated with acetic anhydride] to give the protected amide, ie 10-acetyl-2-methylthiophenothiazine, CID:69367526. Oxidation of this by means of hydrogen peroxide and removal of the acetyl protecting group with potassium carbonate in methanol solution gives 2-methylsulfonylphenothiazine [23503-68-6] (3). Introduction of the sidechain by alkylation with 2-(2-chlorethyl)-1-methylpiperidine [50846-01-0] (6) in the presence of sodamide, afforded the desired mesoridazine (5).
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Thioridazine is a first generation antipsychotic drug belonging to the phenothiazine drug group and was previously widely used in the treatment of schizophrenia and psychosis. The branded product was withdrawn worldwide in 2005 because it caused severe cardiac arrhythmias. However, generic versions are still available in the US.
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The total synthesis of the complex biomolecule vitamin B12 was accomplished in two different approaches by the collaborating research groups of Robert Burns Woodward at Harvard and Albert Eschenmoser at ETH in 1972. The accomplishment required the effort of no less than 91 postdoctoral researchers (Harvard: 77, ETH: 14), and 12 Ph.D. students (at ETH) from 19 different nations over a period of almost 12 years. The synthesis project induced and involved a major change of paradigm in the field of natural product synthesis.
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↑ Gershon S, Sakalis G, Bowers PA (December 1981). "Mesoridazine -- a pharmacodynamic and pharmacokinetic profile". The Journal of Clinical Psychiatry. 42 (12): 463–9. PMID7031039.
↑ American Society of Health-System Pharmacists (AHFS). "Mesoridazine". Medline Plus. U.S. National Library of Medicine.
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