Synthesis of the N-Oxides of Phenothiazine Antipsychotic Agents

Chlorpromazine N-oxide, fluphenazine N4’-oxide, prochlor-perazine N4’-oxide, sulforidazine N-oxide, and trifluoperazine N4’-oxide were synthesized by oxidation of the designated nitrogen atom in the N-10 side chain of the respective parent drug with 3-chloroperoxybenzoic acid. In the case of trifluo...

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Bibliographic Details
Published in:Journal of pharmaceutical sciences 1993-03, Vol.82 (3), p.330-333
Main Authors: Jaworski, T.J., Sardessai, M.S., Aravagiri, M., Lin, G., Shi, Y.Y., Hawes, E.M., Hubbard, J.W., Mckay, G., Midha, K.K.
Format: Article
Language:English
Subjects:
Antipsychotic Agents - chemical synthesis
Biological and medical sciences
Cyclic N-Oxides - chemical synthesis
Medical sciences
Neuropharmacology
Pharmacology. Drug treatments
Phenothiazines
Psycholeptics: tranquillizer, neuroleptic
Psychology. Psychoanalysis. Psychiatry
Psychopharmacology
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Summary:Chlorpromazine N-oxide, fluphenazine N4’-oxide, prochlor-perazine N4’-oxide, sulforidazine N-oxide, and trifluoperazine N4’-oxide were synthesized by oxidation of the designated nitrogen atom in the N-10 side chain of the respective parent drug with 3-chloroperoxybenzoic acid. In the case of trifluoperazine, a stepwise increase in the amount of oxidant yielded the N1,N4 -dioxide and N1’,N4’,S-trioxide. The N’,S-dioxides of chlorpromazine and sulforidazine were obtained by hydrogen peroxide oxidation of the appropriate parent drug.
ISSN:0022-3549
1520-6017
DOI:10.1002/jps.2600820323