Journal
JOURNAL OF MASS SPECTROMETRY
Volume 57, Issue 7, Pages -Publisher
WILEY
DOI: 10.1002/jms.4871
Keywords
forced degradation; impurity; LC-MS; lurasidone; structure elucidation
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Lurasidone, an antipsychotic drug for schizophrenia and bipolar disorder, was found to generate two novel degradation products under free radical-mediated oxidative and solution photolytic conditions.
Lurasidone is an antipsychotic drug clinically used for the treatment of schizophrenia and bipolar disorder. During a mechanism-based forced degradation study of lurasidone, two novel degradation products were observed under free radical-mediated oxidative (via AIBN) and solution photolytic conditions. The structures of the two novel degradants were identified through an approach combining HPLC, LC-MSn (n = 1, 2), preparative HPLC purification and NMR spectroscopy. The degradant formed under the free radical-mediated condition is an oxidative degradant with half of the piperazine ring cleaved to form two formamides; a mechanism is proposed for the formation of the novel N,N '-diformyl degradant, which should be readily applicable to other drugs that contain a piperazine moiety that is widely present in drug molecules. The degradant observed under the solution photolytic condition is identified as the photo-induced isomer of lurasidone with the benzisothiazole ring altered into a benzothiazole ring.
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