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  • Title: Characterization of imatinib metabolites in rat and human liver microsomes: differentiation of hydroxylation from N-oxidation by liquid chromatography/atmospheric pressure chemical ionization mass spectrometry.
    Author: Ma S, Xu Y, Shou M.
    Journal: Rapid Commun Mass Spectrom; 2009 May; 23(10):1446-50. PubMed ID: 19353558.
    Abstract:
    In vitro metabolism of imatinib was investigated in rat and human liver microsomes. Atmospheric pressure chemical ionization (APCI) mass spectrometry (MS) was applied in differentiating hydroxyl metabolites from N-oxides of imatinib because N-oxides are known to undergo deoxygenation during APCI. In addition, the major oxidative metabolite (M9, N-oxidation on the piperazine ring) was observed to undergo in-source fragmentation by elimination of formaldehyde. This fragment ion resulted from Meisenheimer rearrangement with migration of the N-methyl group to the corresponding N-methoxyl piperazine, followed by elimination of formaldehyde due to thermal energy activation at the vaporizer of APCI source. The presence of this fragment ion distinguished not only N-oxide from isomeric hydroxylated metabolite, but also unambiguously indicated that oxidation occurred on the N-4 of the piperazine ring where the methyl group was attached.
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