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Structural characterization of sulfadiazine metabolites using H/D exchange combined with various MS/MS experiments

Structural characterization of sulfadiazine metabolites using H/D exchange combined with various MS/MS experiments,10.1016/j.jasms.2005.06.008,Journal

Structural characterization of sulfadiazine metabolites using H/D exchange combined with various MS/MS experiments   (Citations: 10)
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Two major metabolites and one minor metabolite of sulfadiazine were found in pig manure, using a special combination of different MS techniques like parent and product ion scans, H/D exchange, accurate mass measurement, and MS/MS experiments with substructures. N4-acetylsulfadiazine and 4-hydroxysulfadiazine were identified as major metabolites. N4-acetylsulfadiazine could be verified by H/D exchange and comparison with product ion spectra of a synthetic reference compound. In the case of 4-hydroxysulfadiazine, the majority of possible isomers could be discounted after H/D exchange. Substructure-specific MS/MS experiments with fragment ions and comparison with product ion spectra of two references revealed the presence of 4-hydroxysulfadiazine. The minor metabolite was characterized to some degree using H/D exchange and tandem mass spectrometry in combination with a high-resolution time of flight mass spectrometer. The aminopyrimidine moiety contained an additional modification with a likely elemental composition of C2H4O and no further acidic hydrogen.
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    • ...5-Hydroxysulfadiazine was synthesized following a method described by Pfeifer et al. [26]...
    • ...Furthermore, a hydroxylated metabolite was previously described in the literature as 4-OH-SDZ [26]...
    • ...Using in-source CID followed by additional fragmentation via MS/MS the resulting spectra exhibited a prominent peak at m/z 70, which might be easily explained by the structure bearing an hydroxyl group at the fourth position (Figs. 1 and 4) of the aminopyrimidine ring [26]...

    Marc Lamshöftet al. Metabolism of 14 C-labelled and non-labelled sulfadiazine after admini...

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