薬剤の安定性に関する研究(第22報) : ベンゾサイアダイアジン系化合物の安定性その12クロロサイアザイドの分解機構について

概要

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Difference in the intermediates formed in the degradation of chlorothiazide (I), which was hydrolyzed ultimately to 5-chloro-2,4-disulfamoylaniline (IV) via N-(2-amino-4-chloro-5-sulfamoylphenylsulfonyl) formamide (II) in an alkaline medium and via 5-chloro-2,4-disulfamoylformanilide (III) in an acidic medium, was investigated using a molecular orbital method, in order to understand the hydrolysis mechanism of I. The hydrolysis pathway of I can be explained by the electronegativity of the atoms involved in the postulated activated-complex, 3-hydroxyhydrochlorothiazide (V). However, the stabilities of II and III in acidic and basic media are a possible reason for the above phenomenon, because there is little difference in electronegativities between the positions 2 and 3 in V and the same positions in the anion type of V, namely V^-.
公益社団法人日本薬学会の論文
1972-03-25