Determination of Acid Dissociation Constants of Hydrochlorothiazide and Its Degradant through Measurement of the Effective Electrophoretic Mobilities in CZE

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  • TAKAYANAGI Toshio
    Department of Applied Chemistry, Graduate School of Science and Technology, Tokushima University Department of Chemical Science and Technology, Faculty of Engineering, Tokushima University Department of Chemical Science and Technology, Graduate School of Advanced Technology and Science, Tokushima University
  • ISODA Masashi
    Department of Chemical Science and Technology, Faculty of Engineering, Tokushima University
  • ITOH Daichi
    Department of Chemical Science and Technology, Graduate School of Advanced Technology and Science, Tokushima University
  • MIZUGUCHI Hitoshi
    Department of Applied Chemistry, Graduate School of Science and Technology, Tokushima University Department of Chemical Science and Technology, Faculty of Engineering, Tokushima University Department of Chemical Science and Technology, Graduate School of Advanced Technology and Science, Tokushima University

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Other Title
  • CZEによる電気泳動移動度測定に基づくヒドロクロロチアジドとその分解生成物の酸解離定数の決定
  • CZE ニ ヨル デンキ エイドウ イドウド ソクテイ ニ モトズク ヒドロクロロチアジド ト ソノ ブンカイ セイセイブツ ノ サン カイリ テイスウ ノ ケッテイ

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Abstract

Hydrochlorothiazide, one of the popular diuretics, is degradable in an aqueous solution by hydrolysis, gradually forming 4-amino-6-chloro-m-benzenedisulfonamide. Upon determining the physicochemical constants such as acid dissociation constant (pKa), the coexistence of any degraded species is not desirable. However, equilibrium analysis with the effective electrophoretic mobility measured by capillary zone electrophoresis (CZE) can allow the coexistence of such degraded substances. In this study, acid dissociation constants were determined by CZE with hydrochlorothiazide (HCT) under its degraded conditions. Two steps of the successive acid-dissociation constants have been determined with HCT as pKa1 = 8.95±0.04 and pKa2 = 10.66±0.07; the values agree well with those determined with a freshly prepared HCT solution. Further, two steps of the successive acid-dissociation constants were also determined with the degradant from HCT, 4-amino-6-chloro-m-benzenedisulfonamide, by the CZE analysis utilizing the resolution of the degradant from HCT; pKa1 = 9.27±0.06 and pKa2 = 10.79±0.10 were determined. The potential of the equilibrium analysis by CZE was demonstrated with the degradable HCT.

Journal

  • BUNSEKI KAGAKU

    BUNSEKI KAGAKU 66 (7), 509-514, 2017

    The Japan Society for Analytical Chemistry

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