フロセミドのアルコール-水混合溶媒中における酸加水分解

概要

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As a part of the investigations on the stability of furosemide (4-chloro-N-furfuryl-5-sulfamoylanthranilic acid) (1), acid hydrolysis of 1 was kinetically examined in alcoholwater mixtures. 1 was hydrolyzed with hydrochloric acid in the mixtures to yield 4-chloro-5-sulfamoylanthranilic acid (2) as a main decomposition product, and this degradation of 1 proceeded in pseudo first-order reaction. The hydrolysis rate constant (k_<obs>), when determined at various values of ionic strength (μ), dielectric constant (D) and temperature (T), became greater as these parameters were raised. The activation energies at μ=0.5 and D=55,calculated by Arrhenius equation, were 34.0 kcal/mol in a methanol-water mixture and 39.7 kcal/mol in an ethanol-water mixture. The half-lives (t_<1/2>) at 20°were 19 days and 79 days in methanol-and ethanol-water mixtures, respectively.
公益社団法人日本薬学会の論文
1981-05-25