Radical-derived oxidation products of 5-aminosalicylic acid and N-acetyl-5-aminosalicylic acid.
5-Aminosalicylic acid is an agent effective in the treatment of chronic inflammatory bowel diseases. Its ability to scavenge radicals is considered to be a major factor responsible for its therapeutic efficacy. In this study oxidation products of aminosalicylates with hydroxyl radicals were produced. The compounds that could be discovered by gas chromatographic-mass spectrometric analysis originate from a 1,4-benzoquinone monoimine intermediate which subsequently undergoes multiple reactions such as hydrolysis, reductive 1,4-Michael addition, reoxidation and decarboxylation. Some of these products could represent metabolites formed under in vivo conditions and thus provide a tool for screening biological material from subjects under different clinical conditions.
Fischer
C
C
Dr. Margarete Fischer-Bosch Institute of Clinical Pharmacology, Stuttgart, Germany.
Klotz
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U
D000636:Aminosalicylic Acids / Q000032:analysis / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D016166:Free Radical Scavengers; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods*; D008623:Mercaptoethanol; D019804:Mesalamine; D010084:Oxidation-Reduction
D000636:Aminosalicylic Acids; D016166:Free Radical Scavengers; D019804:Mesalamine; D008623:Mercaptoethanol; C028836:N-acetyl-5-aminosalicylic acid