Stabilization of Ampicillin Analogs in Aqueous Solution. III. Kinetics of Degradation of Ampicillin with Furfural in Aqueous Solution and Physical Properties of Ampicillin-aldehyde Adducts

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The degradation of ampicillin was found to be inhibited due to the formation of a 1 : 1 molar adduct between ampicillin and furfural in alkaline solution. Further, specific base catalysis for the ampicillin-furfural adduct was smaller, about one hundredth, than that for ampicillin-benzaldehyde adduct. Since the adduct formation was not observed at pH<6.00 and the formation constant of the adduct increased with increase of pH, the α-amino group of ampicillin was concluded to participate in the adduct formation. Thus, to estimate the structure of the adduct, various physical properties of samples prepared by freeze-drying of alkaline solution containing ampicillin and an aldehyde (furfural or benzaldehyde) were studied and compared. Nuclear magnetic resonance (NMR) spectra (^1H and ^<13>C), infrared (IR) spectra and the chemical properties of the adducts suggested that they have a Schiff base structure formed from the aldehyde moiety and the free amino group of ampicillin.
社団法人日本薬学会の論文
1982-09-25