Autocatalytic Degradation and Stability of Obidoxime

The degradation of obidoxime chloride (toxogonin), a reactivator of inhibited cholinesterase in organophosphorus poisoning, in concentrated (250 mg mL(-1)) acidic solutions was studied by HPLC at several temperatures to determine the degradation mechanism. The degradation had an autocatalytic profile, which was found to result from the formation of formaldehyde during the degradation process. The activation energy of the hydrolysis was 26.2 kcal mol(-1). The shelf-life (t90, the time by which 10% of the drug has degraded) at 25 degrees C was calculated by several methods and found to be more than 37 years. Autocatalysis, a mechanism found only rarely in the degradation of pharmaceuticals, has not been reported in previous studies of obidoxime hydrolysis.