Hydroxylamine inactivation of cephalosporins: nucleophilic attack on beta-lactam structures

Cephalosporins are not degraded by hydroxylamine (NH2OH) in neutral and acidic solutions. Their reaction with NH2OH in slightly alkaline solutions leads to microbiological inactivation which seems to be a structure dependent phenomenon. In these experiments the mandelic acid-type compounds appear to be quite stable to the effect of NH2OH, whereas, cefazolin is gradually degraded and the straight chain-containing cephalosporins are variably inactivated. The phenylglycine-type oral cephalosporins were generally sensitive to the alkaline conditions used in these tests and apparently are not inactivated by NH2OH. On the contrary, the phenylglycine-type cephalosporins seem to be somewhat stabilized in the presence of NH2OH.