Aminolysis of Benzylpenicillin by Aliphatic Diamines

Kinetics and mechanism of penicillin aminolysis involved in penicillin allergy

“…A knowledge of penicillin aminolysis and other related reactions is fundamental to the understanding of the mechanism for penicillin allergy. Despite of the large amount of works on such reactions (Bundgaard, 1971(Bundgaard, , 1972aSchwartz, 1968Schwartz, , 1969bSchwartz & Wu, 1966;Schneider & de Weck, 1968;Wagner, Davis & Gorman, 1969), the systematic kinetic studies are still lacking. We now report results of more extensive study of the reactions of benzylpenicillin (BPC) with various amines.…”

Chemical aspects of penicillin allergy: imidazole-catalysed penicilloylation

“…In the understanding of penicillin allergy, the most important problem is how to explain the rapid penicilloylation with the €-amino group of tissue protein under physiological pH and temperature. The following chemical aspects for the in vivo formation of penicillin antigen are more acceptable than other possibilities (e.g., see Schneider, 1970) ; (I) intramolecular rapid penicilloylation via combination of the neighbouring functional groups and the €-amino group of lysine (Schneider & de Weck, 1968 ;Schwartz, 1968Schwartz, , 1969. (2) imidazole-catalysed penicilloylation via the highly reactive intermediates of N-penicilloylimidazole (Bundgaard, 1972c;Schneider & de Weck, 1974) or its isomerized product, the penicillenic acid (Bundgaard, 1971(Bundgaard, , 1972a.…”

Pharmaceutical Sciences—1968. A Literature Review of Pharmaceutics

“…In another study, eight antibiotics were used in an investigation of the effect of several organic and inorganic compounds used as adsorbing, suspending, and solubilizing agents (21 8). These included the aminolysis of benzylpenicillin by aliphatic diamines, the catalytic effect of buffers on the degradation of phenoxymethylpenicillin, the stability of aqueous penicillins, and the effect of freezing on the stability of sodium methicillins (219)(220)(221)(222)(223). These included the aminolysis of benzylpenicillin by aliphatic diamines, the catalytic effect of buffers on the degradation of phenoxymethylpenicillin, the stability of aqueous penicillins, and the effect of freezing on the stability of sodium methicillins (219)(220)(221)(222)(223).…”