Demonstration of penicillamine as a product in benzylpenicillenic acid degradation in neutral media using differential pulse polarography.
During the study of the temporal changes of benzylpenicillenic acid in aqueous buffers using differential pulse polarography, penicillamine was found to be a degradation product at neutral pH. Since this result was not previously reported, the effects of pH and buffer concentration on penicillamine formation were investigated. The amount of penicillamine produced was greatest under conditions producing maximum benzylpenicillenic acid stability. Penicillamine was not obtained from benzylpenicilloic acid, the reported degradation product of benzylpenicillenic acid at neutral pH. Penicillamine also was detected in penicillin G solutions of neutral pH. Therefore, it is suggested that penicillamine found in penicillin G solutions arises from benzylpenicillenic acid degradation which, in turn, is produced from penicillin G isomerization. A pathway is proposed to show that penicillamine originates from the UV-absorbing isomer of benzylpenicillenic acid.
D055598:Chemical Phenomena; D002621:Chemistry; D004355:Drug Stability; D006863:Hydrogen-Ion Concentration; D010396:Penicillamine / Q000032:analysis*; D010400:Penicillin G / Q000031:analogs & derivatives*; D011048:Polarography / Q000379:methods
C016262:benzylpenicillenic acid; D010396:Penicillamine; D010400:Penicillin G