Deactivation and transformation products in biodegradability testing of β-lactams amoxicillin and piperacillin

Antibiotics have increasingly been detected in effluents and the environment. However, information on the degree of deactivation and mineralization, and the nature of possible formed dead-end transformation products is scarce but desirable for proper risk assessment. An important group of antibiotics is the beta-lactams. We studied the transformation of the closely structurally related beta-lactams piperacillin and amoxicillin in two OECD biodegradability batch tests. None of the antibiotics was biodegraded in the closed bottle test (CBT). However, primary abiotic elimination as monitored by HPLC-UV-VIS was 20% and 100% in the CBT within 14 days, respectively. With HPLC-UV-VIS and ion trap LC-MS/MS primary elimination was shown to be more than 94% for both antibiotics within seven days in the Zahn-Wellens test (ZWT). Both compounds were deactivated by hydrolysis. For piperacillin, a dead-end transformation product resulted after hydrolysis of the beta-lactam ring. For amoxicillin full mineralization of the transformation products was observed. (C) 2008 Elsevier Ltd. All rights reserved.