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Metabolism of niclosamide in sediment and water systems

Graebing, P. W., Chib, J. S., Hubert, T. D., and Gingerich, W. H., 2004, Metabolism of niclosamide in sediment and water systems: Journal of Agricultural and Food Chemistry, v. 52, no. 19, p. 5924-5932.

Abstract

A series of experiments analyzed the kinetics and mechanisms of [¹⁴C]niclosamide degradation. The aerobic aquatic metabolism of [¹⁴C]niclosamide was studied in nonsterile river water/sediment mixtures. Test systems, maintained under aerobic conditions, were treated with niclosamide and incubated in the dark at 25.0 ± 1.0 °C for 30 days. Half-lives of 4.9 and 5.4 days were calculated for the chlorosalicylic acid- and chloronitroaniline-labeled test systems, respectively. From 0 to 21 days after treatment (DAT), the only metabolism product observed in either test system was aminoniclosamide. At the final sampling interval, five peaks were resolved from the chlorosalicylic acid label, and three peaks were resolved from the chloronitroaniline label test substance. By 30 DAT, sediment-bound residues represented ~ 70% of the observed radioactivity. For the anaerobic aquatic metabolism of [¹⁴C]niclosamide, test systems were incubated under anaerobic conditions for 365 days. Half-lives of 0.65 day for the chlorosalicylic acid label and 2.79 days for the chloronitroaniline label were calculated. From 0 to 3 DAT, niclosamide was first transformed into aminoniclosamide. Aminoniclosamide is readily formed, as it was observed in the chlorosalicylic acid label 0 DAT sampling. Several minor metabolites were observed in the water and sediment extracts. None of these metabolites were formed to a significant amount until the parent niclosamide dissipated below the detection limit. Two of the byproducts from these metabolism studies are polar unknowns eluting at 3 and 5 min by HPLC, similar to the unknowns observed in aqueous photolysis studies.

Keywords

niclosamide, lampricide, half-life, aerobic soil metabolism, anaerobic soil metabolism, routine treatment, en laboratoire, rapid loss, lampricide