Analysis, fate and toxicity of chiral non-steroidal anti-inflammatory drugs in wastewaters and the environment: a review
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REVIEW
Analysis, fate and toxicity of chiral non‑steroidal anti‑inflammatory drugs in wastewaters and the environment: a review Bruce Petrie1 · Dolores Camacho‑Muñoz1 Received: 10 July 2020 / Accepted: 29 July 2020 © The Author(s) 2020
Abstract Non-steroidal anti-inflammatory drugs (NSAIDs) are found in the aquatic environment globally. Such drugs including naproxen, ibuprofen and ketoprofen are chiral molecules. Enantiomers of those drugs have identical physicochemical properties but can behave and interact differently in chiral environments due to differences in their three-dimensional shape. This results in enantiospecific differences in environmental fate and toxicity, which is often overlooked. Therefore, we review the analytical methods, occurrence and fate, and toxicity of chiral non-steroidal anti-inflammatory drugs at the enantiomeric level. The advancement of enantioselective chromatography methods, particularly the use of polysaccharide-based stationary phases, has enabled trace determination of enantiomers in complex environmental matrices. Macrocosm and microcosm studies of engineered and natural environments revealed that such drugs can undergo both enantioselective degradation and chiral inversion. Enantioselectivity has been reported during wastewater treatment, in surface waters and in agricultural soils. The use of microcosms spiked with individual enantiomers over racemates is essential to evaluate these degradation and inversion fate processes. The chiral inversion process whereby one enantiomer converts into its antipode can be significant if the more toxic enantiomers are formed. Existing enantiospecific effect studies report less than an order of magnitude difference in enantiomer toxicity. However, toxicity data for enantiomers are limited and further research is needed to better appreciate the environmental risk at the enantiomeric level. Keywords Emerging contaminant · Enantiomeric fraction · Metabolite · River · Soil · LC–MS/MS
Introduction The presence of pharmaceutical drugs in the environment has been an increasingly active area of research over the last 20 years. NSAIDs are a common therapeutic group of pharmaceuticals used to relieve pain and reduce inflammation. They act via inhibition of the cyclooxygenane isoenzymes (Brune and Patrignani 2015). NSAIDs are mainly excreted in urine as metabolites with a small proportion of the consumed dose being excreted unchanged. For example, 1% or less of naproxen, ibuprofen and ketoprofen is reported to be excreted unchanged in urine (Upton et al. 1980). The extensive use of NSAIDs as prescription and overthe-counter medication results in the presence of µg L−1 concentrations in untreated wastewater (Camacho-Muñoz * Bruce Petrie [email protected] 1
School of Pharmacy and Life Sciences, Robert Gordon University, Aberdeen AB10 7GJ, UK
et al. 2014; Cizmas et al. 2015; Gardner et al. 2013; Kasprzyk-Hordern et al. 2009; Larsson et al. 2014; Petrie et al. 2015; Roberts and Thomas 2006; Tijani et al. 2016). Furthermore, it is not uncommo
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