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Analysis, fate and toxicity of chiral non-steroidal anti-inflammatory drugs in wastewaters and the environment: a review.




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.


PETRIE, B. and CAMACHO-MUÑOZ, D. 2021. Analysis, fate and toxicity of chiral non-steroidal anti-inflammatory drugs in wastewaters and the environment: a review. Environmental chemistry letters [online], 19(1), pages 43-75. Available from:

Journal Article Type Review
Acceptance Date Jul 29, 2020
Online Publication Date Aug 20, 2020
Publication Date Feb 28, 2021
Deposit Date Aug 7, 2020
Publicly Available Date Aug 20, 2020
Journal Environmental chemistry letters
Print ISSN 1610-3653
Electronic ISSN 1610-3661
Publisher Springer
Peer Reviewed Peer Reviewed
Volume 19
Issue 1
Article Number 43-75
Keywords Water treatments; Wastewater; Drugs and the environment; Emerging contaminant; Enantiomeric fraction; Metabolite; River; Soil; LC-MS/MS
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