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.

在全球水生环境中都发现了非甾体类抗炎药（NSAID）。包括萘普生，布洛芬和酮洛芬的这类药物是手性分子。这些药物的对映异构体具有相同的理化性质，但由于其三维形状的差异，它们在手性环境中的行为和相互作用可能不同。这导致环境命运和毒性的对映体特异性差异，而这种差异常常被忽视。因此，我们综述了手性非甾体类抗炎药在对映体水平上的分析方法，发生和结局以及毒性。对映选择性色谱方法的发展，特别是基于多糖的固定相的使用，使得痕量测定复杂环境基质中的对映异构体成为可能。工程环境和自然环境的宏观和微观研究表明，此类药物可以同时经历对映选择性降解和手性倒置。在废水处理，地表水和农业土壤中，据报道对映选择性。使用外消旋体上掺有单个对映体的缩微缩微胶对于评估这些降解和倒置命运过程至关重要。如果形成毒性更大的对映异构体，则一种对映异构体转化成其对映体的手性转化过程可能很重要。现有的对映体特异性作用研究报告对映体毒性差异小于一个数量级。然而，对映体的毒性数据有限，需要进一步研究以更好地了解对映体水平的环境风险。