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Stereoisomeric profiling of chiral pharmaceutically active compounds in wastewaters and the receiving environment: a catchment-scale and a laboratory study.

Camacho-Muñoz, Dolores; Petrie, Bruce; Lopardo, Luigi; Proctor, Kathryn; Rice, Jack; Youdan, Jane; Barden, Ruth; Kasprzyk-Hordern, Barbara


Dolores Camacho-Muñoz

Luigi Lopardo

Kathryn Proctor

Jack Rice

Jane Youdan

Ruth Barden

Barbara Kasprzyk-Hordern


Chiral pharmaceutically active compounds (cPACs) are not currently governed by environmental regulation yet are expected to be in the future. As cPACs can exert stereospecific toxicity in the aquatic environment, it is essential to better understand their stereoselective behaviour here. Therefore, this study aims to provide a new perspective towards comprehensive evaluation of cPACs at a river catchment level, including their stereochemistry as a chemical phenomenon driving fate of chiral molecules in the environment. A large spatial and temporal monitoring program was performed in Southwest England. It included 5 sewage treatment works and the receiving waters of the largest river catchment in Southwest England. Simultaneously, lab-scale microcosm studies in simulated activated sludge bioreactors and river water microcosm were performed to evaluate stereoselective degradation of cPACs. A multi-residue enantioselective method allowed the analysis of a total of 18 pairs of enantiomers and 3 single enantiomers in wastewater and river water samples. Our monitoring program revealed: (1) spatial and temporal variations of cPACs in influent wastewaters resulting from different patterns of usage as well as an (2) enantiomeric enrichment of cPACs, likely due to human metabolism, despite their commercialization as racemic mixtures. A similar chiral signature was observed in effluent and receiving waters. Stereoselective degradation was observed in trickling filters (TF) for naproxen, ketoprofen, cetirizine and 10,11-dihydroxy-10-hydroxycarbamazepine, in sequencing batch reactors (SBR) for ifosfamide and in activated sludge (AS) for cetirizine. The extent of enantiomer-specific fate was wastewater treatment dependent in the case of naproxen (TF showed higher stereoselectivity than AS and SBR) and cetirizine (TF and AS showed higher stereoselectivity than SBR) due to differing microbial population. Furthermore, stereoselective degradation of naproxen was highly variable among STWs using similar treatments (TF) and operating in the same region. Microbial stereoselective degradation was also confirmed by both activated and river water simulated microcosm for chloramphenicol, ketoprofen, indoprofen, naproxen and 10,11-dihydroxy-10-hydroxycarbamazepine. Results from our large scale river catchment monitoring study and lab simulated microcosm show wide-ranging implications of enantiomerism of cPACs on environmental risk assessment (ERA). As two enantiomers of the same compound show different biological effects (e.g. toxicity), their non-racemic presence in the environment might lead to inaccurate ERA. This is because current ERA approaches do not require analysis at enantiomeric level.


CAMACHO-MUÑOZ, D., PETRIE, B., LOPARDO, L., PROCTOR, K., RICE, J., YOUDAN, J., BARDEN, R. and KASPRZYK-HORDON, B. 2019. Stereoisomeric profiling of chiral pharmaceutically active compounds in wastewaters and the receiving environment: a catchment-scale and a laboratory study. Environment international [online], 127, pages 558-572. Available from:

Journal Article Type Article
Acceptance Date Mar 21, 2019
Online Publication Date Apr 11, 2019
Publication Date Jun 30, 2019
Deposit Date Apr 12, 2019
Publicly Available Date Apr 15, 2019
Journal Environment International
Print ISSN 0160-4120
Electronic ISSN 1873-6750
Publisher Elsevier
Peer Reviewed Peer Reviewed
Volume 127
Pages 558-572
Keywords Enantioselectivity; Chiral; Microcosm; Activated sludge; River water
Public URL


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