Evidencing generation of persistent ozonation products of antibiotics roxithromycin and trimethoprim

Environmental Science and Technology

Volumn 43, Issue 17, 2009, Pages 6808-6815

  Radjenovic J ^a   Godehardt, M ^a   Petrovic M ^a   Hein, A ^a   Farre M ^a   Jekel, M ^a   Barcelo D ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

ANTI-MICROBIAL ACTIVITY; ANTI-MICROBIAL AGENT; DIHYDROFOLATE REDUCTASE; DISTILLED WATER; LABORATORY SCALE; MACROLIDES; MATRIX; OH RADICAL; OXIDATION PATHWAY; OZONATION; OZONATION PRODUCTS; PARENT COMPOUNDS; PRODUCT FORMATION; ROXITHROMYCIN; TERTIARY AMINE; TIME OF FLIGHT; TRIMETHOPRIM; TWO-PRODUCT; WASTEWATER EFFLUENTS;

AMINES; ANTIBIOTICS; CHEMICAL OXYGEN DEMAND; FREE RADICALS; OZONE; OZONE WATER TREATMENT; OZONIZATION; WASTEWATER;

EFFLUENTS;

HYDROXIDE; OZONE; RADICAL; ROXITHROMYCIN; TRIMETHOPRIM; WATER;

ANTIBIOTICS; ANTIMICROBIAL ACTIVITY; CHEMICAL COMPOSITION; ENZYME ACTIVITY; OXIDATION; OZONE; REACTION KINETICS; WASTEWATER;

ARTICLE; CHEMICAL REACTION; EFFLUENT; LABORATORY TEST; OXIDATION; OZONATION; TIME OF FLIGHT MASS SPECTROMETRY; WASTE WATER; WASTE WATER MANAGEMENT;

ANIMALS; ANTI-BACTERIAL AGENTS; DAPHNIA; MOLECULAR STRUCTURE; OZONE; ROXITHROMYCIN; TRIMETHOPRIM; WATER POLLUTANTS, CHEMICAL; WATER PURIFICATION;

EID: 69549103661     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es900965a     Document Type: Article

References (24)

1. Hirsch, R.; Ternes, T.; Haberer, K.; Kratz, K.-L. Occurrence of antibiotics in the aquatic environment. Sci. Total Environ. 1999, 225 (1-2), 109-118.
2. Harwood, V. J.; Whitlock, J.; Withington, V. Classification of antibiotic resistance patterns of indicator bacteria by discriminant analysis: Use in predicting the source of fecal contamination in subtropical waters. Appl. Environ. Microbiol. 2000, 66 (9), 3698-3704. (Pubitemid 30691842)
3. Vieno, N. M.;Härkki, H.; Tuhkanen, T.; Kronberg, L. Occurrence of pharmaceuticals in river water and their elimination in a pilot-scale drinking water treatment plant. Environ. Sci. Technol. 2007, 41 (14), 5077-5084.
4. Ternes, T. A.; Stüber, J.; Herrmann, N.; McDowell, D.; Ried, A.; Kampmann, M.; Teiser, B. Ozonation: a tool for removal of pharmaceuticals, contrast media and musk fragrances from wastewater. Water Res. 2003, 37 (8), 1976-1982. (Pubitemid 36403639)
5. Huber, M. M.; Gȯbel, A.; Joss, A.; Hermann, N.; Loḟfler, D.; McArdell, C. S.; Ried, A.; Siegrist, H.; Ternes, T. A.; Von Gunten, U. Oxidation of pharmaceuticals during ozonation of municipal wastewater effluents: A pilot study. Environ. Sci. Technol. 2005, 39 (11), 4290-4299. (Pubitemid 40770262)
6. Von Gunten, U. Ozonation of drinking water: Part I. Oxidation kinetics and product formation. Water Res. 2003, 37 (7), 1443-1467. (Pubitemid 36207560)
7. Buffle, M.-O.; Schumacher, J.; Salhi, E.; Jekel, M.; von Gunten, U. Measurement of the initial phase of ozone decomposition in water and wastewater by means of a continuous quench- flow system: Application to disinfection and pharmaceutical oxidation. Water Res. 2006, 40 (9), 1884-1894.
8. Hoigné, J.; Bader, H. Rate constants of reactions of ozone with organic and inorganic compounds in waters - II: Dissociating organic compounds. Water Res. 1983, 17 (2), 185-194. (Pubitemid 13184984)
9. Huber, M. M.; Ternes, T. A.; Von Gunten, U. Removal of estrogenic activity and formation of oxidation products during ozonation of 17α-ethinylestradiol. Environ. Sci. Technol. 2004, 38 (19), 5177-5186. (Pubitemid 39332051)
10. Mcdowell, D. C.; Huber, M. M.; Wagner, M.; Von Gunten, U.; Ternes, T. A. Ozonation of carbamazepine in drinking water: Identification and kinetic study of major oxidation products. Enivron. Sci. Technol. 2005, 39 (20), 8014-8022.
11. Huber,M.M.; Canonica, S.; Park, G.-Y.;VonGunten, U. Oxidation of pharmaceuticals during ozonation and advanced oxidation processes. Enivron. Sci. Technol. 2003, 37 (5), 1016-1024.
12. Gagné, F.; Blaise, C.; André, C. Occurrence of pharmaceutical products in a municipal effluent and toxicity to rainbow trout (Oncorhynchus mykiss) hepatocytes. Ecotoxicol. Environ. Saf. 2006, 64 (3), 329-336.
13. Yang, L. H.; Ying, G. G.; Su, H. C.; Stauber, J. L.; Adams, M. S.; Binet, M. T. Growth-inhibiting effects of 12 antibacterial agents and their mixtures on the freshwater microalga Pseudokirchneriella subcapitata. Environ. Toxicol. Chem. 2008, 27 (5), 1201-1208.
14. Syracuse Research Corporation Physical Properties database, www.syrres.com.
15. Eichhorn, P.; Ferguson, P. L.; Peérez, S.; Aga, D. S. Application of ion trap-MS with H/D exchange and QqTOF-MS in the identification of microbial degradates of trimethoprim in nitrifying activated sludge. Anal. Chem. 2005, 77 (13), 4176-4184.
16. Drewes, J. E.; Jekel,M.Behavior ofDOCandAOXusing advanced treated wastewater and groundwater recharge. Water Res. 1998, 32 (10), 3125-3133.
17. Dodd, M. C.; Buffle, M.-O.; von Gunten, U. Oxidation of antibacterial molecules by aqueous ozone: moiety-specific reaction kinetics and application to ozone-based wastewater treatment. Environ. Sci. Technol. 2006, 40 (6), 1969-1977.
18. Pérez-Estrada, L. A.; Malato, S.; Gernjak, W.;Agu̇era, A.; Thurman, E. M.; Ferrer, I.; Fernández-Alba, A. R. Photo-fenton degradation of diclofenac: Identification of main intermediates and degradation pathway. Environ. Sci. Technol. 2005, 39 (21), 8300-8306.
19. Schlu̇nzen, F.; Zarivach, R.; Harms, J.; Bashan, A.; Tocilj, A.; Albrecht, R.; Yonath, A.; Franceschi, F. Structural basis for the interaction of antibiotics with the peptidyl transferase centre in eubacteria. Nature 2001, 413 (6858), 814-821. (Pubitemid 33026843)
20. Lange, F.; Cornelissen, S.; Kubac, D.; Sein, M. M.; von Sonntag, J.; Hannich, C. B.; Golloch, A.; Heipieper, H. J.; Moḋer, M.; von Sonntag, C. Degradation of macrolide antibiotics by ozone: A mechanistic case study with clarithromycin. Chemosphere 2006, 65 (1), 17-23. (Pubitemid 44150591)
21. Qiang, Z. M.; Adams, C. Potentiometric determination of acid dissociation constants (pK(a)) for human and veterinary antibiotics. Water Res. 2004, 38 (12), 2874-2890. (Pubitemid 38829579)
22. Roth, B.; Strelitz, J. Z. The protonation of 2,4-diaminopyrimidines. I. Dissociation constants and substituent effects. J. Org. Chem. 1969, 34, 821-836.
23. Bailey, P. S. The reactions of ozone with organic compounds. Chem. Rev. 1958, 58 (5), 925-1010.
24. Walsh, C. Antibiotics: Actions, Origins, Resistance; ASM Press: Washington, DC, 2003.