Oxidation kinetics of cyclophosphamide and methotrexate by ozone in drinking water

Chemosphere

Volumn 79, Issue 11, 2010, Pages 1056-1063

  Garcia Ac, Araceli ^a   Broséus, Romain ^b   Vincent, Simon ^b   Barbeau, Benoit ^b   Prévost, Michèle ^b   Sauvé, Sébastien ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

^b Université Laval   (Canada)

Author keywords

Cytostatic drugs; Drinking water; Mass spectrometry; Ozone; Water treatment

Indexed keywords

DEGRADATION; KINETICS; MASS SPECTROMETRY; OXIDATION; OZONE; OZONIZATION; PHASE SEPARATION; POTABLE WATER; RATE CONSTANTS; WATER QUALITY; WATER TREATMENT;

BENCH SCALE EXPERIMENTS; CYTOSTATIC; DEGRADATION RATE CONSTANTS; ON-LINE SOLID PHASE EXTRACTION; OXIDANT CONCENTRATIONS; SECOND ORDER KINETICS; SIMULTANEOUS DETECTION; TANDEM MASS SPECTROMETRY;

OZONE WATER TREATMENT;

CYCLOPHOSPHAMIDE; DRINKING WATER; HYDROXYL RADICAL; METHOTREXATE; ORGANIC COMPOUND; OZONE;

BIODEGRADATION; BUFFERING; DETECTION METHOD; DRINKING WATER; DRUG; EXPERIMENTAL STUDY; EXTRACTION METHOD; HYDROXYL RADICAL; LINEARITY; MASS SPECTROMETRY; MATRIX; ORGANOCHLORINE; OXIDATION; OZONE; PH; REACTION KINETICS; REACTION RATE; WATER TREATMENT;

ARTICLE; BIODEGRADATION; CONTROLLED STUDY; DEGRADATION KINETICS; DRUG STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; LIQUID CHROMATOGRAPHY; OXIDATION KINETICS; OZONATION; PH; SOLID PHASE EXTRACTION; STRUCTURE ANALYSIS; TANDEM MASS SPECTROMETRY; WASTE WATER MANAGEMENT; WATER ANALYSIS; WATER CONTAMINATION; WATER QUALITY;

CANADA; QUEBEC [CANADA];

EID: 77952550514     PISSN: 00456535     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2010.03.032     Document Type: Article

References (65)

1. 2. J. Am. Water Works Assoc. 2001, 93:90-100.
2. Aherne G.W., Hardcastle A., Nield A.H. Cytotoxic drugs and the aquatic environment - estimation of bleomycin in river and water samples. J. Pharm. Pharmacol. 1990, 42:741-742.
3. Barbeau B., Desjardins R., Mysore C., Prevost M. Impacts of water quality on chlorine and chlorine dioxide efficacy in natural waters. Water Res. 2005, 39:2024-2033.
4. Barbieri A., Sabatini L., Indiveri P., Bonfiglioli R., Lodi V., Violante F.S. Simultaneous determination of low levels of methotrexate and cyclophosphamide in human urine by micro liquid chromatography/electrospray ionization tandem mass spectrometry. Rapid Commun. Mass Sp. 2006, 20:1889-1893.
5. Benotti M.J., Trenholm R.A., Vanderford B.J., Holady J.C., Stanford B.D., Snyder S.A. Pharmaceuticals and endocrine disrupting compounds in US drinking water. Environ. Sci. Technol. 2009, 43:597-603.
6. Buerge I.J., Buser H.R., Poiger T., Muller M.D. Occurrence and fate of the cytostatic drugs cyclophosphamide and ifosfamide in wastewater and surface waters. Environ. Sci. Technol. 2006, 40:7242-7250.
7. Calisto V., Esteves V.I. Psychiatric pharmaceuticals in the environment. Chemosphere 2009, 77:1257-1274.
8. Carballa M., Omil F., Lema J.M. Comparison of predicted and measured concentrations of selected pharmaceuticals, fragrances and hormones in Spanish sewage. Chemosphere 2008, 72:1118-1123.
9. Castiglia L., Miraglia N., Pieri M., Genovese G., Simonelli A., Basilicata P., Sannolo N., Acampora A. Mono- and di-iodocyclophosphamide as possible internal standards for cyclophosphamide quantification: characterization by ion trap multi-stage mass spectrometry and effects of iodine-chlorine substitution on the fragmentation pattern. Rapid Commun. Mass Sp. 2005, 19:1858-1866.
10. Chen Z., Park G., Herckes P., Westerhoff P. Physicochemical treatment of three chemotherapy drugs: irinotecan, tamoxifen, and cyclophosphamide. J. Adv. Oxid. Technol. 2008, 11:254-260.
11. Clara M., Kreuzinger N., Strenn B., Gans O., Kroiss H. The solids retention time - a suitable design parameter to evaluate the capacity of wastewater treatment plants to remove micropollutants. Water Res. 2005, 39:97-106.
12. Daly R.I., Ho L., Brookes J.D. Effect of chlorination on Microcystis aeruginosa cell integrity and subsequent microcystin release and degradation. Environ. Sci. Technol. 2007, 41:4447-4453.
13. Daughton C.G., Ternes T.A. Pharmaceuticals and personal care products in the environment: agents of subtle change?. Environ. Health Persp. 1999, 107:907-938.
14. Elovitz M.S., von Gunten U. Hydroxyl radical ozone ratios during ozonation processes. I-The R-ct concept. Ozone: Sci. Eng. 1999, 21:239-260.
15. Gagnon C., Lajeunesse A., Cejka P., Gagne F., Hausler R. Degradation of selected acidic and neutral pharmaceutical products in a primary-treated wastewater by disinfection processes. Ozone: Sci. Eng. 2008, 30:387-392.
16. Garcia-Ac A., Segura P.A., Gagnon C., Sauve S. Determination of bezafibrate, methotrexate, cyclophosphamide, orlistat and enalapril in waste and surface waters using on-line solid-phase extraction liquid chromatography coupled to polarity-switching electrospray tandem mass spectrometry. J. Environ. Monit. 2009, 11:830-838.
17. Halling-Sorensen B., Nielsen S.N., Lanzky P.F., Ingerslev F., Lutzhoft H.C.H., Jorgensen S.E. Occurrence, fate and effects of pharmaceutical substances in the environment - a review. Chemosphere 1998, 36:357-394.
18. Harris D.C. Quantitative Chemical Analysis 2003, W.H. Freeman & Co., New York.
19. Heberer T., Dunnbier U., Reilich C., Stan H.J. Detection of drugs and drug metabolites in ground water samples of a drinking water treatment plant. Fresen. Environ. Bull. 1997, 6:438-443.
20. Hernandez C., Ramos Y., Fernandez L.A., Ledea O., Bataller M., Veliz E., Besada V., Rosado A. Ozonation of cisplatin in aqueous solution at pH 9. Ozone: Sci. Eng. 2008, 30:189-196.
21. Huber M.M., Canonica S., Park G.Y., Von Gunten U. Oxidation of pharmaceuticals during ozonation and advanced oxidation processes. Environ. Sci. Technol. 2003, 37:1016-1024.
22. Huber M.M., Gobel A., Joss A., Hermann N., Loffler 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, 39:4290-4299.
23. Ikehata K., Naghashkar N.J., Ei-Din M.G. Degradation of aqueous pharmaceuticals by ozonation and advanced oxidation processes: a review. Ozone: Sci. Eng. 2006, 28:353-414.
24. Johnson A.C., Jurgens M.D., Williams R.J., Kummerer K., Kortenkamp A., Sumpter J.P. Do cytotoxic chemotherapy drugs discharged into rivers pose a risk to the environment and human health? An overview and UK case study. J. Hydrol. 2008, 348:167-175.
25. Jolivet J., Cowan K.H., Curt G.A., Clendeninn N.J., Chabner B.A. The pharmacology and clinical use of methotrexate. N. Engl. J. Med. 1983, 309:1094-1104.
26. Jones O.A., Lester J.N., Voulvoulis N. Pharmaceuticals: a threat to drinking water?. Trends Biotechnol. 2005, 23:163-167.
27. Joss A., Andersen H., Ternes T., Richle P.R., Siegrist H. Removal of estrogens in municipal wastewater treatment under aerobic and anaerobic conditions: consequences for plant optimization. Environ. Sci. Technol. 2004, 38:3047-3055.
28. 2. Water Sci. Technol. 2008, 57:195-200.
29. Kummerer K. Antibiotics in the aquatic environment - a review - Part I. Chemosphere 2009, 75:417-434.
30. Kummerer K. Antibiotics in the aquatic environment - a review - Part II. Chemosphere 2009, 75:435-441.
31. Kummerer K., StegerHartmann T., Meyer M. Biodegradability of the anti-tumour agent ifosfamide and its occurrence in hospital effluents and communal sewage. Water Res. 1997, 31:2705-2710.
32. Kummerer K., Al-Ahmad A., Bertram B., Wiessler M. Biodegradability of antineoplastic compounds in screening tests: influence of glucosidation and of stereochemistry. Chemosphere 2000, 40:767-773.
33. Kuo C.Y., Wu H.L., Kou H.S., Chiou S.S., Wu D.C., Wu S.M. Simultaneous determination of methotrexate and its eight metabolites in human whole blood by capillary zone electrophoresis. J. Chromatogr. A 2003, 1014:93-101.
34. Lenz K., Hann S., Koellensperger G., Stefanka Z., Stingeder G., Weissenbacher N., Mahnik S.N., Fuerhacker M. Presence of cancerostatic platinum compounds in hospital wastewater and possible elimination by adsorption to activated sludge. Sci. Total Environ. 2005, 345:141-152.
35. Liu Z.F., Chan K.K., Wang J.J. Tandem mass spectrometric analysis of cyclophosphamide, ifosfamide and their metabolites. Rapid Commun. Mass Sp. 2005, 19:2581-2590.
36. Ljubic I., Sabljic A. Theoretical study of the mechanism and kinetics of gas-phase ozone additions to ethene, fluoroethene, and chloroethene: a multireference approach. J. Phys. Chem. A 2002, 106:4745-4757.
37. Mahnik S.N., Lenz K., Weissenbacher N., Mader R.M., Fuerhacker M. Fate of 5-fluorouracil, doxorubicin, epirubicin, and daunorubicin in hospital wastewater and their elimination by activated sludge and treatment in a membrane-bio-reactor system. Chemosphere 2007, 66:30-37.
38. Matamoros V., Hijosa M., Bayona J.M. Assessment of the pharmaceutical active compounds removal in wastewater treatment systems at enantiomeric level. Ibuprofen and naproxen. Chemosphere 2009, 75:200-205.
39. Mompelat S., Le Bot B., Thomas O. Occurrence and fate of pharmaceutical products and by-products, from resource to drinking water. Environ. Int. 2009, 35:803-814.
40. Ning B., Graham N.J.D. Ozone degradation of iodinated pharmaceutical compounds. J. Environ. Eng. ASCE 2008, 134:944-953.
41. Radjenovic J., Godehardt M., Petrovic M., Hein A., Farre M., Jekel M., Barcelo D. Evidencing generation of persistent ozonation products of antibiotics roxithromycin and trimethoprim. Environ. Sci. Technol. 2009, 43:6808-6815.
42. Reid T., Yuen A., Catolico M., Carlson R.W. Impact of omeprazole on the plasma-clearance of methotrexate. Cancer Chemoth. Pharm. 1993, 33:82-84.
43. Rey R.P., Padron A.S., Leon L.G., Pozo M.M., Baluja C. Ozonation of cytostatics in water medium. Nitrogen bases. Ozone: Sci. Eng. 1999, 21:69-77.
44. Rowney N.C., Johnson A.C., Williams R.J. Cytotoxic drugs in drinking water: a prediction and risk assessment exercise for the Thames catchment in the United Kingdom. Environ. Toxicol. Chem. 2009, 28:2733-2743.
45. Sabljic A., Peijnenburg W. Modeling lifetime and degradability of organic compounds in air, soil, and water systems - (IUPAC technical report). Pure Appl. Chem. 2001, 73:1331-1348.
46. Sanderson H., Thomsen M. Comparative analysis of pharmaceuticals versus industrial chemicals acute aquatic toxicity classification according to the United Nations classification system for chemicals. Assessment of the (Q)SAR predictability of pharmaceuticals acute aquatic toxicity and their predominant acute toxic mode-of-action. Toxicol. Lett. 2009, 187:84-93.
47. Segura P.A., Garcia-Ac A., Lajeunesse A., Ghosh D., Gagnon C., Sauve S. Determination of six anti-infectives in wastewater using tandem solid phase extraction and liquid chromatography-tandem mass spectrometry. J. Environ. Monit. 2007, 9:307-313.
48. Snyder S.A., Wert E.C., Rexing D.J., Zegers R.E., Drury D.D. Ozone oxidation of endocrine disruptors and pharmaceuticals in surface water and wastewater. Ozone: Sci. Eng. 2006, 28:445-460.
49. Snyder, S.A., Wert, E., Lei, H.D., Westerhoff, P., Yoon, Y., 2007. Removal of EDCs and pharmaceuticals in drinking and reuse treatment processes. American Water Works Association Research Founfation (AWWARF), Denver, Colorado, USA.
50. Speitel G.E., Symons J.M., Diehl A.C., Sorensen H.W., Cipparone L.A. Effect of ozone dosage and subsequent biodegradation on removal of DBP precursors. J. Am. Water Works Assoc. 1993, 85:86-95.
51. Stackelberg P.E., Furlong E.T., Meyer M.T., Zaugg S.D., Henderson A.K., Reissman D.B. Persistence of pharmaceutical compounds and other organic wastewater contaminants in a conventional drinking-water treatment plant. Sci. Total Environ. 2004, 329:99-113.
52. Statistica 7.0, S., Inc., Okla., USA.
53. StegerHartmann T., Kummerer K., Hartmann A. Biological degradation of cyclophosphamide and its occurrence in sewage water. Ecotox. Environ. Safe. 1997, 36:174-179.
54. Ternes T.A., Hirsch R., Mueller J., Haberer K. Methods for the determination of neutral drugs as well as betablockers and beta(2)-sympathomimetics in aqueous matrices using GC/MS and LC/MS/MS. Fresen. J. Anal. Chem. 1998, 362:329-340.
55. Ternes T.A., Meisenheimer M., McDowell D., Sacher F., Brauch H.J., Gulde B.H., Preuss G., Wilme U., Seibert N.Z. Removal of pharmaceuticals during drinking water treatment. Environ. Sci. Technol. 2002, 36:3855-3863.
56. Ternes T.A., Stuber 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, 37:1976-1982.
57. 2 molar concentration ratio at different pH values on cyclophosphamide degradation. J. Water Supply Res. T. 2005, 54:403-410.
58. Vieno N.M., Harkki H., Tuhkanen T., Kronberg L. Occurrence of pharmaceuticals in river water and their elimination a pilot-scale drinking water treatment plant. Environ. Sci. Technol. 2007, 41:5077-5084.
59. von Gunten U. Ozonation of drinking water: Part I. Oxidation kinetics and product formation. Water Res. 2003, 37:1443-1467.
60. Wang L., Albasi C., Faucet-Marquis V., Pfohl-Leszkowicz A., Dorandeu C., Marion B., Causserand C. Cyclophosphamide removal from water by nanofiltration and reverse osmosis membrane. Water Res. 2009, 43:4115-4122.
61. Westerhoff P., Yoon Y., Snyder S., Wert E. Fate of endocrine-disruptor, pharmaceutical, and personal care product chemicals during simulated drinking water treatment processes. Environ. Sci. Technol. 2005, 39:6649-6663.
62. Xagoraraki I., Harrington G.W., Zulliger K., Zeier B., Krick W., Karner D.A., Standridge J.H., Westrick J. Inactivation kinetics of the cyanobacterial toxin microcystin-LR by free chlorine. J. Environ. Eng. ASCE 2006, 132:818-823.
63. Zhang Y.J., Geissen S.U., Gal C. Carbamazepine and diclofenac: removal in wastewater treatment plants and occurrence in water bodies. Chemosphere 2008, 73:1151-1161.
64. Zounkova R., Odraska P., Dolezalova L., Hilscherova K., Marsalek B., Blaha L. Ecotoxicity and genotoxicity assessment of cytostatic pharmaceuticals. Environ. Toxicol. Chem. 2007, 26:2208-2214.
65. Zuccato E., Calamari D., Natangelo M., Fanelli R. Presence of therapeutic drugs in the environment. Lancet 2000, 355:1789-1790.