Reaction of phenazone-type drugs and metabolites with chlorine and monochloramine
| Autor: | Rafael Cela, Benigno José Sieira, Rosario Rodil, José Benito Quintana |
|---|---|
| Přispěvatelé: | Universidade de Santiago de Compostela. Departamento de Química Analítica, Nutrición e Bromatoloxía, Universidade de Santiago de Compostela. Instituto de Investigación e Análises Alimentarias |
| Rok vydání: | 2020 |
| Předmět: |
Environmental Engineering
010504 meteorology & atmospheric sciences Halogenation Kinetics chemistry.chemical_element 010501 environmental sciences Pyrazole Phenazone 01 natural sciences Medicinal chemistry Water Purification Chemical kinetics chemistry.chemical_compound Reaction rate constant medicine Chlorine Environmental Chemistry Chlorination Monochloramine Waste Management and Disposal Propyphenazone 0105 earth and related environmental sciences Metamizole Chemistry Chloramines Pollution Transformation products Quadrupole-time of flight mass spectrometry Pharmaceutical Preparations Ultrapure water Pharmaceuticals Antipyrine Water Pollutants Chemical medicine.drug |
| Zdroj: | Minerva. Repositorio Institucional de la Universidad de Santiago de Compostela instname |
| ISSN: | 1879-1026 2017-8476 |
| Popis: | This work studies the chlorination and monochloramination reaction kinetics of two phenazone-type drugs (phenazone – Phe and propyphenazone – PrPhe) and three metabolites of phenazone-type drugs (4-formylaminoantipyrine – FAA, 4-aminoantipyrine - AA and 4-acetoamidoantipyrine - AAA). Kinetics were faster with chlorine (apparent second-order constants between 100 and 66,500 times higher) than with monochloramine. For FAA and AAA, no significant reaction was observed during monochloramination. Further, apparent rate constants decreased as the pH increased from pH 5.7 to 8.3, except during chlorination of AA. The transformation products (TPs) formed were also elucidated by liquid chromatography-high resolution mass spectrometry. The main transformation pathway for Phe and PrPhe consisted of halogenations, hydroxylations and dealkylations, while AAA and FAA were firstly transformed to AA, then followed by pyrazole ring opening and hydroxylations. The extend of the reaction was also tested in real water samples, where, in general, slower reaction kinetics were obtained during monochloramination, while the chlorination reaction showed similar half-lives to ultrapure water. Finally, acute and chronic toxicity of the TPs were estimated using two quantitative structure-activity relationship (QSAR) software (ECOSAR and TEST), showing that some TPs could be more toxic than their precursor compounds This research was funded by Xunta de Galicia (ED431C2017/36), Spanish Agencia Estatal de Investigación (ref. CTM2017-84763-C3-R-2) and FEDER/ERDF funds. This research has been co-financed by the European Regional Development Fund through the Interreg V-A Spain-Portugal Programme (POCTEP) 2014–2020 (ref. 0725_NOR_WATER_1_P). It only reflects the author's view, thus Programme authorities are not liable for any use that may be made of the information contained therein. SI |
| Databáze: | OpenAIRE |
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