RT Journal Article
T1 Reaction of phenazone-type drugs and metabolites with chlorine and monochloramine
A1 Sieira Novoa, Benigno José
A1 Quintana Álvarez, José Benito
A1 Cela Torrijos, Rafael
A1 Rodil Rodríguez, María del Rosario
K1 Pharmaceuticals
K1 Transformation products
K1 Chlorination
K1 Monochloramine
K1 Metamizole
K1 Quadrupole-time of flight mass spectrometry
AB 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
PB Elsevier
SN 0048-9697
YR 2020
FD 2020
LK http://hdl.handle.net/10347/26981
UL http://hdl.handle.net/10347/26981
LA eng
NO B. Sieira et al. Science of the Total Environment, 2021, 757, 143770
NO 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.
DS Minerva
RD 7 jun 2026