High-resolution MS and MSn investigation of ozone oxidation products from phenazone-type pharmaceuticals and metabolites

Favier, Maxime; Dewil, Raf; Eyck, Kwinten Van; Schepdael, Ann Van; Cabooter, Deirdre

doi:10.1016/j.chemosphere.2015.04.010

Cited by 32 publications

(13 citation statements)

References 27 publications

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“…This mechanism was previously described by Gómez and coworkers [10] for methylaminoantipyrine (MAA, an intermediate in the metabolic pathway of metamizole) and is adapted to the molecules studied here. The same ring opening mechanism has also been observed during the ozonation of phenazone by Favier and coworkers [27]. UV photodegradation experiments on FAA have also been conducted by Gómez et al [10], using simulated solar UV radiation over 209 hours of exposure.…”

Section: Identification Of Photolysis Degradation Productssupporting

confidence: 57%

“…This reconstruction was facilitated by the fact that the structure of the parent compound was known, making the transformation products "known unknowns" as they are unknown compounds originating from a known compound. This approach has been reported previously [6,10,27]. The exact masses of the transformation products identified in this study and their MS n fragments (where available) are given in Section S-2 in the supporting information, together with their proposed molecular formula, ring double bond (RDB) values and mass accuracy (in ppm).…”

Section: Lc/ms Methodologymentioning

confidence: 81%

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High-Resolution MS and MSn Investigation of UV Oxidation Products of Phenazone-type Pharmaceuticals and Metabolites

2018

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The occurrence of phenazone-type analgesics, such as aminopyrine, metamizole, phenazone and propyphenazone, has been reported in the effluent of wastewater treatment plants in µg/L concentrations. The presence of the main metabolites of aminopyrine and metamizoleacetamido antipyrine and formyl aminoantipyrinehas even been detected in sub µg/L concentrations in surface water and water bodies used to produce drinking water. This points at their high persistence and the need for adequate removal strategies. The degradation of phenazone, propyphenazone, acetamido antipyrine and formyl aminoantipyrine by UV radiation was investigated under laboratory conditions. An elucidation approach based on high-resolution mass spectrometry resulted in the identification of 11 degradation products. A mechanism of ring opening via the oxidation of the N-N bond of the pyrazolone ring was observed as well as the more typical oxidation of carbon-carbon double bonds. Aside from the degradation products, the capacity of formyl aminoantipyrine to produce trimers and dimers was demonstrated. The dimers were shown to be persistent despite continuous UV radiation. The toxicity of the degradation products was assessed by quantitative structure-activity relationships. It was shown that, when the carbon-carbon double bond is partially oxidized to an epoxy, the toxicity towards fish and daphnids is increased with respect to the parent compound.

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Section: Identification Of Photolysis Degradation Productssupporting

confidence: 57%

Section: Lc/ms Methodologymentioning

confidence: 81%

High-Resolution MS and MSn Investigation of UV Oxidation Products of Phenazone-type Pharmaceuticals and Metabolites

2018

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“…To assess the potential acute and chronic toxicity of the identified degradation products, the ECOSAR (ECOlogical Structure-Activity Relationship) predictive model, developed by the US Environmental Protection Agency was used as done in previous literature [19,20]. In terms of acute toxicity, 96-h Half Lethal Concentration (LC 50 ) for fish, 48-h LC 50 for daphnia and 96-h…”

Section: Ecosar Screeningmentioning

confidence: 99%

Degradation of sulfamethoxazole by heat-activated persulfate oxidation: Elucidation of the degradation mechanism and influence of process parameters

Milh

Schoenaers

Stesmans

et al. 2020

Chemical Engineering Journal

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“…The level of pharmaceutical metabolites and parent compounds in surface waters has increased in both treated waste water and drinking water. This problem was addressed when a LTQ Orbitrap was used to provide better data for these complex matrices [ 52 ]. Mycotoxins and pesticide residues in agricultural products have become a serious human health concern.…”

Section: Orbitrapmentioning

confidence: 99%

Fourier Transform Mass Spectrometry: The Transformation of Modern Environmental Analyses

Lim

Yan

Bach

et al. 2016

IJMS

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Unknown compounds in environmental samples are difficult to identify using standard mass spectrometric methods. Fourier transform mass spectrometry (FTMS) has revolutionized how environmental analyses are performed. With its unsurpassed mass accuracy, high resolution and sensitivity, researchers now have a tool for difficult and complex environmental analyses. Two features of FTMS are responsible for changing the face of how complex analyses are accomplished. First is the ability to quickly and with high mass accuracy determine the presence of unknown chemical residues in samples. For years, the field has been limited by mass spectrometric methods that were based on knowing what compounds of interest were. Secondly, by utilizing the high resolution capabilities coupled with the low detection limits of FTMS, analysts also could dilute the sample sufficiently to minimize the ionization changes from varied matrices.

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High-resolution MS and MSn investigation of ozone oxidation products from phenazone-type pharmaceuticals and metabolites

Cited by 32 publications

References 27 publications

High-Resolution MS and MSn Investigation of UV Oxidation Products of Phenazone-type Pharmaceuticals and Metabolites

High-Resolution MS and MSn Investigation of UV Oxidation Products of Phenazone-type Pharmaceuticals and Metabolites

Degradation of sulfamethoxazole by heat-activated persulfate oxidation: Elucidation of the degradation mechanism and influence of process parameters

Fourier Transform Mass Spectrometry: The Transformation of Modern Environmental Analyses

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