Photolytic and photocatalytic degradation of nitrofurantoin and its photohydrolytic products

Szabó-Bárdos, Erzsébet; Cafuta, Andrea; Hegedűs, Péter; Fónagy, Orsolya; Kiss, Gyula; Babić, Sandra; Škorić, Irena; Horváth, Ottó

doi:10.1016/j.jphotochem.2019.112093

Cited by 27 publications

(8 citation statements)

References 34 publications

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“…This can lead to a decrease in performance, unstable absorption, and undocumented side effects. Cocrystallization proves to be an effective strategy to prevent drug degradation on exposure to light. , For instance, NFT is prone to photoisomerization on a CN double bond, leading to its decomposition into 5-nitro-2-furaldehyde and 1-aminohydantoin, while NFT cocrystals have been reported to possess higher photostability in comparison to the original drug. , …”

Section: Resultsmentioning

confidence: 99%

“…Cocrystallization proves to be an effective strategy to prevent drug degradation on exposure to light. 128,129 For instance, NFT is prone to photoisomerization on a CN double bond, leading to its decomposition into 5nitro-2-furaldehyde and 1-aminohydantoin, 130 while NFT cocrystals have been reported to possess higher photostability in comparison to the original drug. 40,41 In the present work, the photostability of nitrofurantoin cocrystals has also been studied.…”

Section: Solubility and Solutionmentioning

confidence: 99%

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Extending the Range of Nitrofurantoin Solid Forms: Effect of Molecular and Crystal Structure on Formation Thermodynamics and Physicochemical Properties

Surov

Voronin

Drozd

et al. 2022

Crystal Growth & Design

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In this work, four novel pharmaceutical cocrystals of nitrofurantoin, an antibacterial drug, with isonicotinamide, picolinamide, 2-hydroxybenzamide, and 2-aminobenzamide have been obtained and thoroughly characterized by various analytical techniques. The crystal structures of the solid forms have been elucidated by single-crystal X-ray diffraction, and the energy distribution of intermolecular interactions has been further quantified on the basis of QTAIMC analysis. Eight distinct supramolecular heterosynthons of hydrogen bonding have been identified in the studied crystals, and their relative stability has been ranked in terms of total interaction energies. The thermodynamics of the cocrystallization reactions has been systematically investigated using two independent experimental techniques, namely solution calorimetry and phase solubility diagram, which allowed us to assess both the enthalpic and the entropic contributions to the cocrystal formation driving force. The pH-solubility behavior of the cocrystals has been investigated at different pH values using eutectic concentrations of the components. Although all of the cocrystals reported here were found to be more soluble than the parent drug, their advantage in thermodynamic solubility did not translate into enhanced dissolution performance due to a rapid solution-mediated phase transformation in aqueous media. In addition, the effect of cocrystallization on other pharmaceutically relevant properties of nitrofurantoin, including photostability and membrane permeability, has been considered and analyzed.

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Section: Resultsmentioning

confidence: 99%

Section: Solubility and Solutionmentioning

confidence: 99%

Extending the Range of Nitrofurantoin Solid Forms: Effect of Molecular and Crystal Structure on Formation Thermodynamics and Physicochemical Properties

Surov

Voronin

Drozd

et al. 2022

Crystal Growth & Design

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“…However, to obtain such efficiency, a UV source of relatively high power (250 W) was applied. Szabó-Bárdos et al [ 25 ] focused on nitrofurantoin photodegradation, and starting with a concentration of 10 mg L −1 , they obtained nearly 100% degradation after 80 min. Nevertheless, in both mentioned papers, no information was given on total mineralization; thus only an estimation of the degradation effectiveness could have been made.…”

Section: Discussionmentioning

confidence: 99%

“…At first, the double bond configuration in the NFZ molecule changes (photoisomerization occurs), and these changes are followed by the shortening of the molecule’s chain at the furan ring. Assuming that the breakdown will be analogous to that of nitrofurantoin (described by [ 25 ]), the resulting compounds contain more hydroxyl groups than NFZ and practically no amino groups. Moreover, the furan ring is relatively stable and degrades at further stages of the process.…”

Section: Discussionmentioning

confidence: 99%

Nitrofurazone Removal from Water Enhanced by Coupling Photocatalysis and Biodegradation

Smułek

Bielan

Pacholak

et al. 2021

IJMS

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(1) Background: Environmental contamination with antibiotics is particularly serious because the usual methods used in wastewater treatment plants turn out to be insufficient or ineffective. An interesting idea is to support natural biodegradation processes with physicochemical methods as well as with bioaugmentation with efficient microbial degraders. Hence, the aim of our study is evaluation of the effectiveness of different methods of nitrofurazone (NFZ) degradation: photolysis and photodegradation in the presence of two photocatalysts, the commercial TiO2-P25 and a self-obtained Fe3O4@SiO2/TiO2 magnetic photocatalyst. (2) Methods: The chemical nature of the photocatalysis products was investigated using a spectrometric method, and then, they were subjected to biodegradation using the strain Achromobacter xylosoxidans NFZ2. Additionally, the effects of the photodegradation products on bacterial cell surface properties and membranes were studied. (3) Results: Photocatalysis with TiO2-P25 allowed reduction of NFZ by over 90%, demonstrating that this method is twice as effective as photolysis alone. Moreover, the bacterial strain used proved to be effective in the removal of NFZ, as well as its intermediates. (4) Conclusions: The results indicated that photocatalysis alone or coupled with biodegradation with the strain A. xylosoxidans NFZ2 leads to efficient degradation and almost complete mineralization of NFZ.

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“…However, the degradation of tetracycline has been explored using a variety of other metal oxide nanomaterials, often in photo-responsive heterojunctions, such as those based on ZnO [180,181], tungsten oxides [182,183], or bismuthmolybdenum mixed oxide [184]. Other antibiotics raising interest as water contaminants are levofloxacin [185], nitrofurantoin [186], metronidazole [187], and sulfamethoxazole [188]. Metal oxide nanomaterials have been also used in the catalytic and photocatalytic degradation of several anti-inflammatory and analgesic compounds, such as acetaminophen (well-known as paracetamol) through catalysts based on TiO 2 [189], WO 3 [190], ZnO [191], CuO Fe x O y or Co 3 O 4 [141,192].…”

Section: Other Pharmaceuticalsmentioning

confidence: 99%

Recent Advances in Endocrine Disrupting Compounds Degradation through Metal Oxide-Based Nanomaterials

et al. 2022

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Endocrine Disrupting Compounds (EDCs) comprise a class of natural or synthetic molecules and groups of substances which are considered as emerging contaminants due to their toxicity and danger for the ecosystems, including human health. Nowadays, the presence of EDCs in water and wastewater has become a global problem, which is challenging the scientific community to address the development and application of effective strategies for their removal from the environment. Particularly, catalytic and photocatalytic degradation processes employing nanostructured materials based on metal oxides, mainly acting through the generation of reactive oxygen species, are widely explored to eradicate EDCs from water. In this review, we report the recent advances described by the major publications in recent years and focused on the degradation processes of several classes of EDCs, such as plastic components and additives, agricultural chemicals, pharmaceuticals, and personal care products, which were realized by using novel metal oxide-based nanomaterials. A variety of doped, hybrid, composite and heterostructured semiconductors were reported, whose performances are influenced by their chemical, structural as well as morphological features. Along with photocatalysis, alternative heterogeneous advanced oxidation processes are in development, and their combination may be a promising way toward industrial scale application.

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Photolytic and photocatalytic degradation of nitrofurantoin and its photohydrolytic products

Cited by 27 publications

References 34 publications

Extending the Range of Nitrofurantoin Solid Forms: Effect of Molecular and Crystal Structure on Formation Thermodynamics and Physicochemical Properties

Extending the Range of Nitrofurantoin Solid Forms: Effect of Molecular and Crystal Structure on Formation Thermodynamics and Physicochemical Properties

Nitrofurazone Removal from Water Enhanced by Coupling Photocatalysis and Biodegradation

Recent Advances in Endocrine Disrupting Compounds Degradation through Metal Oxide-Based Nanomaterials

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