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Acta Crystallographica. Section E,... Mar 2008The title compound, C(19)H(17)ClN(4)O(3)S, is a Schiff base compound of 5-chloro-salicylaldehyde and sulfamethazine...
The title compound, C(19)H(17)ClN(4)O(3)S, is a Schiff base compound of 5-chloro-salicylaldehyde and sulfamethazine [4-amino-N-(4,6-dimethyl-2-pyrimidin-yl)benzene-sulfonamide]. The geometry around the S atom is distorted tetra-hedral, comprising two O atoms of the sulfonyl group, a C atom of a benzene ring and the amino N atom. The title compound has an intra-molecular O-H⋯N hydrogen bond and two inter-molecular C-H⋯O and N-H⋯O hydrogen bonds, which link neighbouring mol-ecules into 10-membered rings. As a result of an unavoidable conformational arrangement, a slightly short intra-molecular contact of distance 2.59 Å exists between an O atom of the sulfonyl group and an H atom of the sulfamethazine benzene ring.
PubMed: 21202046
DOI: 10.1107/S1600536808005606 -
Ecotoxicology and Environmental Safety Oct 2022Antibiotic residue has become an emerging environmental contaminant, while the toxicological effects and underlying mechanisms caused by the co-exposure to multiple...
Antibiotic residue has become an emerging environmental contaminant, while the toxicological effects and underlying mechanisms caused by the co-exposure to multiple veterinary antibiotics were rarely studied. In this study, male Sprague Dawley rats were exposed to monensin (M) (1, 2, 10 mg/(kg·body weight (BW)) combined with sulfamethazine (S) (60, 120, 600 mg/(kg·BW)) or single drugs for 28 consecutive days. The body weight, hematological and blood biochemical parameters, organ coefficients, and histopathology were analyzed to discover their combined toxicity effect. Transcriptomic analysis was used to reveal the possible mechanisms of their joint toxicity. Compared with the control group, the weight gain rate was significantly reduced in the H-M+S and H-S, and alkaline phosphatase in H-M+S was significantly increased. Furthermore, relative liver and kidneys weight was significantly increased, and the liver of H-M+S showed more severe lesions in histopathological analysis. For H-M+S, H-M and H-S, transcriptomic results showed that 344, 246, and 99 genes were differentially expressed, respectively. The Gene Ontology terms mainly differ in sterol biosynthetic process and steroid hydroxylase activity. The Kyoto Encyclopedia of Genes and Genome pathways showed abnormal retinol metabolism, metabolism of xenobiotics by cytochrome P450, and drug metabolism-cytochrome 450; the common 30 genes were screened from the network of protein-protein interaction. The results showed that mixed contamination of M and S produces hepatotoxicity by interfering with linoleic acid metabolism, retinol metabolism and CYP450 enzyme-dominated drug metabolism. Further analysis showed that Cyp1a2, Cyp2c61, Ugt1a3, and Ugt1a5 might be the key genes. These findings could provide more evidence for investigating the toxic effects and metabolism of mixed antibiotics contamination in mammals.
Topics: Alkaline Phosphatase; Animals; Anti-Bacterial Agents; Body Weight; Cytochrome P-450 CYP1A2; Cytochrome P-450 Enzyme System; Linoleic Acid; Liver; Male; Mammals; Monensin; Rats; Rats, Sprague-Dawley; Steroid Hydroxylases; Sterols; Sulfamethazine; Transcriptome; Vitamin A; Xenobiotics
PubMed: 36155339
DOI: 10.1016/j.ecoenv.2022.114110 -
International Journal of Environmental... Feb 2022Duckweed () has the potential to treat anaerobically digested swine wastewater (ADSW), but the effects of antibiotics and heavy metals in ADSW on the treatment...
Duckweed () has the potential to treat anaerobically digested swine wastewater (ADSW), but the effects of antibiotics and heavy metals in ADSW on the treatment performance and mechanism of are not clear. Herein, an experiment was conducted to investigate the effects of sulfamethazine (SMZ) and cupric ion on NH4+-N and total phosphorus (TP) removal from synthetic ADSW. The activity of superoxide dismutase (SOD) and the contents of photosynthetic pigments, vitamin E, and proteins in duckweed were also evaluated. Under the stress of SMZ, duckweed showed excellent removal efficiency of nutrients, and the results of SOD activity and photosynthetic pigments content indicated that duckweed had good tolerance to SMZ. Interestingly, a combined application of SMZ and cupric ion would inhibit the nutrient removal by duckweed, but significantly increased the contents of photosynthetic pigments, proteins, and vitamin E. In addition, the consequence indicated that high value-added protein and vitamin E products could be produced and harvested by cultivating duckweed in ADSW. Furthermore, possible degradation pathways of SMZ in the duckweed system were proposed based on the analysis with LC-MS/MS. This research proposed a novel view for using duckweed system to remove nutrients from ADSW and produce value-added products under the stress of SMZ and cupric ion.
Topics: Animals; Araceae; Chromatography, Liquid; Sulfamethazine; Swine; Tandem Mass Spectrometry; Wastewater
PubMed: 35206138
DOI: 10.3390/ijerph19041949 -
Biophysical Reviews Apr 2021Sulfonamide (or sulphonamide) functional group chemistry (SN) forms the basis of several groups of drug. In vivo sulfonamides exhibit a range of pharmacological... (Review)
Review
Sulfonamide (or sulphonamide) functional group chemistry (SN) forms the basis of several groups of drug. In vivo sulfonamides exhibit a range of pharmacological activities, such as anti-carbonic anhydrase and anti-t dihydropteroate synthetase allowing them to play a role in treating a diverse range of disease states such as diuresis, hypoglycemia, thyroiditis, inflammation, and glaucoma. Sulfamethazine (SMZ) is a commonly used sulphonamide drug in veterinary medicine that acts as an antibacterial compound to treat livestock diseases such as gastrointestinal and respiratory tract infections. Sulfadiazine (SDZ) is another frequently employed sulphonamide drug that is used in combination with the anti-malarial drug pyrimethamine to treat toxoplasmosis in warm-blooded animals. This study explores the research findings and the work behaviours of SN (SMZ and SDZ) drugs. The areas covered include SN drug structure, SN drug antibacterial activity, SN drug toxicity, and SN environmental toxicity.
PubMed: 33936318
DOI: 10.1007/s12551-021-00795-9 -
International Journal of Nanomedicine 2021Sulfamethazine (SMZ) exposed in the environment can enter the human body through the food chain and pose a serious threat to human health. Therefore, it is important to...
PURPOSE
Sulfamethazine (SMZ) exposed in the environment can enter the human body through the food chain and pose a serious threat to human health. Therefore, it is important to develop a rapid and sensitive method for detecting SMZ in environmental samples. In order to fastly and quantitatively detect SMZ in environmental samples, we developed a label-free fluorescent aptasensor based on specific aptamer (SMZ1S) and fluorescence resonance energy transfer (FRET) between gold nanoparticles (AuNPs) and rhodamine B (RhoB).
METHODS
In the absence of SMZ, SMZ1S was adsorbed on the surface of AuNPs, which led to dispersion of the AuNPs in high concentration saline solution, thus effectively quenching the fluorescence of RhoB. With the increase of the SMZ concentration, the specific binding of SMZ1S and SMZ led to the aggregation of AuNPs in the presence of NaCl, which reduced the quenching of RhoB fluorescence and increased the fluorescence intensity. The sensitivity and linearity curve of the label-free fluorescent aptasensor were determined with different concentrations of sulfamethazine standard solutions. The specificity of this fluorescent aptasensor was determined by replacing sulfamethazine with different antibiotics. In addition, the actual water and soil samples were spiked and recovered.
RESULTS
Under optimized conditions, the proposed fluorescent aptasensor demonstrated a good linear detection of SMZ in binding buffer from 1.25 ng mL to 40 ng mL and the limit of detection was 0.82 ng mL. The spiked recoveries for SMZ were 94.4% to 108.8% with a relative standard deviation of 1.8-10.3% in water and soil samples, respectively.
CONCLUSION
The label-free fluorescent aptasensor investigated in the current study is a promising tool to detect and quantify SMZ in water and soil samples.
Topics: Aptamers, Nucleotide; Biosensing Techniques; Dynamic Light Scattering; Gold; Humans; Limit of Detection; Metal Nanoparticles; Soil; Spectrometry, Fluorescence; Staining and Labeling; Sulfamethazine; Water
PubMed: 33859476
DOI: 10.2147/IJN.S307080 -
Environmental Monitoring and Assessment Jan 2022The effects of pharmaceuticals on the nitrogen cycle in water and soil have recently become an increasingly important issue for environmental research. However, a few... (Review)
Review
The effects of pharmaceuticals on the nitrogen cycle in water and soil have recently become an increasingly important issue for environmental research. However, a few studies have investigated the direct effects of pharmaceuticals on the nitrogen cycle in water and soil. Pharmaceuticals can contribute to inhibition and stimulation of nitrogen cycle processes in the environment. Some pharmaceuticals have no observable effect on the nitrogen cycle in water and soil while others appeared to inhibit or stimulate for it. This review reports on the most recent evidence of effects of pharmaceuticals on the nitrogen cycle processes by examination of the potential impact of pharmaceuticals on nitrogen fixation, nitrification, ammonification, denitrification, and anammox. Research studies have identified pharmaceuticals that can either inhibit or stimulate nitrification, ammonification, denitrification, and anammox. Among these, amoxicillin, chlortetracycline, ciprofloxacin, clarithromycin, enrofloxacin, erythromycin, narasin, norfloxacin, and sulfamethazine had the most significant effects on nitrogen cycle processes. This review also clearly demonstrates that some nitrogen transformation processes such as nitrification show much higher sensitivity to the presence of pharmaceuticals than other nitrogen transformations or flows such as mineralization or ammonia volatilization. We conclude by suggesting that future studies take a more comprehensive approach to report on pharmaceuticals' impact on the nitrogen cycle process.
Topics: Anaerobic Ammonia Oxidation; Denitrification; Environmental Monitoring; Nitrification; Nitrogen; Nitrogen Cycle; Pharmaceutical Preparations; Soil; Water
PubMed: 35044585
DOI: 10.1007/s10661-022-09754-7 -
Acta Crystallographica. Section E,... Feb 2013In the asymmetric unit of the title co-crystal, C(12)H(14)N(4)O(2)S·C(7)H(5)NO(4), the sulfamethazine and 2-nitro-benzoic acid mol-ecules form a heterodimer through...
In the asymmetric unit of the title co-crystal, C(12)H(14)N(4)O(2)S·C(7)H(5)NO(4), the sulfamethazine and 2-nitro-benzoic acid mol-ecules form a heterodimer through inter-molecular amide-carb-oxy-lic acid N-H⋯O and carb-oxy-lic acid-pyrimidine O-H⋯N hydrogen-bond pairs, giving a cyclic motif [graph set R(2) (2)(8)]. The dihedral angle between the two aromatic ring systems in the sulfamethazine mol-ecule is 88.96 (18)° and the nitro group of the acid is 50% rotationally disordered. Secondary aniline N-H⋯O(sulfone) hydrogen-bonding associations give a two-dimensional structure lying parallel to the ab plane.
PubMed: 23424513
DOI: 10.1107/S1600536813000779 -
Acta Crystallographica. Section C,... Mar 2023Sulfamethazine [N-(4,6-dimethylpyrimidin-2-yl)sulfanilamide] is an antimicrobial drug that possesses functional groups capable of acting as hydrogen-bond donors and...
Sulfamethazine [N-(4,6-dimethylpyrimidin-2-yl)sulfanilamide] is an antimicrobial drug that possesses functional groups capable of acting as hydrogen-bond donors and acceptors, which make it a suitable supramolecular building block for the formation of cocrystals and salts. We report here the crystal structure and solid-state characterization of the 1:1 salt piperidinium sulfamethazinate (PPD·SUL, CHN·CHNOS) (I). The salt was obtained by the solvent-assisted grinding method and was characterized by IR spectroscopy, powder X-ray diffraction, solid-state C NMR spectroscopy and thermal analysis [differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA)]. Salt I crystallized in the monoclinic space group P2/n and showed a 1:1 stoichiometry revealing proton transfer from SUL to PPD to form salt I. The PPD and SUL ions are connected by N-H...O and N-H...N interactions. The self-assembly of SUL anions displays the amine-sulfa C(8) motif. The supramolecular architecture of salt I revealed the formation of interconnected supramolecular sheets.
PubMed: 36871288
DOI: 10.1107/S2053229622012050 -
Yakugaku Zasshi : Journal of the... 2018The increasing prevalence of antimicrobial resistance (AMR) has caused intractable infections worldwide. Nearly 50% of the healthy population of Southeast Asia... (Review)
Review
The increasing prevalence of antimicrobial resistance (AMR) has caused intractable infections worldwide. Nearly 50% of the healthy population of Southeast Asia carries extended-spectrum β-lactamase (ESBL)-producing Escherichia coli. The overuse of antimicrobial agents in the agriculture, aquaculture, and medical care sectors causes environmental pollution, facilitating the spread of AMR. However, there is a lack of data pertaining to antimicrobial residues in environmental water in such regions. We investigated a total of 49 chemicals, including β-lactams, sulfonamides, quinolones, and tetracyclines. Water samples were collected from rivers in city centers, and ponds in livestock and aquaculture farms, in Ha Noi, Thai Binh, and Can Tho in Vietnam. We detected antimicrobial agents at 87 of 111 sampling sites (78.4%). Among the target analytes, sulfamethoxazole, sulfamethazine, trimethoprim, cephalexin, and ofloxacin were detected frequently. The residual levels of each antimicrobial agent ranged from 0.1 to 10000 ng/L. Moreover, we detected multi-drug resistant E. coli in fishes sampled from these rivers, suggesting unwanted effects of antimicrobial residues in the environment.
Topics: Animals; Anti-Bacterial Agents; Drug Resistance, Multiple; Escherichia coli; Fishes; Fresh Water; Vietnam; Water Pollutants, Chemical; Water Pollution, Chemical
PubMed: 29503415
DOI: 10.1248/yakushi.17-00177-1 -
Veterinary World Dec 2019Sulfamethazine (SMZ) is an important and widely used antibiotic in poultry industry due to its high efficacy in fighting diseases and promoting growth. In addition, SMZ...
BACKGROUND AND AIM
Sulfamethazine (SMZ) is an important and widely used antibiotic in poultry industry due to its high efficacy in fighting diseases and promoting growth. In addition, SMZ is a possible human carcinogen and has been found in many food types including poultry meat. Accordingly, this study aimed to survey the contamination level and estimated daily intake (EDI) of SMZ in domestic and imported poultry meat samples in Jordan.
MATERIALS AND METHODS
A total of 120 samples; 60, 30, and 30 of fresh and frozen domestic and frozen imported poultry samples, respectively, were collected from different cities in Jordan. Poultry samples were analyzed for SMZ incidence rate and contamination level using a competitive enzyme-linked immunosorbent assay technique. EDI values were calculated from the SMZ concentration, average poultry daily consumption rate, and adult body weight (b.w.).
RESULTS
Of the 120 surveyed samples, 20 samples (16.7%) were SMZ violative positive and exceeded the European Union maximum limit (100 µg/kg) and accordingly were unfit for human consumption. Whereas, 51 samples (42.5%) were with SMZ concentrations of 10-100 µg/kg. The average SMZ concentration was 235.58 µg/kg, with a range of 11.47-800 µg/kg poultry meat. It is also noteworthy the high EDI of SMZ by Jordanian adults, 0.286 µg SMZ/kg b.w./day. Moreover, results prevailed that the highest SMZ incidence rate and contamination level were for imported poultry samples followed by domestic poultry samples, which may indicate that SMZ contamination in poultry meat is an international issue.
CONCLUSION
The current study prevailed high SMZ incidence rate, contamination level, and EDI values, which is likely due to indiscriminate use of SMZ in poultry production. Results also prevailed the high risk that consumers in Jordan may expose due to SMZ residues. Therefore, more strict program and good agricultural practices should be applied to monitor antibiotic withdrawal periods in animals used for human consumption to ensure the legal residue requirements of these antibiotics.
PubMed: 32095052
DOI: 10.14202/vetworld.2019.1992-1997