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Acta Crystallographica. Section E,... Jun 2015In the title zwitterionic compound, C20H15N3O3S2, the 2-hy-droxy-naphthalene-1-carbaldehyde group A, the anilinic unit B and the 1,3-thia-zol-2(3H)-imine group C are...
In the title zwitterionic compound, C20H15N3O3S2, the 2-hy-droxy-naphthalene-1-carbaldehyde group A, the anilinic unit B and the 1,3-thia-zol-2(3H)-imine group C are each approximately planar with r.m.s. deviation of 0.0721, 0.0412 and 0.0125 Å, respectively. The dihedral angles between A/B, A/C and B/C are 24.70 (10), 79.97 (7) and 83.14 (6)°, respectively. There is an intra-molecular S(6) motif involving the imine N-H and the naphtho-late O atom. In the crystal, inversion-related mol-ecules form dimers as a result of N-H⋯N and N-H⋯O hydrogen bonds with R 2 (2)(8) and R 1 (2)(4) motifs, respectively. Weak π-π inter-actions between the benzene and naphthyl rings of inversion-related mol-ecules have ring centroid-centroid distances of 3.638 (2) and 4.041 (2) Å. A C-H⋯π inter-action occurs between the thia-zol ring and the benzene ring of an adjacent mol-ecule.
PubMed: 26090203
DOI: 10.1107/S2056989015009640 -
British Medical Journal Jun 1940
PubMed: 20783164
DOI: No ID Found -
The Cochrane Database of Systematic... Aug 2013Measles is the leading killer among vaccine-preventable diseases; it is responsible for an estimated 44% of the 1.7 million vaccine-preventable deaths among children... (Meta-Analysis)
Meta-Analysis Review
BACKGROUND
Measles is the leading killer among vaccine-preventable diseases; it is responsible for an estimated 44% of the 1.7 million vaccine-preventable deaths among children annually.
OBJECTIVES
To assess the effects of antibiotics given to children with measles to prevent complications and reduce pneumonia, other morbidities and mortality.
SEARCH METHODS
We searched CENTRAL 2013, Issue 4, MEDLINE (1966 to May week 4, 2013) and EMBASE (1980 to May 2013).
SELECTION CRITERIA
Randomised controlled trials (RCTs) and quasi-RCTs comparing antibiotics with placebo or no treatment, to prevent complications in children with measles.
DATA COLLECTION AND ANALYSIS
Two review authors independently extracted data and assessed trial quality.
MAIN RESULTS
Seven trials with 1263 children were included. The methodological quality of most studies was poor. Only two studies were randomized, double-blind trials. There was variation in antibiotics used, their doses, schedule and evaluation of outcome. Pooled study data showed that the incidence of pneumonia was lower in the treatment group compared to the control group. However, the difference was not statistically significant. Of the 654 children who received antibiotics, 27 (4.1%) developed pneumonia; while out of 609 children in the control group, 59 (9.6%) developed pneumonia (odds ratio (OR) 0.35; 95% confidence interval (0.12 to 1.01). The one trial that showed an increase in the rate of pneumonia with antibiotics was conducted in 1942 and compared oral sulfathiazole with symptomatic treatment. If the results of this trial are removed from the meta-analysis, there is a statistically significant reduction in the incidence of pneumonia in children receiving antibiotics (OR 0.26; 95% CI 0.12 to 0.60). The incidence of other complications was significantly lower in children receiving antibiotics: purulent otitis media (OR 0.34; 95% CI 0.16 to 0.73) and tonsillitis (OR 0.08; 95% CI 0.01 to 0.72). There was no difference in the incidence of conjunctivitis (OR 0.39; 95% CI 0.15 to 1.0), diarrhea (OR 0.53; 95% CI 0.23 to 1.22) or croup (OR 0.16; 95% CI 0.01 to 4.06). No major adverse effects attributable to antibiotics were reported.
AUTHORS' CONCLUSIONS
The studies reviewed were of poor quality and used older antibiotics. This review suggests a beneficial effect of antibiotics in preventing complications such as pneumonia, purulent otitis media and tonsillitis in children with measles. On the basis of this review, it is not possible to recommend definitive guidelines on the type of antibiotic, duration or the day of initiation. There is a need for more evidence from high-quality RCTs to answer these questions.
Topics: Anti-Bacterial Agents; Child; Conjunctivitis, Bacterial; Croup; Diarrhea; Humans; Measles; Otitis Media; Pneumonia; Randomized Controlled Trials as Topic; Tonsillitis
PubMed: 23943263
DOI: 10.1002/14651858.CD001477.pub4 -
Journal of Food Protection Sep 1994The plasma pharmacokinetics and tissue penetration of sulfathiazole (ST) and sulfamethazine (SM) after intravenous and intramuscular injection in pigs were studied....
The plasma pharmacokinetics and tissue penetration of sulfathiazole (ST) and sulfamethazine (SM) after intravenous and intramuscular injection in pigs were studied. Following a single intravenous dose of 40 mg ST/kg of bodyweight or 80 mg SM/kg of bodyweight, the plasma ST and SM concentrations were best fitted to a two-compartment model. The areas under the curve were 447 ± 39 and 1485 ± 41 mg/h/L, clearances were 0.090 ± 0.007 and 0.054 ± 0.001 L/kg/h, volumes of distribution were 1.16 ± 0.16 and 0.77 ± 0.06 L/kg, half-lifes in distribution phase were l.18 ± 0.57 and 0.23 ± 0.16 h and half-lifes in eliminations phase were 9.0 ± l.6 and 9.8 ± 0.6 h. When the two compounds were administered simultaneously as a single intravenous injection, the pharmacokinetic parameters for ST were not significantly different. The values for SM show statistical differences for some important parameters: α, β and the AUC were significantly decreased and tα, Vd and CIB were significantly increased. It can be concluded that after a single intravenous injection of 40 mg/kg, sulfathiazole has a high tβ resulting in higher tissue concentrations. This half-life, which is higher than what is reported in the literature, is not influenced by the simultaneous presence of sulfamethazine. The tβ for sulfamethazine after a single intravenous injection of 80 mg/kg is comparable to the data from the literature and is not influenced by the presence of sulfathiazole. Sulfathiazole and SM were also administered simultaneously as an intramuscular injection to healthy pigs at a dosage of 40 and 80 mg/kg bodyweight. Pharmacokinetic experiments were conducted on three pigs. From this pharmacokinetic study it can be concluded that upon a single intramuscular administration of 40 mg/kg of ST and 80 mg/kg of SM the absolute bioavailability in pigs is 0.92 ± 0.04 for ST and l.01 ± 0.07 for SM. Six pigs received five intramuscular im) injections as a single dose of ST and SM every 24 h for five consecutive days for the residue study. The pigs were slaughtered at different times after the last dose was given and samples were taken from various tissues and organs. Concentrations were determined by a microbiological method and a HPTLC method. No edible tissue contained more than 100 μg/kg of the individual sulfonamides after 10 days of withdrawal. It means that adult animals which have a shorter half-life and thus lower tissue concentrations will certainly meet the economic community EC) maximum residue limits after a 10 days withdrawal period.
PubMed: 31121795
DOI: 10.4315/0362-028X-57.9.796 -
Journal of Molecular Biology Aug 2019Microcin B17 (MccB17) is an antibacterial peptide produced by strains of Escherichia coli harboring the plasmid-borne mccB17 operon. MccB17 possesses many notable... (Review)
Review
Microcin B17 (MccB17) is an antibacterial peptide produced by strains of Escherichia coli harboring the plasmid-borne mccB17 operon. MccB17 possesses many notable features. It is able to stabilize the transient DNA gyrase-DNA cleavage complex, a very efficient mode of action shared with the highly successful fluoroquinolone drugs. MccB17 stabilizes this complex by a distinct mechanism making it potentially valuable in the fight against bacterial antibiotic resistance. MccB17 was the first compound discovered from the thiazole/oxazole-modified microcins family and the linear azole-containing peptides; these ribosomal peptides are post-translationally modified to convert serine and cysteine residues into oxazole and thiazole rings. These chemical moieties are found in many other bioactive compounds like the vitamin thiamine, the anti-cancer drug bleomycin, the antibacterial sulfathiazole and the antiviral nitazoxanide. Therefore, the biosynthetic machinery that produces these azole rings is noteworthy as a general method to create bioactive compounds. Our knowledge of MccB17 now extends to many aspects of antibacterial-bacteria interactions: production, transport, interaction with its target, and resistance mechanisms; this knowledge has wide potential applicability. After a long time with limited progress on MccB17, recent publications have addressed critical aspects of MccB17 biosynthesis as well as an explosion in the discovery of new related compounds in the thiazole/oxazole-modified microcins/linear azole-containing peptides family. It is therefore timely to summarize the evidence gathered over more than 40 years about this still enigmatic molecule and place it in the wider context of antibacterials.
Topics: Anti-Bacterial Agents; Antimicrobial Cationic Peptides; Bacteria; Bacteriocins; Cinoxacin; DNA Cleavage; DNA Gyrase; Drug Development; Drug Resistance, Microbial; Escherichia coli; Fluoroquinolones; Humans; Mutation; Nitro Compounds; Peptides; Protein Processing, Post-Translational; Thiazoles; Toxins, Biological
PubMed: 31181289
DOI: 10.1016/j.jmb.2019.05.050 -
Biochemistry Research International 2021Synthetic modifications of sulfathiazole derivatives become an interesting approach to enhance their biological properties in line with their applications. As a result,...
Synthetic modifications of sulfathiazole derivatives become an interesting approach to enhance their biological properties in line with their applications. As a result, sulfathiazole derivatives become a good candidate and potential class of organic compounds to play an important role towards medicinal chemistry. In present study, one thiazole derivative and two new sulfathiazole derivatives are synthesized with 94% and 72-81% yields, respectively. Furthermore, the synthesized compounds were evaluated for their antibacterial activity against two Gram-negative ( and ) and two Gram-positive bacterial strains ( and ) by disk diffusion method. Among synthesized compounds, compound showed potent inhibitory activity against Gram-negative, with 11.6 ± 0.283 mm zone of inhibition compared to standard drug sulfamethoxazole (15.7 ± 0.707 mm) at 50 mg/mL. The radical scavenging activities of these compounds were evaluated using DPPH radical assay, and compound showed the strongest activity with IC values of 1.655 g/mL. The synthesized compounds were evaluated for their molecular docking analysis using gyrase (PDB ID: 2XCT) and human myeloperoxidase (PDB ID: 1DNU) and were found to have minimum binding energy ranging from -7.8 to -10.0 kcal/mol with 2XCT and -7.5 to -9.7 with 1DNU. Compound showed very good binding score -9.7 kcal/mol with both of the proteins and had promising alignment with results. Compound 11b also showed high binding scores with both proteins. Drug likeness and ADMET of synthesized compounds were predicted. The DFT analysis of synthesized compounds was performed using Gaussian 09 and visualized through Gauss view 6.0. The structural coordinates of the lead compounds were optimized using B3LYP/6-31 G (d,p) level basis set without any symmetrical constraints. Studies revealed that all the synthesized compounds might be candidates for further antibacterial and antioxidant studies.
PubMed: 34950517
DOI: 10.1155/2021/7534561 -
Pharmaceuticals (Basel, Switzerland) Nov 2022This study constructs a machine learning method to simultaneously analyze the thermodynamic behavior of many polymer-drug systems. The solubility temperature of...
This study constructs a machine learning method to simultaneously analyze the thermodynamic behavior of many polymer-drug systems. The solubility temperature of Acetaminophen, Celecoxib, Chloramphenicol, D-Mannitol, Felodipine, Ibuprofen, Ibuprofen Sodium, Indomethacin, Itraconazole, Naproxen, Nifedipine, Paracetamol, Sulfadiazine, Sulfadimidine, Sulfamerazine, and Sulfathiazole in 1,3-bis[2-pyrrolidone-1-yl] butane, Polyvinyl Acetate, Polyvinylpyrrolidone (PVP), PVP K12, PVP K15, PVP K17, PVP K25, PVP/VA, PVP/VA 335, PVP/VA 535, PVP/VA 635, PVP/VA 735, Soluplus analyzes from a modeling perspective. The least-squares support vector regression (LS-SVR) designs to approximate the solubility temperature of drugs in polymers from polymer and drug types and drug loading in polymers. The structure of this machine learning model is well-tuned by conducting trial and error on the kernel type (i.e., Gaussian, polynomial, and linear) and methods used for adjusting the LS-SVR coefficients (i.e., leave-one-out and 10-fold cross-validation scenarios). Results of the sensitivity analysis showed that the Gaussian kernel and 10-fold cross-validation is the best candidate for developing an LS-SVR for the given task. The built model yielded results consistent with 278 experimental samples reported in the literature. Indeed, the mean absolute relative deviation percent of 8.35 and 7.25 is achieved in the training and testing stages, respectively. The performance on the largest available dataset confirms its applicability. Such a reliable tool is essential for monitoring polymer-drug systems' stability and deliverability, especially for poorly soluble drugs in polymers, which can be further validated by adopting it to an actual implementation in the future.
PubMed: 36422535
DOI: 10.3390/ph15111405 -
Toxics Apr 2022Veterinary antibiotics (VAs) released into the environment are a concern because of the possibility for increasing antibiotic-resistance genes. The concentrations of six...
Veterinary antibiotics (VAs) released into the environment are a concern because of the possibility for increasing antibiotic-resistance genes. The concentrations of six VAs, chlortetracycline, oxytetracycline, tetracycline, sulfamethazine, sulfamethoxazole, and sulfathiazole, in manure-based compost, soil, and crops were measured using liquid chromatography-tandem mass spectrometry. Mass balance analysis was conducted based on the measured antibiotic concentration, cultivation area, and amount of manure-based compost applied. The result showed that the detected mean concentration of VAs ranges was 3.52~234.19 μg/kg, 0.52~13.08 μg/kg, and 1.05~39.57 μg/kg in manure-based compost, soil, and crops, respectively, and the substance of VAs detected in different media was also varied. Mass balance analysis showed that the VAs released from the manure-based compost can remain in soil (at rates of 26% to 100%), be taken up by crops (at rates of 0.4% to 3.7%), or dissipated (at rates of 9% to 73%) during the cultivation period. Among the six VAs, chlortetracycline and oxytetracycline mainly remained in the soil, whereas sulfamethoxazole and sulfathiazole were mainly dissipated. Although we did not verify the exact mechanism of the fate and distribution of VAs in this study, our results showed that these can vary depending on the different characteristics of VAs and the soil properties.
PubMed: 35622627
DOI: 10.3390/toxics10050213 -
Ecotoxicology and Environmental Safety Jun 2023Understanding the adsorption behavior of antibiotic molecules on minerals is crucial for determining the environmental fate and transport of antibiotics in soils and...
Understanding the adsorption behavior of antibiotic molecules on minerals is crucial for determining the environmental fate and transport of antibiotics in soils and waters. However, the microscopic mechanisms that govern the adsorption of common antibiotics, such as the molecular orientation during the adsorption process and the conformation of sorbate species, are not well understood. To address this gap, we conducted a series of molecular dynamics (MD) simulations and thermodynamics analyses to investigate the adsorption of two typical antibiotics, tetracycline (TET) and sulfathiazole (ST), on the surface of montmorillonite. The simulation results indicated that the adsorption free energy ranged from - 23 to - 32 kJ·mol, and - 9 to - 18 kJ·mol for TET and ST, respectively, which was consistent with the measured difference of sorption coefficient (K) for TET-montmorillonite of 11.7 L·g and ST-montmorillonite of 0.014 L·g. The simulations also found that TET was adsorbed through dimethylamino groups (85% in probability) with a molecular conformation vertical to the montmorillonite's surface, while ST was adsorbed through sulfonyl amide group (95% in probability) with vertical, tilted and parallel conformations on the surface. The results confirmed that molecular spatial orientations could affect the adsorption capacity between antibiotics and minerals. Overall, the microscopic adsorption mechanisms revealed in this study provide critical insights into the complexities of antibiotics adsorption to soil and facilitate the prediction of adsorption capacity of antibiotics on minerals and their environmental transport and fate. This study contributes to our understanding of the environmental impacts of antibiotic usage and highlights the importance of considering molecular-level processes when assessing the fate and transport of antibiotics in the environment.
Topics: Anti-Bacterial Agents; Clay; Bentonite; Minerals; Soil; Tetracycline; Sulfathiazole; Aluminum Silicates
PubMed: 37148753
DOI: 10.1016/j.ecoenv.2023.114970 -
Molecules (Basel, Switzerland) May 2022The sulfonamide-zinc ion interaction, performing a key role in various biological contexts, is the focus of the present study, with the aim of elucidating ligation...
The sulfonamide-zinc ion interaction, performing a key role in various biological contexts, is the focus of the present study, with the aim of elucidating ligation motifs in zinc complexes of sulfa drugs, namely sulfadiazine (SDZ) and sulfathiazole (STZ), in a perturbation-free environment. To this end, an approach is exploited based on mass spectrometry coupled with infrared multiple photon dissociation (IRMPD) spectroscopy backed by quantum chemical calculations. IR spectra of Zn(HO+SDZ-H) and Zn(HO+STZ-H) ions are consistent with a three-coordinate zinc complex, where ZnOH binds to the uncharged sulfonamide via N(heterocycle) and O(sulfonyl) donor atoms. Alternative prototropic isomers Zn(OH)(SDZ-H) and Zn(OH)(STZ-H) lie 63 and 26 kJ mol higher in free energy, respectively, relative to the ground state Zn(OH)(SDZ) and Zn(OH)(STZ) species and do not contribute to any significant extent in the sampled population.
Topics: Ions; Spectrophotometry, Infrared; Sulfanilamide; Sulfonamides; Zinc
PubMed: 35630621
DOI: 10.3390/molecules27103144