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At least 19 recordsLinked to original sources
PubMed1977

Studies on the in vitro development of drug resistance of Proteeae to sulfonamides, trimethoprim and combinations of a sulfonamide and trimethoprim.

A strain of Proteus mirabilis repeatedly subcultured in the presence of a combination of sulfisoxazole and 0.4 microgram/ml of trimethoprim and a strain of P. vulgaris subcultured in the presence of sulfamethoxazole and trimethoprim combined in a 5:1 ratio gradually developed resistance to the combinations. However, the level of resistance developed by the organisms exposed to the combination was always appreciably lower than the level of resistance developed by the same strains exposed to either the sulfonamide or trimethoprim alone.

Drug Combinations↗
PubMed1977

Determination of ionization state by resonance Raman spectroscopy Sulfonamide binding to carbonic anhydrase.

Resonance Raman (RR) spectroscopy has been used to study the ionization state of the sulfonamide, 4'-sulfamylphenyl-2-azo-7-acetamido-1-hydroxynaphthalene-3,-6-disulfonate (Neoprontosil), bound to carbonic anhydrase. The correlation of effects of pH and deuteration on the spectra of model compounds with these effects on the Neoprotosil spectrum allows us to assign spectral bands in the 900-1000 and 100-1200 cm-1 regions to the SO2NH2 group. Large shifts in these bands occur upon ionization of the sulfonamide. On the basis of the positions of bands in the enzyme complex, it was determined that the sulfonamide was bound to the enzyme as SO2NH2, rather than as SO2NH-. Rates of association and dissociation and the dissociation equilibrium constant were measured as a function of pH. The rate behavior for Neoprontosil is consistent with that observed for other sulfonamides and kdissoc/kassoc = kdissoc, suggesting a one-step binding mechanism. Since RR spectroscopy establishes that the final ionization state of the sulfonamide in the enzyme complex is SO2NH2, protonated sulfonamide must bind directly to basic form of the enzyme. These conclusions suggest that sulfonamides form "outer-space" complexes with metal at the enzyme active site.

Animals↗
PubMed2026

The Role of In Vivo, In Vitro and Pharmacogenomic Diagnostic Approaches to Sulfonamide Allergy.

Sulfonamide antibiotics are commonly reported as a medication allergy, presenting as both immediate IgE-mediated reactions and delayed hypersensitivity reactions ranging from benign cutaneous eruptions to severe cutaneous adverse reactions. Sulfonamide antibiotics have retained importance as treatment for multiple indications and are especially relevant in immunocompromised patients wherein use is indicated for prevention of opportunistic infections. Sulfonamide antibiotic allergy labels may lead to inappropriate avoidance of other "sulfur"-containing medications, because cross-reactivity is unlikely between antibiotic and nonantimicrobial sulfonamides. In this review, we discuss the typical presentation of sulfonamide antibiotic hypersensitivity reactions. We also review risk stratification tools and current in vivo procedures and experimental in vitro evaluation methods. Lastly, we will provide an update on emerging pharmacogenomics data associated with sulfonamide medication adverse reactions.

Humans↗
PubMed2024

Sulfonamide-induced DNA hypomethylation disturbed sugar metabolism in rice (Oryza sativa L.).

DNA methylation is well-accepted as a bridge to unravel the complex interplay between genome and environmental exposures, and its alteration regulated the cellular metabolic responses towards pollutants. However, the mechanism underlying site-specific aberrant DNA methylation and metabolic disorders under pollutant stresses remained elusive. Herein, the multilevel omics interferences of sulfonamides (i.e., sulfadiazine and sulfamerazine), a group of antibiotics pervasive in farmland soils, towards rice in 14 days of 1 mg/L hydroponic exposure were systematically evaluated. Metabolome and transcriptome analyses showed that 57.1-71.4 % of mono- and disaccharides were accumulated, and the differentially expressed genes were involved in the promotion of sugar hydrolysis, as well as the detoxification of sulfonamides. Most differentially methylated regions (DMRs) were hypomethylated ones (accounting for 87-95 %), and 92 % of which were located in the CHH context (H = A, C, or T base). KEGG enrichment analysis revealed that CHH-DMRs in the promoter regions were enriched in sugar metabolism. To reveal the significant hypomethylation of CHH, multi-spectroscopic and thermodynamic approaches, combined with molecular simulation were conducted to investigate the molecular interaction between sulfonamides and DNA in different sequence contexts, and the result demonstrated that sulfonamides would insert into the minor grooves of DNA, and exhibited a stronger affinity with the CHH contexts of DNA compared to CG or CHG contexts. Computational modeling of DNA 3D structures further confirmed that the binding led to a pitch increase of 0.1 Å and a 3.8° decrease in the twist angle of DNA in the CHH context. This specific interaction and the downregulation of methyltransferase CMT2 (log2FC = -4.04) inhibited the DNA methylation. These results indicated that DNA methylation-based assessment was useful for metabolic toxicity prediction and health risk assessment.

DNA Methylation↗
PubMed1979

Metal sulfonamides as antibacterial agents in topical therapy.

The apparent efficacy of zinc and cerium sulfadiazine and the metabolic role of other trace metals suggested that sulfonamide salts of these might be of therapeutic value. There is also a possibility that metal salts of other sulfonamides might be useful. Accordingly other sulfonamide salts of zinc were prepared and studied in vitro and in vivo. Only zinc sulfathiazole and zinc methoxazole were as effective as zinc sulfadiazine in animal studies. The sulfadiazines of aluminum, chromium, cobalt, copper and iron were prepared and compared in vitro and in vivo. Only cobalt sulfadiazine appeared comparable to zinc and cerium sulfadiazine in healing burn wounds in rats. Studies on the molecular structure of silver sulfonamides disclosed the polymeric structure peculiar to silver sulfadiazine which appears to account for its unique properties. It is not yet known whether other metal sulfadiazines have this attribute.

Administration, Topical↗
PubMed1976

[Renal excretion of long term sulfonamides under fluid administration and modification of the urinary pH value].

The renal excretion of sulfaclomide, sulfamerazine and sulfamethoxypyridazine is delayed by increased fluid application in rats. The simultaneous administration of sulfonamides and ammonium chloride or sodium hydrogen carbonate causes, respectively, retardation and acceleration of renal sulfonamide excretion which is consistent with the change in urinary pH value. The retarded renal sulfonamide excretion with increasing diuresis is explained by the ensuing change in the urinary pH value. For clinical uses, a speedy renal excretion of long-time sulfonamides by increased diuresis can be expected only if alkalization of the urine is achieved at the same time.

Ammonium Chloride↗
PubMed1979

Characterization of mutationally altered dihydropteroate synthase and its ability to form a sulfonamide-containing dihydrofolate analog.

Among spontaneous mutants of Escherichia coli selected for resistance against sulfonamides, thermosensitive strains were found. These were shown to possess a changed dihydropteroate synthase (EC 2.5.1.15), which had a substantially higher Km value for its normal substrate, p-aminobenzoic acid, and an about 150-fold higher Km for sulfonamides. The mutationally changed dihydropteroate synthase was found to be thermosensitive by in vitro assays. The thermosensitivity was used as an enzyme marker to demonstrate the complex formation between 2-amino-4-hydroxy-6-pyrophosphorylmethyl pteridine and sulfonamides by partially purified dihydropteroate synthase. The formation of folate from 2-amino-4-hydroxy-6-pyrophosphorylmethyl pteridine and p-aminobenzoylglutamic acid by dihydropteroate synthase was found to be very sensitive to inhibition by sulfonamides and very inefficient with the mutationally changed enzyme.

4-Aminobenzoic Acid↗
PubMed1979

Sulfonamide inhibition of human alkaline phosphatase.

Several sulfonamides used as antibacterial or diuretic drugs are potent alkaline phosphatase inhibitors. The mechanism of inhibition may involve binding of the zinc in the active site of the enzyme by the unbonded electron pair on the sulfonamide group nitrogen atom as well as binding of the drug to a second site. Addition of progressively larger groups to this nitrogen leads to an increasing loss of inhibitory capability. Isoenzymes from human liver, bone, kidney, granulation tissue and intestine are inhibited to a similar extent while the placenta isoenzyme is more resistant. It is suggested that some pharmacologic actions of sulfonamides may be due to inhibition of alkaline phosphatase, rather than carbonic anhydrase.

Alkaline Phosphatase↗
PubMed2026

Deciphering the effects of sulfonamide antibiotics on denitrification from a metagenomic perspective: Inhibition of nitrite reduction and succession patterns of functional microorganisms.

Limited research has thoroughly elucidated the impact mechanisms of antibiotics on the denitrification process at the genomic and gene levels, which has hindered the optimization and development of nitrogen removal technology for antibiotic-containing swine wastewater. Lab-scale sequencing batch reactors were constructed in this study to treat synthetic wastewater containing different sulfonamides and nitrate. Investigations were carried out on denitrification performance, microbial community diversity, denitrifier succession patterns, and functional gene distribution. The stress of sulfonamides inhibited the nitrite reduction process, transforming complete denitrification into partial denitrification and causing significant nitrite accumulation. The average nitrogen removal efficiency in the treatment groups decreased from 81.0% ± 2.2-40.1% ± 6.1%. Alicycliphilus and Thauera were identified as the key taxa, accounting for 32.2% and 16.9% of all potential denitrifying bacteria, respectively. Although metagenome-assembled genomes (MAGs) from Thauera were enriched with genes encoding nitrate reductases (nap, nar) and nitrite reductases (nir), this genus preferentially utilized nitrate as an electron acceptor, resulting in the preferential nitrate reduction and subsequent nitrite accumulation. In contrast, Alicycliphilus MAGs developed tolerance to the sulfonamides stress during later stages, with concomitant enrichment of associated functional genes. They replaced Thauera to reemerge as the dominant group, thereby restoring complete denitrification. This study provides new insights into the regulatory mechanisms governing complete versus partial denitrification in nitrogen removal from antibiotic-containing wastewater.

Denitrifier succession↗
PubMed1975

Proton magnetic resonance studies of carbonic anhydrase. III. Binding of sulfonamides.

Resonances of the histidine region of human carbonic anhydrase B have been studied by proton magnetic resonance spectroscopy in the presence of seven sulfonamide inhibitors. Results of difference spectroscopy and observation of the C-2 resonance of an additional titratable histidine in some of these spectra suggest a conformational change in the enzyme, while the large number of unaltered resonances indicates involvement of only a few residues. Inhibition of carbonic anhydrase by sulfonamides appears to involve: stabilization of an appropriately oriented initial complex by hydrophobic binding of the aromatic ring of the inhibitor to residues of the cavity forming the active site; ionization of the sulfonamido group, facilitated by its proximity to zinc; protonation and displacement of the high pH ligand to the metal controlling catalytic activity, thought here to be a histidine residue; and formation by the sulfonamido group of an ionic bond to zinc and a hydrogen bond to the hydroxyl group of serine or threonine. Diversity of spectra produced with various sulfonamides suggests that substituents on the ring and heteroatoms within the ring interact with additional groups at the active site. Increase in inhibitory potency appears to involve optimizing the number as well as the strength of these interactions. An upper limit for the dissociation rate of these complexes of 10 sec-1 was obtained.

Acetazolamide↗
PubMed1976

Drug eruption associated with sulfonamide treatment of vertebral osteomyelitis in a dog.

Drug eruption was diagnosed in a 4-year-old German Shepherd Dog being treated with sulfonamides for vertebral osteomyelitis due to infection with Nocardia spp. The eruption was characterized by generalized, pruritic, eczematous dermatitis. Diagnosis was based on a history of repeated exposure to sulfonamides, skin biopsy findingd, and clinical recovery on cessation of sulfonamide therapy.

Animals↗
PubMed1979

Multiple attacks of jaundice associated with repeated sulfonamide treatment.

Four women who were treated with sulfonamides because of recurrent urinary tract infections experienced adverse liver reactions with jaundice during their third, fourth and fifth course of treatment, respectively. In spite of this, sulfonamide treatment was reinitiated some years later. Adverse liver reactions with jaundice recurred on all occasions. The clinical picture of the liver reactions was indistinguishable from that of viral hepatitis and a hepatitis-like reaction was also seen histologically. Signs of fibrosis appeared histologically after a third attack of jaundice associated with sulfonamides in one patient, but otherwise no persisting abnormalities were noted.

Adult↗
PubMed1979

Histochemical detection of carbonic anhydrase with diemthylaminonaphthalene-5-sulfonamide.

A new specific method for the detection of carbonic anhydrase, EC 4.2.1.1, in tissues is described. The reaction of carbonic anhydrase with dimethylaminonaphthalene-5-sulfonamide (DNSA) forms a highly fluorescent complex. The specificity of the method is proved by the quenching of this fluorescence with ethoxzolamide (6-ethoxybenzothiazole-5-sulfonamide). The difference in the wavelength makes it possible to absorb the fluorescence of the unbound dimethylaminonaphthalene-5-sulfonamide by filters. Kidney, proventriculus, and bone from chicken have been examined. Carbonic anhydrase has been detected in the cytoplasm of the columnar lining cells, proximal tubule cells, and osteoclasts.

Animals↗
PubMed1979

Treatment of experimental nocardiosis in mice: comparison of amikacin and sulfonamide.

Recent in vitro susceptibility studies have shown that amikacin inhibits more than 90% of isolates of Nocardia. This study was designed to evaluate the effect of treatment with amikacin or sulfonamides on infection caused by Nocardia asteroides with the use of murine models. In an acute lethality model in which infection was induced by intraperitoneal injection, 13 (45%) of 29 mice that had been treated with amikacin survived, in comparison to zero of 39 untreated animals in the control group and one of 39 mice that had been treated with sulfadiazine (P less than 0.001 for amikacin). When infected with a strain of N. asteroides that was resistant to amikacin, all mice that were treated with amikacin and all untreated mice died. Drug therapy was also evaluated in a chronic infection model, in which abscesses were produced by an intraperitoneal injection of N. asteroides in saline. Treatment with either amikacin (P less than 0.001) or sulfonamide (P less than 0.02) for two to three weeks significantly increased the rate of resolution of these abscesses. These murine models demonstrate that amikacin has in vivo activity against Nocardia and may be potentially useful in the treatment of human disease.

Amikacin↗
PubMed1979

A reanalysis of the structure-activity relationships of sulfonamide derivatives.

A reanalysis of correspondence between electronic distribution of sulfonamides and their antibacterial activity is proposed. Correlation equations show that the rate limiting steps for sulfonamide action on E. coli cell-free system and whole cell system have similar dependence on the negative logarithm of the ionization constant. The existence of a "bilinear relationship" demonstrates that the whole class of compounds has a single mechanism of action and that permeability factors are unimportant in both biological processes.

Escherichia coli↗
PubMed1978

Solubility studies of silver sulfonamides.

The solubilities of silver sulfapyridine, silver sulfamethazine, and silver sulfamethizole as a function of pH were determined in nitric acid-potassium nitrate, acetate, and sulfonic acid buffers. All silver sulfonamides showed an increase in solubility with increasing hydrogen-ion concentration, a behavior which closely paralleled the protonation of the p-amino function of the sulfonamide. A silver-ion selective electrode was used to measure silver-ion concentration in solution and the methods of known subtraction and known addition were used to measure total silver. Both silver sulfamethizole and silver sulfamethazine were ionized completely in solution. Silver sulfapyridine was ionized completely only in the more acidic pH 2-3 range. A comparison of the physical properties of the silver salts for which mortality studies were available revealed a unique set of properties for silver sulfadiazine.

Hydrogen-Ion Concentration↗
PubMed1979

Stability-indicating high-performance liquid chromatographic determination of chlorpropamide, tolbutamide, and their respective sulfonamide degradates.

A quantitative high-performance liquid chromatographic method for the determination of chlorpropamide, tolbutamide, and their respective hydrolysis products, p-chlorobenzenesulfonamide and p-toluenesulfonamide, in solid dosage forms was developed. The method is stability indicating and can be used to determine the sulfonamide hydrolysis product and the intact drug in the presence of minor degradates. Method reproducibility, demonstrated by repeated injections of a calibration standard, was 1.21%. The lower limit of quantitation of the hydrolysis products, p-chlorobenzenesulfonamide and p-toluenesulfonamide, was 0.2 microgram/5-microliter injection. The accuracy of the method for intact drugs was determined by comparison of the HPLC results to those obtained by the appropriate USP or BP assays. The mean of the results obtained by the two methods differed by 0.7% for chlorpropamide and 0.3% for tolbutamide. Pure drug samples were spiked with amounts of the hydrolysis products ranging from 20 to 120% of the intact content. The mean percent recovery for p-chlorobenzenesulfonamide was 98.6%; for p-toluenesulfonamide, it was 100.6%. A qualitative TLC procedure for the detection of chlorpropamide, p-chlorobenzenesulfonamide, dipropylurea, propylurea, n-propylamine, tolbutamide, p-toluenesulfonamide, dibutylurea, butylurea, and n-butylamine is also described.

Chlorpropamide↗