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At least 19 recordsLinked to original sources
PubMed2003

Absence of cross-reactivity between sulfonamide antibiotics and sulfonamide nonantibiotics.

BACKGROUND: The safety of sulfonamide nonantibiotics is unclear in patients with prior allergic reactions to sulfonamide antibiotics. METHODS: We conducted a retrospective cohort study using the General Practice Research Database in the United Kingdom, examining the risk of allergic reactions within 30 days after the receipt of a sulfonamide nonantibiotic. Patients with evidence of prior hypersensitivity after the receipt of a sulfonamide antibiotic were compared with those without such evidence. Similar analyses were also performed with the use of penicillins instead of sulfonamides, to determine whether any risk was specific to sulfonamide cross-reactivity. RESULTS: Of 969 patients with an allergic reaction after a sulfonamide antibiotic, 96 (9.9 percent) had an allergic reaction after subsequently receiving a sulfonamide nonantibiotic. Of 19,257 who had no allergic reaction after a sulfonamide antibiotic, 315 (1.6 percent) had an allergic reaction after receiving a sulfonamide nonantibiotic (adjusted odds ratio, 2.8; 95 percent confidence interval, 2.1 to 3.7). However, the risk of allergic reactions was even greater after the receipt of a penicillin among patients with a prior hypersensitivity reaction to a sulfonamide antibiotic, as compared with patients with no such history (adjusted odds ratio, 3.9; 95 percent confidence interval, 3.5 to 4.3). Furthermore, among those with a prior hypersensitivity reaction after the receipt of a sulfonamide antibiotic, the risk of an allergic reaction after the subsequent receipt of a sulfonamide nonantibiotic was lower than the risk of an allergic reaction after the subsequent receipt of a penicillin (adjusted odds ratio, 0.7; 95 percent confidence interval, 0.5 to 0.9). Finally, the risk of an allergic reaction after the receipt of a sulfonamide nonantibiotic was lower among patients with a history of hypersensitivity to sulfonamide antibiotics than among patients with a history of hypersensitivity to penicillins (adjusted odds ratio, 0.6; 95 percent confidence interval, 0.5 to 0.8). CONCLUSIONS: There is an association between hypersensitivity after the receipt of sulfonamide antibiotics and a subsequent allergic reaction after the receipt of a sulfonamide nonantibiotic, but this association appears to be due to a predisposition to allergic reactions rather than to cross-reactivity with sulfonamide-based drugs.

Anti-Bacterial Agents↗
PubMed2004

Likelihood and mechanisms of cross-allergenicity between sulfonamide antibiotics and other drugs containing a sulfonamide functional group.

Concerns about cross-allergenicity between sulfonamide antibiotics and nonantibiotic, sulfonamide-containing drugs persist and can complicate patients' drug therapy unnecessarily. No interaction between the human immune system and the sulfonamide functional group has been demonstrated. The immunologic determinant of type I, immediate hypersensitivity responses to sulfonamide antibiotics is the N1 heterocyclic ring. Nonantibiotic sulfonamides do not contain this structural feature. Non-type I hypersensitivity responses to sulfonamide antibiotics are largely attributable to reactive metabolites that may cause either direct cytotoxicity or immunologic response. Formation of these metabolites is a stereospecific process that occurs at the N4 amino nitrogen of the sulfonamide antibiotics, a structure also not found on any nonantibiotic sulfonamide drugs. The stereospecificity of these reactions implies that cross-reactivity with nonantibiotic sulfonamide-containing drugs is highly unlikely; this assertion is supported by recent literature. However, T-cell recognition of unmetabolized, nonhaptenated parent sulfonamide antibiotic appears to occur in a small subset of hypersensitive patients. Several of the severe cutaneous reactions associated with sulfonamide antibiotics are mediated by T cells. It is not known whether T-cell recognition of antibiotic is related to the sulfonamide functional group. Until the mechanism of this recognition is elucidated, cross-reactivity with nonantibiotic sulfonamides appears to remain at least theoretically possible.

Aged↗
PubMed2000

Acyloxymethyl as a drug protecting group. Part 6: N-acyloxymethyl- and N-[(aminocarbonyloxy)methyl]sulfonamides as prodrugs of agents containing a secondary sulfonamide group.

Tertiary N-acyloxymethyl- and N-[(aminocarbonyloxy)methyl]sulfonamides were synthesised and evaluated as novel classes of potential prodrugs of agents containing a secondary sulfonamide group. The chemical and plasma hydrolyses of the title compounds were studied by HPLC. Tertiary N-acyloxymethylsulfonamides are slowly and quantitatively hydrolysed to the parent sulfonamide in pH 7.4 phosphate buffer, with half-lives ranging from 20 h, for 7d, to 30 days, for 7g. Quantitative formation of the parent sulfonamide also occurs in human plasma, the half-lives being within 0.2-2.0 min for some substrates. The rapid rate of hydrolysis can be ascribed to plasma cholinesterase, as indicated by the complete inhibition observed at [eserine] = 0.10 mM. These results suggest that tertiary N-acyloxymethylsulfonamides are potentially useful prodrugs for agents containing a secondary sulfonamide group, especially with pKa < 8, combining a high stability in aqueous media with a high rate of plasma activation. In contrast, N-[(aminocarbonyloxy)methyl]sulfonamides 7h-j do not liberate the parent sulfonamide either in aqueous buffers or in human plasma and thus appear to be unsuitable for development as sulfonamide prodrugs.

Biotransformation↗
PubMed1998

Carbonic anhydrase inhibitors: novel compounds containing S-NH moieties: sulfenamido-sulfonamides, sulfenimido-sulfonamides and their interaction with isozymes I, II and IV.

Reaction of 2-nitrophenyl- and 4-nitrophenylsulfenyl chlorides with aromatic/heterocyclic sulfonamides/bis-sulfonamides containing a free amino, hydrazino or imino group afforded sulfenamido-sulfonamides, or sulfenimido-sulfonamides. Oxidation of these derivatives with potassium permanganate in acetone led to the corresponding bis-sulfonamides. The obtained compounds were assayed as inhibitors of the zinc enzyme carbonic anhydrase (CA), isozymes hCA I, hCA II (human cytosolic forms from red cells) and bCA IV (bovine membrane-associated form). Good inhibition of the three CA isozymes was observed with some of the new compounds, the bis-sulfonamides being more active than the sulfenamido-sulfonamides. Structure-active correlations for the new series of inhibitors are discussed. Some of the sulfenamido-sulfonamides (but not the corresponding bis-sulfonamides) showed topical intraocular pressure lowering effects when applied as a 2% solution directly into the rabbit eye.

Animals↗
PubMed2005

Use of sulfonamides in layers in Kampala district, Uganda and sulfonamide residues in commercial eggs.

BACKGROUND: Use of antimicrobials like sulfonamides in production of layers is a public health risk since it inevitably results in sulfonamide residues in eggs. The presence of the residues may be influenced by knowledge, attitudes and practices of farmers regarding use of sulfonamides (and other antimicrobials) in poultry. OBJECTIVE: The study aimed at assessing the possible contribution of the knowledge, attitudes and practices of poultry farmers to the presence/levels of sulfonamide residues in hen eggs. METHODS: A descriptive cross sectional study was done in the 5 political divisions (and surroundings) of Kampala district. Sixty farmers were systematically sampled from a list of poultry farmers in Kampala and a semi-structured questionnaire administered. Each farmer provided sixty eggs for analysis of sulfadiazine and sulfamethazine residues. Whole eggs were homogenized in acetonitrile and centrifuged twice, extracts evaporated and residues dissolved in mobile phase (32:68, methanol: potassium di-hydrogen phosphate). Fats were removed using hexane while anhydrous sodium chloride was added to break emulsions. Extracts were analyzed by reverse phase high performance liquid chromatography with photodiode array detector. RESULTS: Ninety-five percent of the farmers never observed withdrawal periods although 80% of them knew the importance of withdrawal periods. However, farmers noted that they play a great role in ensuring a safe food supply. Most farmers attributed the non-observance of withdrawal periods to poverty and fear to lose their investments. Ninety-eight percent of the samples had detectable levels of the sulfonamides. Meanwhile, 98.3% of the samples that had detectable sulfonamide residues came from farmers who applied antimicrobials in feeds/ water. CONCLUSION: Consumers of hen eggs in Kampala district are at high risk of sulfonamide residue exposure due to poor farming/ regulatory practices.

Agriculture↗
PubMed1975

Sulfonamide resistance mechanism in Escherichia coli: R plasmids can determine sulfonamide-resistant dihydropteroate synthases.

Several natural isolate E. coli strains highly resistant to sulfonamides and antibiotics are shown to contain a sulfonamide-resistant dihydropteroate synthase (2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine-diphosphate:4-aminobenzoate 2-amino-4-hydroxydihydropteridine-6-methenyltransferase, EC 2.5.1.15) in addition to the normal sensitive enzyme. The resistant dihydropteroate synthases examined are determined by an R plasmid and are smaller and less heat stable than the normal sulfonamide-sensitive enzyme. One synthase resistant to any sulfonamide tested, and to sulfanilic and arsanilic acids, was still inhibited by several non-sulfonamide analogs of p-aminobenzoate. Citrobacter and Klebsiella pneumoniae strains also show similar mechanisms of sulfonamide resistance.

Aminobenzoates↗
PubMed2001

Carbonic anhydrase inhibitors: allylsulfonamide, styrene sulfonamide, N-allyl sulfonamides and some of their Si, Ge, and B derivatives.

Unsubstituted aromatic, heterocyclic and perfluoroalkylic sulfonamides possessing the general formula RSO2NH2 act as powerful inhibitors of the zinc enzyme carbonic anhydrase (CA). Unsaturated primary/substituted sulfonamides have never been investigated for their interaction with the enzyme. Here it is shown that such compounds, and more precisely allyl-sulfonamide and trans-styrene sulfonamide possessing the above general formula (with R=CH2=CH-CH2- and C6H5-CH=CH-, respectively) behave as nanomolar inhibitors of the physiologically relevant isozymes CAI and CAII. Some other derivatives of these two leads (incorporating Si(IV), Ge(IV) and B(III) moieties among others) were also synthesized and investigated for their interaction with CA, but showed decreased affinity for both isozymes. The structure-activity relationship for this class of CA inhibitors is discussed. Furthermore, it was observed that allylsulfonyl chloride is a strong CA inactivator, probably by reacting with amino acid residues critical for the catalytic cycle.

Boron↗
PubMedDate not supplied

Calf antibiotic and sulfonamide test (CAST) for screening antibiotic and sulfonamide residues in calf carcasses.

The Calf Antibiotic and Sulfonamide Test (CAST), a microbial inhibition screening test, was developed for detecting antibiotics and sulfonamides in bob veal calf carcasses. The test uses Bacillus megaterium ATCC 9885 as the indicator organism and Mueller Hinton agar as the growth medium. Compared to Swab Test on Premises (STOP), developed in 1970, this screening test has higher sensitivity and the ability to detect a wider range of veterinary antimicrobial residual drugs, particularly sulfonamides, at lower concentrations. Carcasses that are tested with CAST and suspected of containing chemical residue above tolerance level are retained for confirmation. Disposition of these carcasses are determined upon laboratory result. Routine testing of bob veal calves with CAST allowed the Food Safety and Inspection Service to release most calf carcasses within 24 h post-slaughter, thus conserving shipping and handling resources. However, changes in the regulation in 1990 dictate that disposition of carcasses found to contain violative levels of sulfonamide residues should be based on laboratory findings. The analysis of the data for the years 1990-1994 and 1998 indicate that the use of CAST over the years was significant, and had a direct impact on reduction of residue violations in veal carcasses. With the use of CAST, potentially harmful antimicrobial chemicals entering the human food chain through veal meat have been minimized.

Animals↗
PubMed2006

Carbonic anhydrase inhibitors: X-ray crystallographic studies for the binding of 5-amino-1,3,4-thiadiazole-2-sulfonamide and 5-(4-amino-3-chloro-5-fluorophenylsulfonamido)-1,3,4-thiadiazole-2-sulfonamide to human isoform II.

The X-ray crystal structures of 5-amino-1,3,4-thiadiazole-2-sulfonamide (the acetazolamide precursor) and 5-(4-amino-3-chloro-5-fluorophenylsulfonamido)-1,3,4-thiadiazole-2-sulfonamide in complex with the human isozyme II of carbonic anhydrase (CA, EC 4.2.1.1) are reported. The thiadiazole-sulfonamide moiety of the two compounds binds in the canonic manner to the zinc ion and interacts with Thr199, Glu106, and Thr200. The substituted phenyl tail of the second inhibitor was positioned in the hydrophobic part of the binding pocket, at van der Waals distance from Phe131, Val 135, Val141, Leu198, Pro202, and Leu204. These structures may help in the design of better inhibitors of these widespread zinc-containing enzymes.

Carbonic Anhydrase Inhibitors↗
PubMed1976

Distribution of sulfonamides and sulfonamide potentiators between red blood cells, proteins and aqueous phases of the blood of different species.

The uptake of sulfonamides and sulfonamide potentiators by plasma albumin, red blood cells and hemoglobin of man, ox, rabbit and mouse has been determined. From the figures obtained the distribution of these compounds between cells, macromolecules and aqueous phases of blood has been calculated. In most cases more than 50% of a total sulfonamide in blood is bound to plasma albumin. The time necessary for establishment of concentration equilibrium of the drugs investigated between erythrocytes and surrounding medium varies between a few seconds and several minutes, differences between the species being encountered. Hemoglobin binding of the drugs is much smaller than albumin binding. Nevertheless, drug concentration within the erythrocytes is generally higher than in the surrounding medium.

Animals↗
PubMed1981

Analytical methods for sulfonamides in foods and feeds. II. Performance characteristics of sulfonamide methods.

Important factors in interpretation of methods for sulfonamides in tissues are value of the blank, use or omission of recovery factors, and precision of the methods. For determining sulfonamide in tissues, no interlaboratory collaborative studies have been performed to provide reproducibility parameters. By assuming comparability with other tissue residue methods at equivalent concentrations, it may be anticipated that the coefficient of variation within-laboratories of the Bratton-Marshall method is about 15% at concentrations of a fraction of a part per million. It is estimated that the limit of reliable measurement of the Bratton-Marshall method is about 0.2 ppm, varying with the individual laboratory. This value is higher than the tolerance it is intended to enforce. Obviously, the method in this case has been stretched beyond its original claimed capabilities. This method also has high blanks and low recoveries. Assignment of sufficient resources to the solution of the problem by regulatory agencies has resulted in methods capable of handling the sulfonamide residue problem at 0.1 ppm.

Animal Feed↗
PubMed1999

Determination of the activity of pyrimethamine, trimethoprim, sulfonamides, and combinations of pyrimethamine and sulfonamides against Sarcocystis neurona in cell cultures.

Equine protozoal myeloencephalitis (EPM) is a neurologic syndrome in horses from the Americas and is usually caused by infection with the apicomplexan parasite, Sarcocystis neurona. The activities of pyrimethamine, trimethoprim, sulfachloropyridazine, sulfadiazine, sulfadimethoxine, sulfamethoxazole, sulfamethazine, and sulfathiazole were examined against developing S. neurona merozoites in bovine turbinate cell cultures. A microtiter plate host cell lesion based assay was used to determine the effects of agents on developing merozoites. A cell culture flask assay was used to determine if selective concentrations of the agents killed or only inhibited development of S. neurona. Pyrimethamine was coccidiocidal at 1.0 microg/ml and trimethoprim was coccidiocidal at 5.0 microg/ml. None of the sulfonamides had activity when used alone at 50.0 or 100.0 microg/ml. Combinations of sulfonamides (5.0 or 10.0 microg/ml) with 0.1 microg/ml pyrimethamine demonstrated improved activity.

Animals↗