PubMed Health⌕ Search

SEARCH · PubMed Health

Results for “Benzenesulfonamides”

Explore indexed PubMed citations for clinical trials, systematic reviews and public health research. Read source abstracts and follow each citation to its original PubMed record.

Quote a phrase for an exact phrase match. Source license links do not imply unrestricted reuse.

At least 19 recordsLinked to original sources
PubMed1979

3-Chloro-4-(phenylsuccinimido)-benzenesulfonamide (GS 385), a new anticonvulsant: its quantitative determination, pharmacokinetics and metabolism using high performance liquid chromatography.

A high-performance liquid chromatographic method (HPLC) involving dual wave length detection was developed for the determination of a new anticonvulsant, 3-chloro-4-(phenylsuccinimido)-benzenesulfonamide (suclofernide, GS 385, Sulfalepsin), and three of its metabolites: 3-chloro-4-(p-hydroxyphenylsuccinimido)-benzenesulfonamide (I), 3-chloro-4-(3'-phenylsuccinamyl)-benzenesulfonamide (II) and 3-chloro-4-(2'-phenylsuccinamyl)-benzenesulfonamide (III). The concentrations of GS 385 in blood samples from epileptic patients under chronic treatment with this drug was found in the range of 8--11 micrograms/ml. Pharmacokinetic curves of GS 385 blood levels in rats receiving single doses of the drug showed a maximum concentration of 22--23 micrograms/ml 1.5 h after oral application. The quantity of GS 385 in rat feces, bile and brain was also estimated. The p-hydroxy (I) and acid (II, III) metabolites of GS 385 were detected in both rat feces and bile, whereas only the acid metabolites were found in rat urine.

Animals↗
PubMed1977

Reactions of benzenesulfonohydrazides and benzenesulfonamides with hydrogen chloride or hydrogen bromide in acetic acid.

Benzenesulfonohydrazides capable of yielding a sulfinic acid intermediate by virtue of a basic nitrogen atom in the second position of the hydrazide moiety produced thiosulfonates when treated with 1 N hydrogen chloride in acetic acid and produced disulfides when treated with 1 N hydrogen bromide in the same solvent. In two cases, a crystalline mixture of P-nitrophenyl p-nitrobenzenethiosulfonate and bis(p-nitrophenyl) disulfide was isolated from the hydrogen chloride reactions. No reaction product was obtained from either the hydrogen chloride or hydrogen bromide reaction with benzenesulfonohydrazides that were unable to form a sulfinic acid intermediate. Reduction of benzenesulfonamides to disulfides appeared to be possible only with hydrogen bromide in acetic acid. No thiosulfonate was isolated from the treatments of benzenesulfonamides with 1 N hydrogen chloride in acetic acid. p-Nitrophenyl p-nitrobenzenethiosulfonate and p-bromophenyl p-bromobenzenethiosulfonate exhibited some antimicrobial activities against Gram-positive bacteria. The latter compound also showed analgesic properties in the phenylquinone test.

Acetates↗
PubMed1979

Correlation of carbonic anhydrase inhibitory activities of benzenesulfonamides with the data obtained by use of nitrogen-14 nuclear quadrupole resonance.

Nitrogen-14 nuclear quadrupole resonance (NQR) spectra of several benzenesulfonamides in their solid state are reported and analyzed in the framework of the Townes and Dailey theory. Satisfactory correlations between the (sigma NH--sigma NS) electron densities at the sulfamyl nitrogen and the in vitro carbonic anhydrase inhibitory activities of the sulfonamides have been found. The correlations are in accord with the results of other studies that show the carbonic anhydrase inhibitory activities to be largely influenced by the electronic property of the sulfamyl group.

Carbonic Anhydrase Inhibitors↗
PubMed1979

High-performance liquid chromatographic determination of azosemide in commercial animal feed.

A high-performance liquid chromatographic (HPLC) method was developed for the assay of 2-chloro-5-(1H-tetrazol-5-yl)-4-[(2-thienylmethyl)amino]benzenesulfonamide (I) in animal feed diet mixtures. The sample is extracted with acetone, an aliquot of the extract is evaporated to dryness, and the residue is dissolved in chloroform. This solution can be subjected to either of two cleanup procedures. The first traps I on a sodium hydroxide-diatomaceuous earth column. Compound I is then recovered using an acetic acid-ethyl acetate-chloroform eluent, which is removed by evaporation, followed by dissolution of the residue in aqueous sodium hydroxide. The second procedure involves the direct extraction of I from the chloroform solution. A linear relationship exists between the HPLC UV detector response at 254 nm and concentration up to 170 microgram/ml. The sodium hydroxide extraction procedure resulted in an overall recovery (+/- SD) of 92.9 +/- 1.6 and 97.4 +/- 1.8% (n = 5) at levels of 200 and 6000 ppm, respectively. Overall recoveries (+/- SD) obtained by the diatomaceous earth column procedure for the 20- and 6000-ppm levels were 90.0 +/- 2.0 and 95.9 +/- 1.6% (n = 5), respectively.

Animal Feed↗
PubMed1978

Mass spectrometry of N-methylsulfonylureas. A re-examination.

Some confusion has arisen in the literature regarding the electron impact mass spectrum of N-methyltolbutamide. The situation is complicated by the thermal lability of this compound which causes the formation of the corresponding N-methylsulfonamide. We present here spectral data at relatively low probe temperatures (and without an intervening gas chromatographic system) which we believe define the mass spectrum of N-methyltolbutamide more accurately than before. Similar data are presented for the analogous N-methylacetohexamide and show a rearrangement process for both substances not reported previously for this class of compounds.

Acetohexamide↗
PubMed1979

Renal sites of action of azosemide.

Azosemide is a new monosulfamyl diuretic with potency and spectrum of effects similar to those of furosemide. Eight normal subjects were studied with clearance techniques during water loading and during hydropenia to assess azosemide's site of action. Solute free water reabsorption decreased from 3.1 +/- 0.3 to 0.5 +/- 0.9 ml/min after azosemide (p less than 0.05), indicating an effect of azosemide at the ascending limb of the loop of Henle. During water loading, despite significant 3.5-fold increases in fractional excretion of sodium and chloride, the per cent increase in free water formation, CH2O/CIN X 100 was not significantly changed by azosemide (10.4 +/- 1.4 control and 14.8 +/- 3.1 after azosemide). This unchanged CH2O/CIN X 100 occurred despite increased osmolal clearance after azosemide, from 2.6 +/- 0.4 to 3.8 +/- 0.4 ml/min (p less than 0.02), indicating that azosemide increased delivery of solute to the diluting segment. Evidence is discussed which implies that azosemide inhibits solute transport of the thick ascending limb of the loop of Henle, but may also affect more proximal sites.

Adult↗
PubMed1979

Effects in normal subjects of long-term administration of azosemide.

Azosemide is a new loop diuretic which has been shown to affect solute transport proximal to the diluting segment. We assessed the effects of chronic administration of azosemide in normal subjects on low and normal salt diets. In both, there was compensatory renin release and aldosterone secretion, but the subjects on the low sodium diet developed striking hyperuricemia and metabolic alkalosis and were symptomatic, whereas those on the normal diet compensated to the extent that there were only minor changes.

Diet, Sodium-Restricted↗
PubMed1979

Bioavailability and dissolution behavior of trisulfapyrimidine suspensions.

The bioavailability of seven commercial trisulfapyrimidine suspensions was studied in 14 adult male volunteers. Fifteen blood samples were collected over a 48-hr period following administration of a 1-g dose of each suspension. Serum was assayed for each component (sulfadiazine, sulfamerazine, and sulfamethazine) by high-pressure liquid chromatography. Analysis of variance indicated several significant differences among the seven commercial preparations with respect to Cmax Tmax, and AUC for sulfadiazine, sulfamerazine, and sulfamethazine, The in vitro behavior of each suspension was then studied by the paddle method of the Food and Drug Administration. A 0.5-ml sample was introduced into 900 ml of hydrochloric acid (2.2 x 10(-4) M) at 37 degree and dissolved using a paddle speed of 25 rpm. Samples withdrawn at 15 and 30 min were analyzed by high-pressure liquid chromatography, and the percent of sulfadiazine, sulfamerazine, and sulfamethazine was calculated. Significant correlation was obtained between an in vivo parameter (Cmax for sulfadiazine) and an in vitro parameter (percent sulfadiazine dissolved in 30 min). Results indicate that this method is suitable for the in vitro screening of trisulapyrimidine suspensions.

Adult↗
PubMed1978

Clinical and pharmacological investigations of the new saluretic azosemid.

Ple 1053 (Azosemid) is a diuretic which resembles furosemide chemically and in its mode of action. When administered intravenously, Ple 1053 was approximately 5 times more potent on a weight basis than furosemide, its dose-response relationship was closer and the slope was steeper. After oral administration Ple 1053 and furosemide were approximately equal in potency. However, the effect of Azosemid in healthy subjects was relatively prolonged and abrupt peaks did not occur.

Administration, Oral↗
PubMed2026

Microbiological analysis and whole-genome sequencing of Neisseria gonorrhoeae from the microbiological failures in the international, zoliflodacin, phase 3, clinical trial for treatment of uncomplicated urogenital gonorrhoea: a retrospective, genomic, observational study.

BACKGROUND: Zoliflodacin, a first-in-class oral bacterial, DNA gyrase (GyrB) inhibitor, showed non-inferiority to ceftriaxone combined with azithromycin in a recent large international, phase 3, randomised controlled trial for treatment of uncomplicated urogenital gonorrhoea. The aim of this study was to describe the microbiological and whole-genome sequencing (WGS) analyses of paired baseline (pre-treatment) and test-of-cure (TOC) gonococcal isolates from the zoliflodacin phase 3, randomised controlled trial to further characterise and evaluate the protocol-specified microbiological failures with zoliflodacin (n=22) or ceftriaxone and azithromycin (n=1). METHODS: In this retrospective, genomic, observational study, results from antimicrobial susceptibility testing (agar dilution method) of isolates (n=960; 936 baseline isolates from 763 participants and 24 TOC isolates [23 with a paired baseline isolate in the same anatomical site] from 20 participants) collected during the zoliflodacin phase 3, randomised controlled trial done in 16 outpatient clinics in Belgium, the Netherlands, South Africa, Thailand, and the USA (Nov 6, 2019-March 16, 2023) are described. WGS analysis was performed on paired baseline and TOC isolates from participants with microbiological failures (zoliflodacin 44 isolates [19 participants]; ceftriaxone and azithromycin two isolates [one participant]), and the three baseline isolates with highest zoliflodacin minimum inhibitory concentration (MIC 0·5 mg/L). FINDINGS: All isolates were inhibited by the same zoliflodacin concentrations (MICs ≤0·008 to 0·5 mg/L) as wild-type strains cultured internationally in 2013-23. In participants with a microbiological failure after zoliflodacin treatment (n=22, 19 participants), zoliflodacin MIC values for baseline and TOC isolates were similar, and resistance selection was lacking. WGS showed that five (23%) of 22 infections (95% CI 10-43 [in four participants]) of zoliflodacin microbiological failures had different strains at TOC versus baseline. In 17 zoliflodacin microbiological failures (15 participants), isolates at baseline and TOC were indistinguishable. 13 of these 17 microbiological failures, corresponding to 59% (95% CI 39-77; 13 of 22) of all zoliflodacin microbiological failures, were in urogenital or rectal sites in 11 participants and the isolates had zoliflodacin MICs less than or equal to 0·008 to 0·25 mg/L. The single microbiological failure after ceftriaxone and azithromycin treatment had different strains at TOC versus at baseline. No sequenced isolates had mutations associated with elevated zoliflodacin MICs. INTERPRETATION: In the zoliflodacin phase 3, randomised controlled trial, 23% of the zoliflodacin microbiological failures and the single ceftriaxone and azithromycin microbiological failure had different gonococcal strains at TOC versus baseline, which suggests reinfections and not treatment failures. In addition, 59% of the zoliflodacin microbiological failures, all in anogenital sites, had no obvious microbiological explanation based on the low zoliflodacin MICs, previous pharmacodynamic studies, and no evidence of resistance selection after zoliflodacin therapy. A reinfection as the cause for these microbiological failures could not be excluded. We recommend that WGS is implemented in future randomised controlled trials for gonorrhoea treatment to further evaluate possible microbiological failures, exclude reinfections (to avoid underestimating the cure rates), and characterise antimicrobial resistance determinants. FUNDING: GARDP through grants from Germany BMFTR (03KA1831), UK DHSC as part of GAMRIF, Japan MHLW, the Netherlands' Ministry of Health, Welfare and Sport and Directorate-General for International Cooperation, the Federal Office of Public Health of Switzerland, the Canton of Geneva, Switzerland, and Örebro University Hospital, Sweden.

Humans↗
PubMed1978

Quantitative thin-layer and high-performance liquid chromatographic determination of the diuretic agent 2-chloro-5-[44-hydroxy-3-methyl-2-(methylimino)-4-thiazolidinyl]benzenesulphonamide hydrochloride in serum and urine.

Sensitive and specific thin-layer (TLC) and high-performance liquid chromatographic (HPLC) methods were developed for the determination of the diuretic agent 2-chloro-5-[4-hydroxy-3-methyl-2-(methylimino)-4-thiazolidinyl]benzenesulphonamide hydrochloride (HOE 740). HOE 740 can be determined in serum by HPLC. The detection is performed at a very short wavelength (202 nm), resulting in a detection limit of 10 ng/ml. By TLC only urine levels that are normally high can be determined directly (the detection limit is 70 ng/ml). For the determination of the lower serum levels it is necessary to convert the drug into its dehydration product, which has a higher absorbance and gives sufficient sensitivity (the detection limit is 10 ng/ml). Serum levels determined by the two methods correlate well. Some pharmacokinetic and excretion-kinetic data were computed using two-compartment open models.

Chromatography, High Pressure Liquid↗
PubMed1979

Effects of possible beta-cell membrane label, metahexamide-isothiocyanate, on insulin release.

To synthetize a specifically and covalently reacting label for the sulfonylurea receptor site, the sulfonylurea metahexmide was converted to its isothiocyano-derivative (MITC), and the effects of MITC on insulin release from the perfused rat pancreas were studied. MITC (2 micrometer) stimulated a large insulin release that persisted after the end of the MITC-infusion. At a higher concentration (50 micrometer) MITC produced only a short lasting stimulation, and thereafter inhibited either the sulfonylurea or the glucose-induced insulin release. It is suggested that the irreversible stimulation of insulin release by MITC reflects the convalent linkage of the label to the sulfonylurea receptor site, while excess isothiocyanate inhibited insulin release by reacting on less specific binding sites involved in the secretion process.

Animals↗
PubMed1977

Pharmacology of Sch 11973, N-(2-phenylisopropyl)-N-p-toluene sulfonyl urea, a potential new antianginal agent.

Antianginal drugs were evaluated on the basis of their ability to protect against subepicardial electrogram changes induced by local ventricular ischemia in anesthetized dogs. Sch 11973 [N-(2-phenylisopropyl)-N-p-toluene sulfonyl urea], a potential new antianginal agent, was also effective against local ventricular ischemia with its maximum effect appearing at 1mg/kg, i.v. or i.d. and with a duration of at least 2 hours. Nitroglycerin, at a dose of 0.04 mg/kg given bucally, exerted less protection, lasting on the average less than 15 minutes. Protection by propranolol at 1 mg/kg, i.v., was not better than nitroglycerin, but lasted up to one hour, while dipyridamole was ineffective when given in a dose range of 0.1-10 mg/kg, i.v. Sch 11973 differed from standard antianginal agents which may act via beta-adrenergic blocking activity or alteration of cardiac or circulatory dynamics since no acute pharmacological changes were observed after Sch 11973 was administered.

Adrenergic beta-Antagonists↗
PubMedDate not supplied

Absorption, metabolism, and excretion of 14C-tosifen in the dog and rat.

14C-tosifen [N-2-(1-phenylpropyl)-N'-p-tolyl sulfonylurea] was readily absorbed in both rats and dogs. The rates of absorption, metabolism, and urinary excretion were higher in the rat than in the dog. More of the drug was excreted via the feces than in the urine of the rat, whereas in the dog, the drug was primarily excreted into the urine. The parent drug was the major radioactive component in the plasma of both species. In the urine, however, only a negligible amount of tosifen was found. The major urinary metabolite was a hydroxymethyl derivative which accounted for about 60% and 40% of the total radioactivity in the urine of the dog and rat, respectively.

Absorption↗