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PubMed1999

[Determination of sulfacetamide sodium and sulfanilamide in shao tang ling ointment by high performance liquid chromatography].

An HPLC method for the determination of sulfacetamide sodium and sulfanilamide in Shao Tang Ling ointment was developed. The chromatographic conditions were: column, Spherisorb C18, mobile phase, methanol-0.25% (V/V)-acetic acid solution (7:93); detector UV-257 nm. The average recoveries were 98.9% (n = 5), RSD = 0.64% for sulfacetamide sodium and 99.3% (n = 5), RSD = 1.58% for sulfanilamide. The analytical method is simple, quick, accurate and reproducible.

Burns↗
PubMed1989

[A new drug sulfaton in the combined treatment of infections with sulfanilamide derivatives and diaminopyrimidine].

Derivatives of diaminopyrimidine as potentiators of the effect of the derivatives of sulfanilamide and other antibacterial drugs are discussed. Experimental data on sulfation, a new combined preparation, based on sulfamonomethoxine (a sulfanilamide derivative) and trimethoprim (a diaminopyrimidine derivative) are presented. Brief clinical characteristics of sulfation, its administration routes, doses, dosage advantages and better tolerance as compared to co-trimethoxazole+ (biseptol) are described.

Animals↗
PubMed1975

Alkylation by secondary alcohols III: Fusion of medicinal sulfanilamides with benzhydrol.

The fusion of certain sulfanilamides with benzhydrol in the presence of anhydrous zinc chloride affords several different products, depending primarily on the temperature at which the reaction is carried out. With sulfanilamide itself, three different products were isolated at 100, 160, and 180 degrees. A sequence of steps is suggested to account for the three products, one of which involves an intramolecular rearrangement of a benzhydryl moiety. The fusion of benzhydrol with p-toludine gives 2,6-dibenzhydrylaniline and not the N,N-dibenzhydryl derivative as previously reported.

Alcohols↗
PubMed1983

Distinction between the tautomeric forms of sulfanilamide derivatives by 13C-NMR.

The application of 13C-NMR for the distinction between amido and imido tautomers of sulfanilamide derivatives in DMSO solution is described. The differentiation is based on delta delta, the change in chemical shift of a sulfanilamide from the neutral form (in DMSO solution) to the anion (in aqueous alkaline solution). The delta delta values of three C atoms (C1, C1', C4) are suitable for the differentiation between the tautomers. The conclusions confirm previous results.

Chemical Phenomena↗
PubMed1987

Quantitative structure-activity analysis in dihydropteroate synthase inhibition by sulfones. Comparison with sulfanilamides.

A set of 25 4'-, eight 2',4'-, and five 2',4',6'-substituted 4-aminodiphenyl sulfones were tested for their inhibitory activity on dihydropteroate synthase of Escherichia coli. Linear regression analysis shows that enzymic inhibition indices correlate well with both quantum chemical and spectroscopic descriptors of the electronic structure of the common moiety 4-NH2-C6H4-SO2 of the sulfones (the above descriptors being expressed in relation to the electronic structure of the enzyme substrate, p-aminobenzoate). Therefore, the biological activity of the sulfones can be related to the electronic structural resemblance between these inhibitors and the substrate of the target enzyme. Since a similar result was previously obtained for a wide series of sulfanilamides in their different (amidic, imidic, and anionic) forms, it appears possible to consider the antibacterial sulfones and sulfanilamides as a congeneric chemical series. On the basis of the present results, the classical theory of antimetabolites would appear to take on a quantitative and sound rationale.

Dihydropteroate Synthase↗
PubMed1995

Thermodynamic study of sulfanilamide polymorphism: (I). Monotropy of the alpha-variety.

PURPOSE: Sulfanilamide was chosen as a model compound in order to gain insights on the stability hierarchy of drug polymorphs from structural and thermodynamic criteria. Despite numerous studies, disagreements remained on the reported enthalpies associated with the mutual interconvertions of the alpha-, beta-, and gamma-forms of sulfanilamide. Therefore, the unambiguous determination of these enthalpies was the purpose of this work. METHODS: Samples, free of solvent inclusions and made of only one form, were prepared, and analyzed combining X-ray powder diffraction and Differential Scanning Calorimetry (DSC). RESULTS: The enthalpy values associated with the alpha- to gamma- and beta- to gamma-transitions were found to be + 10.2 and + 10.9 J g-1, respectively. The calculated enthalpy of the beta- to alpha-transition is consistent with the experimental one (+ 1 J g-1). CONCLUSIONS: The monotropy of the alpha-form was ascertained over the explored temperature range at ordinary pressure.

Calorimetry, Differential Scanning↗
PubMed1976

Thermodynamic characteristics of the adsorption of sulfanilamide, phenol, and n-butanol on bio-gel beads.

The thermodynamic properties of the adsorption of sulfanilamide, phenol and n-butanol on Bio-Gel beads have been studied. Bio-Gel was chosen as the adsorbent as it possesses both hydrophobic and hydrophilic sites on its surface. Adsorption of the former two adsorbates was found to be exothermic, and the relevant thermodynamic parameters at 20 degrees are in the ranges: deltaH degrees = -2.7 to -5.4 kcal/mole; deltaF degrees = -6.0 to -7.6 kcal/mole; deltaS degrees = +7.7 to +11.6 e.u. In the presence of urea, adsorption of sulfanilamide and phenol was partially disrupted. This, together with the large entropy gain of the process, indicates that both hydrogen bonding and hydrophobic bonding contribute cooperatively to the adsorption. On the contrary, adsorption of n-butanol, which was not susceptible to urea, was an endothermic process with the parameters, deltaH degrees = +5.8kcal/mole, deltaF degrees = -1.8 kcal/mole, and deltaS = +26.1 E.U. at 20 degrees. These data conform to the thermodynamic properties of hydrophobic bond formation. Finally, possible implications of these data in the structural assembly of lipoprotein molecules are discussed.

Adsorption↗
PubMed1976

Additional evidence for hydrophobic bond formation in the adsorption of sulfanilamide on bio-gel beads.

We have previously suggested the involvement of both hydrogen binding and hydrophobic bonding in the adsorption of sulfanilamide on Bio-Gel beads. In the present study, we closely examined the concentration dependence of the binding curve and our proposed binding model has been corroborated. For comparison, binding parameters and thermodynamic data pertaining to the sulfanilamide-Sephadex system have been also evaluated.

Adsorption↗
PubMed1977

Nonconjugative plasmids encoding sulfanilamide resistance.

Nonconjugative plasmids encoding sulfanilamide (Sa) resistance were demonstrated at a high frequency in Shigella and Escherichia coli strains resistant to sulfanilamide. These Sa plasmids were all compatible with the standard plasmids used in compatibility testing. The sizes of seven Sa plasmids were measured by electron microscopy and ranged from 1.79 to 2.08 mum, corresponding to 3.5 to 3.9 megadaltons.

Conjugation, Genetic↗
PubMedDate not supplied

Metabolism of sulfadimidine, sulfanilamide, p-aminobenzoic acid, and isoniazid in suspensions of parenchymal and nonparenchymal rat liver cells.

Suspensions of isolated liver cells were prepared from rat livers perfused with Ca++-free buffer and 0.05% collagenase. Primary cell suspensions (containing both parenchymal and nonparenchymal liver cells) metabolized sulfadimidine, sulfanilamide, p-aminobenzoic acid, and isoniazid approximately at first order kinetics for at least 4 hr. Suspensions of parenchymal cells had the same metabolic capacity, although the metabolism of isoniazid proceeded at a somewhat reduced rate compared to the primary cell suspensions. Suspensions of nonparenchymal cells did not metabolize sulfadimidine, sulfanilamide, or p-aminobenzoic acid during 4 hr, although such suspensions acted upon isoniazid to some degree. It was concluded that parenchymal rat liver cells may metabolize (acetylate) all four drugs tested, whereas nonparenchymal cells metabolize only isoniazid to any considerable extent.

4-Aminobenzoic Acid↗
PubMed1986

[Resistance to antibiotics and sulfanilamides of enterobacteria isolated in Ulyanovsk Province].

The data on resistance to 10 antibiotics and sulfanilamides of 178 coprocultures of Enterobacteriaceae isolated from patients in the Ulyanovsk Region are presented. It is indicated that 93.8 per cent of the isolates were resistant to the antibiotics. The majority of the cultures were resistant to ampicillin, tetracycline and streptomycin and sensitive to gentamicin, polymyxin, trimetoprim, rifampicin and nalidixic acid. 43 combinations of the antibiotic resistance types were revealed. 92.7 per cent of the isolates were resistant to the sulfanilamides.

Anti-Bacterial Agents↗
PubMed1988

[Interactions of sulfanilamides, penicillins and acetylsalicylic acid in serum protein binding].

Combined use of sulfalen and sulfadimethoxine with benzylpenicillin and ampicillin resulted in increased binding of sulfalen to serum proteins of man. Acetylsalicylic acid promoted a decrease in the sulfanilamide binding to the serum proteins. The observed changes in the sulfanilamide binding to proteins of human blood serum were due to increased or decreased affinity of the drugs to the protein molecules.

Aspirin↗
PubMedDate not supplied

[Sulfanilamide absorption and acetylation in rats with experimental hyperlipidemia and cellular regulation of the process of acetylation].

Experiments on an isolated ileum of the rat with experimental hyperlipidemia have shown the decreased acetylation rate of sulfalen, sulfamonomethoxin and sulfapyridazine. The absorption rate of the free forms of sulfanilamides was increased (significantly for sulfalen and sulfapyridazine). Isadrin (1 . 10(-8) M) and cAMP (1 . 10(-5) M) introduced into the liquid exposed to the mucosa of the rat ileum raised the acetylation rate of sulfamonomethoxin by the ileic wall while anaprilin (1 . 10(-6) M) led to the reduction of both absorption and acetylation of this sulfanilamide. Addition of cAMP to the incubation mixture of mitochondria and microsomes increased the acetylation rate of sulfamonomethoxin.

Acetylation↗
PubMed1983

[Characteristics of the distribution of long-acting sulfanilamides in purulent pyelonephritis in rats].

Distribution of sulfalen, sulfadimethoxine and sulfamethoxypyridazine in the blood and organs of rats and binding of the drugs to the blood serum proteins of the animals with experimental P. aeruginosa pyelonephritis were studied. It was shown that in rats with P. aeruginosa pyelonephritis the levels of long-acting sulfanilamides in the blood and organs were lower, while the levels of their penetration through the histohematic barriers were higher, which was partially due to the decreased binding of sulfanilamides to blood proteins.

Animals↗
PubMed1981

Spontaneous formation of immunogenic conjugates by a biotransformation product of sulfanilamide.

3-hydroxy-sulfanilamide (3-HS) has been previously shown to be formed in significant amounts in rabbits and humans treated with sulfanilamide. In the present paper we demonstrate that 3-HS reacts readily with proteins at alkaline pH and forms conjugates capable to induce hapten specific antibodies in rabbits. According to our previous observations on ortho-aminophenol (OAP), the haptenic properties of 3-HS are apparently due to the presence in its molecule of an ortho-aminophenolic structure, rendering it capable to form a highly reactive quinoneimine derivative. In spite of a similar mechanism of linking and of the presence of an ortho-aminophenolic structure in the two haptens, 3-HS and OAP immunological systems do not cross react with each other. The data presented here support the hypothesis that 3-HS may represent the hapten or one of the haptens involved in sulfonamide allergy.

Animals↗
PubMed1999

Analysis of tea shoot catechins: spectrophotometric quantitation and selective visualization on two-dimensional paper chromatograms using diazotized sulfanilamide.

A highly specific and sensitive diazotized sulfanilamide reagent is synthesized for determination of tea catechins. The reagent is employed both as spray reagent for selective visualization of tea catechins on two-dimensional paper chromatograms (sensitivity <1 microg of d-(+)-catechin) and for their spectrophotometric quantification in the crude extracts of tea polyphenols isolated from fresh or dried tea shoots. The formation of yellow color (lambda(max) = 425 nm) between catechins and diazotized sulfanilamide was investigated and made the basis of a simple and sensitive spectrophotometric method for estimation of the total and individual catechins in different tea cultivars. At 425 nm, the absorbance was linear (r = 0.999) over the (0.4-8.0 microg/mL) concentration range of d-(+)-catechin.

Catechin↗
PubMedDate not supplied

[Functional status of beta-cells of the pancreas in long-term administration of hypoglycemic sulfanilamides in patients with glucose tolerance disorder].

The levels of immunoreactive insulin and C-peptide were determined against a background of the GTT and GTT + prednisolone in patients with glucose intolerance before and 3-6 mos. after sulfanilamide therapy to study the effect of a prolonged use of glibenclamide (manilil) on compensatory-reserve function of beta-cells. The hypoglycemic effect of these drugs was determined by their extrahepatic action. The normalization of the body sensitivity to insulin was established. A prolonged use of sugar lowering sulfanilamides did not make a depleting effect on beta-cell function. The results obtained were in favor of the administration of glibenclamide to patients with disturbed glucose tolerance.

Adult↗
PubMed2004

Effects of polymorphic differences for sulfanilamide, as seen through 13C and 15N solid-state NMR, together with shielding calculations.

We recorded both carbon-13 and nitrogen-15 NMR spectra of the three solid forms of sulfanilamide most commonly known. This study led to an interpretation of the solid-state effects seen in cross-polarization magic angle spinning spectra. Relaxation times for the different forms were measured. These show different behaviour for the three forms, arising from mobility variations. To obtain information on local environments, static spectra and spinning sideband manifolds were recorded and analysed for the 15N resonances, using isotopically enriched samples. Shielding asymmetries and anisotropies for the two nitrogen nuclei were obtained, showing very different behaviour for the two sites. Shielding calculations were carried out for both 13C and 15N nuclei, and the results are discussed in relation to the experimental values.

Anisotropy↗