Sulfaguanidine

Sulfaguanidine is a sulfonamide used as an anti-infective agent.

Sulfadimethoxine and sulfaguanidine: their sorption potential on natural soils.[Pubmed:22197018]

Chemosphere. 2012 Mar;86(10):1059-65.

Sulfonamides (SAs) are one of the oldest groups of veterinary chemotherapeutic agents. As these compounds are not completely metabolized in animals, a high proportion of the native form is excreted in feces and urine. They are therefore released either directly to the environment in aquacultures and by grazing animals, or indirectly during the application of manure or slurry. Once released into the environment, SAs become distributed among various environmental compartments and may be transported to surface or ground waters. The physicochemical properties of SAs, dosage and nature of the matrix are the factors mainly responsible for their distribution in the natural environment. Although these rather polar compounds have been in use for over half a century, knowledge of their fate and behavior in soil ecosystems is still limited. Therefore, in this work we have determined the sorption potential of sulfadimethoxine and Sulfaguanidine on various natural soils. The influence on sorption of external factors, such as ionic strength and pH, were also determined. The sorption coefficients (K(d)) obtained for the sulfonamides investigated were quite low (from 0.20 to 381.17 mL g(-1) for sulfadimethoxine and from 0.39 to 35.09 mL g(-1) for Sulfaguanidine), which indicated that these substances are highly mobile and have the potential to run off into surface waters and/or infiltrate ground water. Moreover, the sorption of these pharmaceuticals was found to be influenced by OC, soil solution pH and ionic strength, with higher K(d) values for soils of higher OC and lower K(d) values with increasing pH and ionic strength.

Preparation and application of sulfaguanidine-imprinted polymer on solid-phase extraction of pharmaceuticals from water.[Pubmed:25281079]

Talanta. 2015 Jan;131:99-107.

The molecularly imprinted polymers (MIPs) with Sulfaguanidine as a template, methacrylic acid, 4-vinylpyridine, and 2-hydroxyethyl methacrylate as functional monomers, ethylene glycol dimethacrylate as a cross-linker and 2,2'-azobis-isobutyronitrile as an initiator have been prepared through the cross-link reaction of polymerization. Solid-phase extraction (SPE) procedure for the extraction of Sulfaguanidine from water samples using the prepared MIPs and non-imprinted (NIPs) was evaluated. The best MIP in combination with commercial sorbents was applied for simultaneous extraction of eight pharmaceuticals. New SPE cartridges were prepared by combination of optimal produced MIP and Oasis HLB in 6 mL of polypropilene SPE reservoir. The developed method which includes new SPE cartridge (MIPMAA-Oasis HLB, 400mg/6 mL) and thin-layer chromatography was validated. The method provides a linear response over the concentration range of 0.5-150 mug/L, depending on the pharmaceutical with the correlation coefficients>0.9843 in all cases except for norfloxacin (0.9770) and penicillin G procaine (0.9801). Also, the method has revealed low limits of detection (0.25-20 mug/L), good precision (intra and inter-day), a relative standard deviation below 15% and recoveries above 95% for all eight pharmaceuticals. The developed method by using newly prepared SPE cartridge has been successfully applied to the analysis of production wastewater samples from pharmaceutical industry.

Synthesis of novel sulfonamide analogs containing sulfamerazine/sulfaguanidine and their biological activities.[Pubmed:26327456]

J Enzyme Inhib Med Chem. 2016 Dec;31(6):1005-10.

Sulfamerazine and Sulfaguanidine are clenched with p-nitrobenzoyl chloride and the products obtained are reduced to NaxS in ethanol-water. Novel sulfonamides (6a-g and 9a-g) were synthesized by the reaction of these reduced products (4 and 8) with various sulfonyl chlorides (5a-g). The structures of these compounds were characterized using spectroscopic analysis (IR, (1)H-NMR, (13)C-NMR and HRMS) technique. Antimicrobial activity of sulfonamides (3, 4, 7, 8, 6a-g and 9a-g) was evaluated by the agar diffusion method. These compounds showed antimicrobial activity against tested microorganism strains (Gram-positive bacteria, clinic isolate and yeast and mold). Compounds 9d, 9e, 9a, 6d and 6e showed particularly antimicrobial activity against tested Gram-positive (Bacillus cereus and B. subtilis) and Gram-negative (Enterobacter aerogenes) bacteria.

Three-component synthesis and carbonic anhydrase inhibitory properties of novel octahydroacridines incorporating sulfaguanidine scaffold.[Pubmed:27237188]

J Enzyme Inhib Med Chem. 2016;31(sup2):63-69.

Novel Sulfaguanidines incorporating acridine moiety were synthesized by the reaction of cyclohexane-1,3-dione, Sulfaguanidine, and aromatic aldehydes. Synthesis of these compounds was performed in water at room temperature, and their structures were confirmed by using spectral analysis (IR, (1)H-NMR, (13)C-NMR, and HRMS). Human carbonic anhydrase isoenzymes (hCA I and II) were purified from erythrocyte cells with affinity chromatography. hCA I was purified 83.40-fold with a specific activity, 1060.9 EU mg protein(-1), and hCA II was purified 262.32-fold with a specific activity, 3336.8 EU mg protein(-1). The inhibitory effects of newly synthesized Sulfaguanidines and acetazolamide, (AAZ) as a control compound, on hydratase and esterase activities of these isoenzymes have been studied in vitro. Synthesized compounds have moderate inhibition potentials on hCA I and hCA II isoenzymes. IC50 values of compounds for esterase activity are in the range of 118.4 +/- 7.0 muM-257.5 +/- 5.2 muM for hCA I and 86.7 +/- 3.0 muM-249.4 +/- 10.2 muM for hCA II, respectively.