SILVER SUCCINYLSULFADIAZINE AND SILVER SULFADIAZINE IMIDAZOLE - 2-NEW DERIVATIVES OF THE ANTI-BACTERIAL SILVER SULFADIAZINE

Published on Jan 1, 1980in Archiv Der Pharmazie3.751
路 DOI :10.1002/ARDP.19803131208
Hb Klasen4
Estimated H-index: 4
(UG: University of Groningen),
Huub B. Klasen
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Abstract
Because of the low water solubility of silver sulfadiazine (0.34 mg/100 ml) the preparation of more soluble derivatives has been studied. One such derivative was prepared by the introduction of a succinyl group on the aromatic amino group of sulfadiazine. The silver compound had the composition Ag2(succinylsulfadiazine). The water solubility of this compound with respect to silver sulfadiazine was enhanced by the factor 2 for [sulfanilamide] and 60 for [Ag]. A second derivative was prepared by the introduction of imidazole into the first coordination sphere of the silver ion. The composition of the compound was Ag(imidazole)2 sulfadiazine. Its solubility was enhanced by the factor 10 as compared with that of silver sulfadiazine. The MIC values of the compounds are comparable with those of silver sulfadiazine.
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References6
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#1Auke Bult (UG: University of Groningen)H-Index: 1
#2Huub B. Klasen (UG: University of Groningen)H-Index: 1
Abstract The structures of silver sulfonamides were found to depend highly on the substituent at the amide nitrogen of the sulfonamide. Silver is coordinated to that nitrogen and the sulfonamide is in the amido form if no substituent is present or if the substituent is a phenyl, acetyl, or 2-pyrimidyl group. If the substituent is a 2-thiazolyl or 2-pyridinyl group, the sulfonamide is in the imido form and silver coordinates to the nitrogen of the substituent. Depending on the number of suitable ...
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#1Hb Klasen (UG: University of Groningen)H-Index: 4
The structures of 1: 1 compounds of silver with twelve sulfanilamide derivatives are studied. In the compounds with sulfadimethoxine and sulfafenazole the silver ion is coordinated to the deprotonated amido nitrogen (amido-Ag structure). In the compounds with sulfadimidine, sulfamerazine, sulfamethoxazole, sulfamethoxydiazine, sulfamethoxypyrazine, sulfamethoxypyridazine, sulfamethylthiadiazole, sulfamoxol, sulfisomidine and sulfisoxazole the silver ion is coordinated to the nitrogen which is at...
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#1Robert J. Fass (OSU: Ohio State University)H-Index: 32
#2Carol A. Rotilie (OSU: Ohio State University)H-Index: 6
Last. Richard B. Prior (OSU: Ohio State University)H-Index: 14
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The minimal inhibitory concentrations of clindamycin and gentamicin alone and in combinations were determined by a microdilution method for 163 aerobic, facultative, and anaerobic clinical isolates. All 77 strains of Staphylococcus aureus, Diplococcus pneumoniae, Streptococcus pyogenes , and anaerobic bacteria (except for three strains of Clostridium ) were inhibited by 1.6 渭g or less of clindamycin per ml. Gentamicin did not interfere with the activity of clindamycin within the range of concent...
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The role of silver and sulfadiazine in the mechanism of action of silver sulfadiazine on burn wound infections was investigated. Silver, but not sulfadiazine, was bound by bacteria. Sulfadiazine did not act as an antibacterial agent in low concentrations, but exhibited specific synergism in combination with subinhibitory levels of silver sulfadiazine. The efficacy of silver sulfadiazine is thought to result from its slow and steady reactions with serum and other sodium chloride-containing body f...
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#1P.M.J. CoenegrachtH-Index: 10
#2J.P. FrankeH-Index: 1
Last. H.J. MettingH-Index: 1
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Abstract The automatic amperometric and potentiometric microtitration of pharmaceutically important sulfanilamide derivatives by diazotization with nitrite is described. Optimal conditions for diazotization and amperometric indication are discussed. A new cathodic amperometric indication of nitrite in M hydrochloric acid-25% ( w v ) of potassium bromide medium is proposed; the electrode processes involved are interpreted on the basis of current-potential curves. The effects of the hydrochloric a...
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Abstract For the effective treatment of bacterial infection, it is essential to find a new strategy to deliver antibacterial agents. In the present study, the co-delivery of superfine nano-silver with solubilized sulfadiazine (SD) using cyclodextrin metal-organic frameworks (CD-MOF) as carrier exhibited superior antibacterial efficacy to insoluble silver sulfadiazine. The abundant hydroxyl moieties in CD-MOF were utilized to reduce Ag precursor into silver nanoparticles (Ag NPs) of 4-5 nm and im...
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Silver sulfadiazine (AgSD) is the leading topical antibacterial agent for the treatment of burn wound infections. Antibacterial effect of AgSD is limited by its poor aqueous solubility, and antibacterial activity develops only by decomposition of AgSD to silver ions and sulfadiazine. In this study, it is for the first time that application of silver-modified nanoporous silica carriers (MCM-41 or SBA-15) loaded with sulfadiazine (SD), instead of silver sulfadiazine, overcoming the abovementioned ...
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Four different-anion Ag(I) compounds with the ligand norharmane (9H-Pyrido[3,4-b]indole; Hnor) and having the general formula [Ag(Hnor)2](anion) (anion = ClO4鈭, NO3鈭 and BF4鈭) [Ag(Hnor)2(MeCN)](PF6) are reported, and studied in detail regarding their coordination mode and in vitro antiproliferative effects. X-ray structural analysis revealed that the complex with the PF6鈭 anion has a MeCN solvent molecule weakly coordinated to Ag(I), making the metal coordination T-shaped, while the other compou...
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#1An-Rong Lee (NDMC: National Defense Medical Center)H-Index: 11
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Two new zinc sulphadiazine (Zn(SD) 2 )-amine complexes, zinc sulphadiazine-methylamine (Zn(SD) 2 (CH 3 NH 2 ) 2 ) and zinc sulphadiazine-ethylenediamine (Zn(SD) 2 (C 2 HgN 2 ) 3 .H 2 O), were prepared and compared with silver sulphadiazine (AgSD). The compounds were readily obtained by reaction of zinc nitrate hexahydrate with sulphadiazine or its salt in methylamine and ethylenediamine, respectively. Structure was established by X-ray crystallography and ultraviolet-visible, infrared and nuclea...
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#1Zeinab H. Mohamed Usman (LUC: Loyola University Chicago)H-Index: 1
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Abstract A method for determining silver in silver sulfadiazine pharmaceutical creams and ointments has been developed. Organic residues in the products are destroyed with sulfuric acid and nitric acid mixture. After evaporation of acids the silver is reduced with formaldehyde in alkaline solution, pH 11 鈥 12.5, to the metallic state; which is then reoxidized at pH 3.5 with iron(III) in the presence of ferrozine. The resulting absorbance is measured at 562 nm. Average recoveries of 99.7 卤 0.19 %...
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In this study the preparation of five hydrophilic derivatives of sulfadiazine is reported. The common structural element in the compounds is the 2-sulfonamidopyrimidine moiety. Three of these compounds are suitable for the preparation of a photostable 1鈭1 silver compound. These silver compounds are five to ten times more water soluble than silver sulfadiazine. TheIr,1H- and13C-Nmr data point to a similar co-ordination of silver in these compounds as with silver sulfadiazine. The microbiological ...
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