Of sulfathiazoles

The reactivity of sulfathiazoles has been reviewed (65). Methylation in alkaline solution with dimethyl sulfate gives only the ring methylated derivative (85). Mixtures of products are obtained with diazomethane as alkylating agent (see p. 37). Other alkyl halides in aqueous alkali lead also to ring-alkylated products (85. 251, 650. 669-671). 

Action of magnesium sulfate on the sodium salt of sulfathiazole gives its magnesium salt (681). 

The investigations of Jensen and Schmith (45) indicate that in vitro activity of 2-sulfanilamido and 4-methyl-2-sulfanilamido selenazoles against pneumonia infections is comparable to that of sulfathiazole or sulfadiazine. Frisk (47) found that the activity of the selenium compounds was much lower than that of sulfathiazole. 

Sulfonamides prepared from 2-aminoselenazoles by normal methods sometimes possess activity comparable to that of sulfathiazole (45, 47). 

Aminothiazole itself (104a), R, = R2 = H (an intermediate in the preparation of sulfathiazole), was synthetized as early as 1888 from a,p-dihalogenoethylethers, which give chloroacetaldehyde in addic medium (8). Many other derivatives have now been used for this synthesis, and they are listed in Table IT12. All give excellent yields. 

A variation of this procedure is used for sulfisomidine because of the different character of the amino group in the 4-position of a pyrimidine ring. Two moles of the sulfonyl chloride are condensed with one mole of 4-amino-2,6-dimethy1pyrimidine in the presence of triethylamine. The resulting bis(acetylsulfanilyl) derivative is readily hydrolyzed to the product. The formation of the bis(acetylsulfanilyl) derivative has also been employed for other heterocycHc amines, eg, for synthesis of sulfathiazole and sulfamoxole (44), but the 1 1 reaction is probably preferable. 

The large importance of the sulfonamides for chemotherapeutics, and specially the high activity of sulfathiazole toward bacterial infections, indicated that sulfonamido derivatives of selenazole should also be investigated. Backer and de Jonge used for this purpose 2-amino-... 

Much of the development of the chemistry of sulfanilamidoselenazole derivatives is a result of the important role played by sulfonamides in chemotherapy and more particularly the good activity of sulfathiazole against bacterial infections. Backer and De Jonge (44) prepared these derivatives by reaction of 2-amino-4-methvl- and 2-amino-4-phenvl-selenazoles with N-acetvlsulfanilic acid chloride in pyridine. Alkaline... 

In its heyday, DTA analysis was very useful for the study of compound polymorphism and in the characterization of solvate species of drug compounds. It was used to deduce the ability of polymorphs to undergo thermal interconversion, providing information that could be used to deduce whether the system in question was monotropic or enantiotropic in nature. For instance, the enthalpies of fusion and transition were measured for different polymorphs of sulfathiazole and methylprednisolone [24]. The DTA thermograms shown in Fig. 4.5 demonstrate that Form-I is metastable with respect to Form-II, even... 

M. Lopez-Sanchez, M.J. Ruedas-Rama, A. Ruiz-Medina, A. Molina-Diaz and M.J. Ayora-Canada, Pharmaceutical powders analysis using FT-Raman spectrometry Simultaneous determination of sulfathiazole and sulfanilamide, Talanta, 74, 1603-1607 (2008). 

In this paper we present a brief history of the use of sulfathiazole, Terramycin , and Fumidil-B as antimicrobials in beekeeping. Included are some results of our published research, as well as some of our new research in which we show why the precautions - stated explicitly on the current Terramycin label to assure that honey intended for human consumption is free of trace amounts of drug residues - also implicitly apply to medicated colonies from which pollen may be collected for human consumption. 

Figure 2. HPLC chromatograms obtained for sulfathiazole standard compared with a honey control and honey fortified at 1.0 ppm (80% recovery). Mobile phase 95% methylene chloride-5% methanol flow rate 1.5 ml/min 0.2 Pg of sulfathiazole injected as standard extract injected equivalent to 40 mg of honey.

Argauer, R. J., Shimanuki, H., and Knox, D. A. 1982. Determination of Sulfathiazole in Honey from Medicated Honey Bee Colonies by High-Performance Liquid Chromatography on a Cyano-Amino Polar Phase. Environmental Entomology 11 820-23. 

Barry, C. P., MacEachern, G. M. 1983. Reverse Phase Liquid Chromatographic Determination of Sulfathiazole Residues in Honey. J. Assoc. Off. Anal. Chem. 66 4-7. 

Liquid Dosage Forms Sodium nitropruside in aqueous solution for injection will remain stable for up to one year if protected from light however, its shelf life is about 4h when exposed to normal room light [35]. It has been reported that uric acid increases the photostability of sulfathiazole sodium in solutions [36]. Further dZ-methionine increased the photostability of ascorbic acid in solution [37]. The... 

The extent to which a sulfonamide is acetylated depends upon the drug administered and the animal species. Acetylsulfathiazole is the principal metabolite found in the urine of cattle, sheep, and swine after enteral or parenteral administration of sulfathiazole. However, sheep can acetylate only 10% of the dose, while cattle can acetylate 32%, and swine 39%. When sulfamethazine was administered intravenously or orally to cattle, the animals eliminated 11% or 25% of the dose, respectively, in urine as N" -acetylsulfamethazine. The increased acetylation that occurred following tlie oral administration may be related to the increased exposure of sulfamethazine to liver enzymes following its absorption into the portal circulation. The acetylation rate may also be affected by the health status of an animal. Tims, cows suffering from ketosis in cows acetylate sulfonamides at much lower extent. 

Sekiguchi, K. and N. Obi. 1961. Studies on absorption of eutectic mixture. I. A comparison of the behavior of eutectic mixture of sulfathiazole and that of ordinary sulfathiazole in tern Pharm... 

Simonelli, A. P., S. C. Mehta, and W I. Higuchi. 1970. Inhibition of sulfathiazole crystal growth by polyvinylpyrrolidone.J Pharm Sc59 633-638. 

Nicolazzo et al. [52] considered the use of the lipophilic skin penetration enhancers, octisalate and padimate (both used in sunscreens), in comparison to Azone on the buccal absorption of various drugs in vitro. They were found to have limited effect in enhancing the permeation of triamcinolone acetonide (although some increase in tissue uptake was proposed in some cases) relative to Azone, while reducing the penetration of estradiol and caffeine. One interesting report is that of the effect of capsaicin from capsicum, a commonly used food ingredient, which has been reported to enhance the permeability of sulfathiazole in human volunteers [53] presumably by a direct irritation effect on the mucosa. This raised an interesting issue of the effect of diet on oral mucosal permeability. 

Asker AF, Larose M. Influence of uric acid on photostability of sulfathiazole sodium solutions. Drug Dev Ind Pharm 1987 13 2239-2248. 

The structural formulas of several cyclic compounds containing both nitrogen and sulfur are shown in Figure 17.4. Basic to the structures of these compounds is the simple ring structure of thiazole. It is a colorless liquid (bp, 117°C). One of its major uses has been for the manufacture of sulfathiazole, one of the oldest of the sulfonamide class of antibacterial drugs. The use of sulfathiazole is now confined to the practice of veterinary medicine because of its serious side effects. 

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