Drug Sulfanilamide

Massengill stated, as Klumpp reported the conversation (22), "that the drug sulfanilamid[e] had been so exploited by physicians and the press that everyone in the country was going wild... 

In 1937, 107 people died when the drug sulfanilamide was wrongly formulated. 

Many of the sulfur compounds are toxic but essential for life. The gas from elemental sulfur and from most of the compounds of sulfur is poisonous when inhaled and deadly when ingested. This is the reason that sulfur compounds are effective for rat and mice extermination as well an ingredient of insecticides. Sulfa drugs (sulfanilamide and sufadiazine), although toxic, were used as medical antibiotics during World War II before the development of penicillin. They are still used today in veterinary medicine. 

Reduction of the azo dye piontosil to produce the antibacterial drug sulfanilamide (Fig. 4.38) is a well-known example of azo reduction. This reaction is catalyzed by cytochromes P-450 and is also carried out by the reductases in the gut bacteria. The reduction of azo groups in food coloring dyes such as amaranth is catalyzed by several enzymes, including cytochromes P-450, NADPH cytochrome P-450 reductase, and DT-diaphorase, a cytosolic enzyme. 

This substance is a liquid used in antifreeze, paints, polishes, and cosmetics. As it has a sweet taste and is readily available it has been used as a poor man s alcohol, but it may also be ingested accidentally and for suicidal purposes. Diethylene glycol was once used as a vehicle for the drug sulfanilamide, and when used for this, it caused some 76 deaths. 

However, because malonic acid has only one methylene group, it is obvious that no oxidation-reduction can take place. Only association of the enzyme and inhibitor, and dissociation of the I complex, can occur. Another classical example of a competitive inhibitor is the sulfa drug sulfanilamide, which interferes with the biosynthesis of folic acid from the precursor -aminobenzoic acid (PABA). 

A pharmaceutical mixture contains two drugs, sulfanilamide and sulfathiazole. When the UV spectrum of the mixture was obtained, it was found that the two spectra overlapped as shown below in Figure 7.26. Pure samples of each drug were available and the spectrum for each drug was obtained under identical conditions. Using the data tabulated below, calculate the concentrations of each drug in the mixture. 

In the last ten years, the sulfonamide type of diuretic has yielded spectacularly to intensive study. The recognition that certain sulfonamides could have a useful influence upon renal electrolyte excretion is scarcely 15 years old The basic observations for this diuretic development arose from the sulfa drug era, from observations on the side effects of the first sulfa drug, sulfanilamide. Tishler (62) gives a chart depicting the many new drug fields where valuable... 

Replacing sulfa drugs (sulfanilamide derivatives) with novel chhydropter-oate synthase (DHPS) inhibitors 13FMC1331. 

In this experiment, you will prepare the sulfa drug sulfanilamide by the following synthetic scheme. The synthesis involves converting acetanilide to the intermediate p-acetamidobenzenesulfonyl chloride in Step 1. This intermediate is converted to sulfanilamide by way of p-acetamidobenzenesulfonamide in Step 2. 

The drug sulfanilamide (the first of the antibiotics), which is obtained... 

Purpose. You will carry out the multistep synthesis of the epoch-making antibacterial drug, sulfanilamide.You wiU learn the techniques for handling moisture sensitive materials and investigate the strategies involved in solving a synthetic organic problem. 

Purpose. The sequential synthesis is completed and the sulfa drug, sulfanilamide, is obtained by treatment of the sulfonyl chloride intermediate prepared in Experiment [C2], with an aqueous ammonia solution. This interesting product is fully characterized. 

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