P-Aminobenzene sulfonamide

The mode of action of sulfanilamides became known around 1947, when the structure and biosynthesis of folic acid were elucidated. This compound is built by bacteria from the heterocyclic pteroyl moiety, p-aminobenzoate, and glutamate. p-Aminobenzene-sulfonamide (9.89, sulfanilamide) is a competitive inhibitor of the synthase enzyme, acting as an antimetabolite of p-aminobenzoate. Occasionally, the sulfanilamide can even be incorporated into the modified folate, resulting in an inactive compound and thus an inactive enzyme. This theory, proposed by Woods and Fildes in 1940, became the first molecular explanation of drug action. 

The second is a comparably contemporary study94 on both the parent p-aminobenzene-sulfonamide and p-amino-fV-(3,4-dimethyl-5-isoxazolyl)benzenesulfonamide, known in the medicinal community as sulfanilamide and sulfisoxazole, respectively. As solids, the enthalpies of formation are —458.3 1.6 and —180.1 3.8 k.l mol 1, respectively. The former species may be compared with benzenesulfonamide, for which we cite only the most recent enthalpy of formation95, —320.1 1.6 k.l mol 1. As has been so often the case, we cannot reconcile the two sets of values. We are immediately thwarted in the comparison of the latter species. We lack the desired data for the desamino species or for any isoxazolamine-containing species. 

FIGURE 9.7 Typical pH-responsive polyacids (a) poly(acrylic acid) (PAAc) (b) poly(methacrylic acid) (PMAAc) (c) poly(2-ethyl acrylic acid) (PEAAc) (d) poly(2-propyl acrylic acid) (PPAAc) (e) poly(methacrylic amide) contains p-aminobenzene sulfonamide. 

SYNS ALBEXAN ALBOSAL AMBESIDE p-.UIINOBENZENESULFAMIDE p-AMINO-BENZENESULFONAMIDE 4-AMINOBENZENE-SULFONAMIDE p-AMINOPHENYLSULFONAMIDE 4-AMINOPHENYLSULFONAMIDE p-ANILINE-SULFONAMIDE ANILINE-p-SULFONIC AMIDE ANTISTREPT BACTERAMID COLLOMIDE COLSULANYDE COPTICIDE DIPRON ESTREPTOCEDA F 1162 FOURNEAU 1162 GERISON GOMBARDOL LUSIL LYSOCOCCINE... 

Other problems of cross-reactivity frequently encountered include the aminoglycoside antibiotics (streptomycin, kanamycin, neomycin, gentamycin), the p-aminobenzene derivatives (sulfonamides, sulfonylureas, procaine, procainamide, thiazide, carbonic anhydrase inhibitors), local anesthetics containing the p-aminophenyl group, and iodinated contrast media. 

Sulfanilamide (CgHgN202S) = White, odorless crystalline sulfonamide, used in the treatment of various bacterial infections. Synonyms Albexan albosol ambeside p-aminobenzene sulfamide sulfanilamide purified bacteramid 4-amino-benzenesulfonamide. 

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