Chemistry Structure and Function

The sulfonamides are a large group of compounds that are structural analogues of p-aminobenzoic acid (PABA). They differ primarily in the substituents on either the amido group (SO2-NH-R) or the amino group (-NH2) of the sulfanilamide nucleus. Substitutions on the sulfonamide group modify the drug's solubility characteristics, resulting in congeners with different rates of absorption and excretion. One group of sulfonamides remains largely unabsorbed in the gastrointestinal (GI)

tract following oral administration. Sulfadiazine, for example, produces changes only on local gut bacterial flora and finds wide use in presurgical bowel sterilization. Other sulfonamides, such as sulfisoxazole, are rapidly absorbed and highly soluble, and they undergo rapid urinary excretion, mainly in the unaltered form. A third group are rapidly absorbed and slowly excreted and maintain adequate blood levels for up to 24 hours (e.g., sulfamethoxazole). These drugs are useful in treating chronic urinary infections. Finally, some sulfonamides (e.g., sulfacetamide and sulfadiazine [silver salt]) are designed for topical use such as in infection of the eye and in burn patients.

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