Salicylhydroxamic Acid (SHA)

Salicylhydroxamic acid is a drug that is a potent and irreversible inhibitor of bacterial and plant urease usually used for urinary tract infections. The molecule is similar to urea but is not hydrolyzable by the urease enzyme. It is also a trypanocidal agent. When administered orally, it is metabolized to salicylamide which exerts analgesic, antipyretic and antiinflammatory effects. Salicylhydroxamic acid is also a common ligand utilized in the synthesis of metallacrowns. In plants, some fungi and some protists with the alternative oxidase (AOX) enzyme in the mitochondrial electron transport chain system, salicylhdroxamic acid acts as an inhibitor of the enzyme, blocking the largely uninhibited flow of electrons through AOX. AOX acts as a "short circuit" of the normal electron chain, dissipating electrons with a much-decreased translocation of protons, and therefore diminished production of ATP by oxidative phosphorylation.