salicylhydroxamic acid salicylhydroxamic acid salicylhydroxamic acid (sha or sham) is a drug that is a potent and irreversible enzyme inhibitor of the urease enzyme in various bacteria and plants; it is usually used for urinary tract infections. the molecule is similar to urea but is not hydrolyzable by urease; it thus disrupts the bacteria's metabolism through competitive inhibition. it is also a trypanocidal agent. when administered orally, it is metabolized to salicylamide, which exerts analgesic, antipyretic, and anti-inflammatory effects. the drug sham is not to be confused with a sham drug, which is either a legitimate placebo or a quack remedy. salicylhydroxamic acid names preferred iupac name n,2-dihydroxybenzamide other names 2-hydroxybenzenecarbohydroxamic acid identifiers cas number 89-73-6 y 3d model (jsmol) interactive image chebi chebi:45615 y chembl chembl309339 y chemspider 60011 y echa infocard 100.001.759 pubchem cid 66644 unii 8q07182d0t y comptox dashboard (epa) dtxsid5075365 inchi inchi=1s/c7h7no3/c9-6-4-2-1-3-5(6)7(10)8-11/h1-4,9,11h,(h,8,10)key: hbroznqevuilml-uhfffaoysa-ninchi=1/c7h7no3/c9-6-4-2-1-3-5(6)7(10)8-11/h1-4,9,11h,(h,8,10)key: hbroznqevuilml-uhfffaoyax smiles c1=cc=c(c(=c1)c(=o)no)o properties chemical formula c7h7no3 molar mass 153.137 g·mol−1 appearance brownish crystalline powder melting point 175 to 178 °c (347 to 352 °f; 448 to 451 k) except where otherwise noted, data are given for materials in their standard state (at 25 °c , 100 kpa). y verify (what is yn ?) infobox references 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. when aox is blocked by sham, electrons are forced through the cytochrome pathway and through complex iv, allowing observation of the operation of the cytochrome pathway without aox activity. the aox pathway is found to be the exclusive electron transport pathway in trypanosoma brucei, the organism that causes african sleeping sickness, meaning that sham completely shuts down oxygen consumption by this organism.