Salicylhydroxamic acid

Salicylhydroxamic acid

Names
IUPAC name 2-Hydroxybenzenecarbohydroxamic acid
Identifiers
CAS Number	89-73-6 Y
ChEBI	CHEBI:45615 Y
ChEMBL	ChEMBL309339 Y
ChemSpider	60011 Y
Jmol 3D model	Interactive image
PubChem	66644
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-N InChI=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	153.14 g·mol−1
Appearance	Brownish crystalline powder
Melting point	175 to 178 °C (347 to 352 °F; 448 to 451 K)
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Salicylhydroxamic acid (SHA or SHAM) 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. When AOX is blocked by SHAM, electrons are forced through the cytochrome pathway and through cytochrome 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.

See also

• Acetohydroxamic acid