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| Names | |
|---|---|
| Preferred IUPAC name N,2-Dihydroxybenzamide | |
| Other names 2-Hydroxybenzenecarbohydroxamic acid | |
| Identifiers | |
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3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
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| ECHA InfoCard | 100.001.759 |
| UNII | |
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| Properties | |
| 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 theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Salicylhydroxamic acid (SHA orSHAM) is adrug that is a potent and irreversibleenzyme inhibitor of theurease enzyme in variousbacteria andplants; it is usually used forurinary tract infections. The molecule is similar tourea but is nothydrolyzable by urease;[1] it thus disrupts the bacteria'smetabolism throughcompetitive inhibition. It is also atrypanocidal agent. When administeredorally, it is metabolized tosalicylamide, which exertsanalgesic,antipyretic, andanti-inflammatory effects.[citation needed]
Salicylhydroxamic acid is also a commonligand utilized in the synthesis ofmetallacrowns.[citation needed]
In plants, some fungi and some protists with thealternative oxidase (AOX) enzyme in the mitochondrialelectron transport chain system, salicylhdroxamic acid acts as an inhibitor of the enzyme, blocking the largely uninhibited flow of electrons through AOX.[2] 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 byoxidative phosphorylation. When AOX is blocked by SHAM, electrons are forced through the cytochrome pathway and throughcomplex 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 inTrypanosoma brucei, the organism that causesAfrican Sleeping Sickness, meaning that SHAM completely shuts down oxygen consumption by this organism.[3][4]
