Contents

Salicylhydroxamic acid

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-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	153.137 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 [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Salicylhydroxamic acid (SHAorSHAM) 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;^[1] 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.^{[citation needed]}

Salicylhydroxamic acid is also a common ligand utilized in the synthesis of metallacrowns.^{[citation needed]}

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.^[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 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.^[3][4]

See also[edit]

• Acetohydroxamic acid

References[edit]

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