Acetohydroxamic acid

Acetohydroxamic acid (also known as AHA or by the trade name Lithostat) 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.

Acetohydroxamic acid

Clinical data
Trade names	Lithostat
AHFS/Drugs.com	Consumer Drug Information
ATC code	G04BX03 (WHO)
Identifiers
IUPAC name N-Hydroxyacetamide
CAS Number	546-88-3 Y
PubChem CID	1990
DrugBank	DB00551 Y
ChemSpider	1913 Y
UNII	4RZ82L2GY5
KEGG	D00220 Y
ChEBI	CHEBI:49029 Y
ChEMBL	ChEMBL734 Y
CompTox Dashboard (EPA)	DTXSID7022546
ECHA InfoCard	100.008.104
Chemical and physical data
Formula	C2H5NO2
Molar mass	75.067 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(NO)C
InChI InChI=1S/C2H5NO2/c1-2(4)3-5/h5H,1H3,(H,3,4) Y Key:RRUDCFGSUDOHDG-UHFFFAOYSA-N Y
(verify)

Orphan drug

In 1983 the US Food and Drug Administration approved acetohydroxamic acid (AHA) as an orphan drug for "prevention of so-called struvite stones" under the newly enacted Orphan Drug Act of 1983.^[2] AHA cannot be patented because it is a standard chemical compound.^[2]

See also

• Salicylhydroxamic acid