Acetohydroxamic acid

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 ;
PubChem CID	1990;
DrugBank	DB00551 ;
ChemSpider	1913 ;
UNII	4RZ82L2GY5;
KEGG	D00220 ;
ChEBI	CHEBI:49029 ;
ChEMBL	ChEMBL734 ;
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) ; Key:RRUDCFGSUDOHDG-UHFFFAOYSA-N ;
	(verify)

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.

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]

^ Fishbein WN, Carbone PP (June 1965). "Urease Catalysis. Ii. Inhibition of the Enzyme by Hydroxyurea, Hydroxylamine, and Acetohydroxamic Acid". The Journal of Biological Chemistry. 240: 2407–14. doi:10.1016/S0021-9258(18)97338-2. PMID 14304845.
^ ^a ^b Marwick C (July 1983). "New drugs selectively inhibit kidney stone formation". JAMA. 250 (3): 321–2. doi:10.1001/jama.1983.03340030003001. PMID 6854890.