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 namesLithostat
AHFS/Drugs.comConsumer Drug Information
ATC code
Identifiers
IUPAC name
  • N-Hydroxyacetamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.008.104
Chemical and physical data
FormulaC2H5NO2
Molar mass75.067 g·mol−1
3D model (JSmol)
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

References
  1. 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.
  2. Marwick C (July 1983). "New drugs selectively inhibit kidney stone formation". JAMA. 250 (3): 321–2. doi:10.1001/jama.1983.03340030003001. PMID 6854890.
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