Article · Wikipedia archive · Last revised Jun 8, 2026

Acetohydroxamic acid

Acetohydroxamic acid 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 and urinary stone disease. The molecule is similar to urea but is not hydrolyzable by urease; it thus disrupts the bacteria's metabolism through competitive inhibition. It is particularly effective for the prevention and treatment of infection stones.

Last revised
Jun 8, 2026
Read time
≈ 1 min
Length
248 w
Citations
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Source
Wikipedia ↗
Acetohydroxamic acid
Clinical data
Trade namesLithostat
AHFS/Drugs.comConsumer Drug Information
Pregnancy
category
  • X
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • 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)
  • O=C(NO)C
  • InChI=1S/C2H5NO2/c1-2(4)3-5/h5H,1H3,(H,3,4) checkY
  • Key:RRUDCFGSUDOHDG-UHFFFAOYSA-N checkY
  (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 and urinary stone disease. 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 particularly effective for the prevention and treatment of infection stones (struvite stones).2

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 1983.3 AHA cannot be patented because it is a standard chemical compound.3

See also

See also

References

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: 2407–2414. doi:10.1016/S0021-9258(18)97338-2. PMID 14304845.
  2. Karki N, Leslie SW (2026). "Struvite and Triple Phosphate Renal Calculi". StatPearls. Treasure Island (FL): StatPearls Publishing. PMID 33760542. Retrieved 2026-03-17.
  3. Marwick C (July 1983). "New drugs selectively inhibit kidney stone formation". JAMA. 250 (3): 321–322. doi:10.1001/jama.1983.03340030003001. PMID 6854890.