Chemistry:Acetohydroxamic acid

From HandWiki
Short description: Enzyme inhibitor that inhibits urease
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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC2H5NO2
Molar mass75.067 g·mol−1
3D model (JSmol)
  (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

References

  1. "Urease Catalysis. Ii. Inhibition of the Enzyme by Hydroxyurea, Hydroxylamine, and Acetohydroxamic Acid". The Journal of Biological Chemistry 240: 2407–14. June 1965. doi:10.1016/S0021-9258(18)97338-2. PMID 14304845. 
  2. Karki, Niraj; Leslie, Stephen W. (2026). "Struvite and Triple Phosphate Renal Calculi". StatPearls. Treasure Island (FL): StatPearls Publishing. http://www.ncbi.nlm.nih.gov/books/NBK568783/. Retrieved 2026-03-17. 
  3. 3.0 3.1 "New drugs selectively inhibit kidney stone formation". JAMA 250 (3): 321–2. July 1983. doi:10.1001/jama.1983.03340030003001. PMID 6854890.