Acetohydroxamic acid

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Acetohydroxamic acid
Acetohydroxamic acid.svg
Clinical data
Trade names Lithostat
AHFS/ Consumer Drug Information
ATC code
CAS Number
PubChem CID
ECHA InfoCard 100.008.104 Edit this at Wikidata
Chemical and physical data
Formula C2H5NO2
Molar mass 75.07 g·mol−1
3D model (JSmol)

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[edit]

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[edit]


  1. ^ Fishbein, W; Carbone, P (1965). "Urease catalysis. ii. Inhibition of the enzyme by hydroxyurea, hydroxylamine, and acetohydroxamic acid". J Biol Chem. 240: 2407–2414. PMID 14304845.
  2. ^ a b Marwick, Charles (1983). "New drugs selectively inhibit kidney stone formation". The Journal of the American Medical Association. 240 (3): 321–322. doi:10.1001/jama.1983.03340030003001.