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Acetohydroxamic acid

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An enzyme inhibitor that inhibits urease and thus can treat some infections Pharmaceutical compound
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 Edit this at Wikidata
Chemical and physical data
FormulaC2H5NO2
Molar mass75.067 gยทmol
3D model (JSmol)
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; 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. AHA cannot be patented because it is a standard chemical compound.

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: 2407โ€“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): 321โ€“2. doi:10.1001/jama.1983.03340030003001. PMID 6854890.
Urologicals, including antispasmodics (G04B)
Acidifiers
Urinary antispasmodics
(primarily antimuscarinics)
Other urologicals
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Acetohydroxamic acid Add topic