Acetohydroxamic acid

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Acetohydroxamic acid
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Clinical data
Trade namesLithostat
AHFS/Drugs.comConsumer Drug Information
Pregnancy
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  • X
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Legal status
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  • In general: ℞ (Prescription only)
Identifiers
  • N-Hydroxyacetamide
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Chemical and physical data
FormulaC2H5NO2
Molar mass75.067 g·mol−1
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  • O=C(NO)C
  • InChI=1S/C2H5NO2/c1-2(4)3-5/h5H,1H3,(H,3,4) checkY
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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

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  1. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.Karki N, Leslie SW (2026). "Struvite and Triple Phosphate Renal Calculi". StatPearls. Treasure Island (FL): StatPearls Publishing. PMID 33760542. Retrieved 2026-03-17.
  3. ^ a b Page Module:Citation/CS1/styles.css has no content.Marwick C (July 1983). "New drugs selectively inhibit kidney stone formation". JAMA. 250 (3): 321–322. doi:10.1001/jama.1983.03340030003001. PMID 6854890.

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