Acetohydroxamic acid
An enzyme inhibitor that inhibits urease and thus can treat some infections
- G04BX03 (WHO)
- N-Hydroxyacetamide
- 546-88-3 Y
- 1990
- DB00551 Y
- 1913 Y
- 4RZ82L2GY5
- D00220 Y
- CHEBI:49029 Y
- ChEMBL734 Y
- DTXSID7022546
- Interactive image
- O=C(NO)C
InChI
- InChI=1S/C2H5NO2/c1-2(4)3-5/h5H,1H3,(H,3,4) Y
- Key:RRUDCFGSUDOHDG-UHFFFAOYSA-N Y
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
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
References
- ^ 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: 2407–14. doi:10.1016/S0021-9258(18)97338-2. PMID 14304845.
- ^ a b Marwick C (July 1983). "New drugs selectively inhibit kidney stone formation". JAMA. 250 (3): 321–2. doi:10.1001/jama.1983.03340030003001. PMID 6854890.
- v
- t
- e
Urologicals, including antispasmodics (G04B)
(primarily antimuscarinics)
- Urea analogues: Acetohydroxamic acid
- Salicylhydroxamic acid