Acetohydroxamic Acid

Title: Acetohydroxamic Acid
CAS Registry Number: 546-88-3
CAS Name: N-Hydroxyacetamide
Additional Names: N-acetylhydroxylamine; acetic acid oxime; AHA
Trademarks: Lithostat (Mission Pharmacal)
Molecular Formula: C2H5NO2
Molecular Weight: 75.07
Percent Composition: C 32.00%, H 6.71%, N 18.66%, O 42.63%
Line Formula: CH3CONHOH
Literature References: Urease inhibitor. Prepn: A. Miolati, Ber. 25, 699 (1892); W. M. Wise, W. W. Brandt, J. Am. Chem. Soc. 77, 1058 (1955); H. A. Staab et al., Ber. 95, 1275 (1962); G. Sosnovsky, J. A. Krogh, Synthesis 1980, 654. Inhibition of urease activity: K. Kobashi et al., Biochim. Biophys. Acta 65, 380 (1962); W. N. Fishbein et al., Nature 208, 46 (1965); W. N. Fishbein, P. P. Carbone, J. Biol. Chem. 240, 2407 (1965); D. P. Griffith et al., Invest. Urol. 11, 234 (1973). Metabolism: E. Wolpert et al., Proc. Soc. Exp. Biol. Med. 136, 592 (1971); W. N. Fishbein et al., J. Pharmacol. Exp. Ther. 186, 173 (1973). Pharmacokinetics: S. Feldman et al., Invest. Urol. 15, 498 (1978). Clinical studies in treatment of kidney stones: D. B. Griffith et al., J. Urol. 119, 9 (1978); A. Martelli et al., Urology 17, 320 (1981).
Properties: mp 89-92°. pKa 8.70. pH (aq soln): 9.39.
Melting point: mp 89-92°
pKa: pKa 8.70
Therap-Cat: Antiurolithic. Antibacterial adjunct (urinary tract infection).
Keywords: Antiurolithic.
Acetoin Acetomeroctol Acetone Acetone Cyanohydrin Acetone Sodium Bisulfite

Acetohydroxamic acid
Acetohydroxamic acid.svg
Acetohydroxamic-acid-3D-balls.png
Systematic (IUPAC) name
ethanehydroxamic acid
Clinical data
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Identifiers
CAS number 546-88-3 YesY
ATC code G04BX03
PubChem CID 1990
DrugBank DB00551
ChemSpider 1913 YesY
UNII 4RZ82L2GY5 YesY
KEGG D00220 YesY
ChEBI CHEBI:49029 YesY
ChEMBL CHEMBL734 YesY
Chemical data
Formula C2H5NO2 
Mol. mass 75.0666 g/mol
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Acetohydroxamic acid (also known as AHA or Lithostat) is a drug that is a potent and irreversible inhibitor of bacterial and plant urease usually used for urinary tract infections. The molecule is similar to urea but is not hydrolyzable by the urease enzyme (Fishbein and Carbone, 1965).