63. Acetohydroxamic Acid

Nomenclature

CAS number: 546-88-3
N-Hydroxyacetamide; N-acetylhydroxylamine; acetic acid oxime; AHA; Lithostat (Mission Pharmacal).
C2H5NO2; mol wt 75.07.
C 32.00%, H 6.71%, N 18.66%, O 42.63%.
CH3CONHOH.

Description and references

Urease inhibitor. Prepn: A. Miolati, Ber. 25, 699 (1892); W. M. Wise, W. W. Brandt, J. Am. Chem. Soc. 77, 1058 (1955) DOI; H. A. Staab et al., Ber. 95, 1275 (1962) DOI; G. Sosnovsky, J. A. Krogh, Synthesis 1980, 654. Inhibition of urease activity: K. Kobashi et al., Biochim. Biophys. Acta 65, 380 (1962) DOI PubMed; W. N. Fishbein et al., Nature 208, 46 (1965) DOI PubMed; W. N. Fishbein, P. P. Carbone, J. Biol. Chem. 240, 2407 (1965) PubMed; D. P. Griffith et al., Invest. Urol. 11, 234 (1973) PubMed. Metabolism: E. Wolpert et al., Proc. Soc. Exp. Biol. Med. 136, 592 (1971) PubMed; W. N. Fishbein et al., J. Pharmacol. Exp. Ther. 186, 173 (1973) PubMed. Pharmacokinetics: S. Feldman et al., Invest. Urol. 15, 498 (1978) PubMed. Clinical studies in treatment of kidney stones: D. B. Griffith et al., J. Urol. 119, 9 (1978) PubMed; A. Martelli et al., Urology 17, 320 (1981) DOI PubMed.

Properties

White crystalline powder. mp 89-92°. pKa 8.70. pH (aq soln): 9.39. Freely sol in water, alcohol. Very slightly sol in chloroform.

Therapeutic Category

Antiurolithic. Antibacterial adjunct (urinary tract infection).

Keywords

Antiurolithic