4882. Ibuproxam

Nomenclature

CAS number: 53648-05-8
N-Hydroxy-α-methyl-4-(2-methylpropyl)benzeneacetamide; dl-2-(4-isobutylphenyl)propionohydroxamic acid; G-277; Ibudros (Manetti Roberts).
C13H19NO2; mol wt 221.30.
C 70.56%, H 8.65%, N 6.33%, O 14.46%.

Description and references

Hydroxylamine deriv of ibuprofen, q.v., to which it is converted in vivo. Prepn: G. Orzalesi, R. Selleri, DE 2400531; eidem, US 4082707 (1974, 1978 both to Manetti & Roberts). Metabolism in rats: G. Orzalesi et al., Arzneim.-Forsch. 27, 1012 (1977); in humans: eidem, ibid. 30, 1607 (1980). Pharmacological study: eidem, ibid. 27, 1006 (1977). Thermal decomposition: S. Chimichi et al., J. Pharm. Sci. 69, 521 (1980). Physico-chemical properties: M. Mannelli et al., Boll. Chim. Farm. 119, 203 (1980).

Chemical structure

Properties

Crystals from acetone/petr ether, mp 119-121°. Sol in methanol, ethanol, acetone, ethyl ether. Practically insol in water and petr ether. LD50 in mice, rats (g/kg): >2, >3 orally (Orzalesi, Selleri, 1978).

Therapeutic Category

Anti-inflammatory.

Keywords

Anti-inflammatory (Nonsteroidal); Arylpropionic Acid Derivatives