25. Aceglutamide

Nomenclature

CAS number: 2490-97-3
N2-Acetyl-l-glutamine; α-N-acetyl-l-glutamine.
C7H12N2O4; mol wt 188.18.
C 44.68%, H 6.43%, N 14.89%, O 34.01%.

Description and references

Prepn: P. Karrer et al., Helv. Chim. Acta 9, 301 (1926) DOI; GB 792576 (1958 to Merck & Co.); I. J. Maschler, N. Lichtenstein, Biochim. Biophys. Acta 57, 252 (1962) DOI PubMed. Stability in soln: G. Sekules, G. Guadagnini, Farmaco Ed. Prat. 21, 22 (1966). NMR study: W. Voelter et al., Z. Naturforsch. 26B, 213 (1971). HPLC-MS determn in urine: K. Sugahara et al., J. Chromatogr. B 657, 15 (1994) DOI PubMed. Clinical trial as component of total parenteral nutrition: I. Magnusson et al., Metabolism 38, Suppl. 1, 82 (1989) DOI PubMed.

Chemical structure

Properties

Crystals from ethanol, mp 197°. [α]20D 12.5° (c = 2.9 in water). Stable in neutral aqueous solns.

Derivative

Aluminum complex.

Nomenclature

CAS number: 12607-92-0
Pentakis (N2-acetyl-l-glutaminato)tetrahydroxytrialuminum; aceglutamide aluminum; KW-110; Glumal (Kyowa).
C35H59Al3N10O24; mol wt 1084.84.
C 38.75%, H 5.48%, Al 7.46%, N 12.91%, O 35.40%.

Description and references

Prepn: T. Kagawa et al., DE 2127176; eidem, US 3787466 (1971, 1974 both to Kyowa). Physico-chemical properties: E. Hayakawa et al., Yakugaku Zasshi 97, 731 (1977) PubMed, C.A. 87, 141198 (1977). Cytoprotective effect: H. Tanaka, Arzneim.-Forsch. 36, 1485 (1986).

Properties

White powder, mp 221° (dec). Sol in water. Practically insol in methanol, ethanol, acetone. LD50 in male mice, rats (g/kg): 14.3, >14.5 orally; 5.0, 4.2 i.p.; 0.46, 0.40 i.v. (Kagawa).

Therapeutic Category

Nutritional supplement (glutamine source). Aluminum complex as antiulcerative.

Keywords

Replenishers/Supplements; Nutrient

Aceglutamide Aluminum Complex: Antiulcerative; Cytoprotectant (Gastric)