Aceglutamide

Title: Aceglutamide
CAS Registry Number: 2490-97-3
CAS Name: N2-Acetyl-L-glutamine
Additional Names: a-N-acetyl-L-glutamine
Trademarks: Acutil-S (ISF)
Molecular Formula: C7H12N2O4
Molecular Weight: 188.18
Percent Composition: C 44.68%, H 6.43%, N 14.89%, O 34.01%
Literature References: Prepn: P. Karrer et al., Helv. Chim. Acta 9, 301 (1926); GB 792576 (1958 to Merck & Co.), C.A. 53, 2109a (1959); I. J. Maschler, N. Lichtenstein, Biochim. Biophys. Acta 57, 252 (1962). Stability study: G. Sekules, G. Guadagnini, Farmaco Ed. Prat. 21, 22 (1966). NMR study: W. Voelter et al., Z. Naturforsch. 26B, 213 (1971). Fermentation study: T. Nakanishi, J. Ferment. Technol. 56, 573 (1978). Prepn of the aluminum complex: T. Kagawa et al., DE 2127176 corresp to US 3787466 (1971, 1974 both to Kyowa). Physico-chemical properties: E. Hayakawa et al., Yakugaku Zasshi 97, 731 (1977), C.A. 87, 141198 (1977). Effect on exptl chronic gastric ulcer: H. Tanaka et al., Oyo Yakuri 7, 1035 (1973), C.A. 81, 33283v (1974). Cytoprotective effect: H. Tanaka, Arzneim.-Forsch. 36, 1485 (1986).
Properties: Crystals from ethanol, mp 197°. [a]20D -12.5° (c = 2.9 in water).
Melting point: mp 197°
Optical Rotation: [a]20D -12.5° (c = 2.9 in water)
Derivative Type: Aluminum complex
CAS Registry Number: 12607-92-0
Additional Names: Pentakis (N2-acetyl-L-glutaminato)tetrahydroxytrialuminum; aceglutamide aluminum
Manufacturers' Codes: KW-110
Trademarks: Glumal (Kyowa)
Molecular Formula: C35H59Al3N10O24
Molecular Weight: 1084.84
Percent Composition: C 38.75%, H 5.48%, Al 7.46%, N 12.91%, O 35.40%
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).
Melting point: mp 221° (dec)
Toxicity data: 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)
Therap-Cat: Free acid as nootropic; aluminum complex as antiulcerative.
Keywords: Nootropic.
Acemannan Acemetacin Acenaphthene Acenocoumarol Aceperone

Aceglutamide
Stereo, skeletal formula of aceglutamide (S)
Identifiers
CAS number 2490-97-3 S YesY
PubChem 25561, 444019 R, 182230 S
ChemSpider 23836 YesY, 392045 R YesY, 158492 S YesY
UNII 01J18G9G97 YesY
EC number 219-647-7
DrugBank DB04167
KEGG D07063 YesY
MeSH aceglutamide
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C7H12N2O4
Molar mass 188.18 g mol−1
Appearance White crystals
Melting point 197 °C; 387 °F; 470 K
Related compounds
Related alkanoic acids
  • N-Acetylaspartic acid
  • N-Acetylglutamic acid
  • Citrulline
  • Pivagabine
Related compounds
  • Bromisoval
  • Carbromal
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Aceglutamide is a psychostimulant and nootropic[1] used to improve memory and concentration.[2] Chemically, it is the acetyl derivative of the amino acid L-glutamine.

The salt aceglutamide aluminum (also known as KW-110 and Glumal) is effective in the treatment of ulcers.[3][4][5][6]

Aceglutamide can also be used as a liquid-stable source of glutamine to prevent damage from protein energy malnutrition.[7][8][9]