N(2)-acetylglutamine

Also known as GlcNAc, Aceglutamide [INN], N-Acetylglutamine, Acetylglutamine, 2-acetamido-4-aminocarbonyl-butanoic acid, 2-acetamido-4-carbamoyl-butanoic acid, L-2-Acetamidoglutaramic acid, N2-acetylglutamine

Aceglutamide (brand name Neuramina), or aceglutamide aluminium (brand name Glumal), also known as acetylglutamine, is a psychostimulant, nootropic, and antiulcer agent that is marketed in Spain and Japan. It is an acetylated form of the amino acid L-glutamine, the precursor of glutamate in the body and brain. Aceglutamide functions as a prodrug to glutamine with improved potency and stability.

Chemical data

Formula: C7H12N2O4
Molecular weight: 188.18 g/mol
IUPAC name: 2-acetamido-5-amino-5-oxopentanoic acid
SMILES: CC(=O)NC(CCC(=O)N)C(=O)O
InChIKey: KSMRODHGGIIXDV-UHFFFAOYSA-N
XLogP: -1.4
Polar surface area: 109 Å²
H-bond donors: 3
H-bond acceptors: 4
Formal charge: 0

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Drug data · ChEMBL

Molecule type: Small molecule

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Wikidata facts

Subclass of: chemical compound
Mass: 188.08

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chemical formula: C₇H₁₂N₂O₄
canonical SMILES: CC(=O)NC(CCC(=O)N)C(=O)O
medical condition treated: peptic ulcer disease
found in taxon: Caenorhabditis elegans
subject has role: nootropic

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Aceglutamide is used as a psychostimulant and nootropic, while aceglutamide aluminium is used in the treatment of ulcers. Aceglutamide can also be used as a liquid-stable source of glutamine to prevent damage from protein energy malnutrition. The drug has shown neuroprotective effects in an animal model of cerebral ischemia.

Excerpted from Wikipedia’s “N(2)-acetylglutamine” article, available under the CC BY-SA 4.0 licence.

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