Aceglutamide

Aceglutamide

Names
IUPAC name 2-(Acetylamino)-glutaramidic acid
Other names KW-110; α-N-Acetylglutamine[1]
Identifiers
CAS Number	2490-97-3 S
3D model (Jmol)	Interactive image Interactive image
ChemSpider	23836 392045 R 158492 S
DrugBank	DB04167
ECHA InfoCard	100.017.862
EC Number	219-647-7
KEGG	D07063
MeSH	aceglutamide
PubChem	25561 444019 R 182230 S
UNII	01J18G9G97
InChI InChI=1S/C7H12N2O4/c1-4(10)9-5(7(12)13)2-3-6(8)11/h5H,2-3H2,1H3,(H2,8,11)(H,9,10)(H,12,13) Key: KSMRODHGGIIXDV-UHFFFAOYSA-N
SMILES Cc(:[o]):[nH]C(CCc(:[nH2]):[o])c(:[o]):[oH] CC(=O)NC(CCC(N)=O)C(O)=O
Properties
Chemical 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 otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Aceglutamide (INN, JAN) (brand name Neuramina), or aceglutamide aluminum (JAN, USAN) (brand name Glumal), also known as acetylglutamine, is a psychostimulant, nootropic, and antiulcer agent that is marketed in Spain and Japan.^[1][2][3][4] It is an acetylated form of the amino acid L-glutamine, the precursor of glutamate in the body and brain.^[5] Aceglutamide functions as a prodrug to glutamine with improved potency and stability.^[5] Aceglutamide is used as a psychostimulant and nootropic, while aceglutamide aluminum is used in the treatment of ulcers.^[6][7][8][9] Aceglutamide can also be used as a liquid-stable source of glutamine to prevent damage from protein energy malnutrition.^[10][11][12] The drug has shown neuroprotective effects in an animal model of cerebral ischemia.^[5]

See also

• Aceburic acid
• Aceturic acid
• N-Acetylglutamic acid

References

1. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 3–. ISBN 978-1-4757-2085-3.
2. Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 6–. ISBN 978-3-88763-075-1.
3. William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 35–. ISBN 978-0-8155-1856-3.
4. I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 3–. ISBN 978-94-011-4439-1.
5. Zhang, Rui; Yang, Nan; Ji, Chao; Zheng, Ji; Liang, Zhen; Hou, Chun-Ying; Liu, Yan-Yong; Zuo, Ping-Ping (2015). "Neuroprotective effects of Aceglutamide on motor function in a rat model of cerebral ischemia and reperfusion". Restorative Neurology and Neuroscience. 33 (5): 741–759. doi:10.3233/RNN-150509. ISSN 0922-6028.
6. Ito, M; Yokochi, E; Kobayashi, C; Suzuki, Y (1982). "Studies on defensive factors of experimental ulcers (2). Increasing action of aceglutamide aluminum on defensive factors in acetic acid ulcers of rats (author's transl)". Nihon yakurigaku zasshi. Folia pharmacologica Japonica. 79 (4): 327–34. PMID 7095654.
7. Harada, Masatoshi; Yano, Shingo (1974). "Inhibitory effect of N-acetyl-L-glutamine aluminum complex (KW-110) and related compounds on gastric erosion and motility in stressed animals". Oyo Yakuri. 8 (1): 1–6.
8. Varas Lorenzo, MJ; López Martínez, A; Gordillo Bernal, J; Mundet Surroca, J (1991). "Comparative study of 3 drugs (aceglutamide aluminum, zinc acexamate, and magaldrate) in the long-term maintenance treatment (1 year) of peptic ulcer". Revista espanola de enfermedades digestivas : organo oficial de la Sociedad Espanola de Patologia Digestiva. 80 (2): 91–4. PMID 1790087.
9. Tanaka, H; Shuto, K; Marumo, H (1982). "Effect of N-acetyl-L-glutamine aluminum complex (KW-110), an antiulcer agent, on the non-steroidal anti-inflammatory drug-induced exacerbation of gastric ulcer in rats". Japanese journal of pharmacology. 32 (2): 307–13. doi:10.1254/jjp.32.307. PMID 7098147.
10. Lopez-Pedrosa Jose M; Manzano Manuel; Baxter Jeffrey H; Rueda Ricardo (2007). "N-acetyl-L-glutamine, a liquid-stable source of glutamine, partially prevents changes in body weight and on intestinal immunity induced by protein energy malnutrition in pigs". Digestive diseases and sciences. 52 (3): 650–658. doi:10.1007/s10620-006-9500-y. PMID 17253138.
11. JP 10101576 
12. US 2003099722