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Aceglutamide

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Aceglutamide
Stereo, skeletal formula of aceglutamide (S)
Names
Preferred IUPAC name
2-Acetamido-5-amino-5-oxopentanoic acid
Other names
2-(Acetylamino)-glutaramidic acid
α-N-Acetylglutamine;[1]
N-Acetylglutamine
N-Acetyl-L-glutamine
Identifiers
3D model (JSmol)
ChemSpider
DrugBank
ECHA InfoCard 100.017.862 Edit this at Wikidata
EC Number
  • 219-647-7
KEGG
MeSH aceglutamide
UNII
  • 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) checkY
    Key: KSMRODHGGIIXDV-UHFFFAOYSA-N checkY
  • CC(=O)NC(CCC(N)=O)C(O)=O
Properties
C7H12N2O4
Molar mass 188.183 g·mol−1
Appearance White crystals
Melting point 197 °C (387 °F; 470 K)
Related compounds
Related alkanoic acids
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.[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 aluminium 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

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References

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  1. ^ a b Elks J (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. ^ Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 3–. ISBN 978-94-011-4439-1.
  5. ^ a b c Zhang R, Yang N, Ji C, Zheng J, Liang Z, Hou CY, et al. (2015). "Neuroprotective effects of Aceglutamide on motor function in a rat model of cerebral ischemia and reperfusion". Restorative Neurology and Neuroscience. 33 (5): 741–59. doi:10.3233/RNN-150509. PMID 26444640.
  6. ^ Ito M, Yokochi E, Kobayashi C, Suzuki Y (April 1982). "[Studies on defensive factors of experimental ulcers (2). Increasing action of aceglutamide aluminium on defensive factors in acetic acid ulcers of rats (author's transl)]". Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica. 79 (4): 327–34. doi:10.1254/fpj.79.327. PMID 7095654.
  7. ^ Harada M, Yano S (1974). "Inhibitory effect of N-acetyl-L-glutamine aluminium 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 (August 1991). "[Comparative study of 3 drugs (aceglutamide aluminium, zinc acexamate, and magaldrate) in the long-term maintenance treatment (1 year) of peptic ulcer]". Revista Espanola de Enfermedades Digestivas. 80 (2): 91–4. PMID 1790087.
  9. ^ Tanaka H, Shuto K, Marumo H (April 1982). "Effect of N-acetyl-L-glutamine aluminium 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. ^ López-Pedrosa JM, Manzano M, Baxter JH, Rueda R (March 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): 650–8. doi:10.1007/s10620-006-9500-y. PMID 17253138. S2CID 37484555.
  11. ^ JP H10101576, Sasaki, Kazuyuki & Hayakawa, Toru, "Treating medicine for digestive organ disease", published 1998-04-21, assigned to Nisshin Flour Milling Co Ltd. 
  12. ^ US application 2003099722, Baxter, Jeffrey, "Methods and compositions for providing glutamine", published 2003-05-29, assigned to Abbott Laboratories , abandoned during patent examination
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