aceglutamide

{{chembox

| ImageFile = Aceglutamide.svg

| ImageClass = skin-invert-image

| ImageFile_Ref = {{chemboximage|correct|??}}

| ImageSize = 160

| ImageName = Stereo, skeletal formula of aceglutamide (S)

| PIN = 2-Acetamido-5-amino-5-oxopentanoic acid

| OtherNames = 2-(Acetylamino)-glutaramidic acid
α-N-Acetylglutamine;
N-Acetylglutamine
N-Acetyl-L-glutamine

|Section1={{Chembox Identifiers

| CASNo = 5817-09-4

| CASNo_Ref = {{cascite|correct|??}}

| CASNo_Comment = R/S

| CASNo1 =161579-61-9

| CASNo1_Comment =R

| CASNo2 =2490-97-3

| CASNo2_Comment =S

| PubChem = 25561

| PubChem_Comment = R/S

| PubChem1 = 444019

| PubChem1_Comment = R

| PubChem2 = 182230

| PubChem2_Comment = S

| ChemSpiderID = 23836

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID_Comment = R/S

| ChemSpiderID1 = 392045

| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID1_Comment = R

| ChemSpiderID2 = 158492

| ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID2_Comment = S

| UNII = 01J18G9G97

| UNII_Ref = {{fdacite|correct|FDA}}

| EINECS = 219-647-7

| DrugBank = DB04167

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| KEGG = D07063

| KEGG_Ref = {{keggcite|correct|kegg}}

| MeSHName = aceglutamide

| SMILES = CC(=O)NC(CCC(N)=O)C(O)=O

| StdInChI = 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)

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = KSMRODHGGIIXDV-UHFFFAOYSA-N

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

}}

|Section2={{Chembox Properties

| C=7 | H=12 | N=2 | O=4

| Appearance = White crystals

| MeltingPtC = 197

}}

|Section3={{Chembox Related

| OtherFunction_label = alkanoic acids

| OtherFunction = {{unbulleted list|N-Acetylaspartic acid|N-Acetylglutamic acid|Citrulline|Pivagabine}}

| OtherCompounds = {{unbulleted list|Bromisoval|Carbromal}}

}}

}}

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.{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA3|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=3–}}{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA6|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=6–}}{{cite book|author=William Andrew Publishing|title=Pharmaceutical Manufacturing Encyclopedia, 3rd Edition|url=https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA35|date=22 October 2013|publisher=Elsevier|isbn=978-0-8155-1856-3|pages=35–}}{{cite book| vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA3|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=3–}} It is an acetylated form of the amino acid L-glutamine, the precursor of glutamate in the body and brain.{{cite journal | vauthors = Zhang R, Yang N, Ji C, Zheng J, Liang Z, Hou CY, Liu YY, Zuo PP | display-authors = 6 | title = Neuroprotective effects of Aceglutamide on motor function in a rat model of cerebral ischemia and reperfusion | journal = Restorative Neurology and Neuroscience | volume = 33 | issue = 5 | pages = 741–59 | year = 2015 | pmid = 26444640 | doi = 10.3233/RNN-150509 }} Aceglutamide functions as a prodrug to glutamine with improved potency and stability.

Aceglutamide is used as a psychostimulant and nootropic, while aceglutamide aluminium is used in the treatment of ulcers.{{cite journal | vauthors = Ito M, Yokochi E, Kobayashi C, Suzuki Y | title = [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)] | journal = Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica | volume = 79 | issue = 4 | pages = 327–34 | date = April 1982 | pmid = 7095654 | doi = 10.1254/fpj.79.327 | doi-access = free }}{{cite journal | title = Inhibitory effect of N-acetyl-L-glutamine aluminium complex (KW-110) and related compounds on gastric erosion and motility in stressed animals | vauthors = Harada M, Yano S | journal = Oyo Yakuri | year = 1974 | volume = 8 | issue = 1 | pages = 1–6}}{{cite journal | vauthors = Varas Lorenzo MJ, López Martínez A, Gordillo Bernal J, Mundet Surroca J | title = [Comparative study of 3 drugs (aceglutamide aluminium, zinc acexamate, and magaldrate) in the long-term maintenance treatment (1 year) of peptic ulcer] | journal = Revista Espanola de Enfermedades Digestivas | volume = 80 | issue = 2 | pages = 91–4 | date = August 1991 | pmid = 1790087 }}{{cite journal | vauthors = Tanaka H, Shuto K, Marumo H | title = 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 | journal = Japanese Journal of Pharmacology | volume = 32 | issue = 2 | pages = 307–13 | date = April 1982 | pmid = 7098147 | doi = 10.1254/jjp.32.307 | doi-access = free }} Aceglutamide can also be used as a liquid-stable source of glutamine to prevent damage from protein energy malnutrition.{{cite journal | vauthors = López-Pedrosa JM, Manzano M, Baxter JH, Rueda R | title = 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 | journal = Digestive Diseases and Sciences | volume = 52 | issue = 3 | pages = 650–8 | date = March 2007 | pmid = 17253138 | doi = 10.1007/s10620-006-9500-y | s2cid = 37484555 }}{{cite patent|country=JP|number=H10101576|pubdate=1998-04-21|title=Treating medicine for digestive organ disease|assign1=Nisshin Flour Milling Co Ltd.|inventor1-last=Sasaki|inventor1-first=Kazuyuki|inventor2-last=Hayakawa|inventor2-first=Toru}}{{cite patent|country=US|number=2003099722|status=application|pubdate=2003-05-29|title=Methods and compositions for providing glutamine|assign1=Abbott Laboratories|inventor1-last=Baxter|inventor1-first=Jeffrey}}, abandoned during patent examination The drug has shown neuroprotective effects in an animal model of cerebral ischemia.