Page last updated: 2024-11-07

alanylglutamine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

alanylglutamine: RN refers to (L-Glu)-isomer; dipeptiven is for parenteral use [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Ala-Gln : A dipeptide formed from L-alanyl and L-glutamine residues. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID123935
CHEMBL ID3707366
CHEBI ID73788
SCHEMBL ID133887
MeSH IDM0153017

Synonyms (59)

Synonym
l-alanyl-l-glutamine ,
ala-gln, bioreagent, suitable for cell culture, suitable for insect cell culture
ala-gln, >=98% (tlc)
alanylglutamine
A1261
h-ala-gln-oh
39537-23-0
(2s)-5-amino-2-[[(2s)-2-aminopropanoyl]amino]-5-oxopentanoic acid
l-alanyl-l-glutamin
ala-gln
dipeptiven
alanyl-glutamine
n(2)-l-alanyl-l-glutamine
AKOS010366801
l-alany-l-glutamine
dipeptamin
sustamine
glutamax
n(2)-l-alanine l-glutamine dipeptide
unii-u5jdo2770z
l-glutamine, n2-l-alanyl-
glutamax i
u5jdo2770z ,
dipeptide alanyl-glutamine
AM20100042
CHEBI:73788
l-ala-l-gln
alanyl glutamine [inci]
glutamine, n2-l-alanyl-
l-alanyl-l-glutamine amino acid
alanyl glutamine [who-dd]
fema no. 4712
l-alanyl-l-glutamine [usp-rs]
alanyl-glutamine dipeptide
alanyl glutamine
l-glutamine, l-alanyl-
S5801
SCHEMBL133887
CHEMBL3707366
210541-56-3
l-alanine-l-glutamine
mfcd00133046
DTXSID20192658
l-alanyl-l-glutamine, united states pharmacopeia (usp) reference standard
l-alanyl-l-glutamine 1-hydrate
alanine-glutamine dipeptide
a-q dipeptide
alanine glutamine dipeptide
aq dipeptide
DB11876
Q27144111
(s)-5-amino-2-((s)-2-aminopropanamido)
n(2)-l-alanyl-l-glutamine,(s)
-5-oxopentanoic acid
AS-12601
CS-W014818
(s)-5-amino-2-((s)-2-aminopropanamido)-5-oxopentanoic acid
HY-W014102
(s)-5-amino-2-((s)-2-aminopropanamido)-5-oxopentanoicacid

Research Excerpts

Overview

Alanylglutamine (AG) is a dipeptide that fuels enterocytes and has a coadjuvant role during gut healing.

ExcerptReferenceRelevance
"Alanylglutamine (AG) is a dipeptide that fuels enterocytes and has a coadjuvant role during gut healing. "( Alanyl-glutamine Heals Indomethacin-induced Gastric Ulceration in Rats Via Antisecretory and Anti-apoptotic Mechanisms.
Abdallah, DM; El-Abhar, HS; El-Lekawy, AM, 2019
)
1.96

Treatment

ExcerptReferenceRelevance
"Treatment with alanylglutamine (Ala-Gln) or growth hormone (GH) did not alter Caco-2 Gly-Sar transport in the absence of H(2)O(2)."( Alanylglutamine dipeptide and growth hormone maintain PepT1-mediated transport in oxidatively stressed Caco-2 cells.
Alteheld, B; Evans, ME; Ganapathy, V; Gu, LH; Jones, DP; Leibach, FH; Ziegler, TR, 2005
)
2.11

Toxicity

ExcerptReferenceRelevance
" All the experiments were performed by a matricial-predefined protocol that allows the evaluation of the protective or toxic effects of each of these 19 compounds."( Paradoxical toxicity of cardioplegic compounds on ischemic cardiomyocyte using optimal design strategy.
Ferrera, R; Michel, P; Ovize, M, 2005
)
0.33
"After the 24-hour incubation period, pyruvate (5 mmol/liter), polyethylene glycol (5 mmol/liter), Ala-Gln (20 mmol/liter), and reduced glutathione (3 mmol/liter) showed toxic effects, whereas ethanol (1%) and calcium chloride (2 mmol/liter) seemed to be protective."( Paradoxical toxicity of cardioplegic compounds on ischemic cardiomyocyte using optimal design strategy.
Ferrera, R; Michel, P; Ovize, M, 2005
)
0.33
" l-AG was not acutely toxic when administered to Sprague-Dawley rats by gavage at 2000mg/kg bw."( Safety studies of l-alanyl-l-glutamine (l-AG).
Bowles, AJ; Durward, R; Lynch, B; Mullaney, T; Oda, S; Sugimura, Y, 2008
)
0.35
"Forty-four patients with gastric or colorectal cancer developing WHO side-effect grading system of grade 2 or higher were randomized to either control group (n = 22) or Gln group (n = 22) during next cycle of chemotherapy."( Clinical trial: prophylactic intravenous alanyl-glutamine reduces the severity of gastrointestinal toxicity induced by chemotherapy--a randomized crossover study.
Li, J; Li, Y; Liu, F; Ni, X; Ping, X; Yu, B, 2009
)
0.35
" There were no clinical or statistical differences in adverse events, safety and efficacy parameters between both groups."( Efficacy and safety of a parenteral amino acid solution containing alanyl-glutamine versus standard solution in infants: a first-in-man randomized double-blind trial.
Debauche, C; Schaible, T; Struijs, MC; te Beest, H; Tibboel, D; van Elburg, RM, 2013
)
0.39
"This first-in-man study shows that GLN-AA is safe in infants after surgical interventions, and is well tolerated."( Efficacy and safety of a parenteral amino acid solution containing alanyl-glutamine versus standard solution in infants: a first-in-man randomized double-blind trial.
Debauche, C; Schaible, T; Struijs, MC; te Beest, H; Tibboel, D; van Elburg, RM, 2013
)
0.39

Dosage Studied

ExcerptRelevanceReference
" We conclude that the duration and dosage of glutamine administration (equivalent to 26 gm glutamine per day in a patient weighing 70 kg) used in this study are not sufficient to restore glutamine deficiency of the skeletal muscle in the depleted state."( Glutamine-containing dipeptides as infusion substrates in the septic state.
Fürst, P; Karner, J; Ollenschläger, G; Roth, E; Simmel, A, 1989
)
0.28
" Rats were given hydrocortisone 21-acetate or the dosing vehicle and were infused with alanine (AA) or alanyl-glutamine (AG) at the same concentrations and rates (1."( Alanyl-glutamine prevents muscle atrophy and glutamine synthetase induction by glucocorticoids.
Hickson, RC; Karl, IE; Osborne, DF; Wegrzyn, LE, 1996
)
0.29
" The described mode and dosage of glutamine administration did not produce meaningful benefit in our autologous transplant patients and it was certainly not cost-effective."( Standardized parenteral alanyl-glutamine dipeptide supplementation is not beneficial in autologous transplant patients: a randomized, double-blind, placebo controlled study.
Benes, P; Chocenská, E; Gregora, E; Kozák, T; Patorková, M; Procházka, B; Pytlík, R, 2002
)
0.31
" Nutritional status of patients cannot be improved by the mode and dosage of parenteral glutamine used in our study."( [Parenteral glutamine does not improve the nutritional status in patients during high-dose chemotherapy and autologous peripheral stem cell transplantation].
Andĕl, M; Benes, P; Chocenská, E; Gregora, E; Klepetár, J; Kozák, T; Pat'orková, M; Procházka, B; Pytlík, R, 2002
)
0.31
"This pilot study showed that pharmacologically dosed oral GLN therapy prior to cardiac surgery was safe, well tolerated, and feasible."( Pharmacologically dosed oral glutamine reduces myocardial injury in patients undergoing cardiac surgery: a randomized pilot feasibility trial.
Dauber, I; Hamiel, C; Queensland, K; Rooyackers, O; Sufit, A; Weitzel, LB; Wischmeyer, PE, 2012
)
0.38
"For the first time, microparticles containing AGP were developed and exhibited prolonged in vitro release as well as protection to the drug, and it could be considered as a dosage form for patients who suffer from insulin-induced hypoglycemia and/or nocturnal hypoglycemia."( Formulation and characterization of ethylcellulose microparticles containing .L-alanyl- L-glutamine peptide.
Bazotte, RB; Bruschi, ML; Gonçalves, Mde C; Herculano, Lda S; Medina, AN; Nogueira, AC; Villa Nova, M, 2014
)
0.4
"Determine the minimum dosage of alanyl-glutamine (Ala-Gln) required to improve gut integrity and growth in children at risk of environmental enteropathy (EE)."( Intervention and Mechanisms of Alanyl-glutamine for Inflammation, Nutrition, and Enteropathy: A Randomized Controlled Trial.
Filho, JQ; Guedes, MM; Guerrant, RL; Havt, A; Junior, FS; Lanzarini Lopes, GML; Lima, AAM; Lima, NL; Maier, EA; Mayneris-Perxachs, J; Moore, SR; Perry, M; Quetz, JS; Quinn, LA; Ramprasad, C; Soares, AM; Swann, J, 2020
)
0.56
"This was a double-blinded randomized placebo-controlled dose-response trial."( Intervention and Mechanisms of Alanyl-glutamine for Inflammation, Nutrition, and Enteropathy: A Randomized Controlled Trial.
Filho, JQ; Guedes, MM; Guerrant, RL; Havt, A; Junior, FS; Lanzarini Lopes, GML; Lima, AAM; Lima, NL; Maier, EA; Mayneris-Perxachs, J; Moore, SR; Perry, M; Quetz, JS; Quinn, LA; Ramprasad, C; Soares, AM; Swann, J, 2020
)
0.56
" The average dose was 170 mL of AG or control based on a dosing scheme of 1 g/kg bodyweight."( A randomized double-blind controlled proof-of-concept study of alanyl-glutamine for reduction of post-myomectomy adhesions.
Chizen, DR; De Wilde, RL; Gargiulo, AR; Lim, HJ; Pierson, RA; Rislund, DC; Robertson, LM; Tulandi, T; Velygodskiy, A, 2023
)
0.91
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
dipeptide zwitterionAny peptide zwitterion comprising two amino acid residues. Major structure at pH 7.3.
dipeptideAny molecule that contains two amino-acid residues connected by peptide linkages.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (239)

TimeframeStudies, This Drug (%)All Drugs %
pre-199014 (5.86)18.7374
1990's28 (11.72)18.2507
2000's78 (32.64)29.6817
2010's93 (38.91)24.3611
2020's26 (10.88)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 21.75

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index21.75 (24.57)
Research Supply Index5.84 (2.92)
Research Growth Index4.97 (4.65)
Search Engine Demand Index50.49 (26.88)
Search Engine Supply Index4.00 (0.95)

This Compound (21.75)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials73 (26.94%)5.53%
Reviews10 (3.69%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other188 (69.37%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]