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Details

Stereochemistry ABSOLUTE
Molecular Formula C8H15N3O4
Molecular Weight 217.2227
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALANYL GLUTAMINE

SMILES

C[C@H](N)C(=O)N[C@@H](CCC(N)=O)C(O)=O

InChI

InChIKey=HJCMDXDYPOUFDY-WHFBIAKZSA-N
InChI=1S/C8H15N3O4/c1-4(9)7(13)11-5(8(14)15)2-3-6(10)12/h4-5H,2-3,9H2,1H3,(H2,10,12)(H,11,13)(H,14,15)/t4-,5-/m0/s1

HIDE SMILES / InChI

Molecular Formula C8H15N3O4
Molecular Weight 217.2227
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: The description was created based on several sources, including https://clinicaltrials.gov/ct2/show/NCT02053350 | https://www.ncbi.nlm.nih.gov/pubmed/26518955 | https://clinicaltrials.gov/ct2/show/NCT01832636 | https://www.ncbi.nlm.nih.gov/pubmed/22986234

Alanyl-glutamine is a widely used alternative supplement to L-glutamine in the production of biopharmaceuticals. The primary advantage of using L-alanyl-glutamine in place of L-glutamine is that it reduces the level of ammonia generated during cell culture. L-alanyl glutamine also acts as an antioxidant (peroxide) and anti-apoptosis (LPS-induced) factor. Ala-Glu may be used in cell culture and insect cell culture applications. It can be used in studies on injury and sepsis, and in the effects of irradiation on leucine and protein metabolism in vivo. Alanyl-glutamine is used as dipeptide infusion solution, which is given as part of parenteral and/or enteral nutritional therapy. When the intake of nutrients or food into the mouth or directly into the gut is not possible or it is not enough to supply the body’s needs then nutrients or foods can be given intravenously or through the gastrointestinal tract or a combination of both. This is especially important for people whose bodies are under physical stress from illness or recent surgery. During illness or after surgery the body requires nutrition or food. Amino acids are the building blocks used by the body to make proteins. Dipeptiven is usually given as a supplement to amino acid solutions or an amino acid containing infusion regimen as part of complete nutritional support.

Originator

Sources: Bulletin of the Chemical Society of Japan (1961), 34, 739

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Dipeptiven

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
652 μM
0.5 g/kg 1 times / day steady-state, intravenous
dose: 0.5 g/kg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered:
ALANYL GLUTAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
0.26 h
0.5 g/kg 1 times / day steady-state, intravenous
dose: 0.5 g/kg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered:
ALANYL GLUTAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1 g/kg 1 times / day multiple, intravenous
Highest studied dose
Dose: 1 g/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 1 g/kg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
PubMed

PubMed

TitleDatePubMed
Metabolic changes induced by pre-administration of L-alanyl-glutamine and omega-3 in Wistar rats subjected to sepsis.
2010-12
Randomized clinical trial of gut-specific nutrients in critically ill surgical patients.
2010-11
Immunogenicity and efficacy of oral vaccines in developing countries: lessons from a live cholera vaccine.
2010-10-04
Effects of in ovo injecting disaccharides and alanyl-glutamine dipeptide on the energy status in duck embryos and neonates.
2010-10
The impact of glutamine dipeptide-supplemented parenteral nutrition on outcomes of surgical patients: a meta-analysis of randomized clinical trials.
2010-09-21
Evaluation of HIV protease and nucleoside reverse transcriptase inhibitors on proliferation, necrosis, apoptosis in intestinal epithelial cells and electrolyte and water transport and epithelial barrier function in mice.
2010-08-11
Glutamate exocrine dynamics augmented by plasma glutamine and the distribution of amino acid transporters of the rat pancreas.
2010-06
L-alanyl-glutamine preoperative infusion in patients with critical limb ischemia subjected to distal revascularization reduces tissue damage and protects from oxidative stress.
2010-05
Parenteral nutrition: Revisited.
2010-03
Effect of multidrug-efflux transporter genes on dipeptide resistance and overproduction in Escherichia coli.
2010-03
Examination of the efficacy of acute L-alanyl-L-glutamine ingestion during hydration stress in endurance exercise.
2010-02-03
Effects of supplementation with free glutamine and the dipeptide alanyl-glutamine on parameters of muscle damage and inflammation in rats submitted to prolonged exercise.
2010-01
Glutamine and alanyl-glutamine dipeptide reduce mesenteric plasma extravasation, leukocyte adhesion and tumor necrosis factor-α (TNF-α) release during experimental endotoxemia.
2009-12
Nutrition support with glutamine dipeptide in patients undergoing liver transplantation.
2009-12
Surgery and transplantation - Guidelines on Parenteral Nutrition, Chapter 18.
2009-11-18
Amino acids - Guidelines on Parenteral Nutrition, Chapter 4.
2009-11-18
Clinical trial: prophylactic intravenous alanyl-glutamine reduces the severity of gastrointestinal toxicity induced by chemotherapy--a randomized crossover study.
2009-09-01
Modulation of B-cell endoplasmic reticulum calcium homeostasis by Epstein-Barr virus latent membrane protein-1.
2009-08-03
The effect of intravenous alanyl-glutamine supplementation on plasma glutathione levels in intensive care unit trauma patients receiving enteral nutrition: the results of a randomized controlled trial.
2009-08
Protective effects of glutamine dipeptide and alpha-tocopherol against ischemia-reperfusion injury in the isolated rat liver.
2009-06
L-Glutamine or L-alanyl-L-glutamine prevents oxidant- or endotoxin-induced death of neonatal enterocytes.
2009-05
Amino acids change liver growth factors gene expression in malnourished rats.
2009-04-08
Effects of oral supplementation with glutamine and alanyl-glutamine on glutamine, glutamate, and glutathione status in trained rats and subjected to long-duration exercise.
2009-04
Perioperative application of L-alanyl-L-glutamine in cardiac surgery: effect on the polarized T cell cytokine expression.
2009-03
Intravenous glutamine decreases lung and distal organ injury in an experimental model of abdominal sepsis.
2009
Pilot Study: effects of parenteral glutamine dipeptide supplementation on neutrophil functions and prevention of chemotherapy-induced side-effects in acute myeloid leukaemia patients.
2008-12-20
Protective effects of alanyl-glutamine on acute lung injury induced by lipopolysaccharide in rats.
2008-12
Alanyl-glutamine and glutamine supplementation improves 5-fluorouracil-induced intestinal epithelium damage in vitro.
2008-10
L-alanyl-L-glutamine-supplemented parenteral nutrition decreases infectious morbidity rate in patients with severe acute pancreatitis.
2008-07-04
Efficacy of parenteral nutrition supplemented with glutamine dipeptide to decrease hospital infections in critically ill surgical patients.
2008-07-04
Frequent intravenous pulses of growth hormone together with glutamine supplementation in prolonged critical illness after multiple trauma: effects on nitrogen balance, insulin resistance, and substrate oxidation.
2008-06
Hartree-Fock calculations with linearly scaling memory usage.
2008-05-14
Metabolic effects of enteral versus parenteral alanyl-glutamine dipeptide administration in critically ill patients receiving enteral feeding: a pilot study.
2008-04
Safety studies of l-alanyl-l-glutamine (l-AG).
2008-03
Year in review in Intensive Care Medicine, 2007. I. Experimental studies. Clinical studies: brain injury and neurology, renal failure and endocrinology.
2008-02
Frequent intravenous pulses of growth hormone together with alanylglutamine supplementation in prolonged critical illness after multiple trauma: effects on glucose control, plasma IGF-I and glutamine.
2008-02
Glutamine and alanyl-glutamine accelerate the recovery from 5-fluorouracil-induced experimental oral mucositis in hamster.
2008-02
Impact of alanyl-glutamine dipeptide on severe acute pancreatitis in early stage.
2008-01-21
[Effect of glutamine on serum interleukin-8 and tumor necrosis factor-alpha levels in patients with severe pancreatitis].
2008-01
Depletion of plasma antioxidants in surgical intensive care unit patients requiring parenteral feeding: effects of parenteral nutrition with or without alanyl-glutamine dipeptide supplementation.
2008-01
[Objectivization of the diagnostics and control of treatment of paresis of the gastrointestinal tract in diffuse peritonitis].
2008
L-alanine-L-glutamine supplementation improves the outcome after colorectal surgery for cancer.
2007-11
Short-term alanyl-glutamine dipeptide pretreatment in liver ischemia-reperfusion model: effects on microcirculation and antioxidant status in rats.
2007-10
Specific amino acids in the critically ill patient--exogenous glutamine/arginine: a common denominator?
2007-09
[Effect of early enriched parenteral alanyl-glutamine on heat shock protein 70 (HSP70) expression in critical patients].
2007-08
L-alanin-L-glutamine supplementation improves the outcome after colorectal surgery for cancer.
2007-07
A controlled trial of glutamine effects on bone healing.
2007-05-29
Glutamine kinetics during intravenous glutamine supplementation in ICU patients on continuous renal replacement therapy.
2007-04
Wasting and intestinal barrier function in children taking alanyl-glutamine-supplemented enteral formula.
2007-03
Glutamine induces heat-shock protein and protects against Escherichia coli lipopolysaccharide-induced vascular hyporeactivity in rats.
2007
Patents

Sample Use Guides

Alanyl-Glutamine orally 3g/day for 10 days
Route of Administration: Oral
IEC-6 cells were seeded in 12-well plates in a concentration of 6.25 Ч 104 cells/well and cultivated in DMEM media with 5% FCS (Gibco BRL). IEC-6 cells were confluent after 2 d following seeding. In order to rule out the effect of cell proliferation on cell migration, wells were incubated for 20 min with 5 μg/mL of mitomycin C, which inhibits DNA synthesis and cell mitosis. Wells were then scratched along their diameter and extended 30 mm in length to the right center corner, using a sterile razor blade. Prior to scratching, 50% of the media volume was removed from each study well. The media was changed and the cells were then incubated in DMEM media without glutamine (Gln) with 0, 7, 10, 70 and 100 μg/mL of NFV, diluted in 0.5% DMSO. After one hour of incubation, wells were washed using DMEM media without Gln and incubated with DMEM media without Gln for 12 or 24 h. To evaluate the effect of AQ (Alanyl-glutamine) on cell migration, after incubating the wells with mitomycin C for 20 min and scratching, the wells were incubated with either DMEM media without Gln or DMEM media without Gln supplemented with 1, 5, 10 or 50 mM of AQ.
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:11:40 GMT 2025
Edited
by admin
on Mon Mar 31 19:11:40 GMT 2025
Record UNII
U5JDO2770Z
Record Status FAILED
Record Version
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Name Type Language
L-ALANYL-L-GLUTAMINE
USP-RS  
Preferred Name English
ALANYL GLUTAMINE
INCI   WHO-DD  
INCI  
Official Name English
ALANYL-GLUTAMINE DIPEPTIDE
Common Name English
L-ALANYL-L-GLUTAMINE [USP-RS]
Common Name English
ALANYLGLUTAMINE
Systematic Name English
ALA-GLN
Common Name English
Alanyl glutamine [WHO-DD]
Common Name English
N(2)-L-ALANYL-L-GLUTAMINE
Systematic Name English
DIPEPTAMIN
Brand Name English
N(2)-L-ALANYL-LEVOGLUTAMIDE
Common Name English
L-GLUTAMINE, N2-L-ALANYL-
Systematic Name English
ALANYL-GLUTAMINE
Systematic Name English
GLUTAMINE, N2-L-ALANYL-
Systematic Name English
FEMA NO. 4712
Code English
GLUTAMAX
Common Name English
SUSTAMINE
Brand Name English
L-ALANYL-L-GLUTAMINE AMINO ACID
Common Name English
Classification Tree Code System Code
WHO-ATC B05XB02
Created by admin on Mon Mar 31 19:11:40 GMT 2025 , Edited by admin on Mon Mar 31 19:11:40 GMT 2025
WHO-VATC QB05XB02
Created by admin on Mon Mar 31 19:11:40 GMT 2025 , Edited by admin on Mon Mar 31 19:11:40 GMT 2025
FDA ORPHAN DRUG 611617
Created by admin on Mon Mar 31 19:11:40 GMT 2025 , Edited by admin on Mon Mar 31 19:11:40 GMT 2025
DSLD 3081 (Number of products:109)
Created by admin on Mon Mar 31 19:11:40 GMT 2025 , Edited by admin on Mon Mar 31 19:11:40 GMT 2025
JECFA EVALUATION L-ALANYL-L-GLUTAMINE
Created by admin on Mon Mar 31 19:11:40 GMT 2025 , Edited by admin on Mon Mar 31 19:11:40 GMT 2025
Code System Code Type Description
CAS
39537-23-0
Created by admin on Mon Mar 31 19:11:40 GMT 2025 , Edited by admin on Mon Mar 31 19:11:40 GMT 2025
PRIMARY
CHEBI
74387
Created by admin on Mon Mar 31 19:11:40 GMT 2025 , Edited by admin on Mon Mar 31 19:11:40 GMT 2025
PRIMARY
FDA UNII
U5JDO2770Z
Created by admin on Mon Mar 31 19:11:40 GMT 2025 , Edited by admin on Mon Mar 31 19:11:40 GMT 2025
PRIMARY
JECFA MONOGRAPH
2098
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PRIMARY
SMS_ID
100000127872
Created by admin on Mon Mar 31 19:11:40 GMT 2025 , Edited by admin on Mon Mar 31 19:11:40 GMT 2025
PRIMARY
ChEMBL
CHEMBL3707366
Created by admin on Mon Mar 31 19:11:40 GMT 2025 , Edited by admin on Mon Mar 31 19:11:40 GMT 2025
PRIMARY
PUBCHEM
123935
Created by admin on Mon Mar 31 19:11:40 GMT 2025 , Edited by admin on Mon Mar 31 19:11:40 GMT 2025
PRIMARY
EPA CompTox
DTXSID20192658
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PRIMARY
DRUG BANK
DB11876
Created by admin on Mon Mar 31 19:11:40 GMT 2025 , Edited by admin on Mon Mar 31 19:11:40 GMT 2025
PRIMARY
CHEBI
73788
Created by admin on Mon Mar 31 19:11:40 GMT 2025 , Edited by admin on Mon Mar 31 19:11:40 GMT 2025
PRIMARY
WIKIPEDIA
Alanyl-glutamine
Created by admin on Mon Mar 31 19:11:40 GMT 2025 , Edited by admin on Mon Mar 31 19:11:40 GMT 2025
PRIMARY
NCI_THESAURUS
C127908
Created by admin on Mon Mar 31 19:11:40 GMT 2025 , Edited by admin on Mon Mar 31 19:11:40 GMT 2025
PRIMARY
DAILYMED
U5JDO2770Z
Created by admin on Mon Mar 31 19:11:40 GMT 2025 , Edited by admin on Mon Mar 31 19:11:40 GMT 2025
PRIMARY
RXCUI
1359422
Created by admin on Mon Mar 31 19:11:40 GMT 2025 , Edited by admin on Mon Mar 31 19:11:40 GMT 2025
PRIMARY RxNorm
NCI_THESAURUS
C1505
Created by admin on Mon Mar 31 19:11:40 GMT 2025 , Edited by admin on Mon Mar 31 19:11:40 GMT 2025
CONCEPT Dietary Supplement
RS_ITEM_NUM
1012517
Created by admin on Mon Mar 31 19:11:40 GMT 2025 , Edited by admin on Mon Mar 31 19:11:40 GMT 2025
PRIMARY
DRUG CENTRAL
4319
Created by admin on Mon Mar 31 19:11:40 GMT 2025 , Edited by admin on Mon Mar 31 19:11:40 GMT 2025
PRIMARY
EVMPD
SUB34011
Created by admin on Mon Mar 31 19:11:40 GMT 2025 , Edited by admin on Mon Mar 31 19:11:40 GMT 2025
PRIMARY
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