U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C5H10N2O3
Molecular Weight 146.1447
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GLUTAMINE

SMILES

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

InChI

InChIKey=ZDXPYRJPNDTMRX-VKHMYHEASA-N
InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/t3-/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment:: Description was created based on several sources, including

Glutamine is a non-essential amino acid present abundantly throughout the body and is involved in many metabolic processes. It is synthesized from glutamic acid and ammonia. It is the principal carrier of nitrogen in the body and is an important energy source for many cells. Supplemental L-glutamine's possible immunomodulatory role may be accounted for in a number of ways. L-glutamine appears to play a major role in protecting the integrity of the gastrointestinal tract and, in particular, the large intestine. During catabolic states, the integrity of the intestinal mucosa may be compromised with consequent increased intestinal permeability and translocation of Gram-negative bacteria from the large intestine into the body. The demand for L-glutamine by the intestine, as well as by cells such as lymphocytes, appears to be much greater than that supplied by skeletal muscle, the major storage tissue for L-glutamine. L-glutamine is the preferred respiratory fuel for enterocytes, colonocytes and lymphocytes. Therefore, supplying supplemental L-glutamine under these conditions may do a number of things. For one, it may reverse the catabolic state by sparing skeletal muscle L-glutamine. It also may inhibit translocation of Gram-negative bacteria from the large intestine. L-glutamine helps maintain secretory IgA, which functions primarily by preventing the attachment of bacteria to mucosal cells. L-glutamine appears to be required to support the proliferation of mitogen-stimulated lymphocytes, as well as the production of interleukin-2 (IL-2) and interferon-gamma (IFN-gamma). It is also required for the maintenance of lymphokine-activated killer cells (LAK). L-glutamine can enhance phagocytosis by neutrophils and monocytes. It can lead to an increased synthesis of glutathione in the intestine, which may also play a role in maintaining the integrity of the intestinal mucosa by ameliorating oxidative stress. The exact mechanism of the possible immunomodulatory action of supplemental L-glutamine, however, remains unclear. It is conceivable that the major effect of L-glutamine occurs at the level of the intestine. Perhaps enteral L-glutamine acts directly on intestine-associated lymphoid tissue and stimulates overall immune function by that mechanism, without passing beyond the splanchnic bed. Glutamine is used for nutritional supplementation, also for treating dietary shortage or imbalance.

CNS Activity

Curator's Comment:: glutamine actually does cross the blood brain barrier

Originator

Curator's Comment:: Glutamine was first discovered by Schulze in 1883

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P17812
Gene ID: 1503.0
Gene Symbol: CTPS1
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Nutrestore

Approved Use

Nutrestore® [L-glutamine powder for oral solution] is indicated for the treatment of Short Bowel Syndrome (SBS) in patients receiving specialized nutritional support when used in conjunction with a recombinant human growth hormone that is approved for this indication

Launch Date

1.08673919E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
22.67 μg/mL
2 g single, oral
dose: 2 g
route of administration: Oral
experiment type: SINGLE
co-administered:
GLUTAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
35.34 μg/mL
4 g single, oral
dose: 4 g
route of administration: Oral
experiment type: SINGLE
co-administered:
GLUTAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
31.83 μg × h/mL
2 g single, oral
dose: 2 g
route of administration: Oral
experiment type: SINGLE
co-administered:
GLUTAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
57.13 μg × h/mL
4 g single, oral
dose: 4 g
route of administration: Oral
experiment type: SINGLE
co-administered:
GLUTAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.5 h
2 g single, oral
dose: 2 g
route of administration: Oral
experiment type: SINGLE
co-administered:
GLUTAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1.77 h
4 g single, oral
dose: 4 g
route of administration: Oral
experiment type: SINGLE
co-administered:
GLUTAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
0.86 g/kg 1 times / day multiple, intravenous (total)
Highest studied dose
Dose: 0.86 g/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 0.86 g/kg, 1 times / day
Sources: Page: p.267
unhealthy, 22-88
Health Status: unhealthy
Condition: Multiple organ failure
Age Group: 22-88
Sex: M+F
Sources: Page: p.267
0.7 g/kg 1 times / day multiple, oral (total)
Highest studied dose
Dose: 0.7 g/kg, 1 times / day
Route: oral
Route: multiple
Dose: 0.7 g/kg, 1 times / day
Sources: Page: 2557S
unhealthy, children
n = 6
Health Status: unhealthy
Condition: Cystic fibrosis
Age Group: children
Population Size: 6
Sources: Page: 2557S
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Receptor protein tyrosine kinase EphB4 is up-regulated in colon cancer.
2001
A sensitive and rapid assay for homologous recombination in mosquito cells: impact of vector topology and implications for gene targeting.
2001
Dietary antioxidants protect gut epithelial cells from oxidant-induced apoptosis.
2001
Connexin-mimetic peptide Gap 27 decreases osteoclastic activity.
2001
Cloning, expression and nuclear localization of human NPM3, a member of the nucleophosmin/nucleoplasmin family of nuclear chaperones.
2001
Early response genes induced in chondrocytes stimulated with the inflammatory cytokine interleukin-1beta.
2001
Genomic-scale measurement of mRNA turnover and the mechanisms of action of the anti-cancer drug flavopiridol.
2001
Estimation of apparent L-amino acid diffusion in porcine jejunal enterocyte brush border membrane vesicles.
2001
MtnK, methylthioribose kinase, is a starvation-induced protein in Bacillus subtilis.
2001
HIPK2 overexpression leads to stabilization of p53 protein and increased p53 transcriptional activity by decreasing Mdm2 protein levels.
2001
Gene targeting in mosquito cells: a demonstration of 'knockout' technology in extrachromosomal gene arrays.
2001
Flow cytometric assessment of the reactivity of a panel of monoclonal antibodies (mAb) against two populations of human dendritic cells (DC).
2001
[Proton magnetic-resonance spectroscopy in remitting and secondary-progressive multiple sclerosis].
2001
Biochemical, electron microscopic and immunohistological observations of cationic detergent-extracted cells: detection and improved preservation of microextensions and ultramicroextensions.
2001
Extracting biological information from DNA arrays: an unexpected link between arginine and methionine metabolism in Bacillus subtilis.
2001
Modulation of intracellular calcium and proliferative activity of invertebrate and vertebrate cells by ethylene.
2001
Comparative effects of diet supplementation with l-carnitine and dl-carnitine on ammonia toxicity and hepatic metabolism in rats.
2001 Apr
Heterogeneity of transport systems for L-glutamine in mouse mammary gland.
2001 Aug
L-glutamine.
2001 Aug
The stability constants of copper(II) complexes with some alpha-amino acids in dioxan-water mixtures.
2001 Aug 15
Gamma-glutamyl transpeptidase and glutathione biosynthesis in non-tumorigenic and tumorigenic rat liver oval cell lines.
2001 Dec
Coupled and uncoupled proton movement by amino acid transport system N.
2001 Dec 17
Free and protein-bound glutamine have identical splanchnic extraction in healthy human volunteers.
2001 Jul
Significance of interferon-gamma in coronary artery bypass surgery.
2001 Jul-Sep
Cost-containment with glutamine dipeptide-supplemented TPN.
2001 Jun
Implementation and uses of automated de novo peptide sequencing by tandem mass spectrometry.
2001 Jun 1
Chemo-enzymatic synthesis of a bioactive peptide containing a glutamine-linked oligosaccharide and its characterization.
2001 Jun 15
[Glutamine].
2001 May
Amino acid residues important for substrate specificity of the amino acid permeases Can1p and Gnp1p in Saccharomyces cerevisiae.
2001 Nov
The development of low-grade cerebral edema in cirrhosis is supported by the evolution of (1)H-magnetic resonance abnormalities after liver transplantation.
2001 Nov
Expression of c-myc is not critical for cell proliferation in established human leukemia lines.
2001 Nov 16
Amino acids protect epithelial cells from local toxicity by absorption enhancer, sodium laurate.
2001 Oct
Na+ transport by the neural glutamine transporter ATA1.
2001 Oct
System y+L-like activities account for high and low amino-acid transport phenotypes in chicken erythrocytes.
2001 Oct 1
Human L-type amino acid transporter 1 (LAT1): characterization of function and expression in tumor cell lines.
2001 Oct 1
Signaling to the nucleus by an L-type calcium channel-calmodulin complex through the MAP kinase pathway.
2001 Oct 12
Brain amino acid metabolism and ketosis.
2001 Oct 15
Amino acid supplementation affects hematological and biochemical parameters in elite rugby players.
2001 Sep
Comparison of calcitonin, alendronate and fluorophosphate effects on ovariectomized rat bone.
2001 Sep
[A study for optimal method of separating and cultivating embryonic rat cerebral neurons].
2001 Sep
Characterization of inhibitors acting at the synthetase site of Escherichia coli asparagine synthetase B.
2001 Sep 18
[Use of biologically active substances in preventing the toxic action of some heavy metals].
2001 Sep-Oct
MR proton spectroscopy in liver examinations of healthy individuals in vivo.
2002 Feb
[Association between the genetic polymorphisms of beta2-adrenergic receptor gene and the asthma susceptibility and clinical phenotypes in a Chinese population].
2002 Feb
The effects of high-dose glutamine ingestion on weightlifting performance.
2002 Feb
Glutamine promotes triglyceride absorption in a dose-dependent manner.
2002 Feb
The influence of L-glutamine on the depression of hepatic cytochrome P450 activity in male rats caused by total parenteral nutrition.
2002 Feb
Antiapoptotic and proapoptotic action of various amino acids and analogs in starving MOLT-4 cells.
2002 Feb 1
Characterization of cell death induced by vinflunine, the most recent Vinca alkaloid in clinical development.
2002 Jan 7
Oral bovine serum concentrate improves cryptosporidial enteritis in calves.
2002 Mar
Patents

Sample Use Guides

Usual Adult Dose for Dietary Supplement Average Dose: 10 g orally 3 times per day Dosing range: 5 g to 30 g orally per day
Route of Administration: Oral
Physiological concentration of glutamine (0.5mM) significantly increased the contribution of exogenous oleate to β-oxidation, 1.6-fold, and triglyceride formation, 2.8-fold in rat heart.
Name Type Language
GLUTAMINE
INCI   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF  
USAN   INCI   INN  
Official Name English
GLUTAMINE [INN]
Common Name English
NSC-27421
Code English
2-AMINOGLUTARAMIC ACID
Systematic Name English
L-GLUTAMINE [ORANGE BOOK]
Common Name English
GLUTAMINE [VANDF]
Common Name English
ENDARI
Brand Name English
GLUTAMINE [MI]
Common Name English
LEVOGLUTAMIDE
WHO-DD  
Common Name English
L-GLUTAMINE [FCC]
Common Name English
L-GLUTAMINE [VANDF]
Common Name English
L-GLUTAMINE [JAN]
Common Name English
GLUTAMINE, L-
Systematic Name English
GLUTAMINE [INCI]
Common Name English
GLUTAMINE [ORANGE BOOK]
Common Name English
L-GLUTAMINE [FHFI]
Common Name English
L-GLUTAMINE
FCC   FHFI   JAN   VANDF  
Systematic Name English
GLUTAMINE [USP]
Common Name English
NUTRESTORE
Brand Name English
FEMA NO. 3684
Code English
LEVOGLUTAMIDE [WHO-DD]
Common Name English
GLUTAMINE [USP-RS]
Common Name English
GLUTAMINE [USAN]
Common Name English
GLUTAMINE [MART.]
Common Name English
Classification Tree Code System Code
LOINC 26806-0
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LOINC 13396-7
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LOINC 58921-8
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LOINC 58930-9
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LOINC 2373-9
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LOINC 26894-6
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LOINC 13747-1
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LOINC 15134-0
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DSLD 75 (Number of products:2650)
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LOINC 25920-0
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LOINC 58927-5
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LOINC 56680-2
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FDA ORPHAN DRUG 145901
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LOINC 2374-7
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LOINC 44361-4
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CFR 21 CFR 172.320
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NDF-RT N0000175780
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JECFA EVALUATION L-GLUTAMINE
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LOINC 15144-9
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FDA ORPHAN DRUG 85794
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NDF-RT N0000006806
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LOINC 47630-9
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LOINC 2371-3
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LOINC 2370-5
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NCI_THESAURUS C68442
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LOINC 44362-2
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LOINC 25919-2
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LOINC 32243-8
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EU-Orphan Drug EU/3/12/1011
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WHO-ATC A16AA03
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LOINC 30056-6
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LOINC 22641-5
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LOINC 27043-9
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LOINC 44360-6
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LOINC 2372-1
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LOINC 25430-0
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LOINC 22720-7
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LOINC 16917-7
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WHO-VATC QA16AA03
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LOINC 20643-3
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NCI_THESAURUS C29596
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LOINC 22710-8
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LOINC 32242-0
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Code System Code Type Description
INN
1413
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PRIMARY
NCI_THESAURUS
C522
Created by admin on Fri Jun 25 22:57:00 UTC 2021 , Edited by admin on Fri Jun 25 22:57:00 UTC 2021
PRIMARY
RXCUI
4885
Created by admin on Fri Jun 25 22:57:00 UTC 2021 , Edited by admin on Fri Jun 25 22:57:00 UTC 2021
PRIMARY RxNorm
EVMPD
SUB23331
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PRIMARY
EPA CompTox
56-85-9
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PRIMARY
MESH
D005973
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PRIMARY
EVMPD
SUB08473MIG
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PRIMARY
MERCK INDEX
M5777
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PRIMARY Merck Index
CAS
56-85-9
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PRIMARY
DRUG CENTRAL
1311
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PRIMARY
ECHA (EC/EINECS)
200-292-1
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PRIMARY
FDA UNII
0RH81L854J
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PRIMARY
HSDB
8165
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PRIMARY
USP_CATALOG
1294808
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PRIMARY USP-RS
DRUG BANK
DB00130
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PRIMARY
WIKIPEDIA
GLUTAMINE
Created by admin on Fri Jun 25 22:57:00 UTC 2021 , Edited by admin on Fri Jun 25 22:57:00 UTC 2021
PRIMARY
PUBCHEM
5961
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PRIMARY
ChEMBL
CHEMBL930
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PRIMARY