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

Details

Stereochemistry ABSOLUTE
Molecular Formula C5H10N2O3
Molecular Weight 146.1445
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GLUTAMINE

SMILES

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

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

2004
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
The impact of alanyl-glutamine on clinical safety, nitrogen balance, intestinal permeability, and clinical outcome in postoperative patients: a randomized, double-blind, controlled study of 120 patients.
1999 Sep-Oct
Primary structure, functional characteristics and tissue expression pattern of human ATA2, a subtype of amino acid transport system A.
2000 Jul 31
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
Modulation of intracellular calcium and proliferative activity of invertebrate and vertebrate cells by ethylene.
2001
Calcium-mediated transductive systems and functionally active gap junctions in astrocyte-like GL15 cells.
2001
L-glutamine.
2001 Aug
The glutamine/glutamate couplet and cellular function.
2001 Aug
Effects of the garlic compound diallyl disulfide on the metabolism, adherence and cell cycle of HT-29 colon carcinoma cells: evidence of sensitive and resistant sub-populations.
2001 Aug
Familial isolated primary hyperparathyroidism--a multiple endocrine neoplasia type 1 variant?
2001 Aug
Presence of glutamine:fructose-6-phosphate amidotransferase for glucosamine-6-phosphate synthesis in endothelial cells: effects of hyperglycaemia and glutamine.
2001 Feb
Glutamine and glutathione counteract the inhibitory effects of mediators of sepsis in neonatal hepatocytes.
2001 Feb
Influence of glutamine on cytokine production by human gut in vitro.
2001 Feb 7
Free fatty acid-induced inhibition of glucose and insulin-like growth factor I-induced deoxyribonucleic acid synthesis in the pancreatic beta-cell line INS-1.
2001 Jan
Glutamine metabolism to glucosamine is necessary for glutamine inhibition of endothelial nitric oxide synthesis.
2001 Jan 15
Free and protein-bound glutamine have identical splanchnic extraction in healthy human volunteers.
2001 Jul
Cost-containment with glutamine dipeptide-supplemented TPN.
2001 Jun
Chemo-enzymatic synthesis of a bioactive peptide containing a glutamine-linked oligosaccharide and its characterization.
2001 Jun 15
Characterization of an N-system amino acid transporter expressed in retina and its involvement in glutamine transport.
2001 Jun 29
Production of brown tyrosine pigments by the yeast Yarrowia lipolytica.
2001 Mar
Localized proton MR spectroscopy in infants with urea cycle defect.
2001 May
Regulation of mitochondrial glutamine/glutamate metabolism by glutamate transport: studies with (15)N.
2001 May
Structural basis for the activity and substrate specificity of Erwinia chrysanthemi L-asparaginase.
2001 May 15
Amino acid residues important for substrate specificity of the amino acid permeases Can1p and Gnp1p in Saccharomyces cerevisiae.
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
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
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
NUTRESTORE
Brand Name English
FEMA NO. 3684
Code English
GLUTAMINE [USP MONOGRAPH]
Common Name English
GLUTAMINE [USP-RS]
Common Name English
GLUTAMINE [USAN]
Common Name English
Levoglutamide [WHO-DD]
Common Name English
GLUTAMINE [MART.]
Common Name English
Classification Tree Code System Code
LOINC 26806-0
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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 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 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 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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Code System Code Type Description
NSC
27421
Created by admin on Sat Dec 16 17:06:15 GMT 2023 , Edited by admin on Sat Dec 16 17:06:15 GMT 2023
PRIMARY
CHEBI
28300
Created by admin on Sat Dec 16 17:06:15 GMT 2023 , Edited by admin on Sat Dec 16 17:06:15 GMT 2023
PRIMARY
INN
1413
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PRIMARY
NCI_THESAURUS
C522
Created by admin on Sat Dec 16 17:06:15 GMT 2023 , Edited by admin on Sat Dec 16 17:06:15 GMT 2023
PRIMARY
RXCUI
4885
Created by admin on Sat Dec 16 17:06:15 GMT 2023 , Edited by admin on Sat Dec 16 17:06:15 GMT 2023
PRIMARY RxNorm
EVMPD
SUB23331
Created by admin on Sat Dec 16 17:06:15 GMT 2023 , Edited by admin on Sat Dec 16 17:06:15 GMT 2023
PRIMARY
CHEBI
30011
Created by admin on Sat Dec 16 17:06:15 GMT 2023 , Edited by admin on Sat Dec 16 17:06:15 GMT 2023
PRIMARY
DAILYMED
0RH81L854J
Created by admin on Sat Dec 16 17:06:15 GMT 2023 , Edited by admin on Sat Dec 16 17:06:15 GMT 2023
PRIMARY
EPA CompTox
DTXSID1023100
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PRIMARY
CHEBI
58359
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PRIMARY
USAN
MM-23
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PRIMARY
MESH
D005973
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PRIMARY
EVMPD
SUB08473MIG
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PRIMARY
SMS_ID
100000087590
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PRIMARY
MERCK INDEX
m5777
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PRIMARY Merck Index
JECFA MONOGRAPH
1420
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PRIMARY
CAS
56-85-9
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PRIMARY
DRUG CENTRAL
1311
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PRIMARY
CHEBI
18050
Created by admin on Sat Dec 16 17:06:15 GMT 2023 , Edited by admin on Sat Dec 16 17:06:15 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-292-1
Created by admin on Sat Dec 16 17:06:15 GMT 2023 , Edited by admin on Sat Dec 16 17:06:15 GMT 2023
PRIMARY
FDA UNII
0RH81L854J
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PRIMARY
HSDB
8165
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PRIMARY
DRUG BANK
DB00130
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PRIMARY
WIKIPEDIA
GLUTAMINE
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PRIMARY
PUBCHEM
5961
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PRIMARY
RS_ITEM_NUM
1294808
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PRIMARY
ChEMBL
CHEMBL930
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PRIMARY