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
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
DescriptionSources: http://www.drugbank.ca/drugs/DB00130Curator's Comment: Description was created based on several sources, including
Sources: http://www.drugbank.ca/drugs/DB00130
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
Sources: http://www.calmclinic.com/anxiety/drugs/glutamine
Curator's Comment: glutamine actually does cross the blood brain barrier
Originator
Sources: http://www.aminoacidsguide.com/Gln.html
Curator's Comment: Glutamine was first discovered by Schulze in 1883
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P17812 Gene ID: 1503.0 Gene Symbol: CTPS1 Target Organism: Homo sapiens (Human) Sources: http://www.drugbank.ca/drugs/DB00130 |
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Target ID: CHEMBL2146302 Sources: http://www.drugbank.ca/drugs/DB00130 |
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Target ID: CHEMBL2730 Sources: http://www.drugbank.ca/drugs/DB00130 |
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Target ID: GO:0006915 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27137983 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Nutrestore Approved UseNutrestore® [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 Date2004 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
22.67 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24771050 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24771050 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
31.83 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24771050 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24771050 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24771050 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24771050 |
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
Dose | Population | Adverse 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 |
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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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-667_NutreStore_BioPharmr.pdf#page14 Page: 14.0 |
no |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
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Primary structure, functional characteristics and tissue expression pattern of human ATA2, a subtype of amino acid transport system A. | 2000 Jul 31 |
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A sensitive and rapid assay for homologous recombination in mosquito cells: impact of vector topology and implications for gene targeting. | 2001 |
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Dietary antioxidants protect gut epithelial cells from oxidant-induced apoptosis. | 2001 |
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Connexin-mimetic peptide Gap 27 decreases osteoclastic activity. | 2001 |
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Cloning, expression and nuclear localization of human NPM3, a member of the nucleophosmin/nucleoplasmin family of nuclear chaperones. | 2001 |
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Early response genes induced in chondrocytes stimulated with the inflammatory cytokine interleukin-1beta. | 2001 |
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Genomic-scale measurement of mRNA turnover and the mechanisms of action of the anti-cancer drug flavopiridol. | 2001 |
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Estimation of apparent L-amino acid diffusion in porcine jejunal enterocyte brush border membrane vesicles. | 2001 |
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MtnK, methylthioribose kinase, is a starvation-induced protein in Bacillus subtilis. | 2001 |
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Modulation of intracellular calcium and proliferative activity of invertebrate and vertebrate cells by ethylene. | 2001 |
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Calcium-mediated transductive systems and functionally active gap junctions in astrocyte-like GL15 cells. | 2001 |
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L-glutamine. | 2001 Aug |
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The glutamine/glutamate couplet and cellular function. | 2001 Aug |
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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 |
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Familial isolated primary hyperparathyroidism--a multiple endocrine neoplasia type 1 variant? | 2001 Aug |
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Presence of glutamine:fructose-6-phosphate amidotransferase for glucosamine-6-phosphate synthesis in endothelial cells: effects of hyperglycaemia and glutamine. | 2001 Feb |
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Glutamine and glutathione counteract the inhibitory effects of mediators of sepsis in neonatal hepatocytes. | 2001 Feb |
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Influence of glutamine on cytokine production by human gut in vitro. | 2001 Feb 7 |
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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 |
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Glutamine metabolism to glucosamine is necessary for glutamine inhibition of endothelial nitric oxide synthesis. | 2001 Jan 15 |
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Free and protein-bound glutamine have identical splanchnic extraction in healthy human volunteers. | 2001 Jul |
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Cost-containment with glutamine dipeptide-supplemented TPN. | 2001 Jun |
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Chemo-enzymatic synthesis of a bioactive peptide containing a glutamine-linked oligosaccharide and its characterization. | 2001 Jun 15 |
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Characterization of an N-system amino acid transporter expressed in retina and its involvement in glutamine transport. | 2001 Jun 29 |
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Production of brown tyrosine pigments by the yeast Yarrowia lipolytica. | 2001 Mar |
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Localized proton MR spectroscopy in infants with urea cycle defect. | 2001 May |
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Regulation of mitochondrial glutamine/glutamate metabolism by glutamate transport: studies with (15)N. | 2001 May |
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Structural basis for the activity and substrate specificity of Erwinia chrysanthemi L-asparaginase. | 2001 May 15 |
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Amino acid residues important for substrate specificity of the amino acid permeases Can1p and Gnp1p in Saccharomyces cerevisiae. | 2001 Nov |
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Expression of c-myc is not critical for cell proliferation in established human leukemia lines. | 2001 Nov 16 |
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Amino acids protect epithelial cells from local toxicity by absorption enhancer, sodium laurate. | 2001 Oct |
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System y+L-like activities account for high and low amino-acid transport phenotypes in chicken erythrocytes. | 2001 Oct 1 |
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Human L-type amino acid transporter 1 (LAT1): characterization of function and expression in tumor cell lines. | 2001 Oct 1 |
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Signaling to the nucleus by an L-type calcium channel-calmodulin complex through the MAP kinase pathway. | 2001 Oct 12 |
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Brain amino acid metabolism and ketosis. | 2001 Oct 15 |
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Amino acid supplementation affects hematological and biochemical parameters in elite rugby players. | 2001 Sep |
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Characterization of cell death induced by vinflunine, the most recent Vinca alkaloid in clinical development. | 2002 Jan 7 |
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Oral bovine serum concentrate improves cryptosporidial enteritis in calves. | 2002 Mar |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/glutamine.html
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23201305
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.
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ACTIVE MOIETY