General
Preferred name
L-glutamine
Synonyms
GLUTAMINE (D) ()
GLUTAMINE ()
glutamine-(l) ()
Levoglutamide ()
L-Glutamic acid 5-amide ()
FEMA NO. 3684 ()
Endari ()
Nutrestore ()
NSC-27421 ()
L-Glutamine-d5 ()
P&D ID
PD001524
CAS
6899-04-3
32640-56-5
26700-71-0
585-21-7
56-85-9
14341-78-7
Tags
natural product
drug
available
Approved by
FDA
First approval
2004
Drug Status
nutraceutical
investigational
approved
Drug indication
Short bowel syndrome
Max Phase
Phase 4
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
PHARMACODYNAMICS
Like other amino acids, glutamine is biochemically important as a constituent of proteins. Glutamine is also crucial in nitrogen metabolism. Ammonia (formed by nitrogen fixation) is assimilated into organic compounds by converting glutamic acid to glutamine. The enzyme which accomplishes this is called glutamine synthetase. Glutamine can then be used as a nitrogen donor in the biosynthesis of many compounds, including other amino acids, purines, and pyrimidines.; ; L-glutamine improves nicotinamide adenine dinucleotide (NAD) redox potential [FDA Label].
INDICATION
Used for nutritional supplementation, also for treating dietary shortage or imbalance.; ; Used to reduce the acute complications of sickle cell disease in adult and pediatric patients 5 years of age and older [FDA Label].
TOXICITY
Doses of L-glutamine up to 21 grams daily appear to be well tolerated. Reported adverse reactions are mainly gastrointestinal and not common. They include constipation and bloating. There is one older report of two hypomanic patients whose manic symptoms were exacerbated following the use of 2 to 4 grams daily of L-glutamine. The symptoms resolved when the L-glutamine was stopped. These patients were not rechallenged, nor are there any other reports of this nature.; ; The most common adverse effects observed in clinical trials of Endari were constipation (21%), nausea (19%), headache (18%), abdominal pain (17%), cough (16%), extremity pain (13%), back pain (12%), and chest pain (12%) [FDA Label].
MOA
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.; ; The exact mechanism of L-glutamine's effect on NAD redox potential is unknown but is thought to involve increased amounts of reduced glutathione made available by glutamine supplementation [FDA Label]. This improvement in redox potential reduces the amount of oxidative damage which sickle red blood cells are more susceptible to. The reduction in cellular damage is thought to reduce chronic hemolysis and vaso-occlusive events.
DESCRIPTION
Excitatory amino acid
(LOPAC library)
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Compound Sets
24
ChEMBL Approved Drugs
ChEMBL Drugs
Drug Repurposing Hub
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMAP
DrugMAP Approved Drugs
Enamine BioReference Compounds
JUMP-Target 1 Compound Set
LOPAC library
MedChem Express Bioactive Compound Library
NCATS Inxight Approved Drugs
NPC Screening Collection
ReFrame library
Selleckchem Bioactive Compound Library
The Spectrum Collection
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
75
Molecular Weight
146.07
Hydrogen Bond Acceptors
3
Hydrogen Bond Donors
3
Rotatable Bonds
4
Ring Count
0
Aromatic Ring Count
0
cLogP
-1.34
TPSA
106.41
Fraction CSP3
0.6
Chiral centers
1.0
Largest ring
0.0
QED
0.46
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
MOA
GluR
Pathway
Neuroscience
Apoptosis
GPCR/G protein
Metabolic Enzyme/Protease
Neuronal Signaling
Indication
diarrhea, mucositis, muscle pain, joint pain, peptic ulcer disease (PUD), ulcerative colitis, Crohn's disease, anxiety, insomnia
Disease Area
gastroenterology, dental, neurology/psychiatry, rheumatology
Target
CTPS1, GLUL, GPRC6A, PPAT
PPAT
Endogenous Metabolite
Ferroptosis
mGluR
Source data
