Glutamine

L-glutamine oral powder
Clinical data
Trade names	Endari, Nutrestore
AHFS/Drugs.com	Monograph
MedlinePlus	a617035
License data	US DailyMed: Glutamine;
Routes of; administration	By mouth
Drug class	Gastrointestinal agent
ATC code	A16AA03 (WHO) ;
Legal status
Legal status	US: ℞-only;
Identifiers
	IUPAC name (S)-2,5-diamino-5-oxopentanoic acid;
CAS Number	56-85-9;
PubChem CID	5961;
DrugBank	DB00130;
ChemSpider	5746;
UNII	0RH81L854J;
KEGG	D00015; C00064;
ChEBI	CHEBI:58359;
ChEMBL	ChEMBL930;
PDB ligand	GLN (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID1023100 ;
ECHA InfoCard	100.000.266
Chemical and physical data
Formula	C5H10N2O3
Molar mass	146.146 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C(CC(=O)N)C(C(=O)O)N;
	InChI 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; Key:ZDXPYRJPNDTMRX-VKHMYHEASA-N;
Data page
	Glutamine (data page)

Glutamine
	; Skeletal formula of L-glutamine
Ball-and-stick model	Space-filling model
Names
	IUPAC name Glutamine
	Other names L-Glutamine ; (levo)glutamide ; 2,5-Diamino-5-oxopentanoic acid ; 2-Amino-4-carbamoylbutanoic acid; Endari
Identifiers
CAS Number	56-85-9 ;
3D model (JSmol)	Interactive image; Zwitterion: Interactive image;
Abbreviations	Gln, Q
ChEBI	CHEBI:18050 ;
ChEMBL	ChEMBL930 ;
ChemSpider	5746 ;
DrugBank	DB00130 ;
ECHA InfoCard	100.000.266
EC Number	200-292-1;
IUPHAR/BPS	723;
KEGG	C00303 ;
PubChem CID	5961;
UNII	0RH81L854J ;
CompTox Dashboard (EPA)	DTXSID1023100 ;
	InChI 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 Key: ZDXPYRJPNDTMRX-VKHMYHEASA-N ;
	SMILES O=C(N)CCC(N)C(=O)O; Zwitterion: O=C(N)CCC([NH3+])C(=O)[O-];
Properties
Chemical formula	C5H10N2O3
Molar mass	146.146 g·mol−1
Melting point	decomposes around 185°C
Solubility in water	soluble
Acidity (pKa)	2.2 (carboxyl), 9.1 (amino)
Chiral rotation ([α]D)	+6.5º (H2O, c = 2)
Pharmacology
ATC code	A16AA03 (WHO)
Supplementary data page
	Glutamine (data page)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Glutamine (symbol Gln or Q) is an α-amino acid that is used in the biosynthesis of proteins. Its side chain is similar to that of glutamic acid, except the carboxylic acid group is replaced by an amide. It is classified as a charge-neutral, polar amino acid. It is non-essential and conditionally essential in humans, meaning the body can usually synthesize sufficient amounts of it, but in some instances of stress, the body's demand for glutamine increases, and glutamine must be obtained from the diet. It is encoded by the codons CAA and CAG.

In human blood, glutamine is the most abundant free amino acid.

The dietary sources of glutamine include especially the protein-rich foods like beef, chicken, fish, dairy products, eggs, vegetables like beans, beets, cabbage, spinach, carrots, parsley, vegetable juices and also in wheat, papaya, Brussels sprouts, celery, kale and fermented foods like miso.

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