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L-Glutamine

Catalog No. DB00130 Name DrugBank
CAS Number 56-85-9 Website http://www.ualberta.ca/
M. F. C5H10N2O3 Telephone (780) 492-3111
M. W. 146.1445 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 16

SYNONYMS

IUPAC name
(2S)-2-amino-4-carbamoylbutanoic acid
IUPAC Traditional name
L-glutamine
Brand Name
Glutamine Express (Genetic Evolutionary Nutrition)
Glutamine Fuel Mega (Twinlab)
Saforis
Glutamine Fuel Powder (Twinlab)
L-Glutamine Power (Champion Nutrition)
Earthlink Science Glutamine Chews Chocolate (Amerifit)
Cebrogen
Stimulina
Glavamin
Synonyms
AES-14
2-Aminoglutaramic acid
Glutamine
L-glutamine

DATABASE IDS

PubChem CID 5961
CAS Number 56-85-9
PubChem SID 46505866

PROPERTIES

Hydrophobicity(logP) -4.1
Solubility Slight (0.1-1%)

DETAILS

Description (English)
Item Information
Drug Groups approved; nutraceutical; investigational
Description 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. [PubChem]
Indication Used for nutritional supplementation, also for treating dietary shortage or imbalance.
Pharmacology 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.
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.
Affected Organisms
Humans and other mammals
Biotransformation Enterocytes, Hepatic
Absorption Absorption is efficient and occurs by an active transport mechanism
References
Boza JJ, Dangin M, Moennoz D, Montigon F, Vuichoud J, Jarret A, Pouteau E, Gremaud G, Oguey-Araymon S, Courtois D, Woupeyi A, Finot PA, Ballevre O: Free and protein-bound glutamine have identical splanchnic extraction in healthy human volunteers. Am J Physiol Gastrointest Liver Physiol. 2001 Jul;281(1):G267-74. [Pubmed]
McAnena OJ, Moore FA, Moore EE, Jones TN, Parsons P: Selective uptake of glutamine in the gastrointestinal tract: confirmation in a human study. Br J Surg. 1991 Apr;78(4):480-2. [Pubmed]
Morlion BJ, Stehle P, Wachtler P, Siedhoff HP, Koller M, Konig W, Furst P, Puchstein C: Total parenteral nutrition with glutamine dipeptide after major abdominal surgery: a randomized, double-blind, controlled study. Ann Surg. 1998 Feb;227(2):302-8. [Pubmed]
Jian ZM, Cao JD, Zhu XG, Zhao WX, Yu JC, Ma EL, Wang XR, Zhu MW, Shu H, Liu YW: 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. JPEN J Parenter Enteral Nutr. 1999 Sep-Oct;23(5 Suppl):S62-6. [Pubmed]
External Links
Wikipedia
PDRhealth

REFERENCES

  • Boza JJ, Dangin M, Moennoz D, Montigon F, Vuichoud J, Jarret A, Pouteau E, Gremaud G, Oguey-Araymon S, Courtois D, Woupeyi A, Finot PA, Ballevre O: Free and protein-bound glutamine have identical splanchnic extraction in healthy human volunteers. Am J Physiol Gastrointest Liver Physiol. 2001 Jul;281(1):G267-74. Pubmed
  • McAnena OJ, Moore FA, Moore EE, Jones TN, Parsons P: Selective uptake of glutamine in the gastrointestinal tract: confirmation in a human study. Br J Surg. 1991 Apr;78(4):480-2. Pubmed
  • Morlion BJ, Stehle P, Wachtler P, Siedhoff HP, Koller M, Konig W, Furst P, Puchstein C: Total parenteral nutrition with glutamine dipeptide after major abdominal surgery: a randomized, double-blind, controlled study. Ann Surg. 1998 Feb;227(2):302-8. Pubmed
  • Jian ZM, Cao JD, Zhu XG, Zhao WX, Yu JC, Ma EL, Wang XR, Zhu MW, Shu H, Liu YW: 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. JPEN J Parenter Enteral Nutr. 1999 Sep-Oct;23(5 Suppl):S62-6. Pubmed