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L-Arginine

Catalog No. DB00125 Name DrugBank
CAS Number 74-79-3 Website http://www.ualberta.ca/
M. F. C6H14N4O2 Telephone (780) 492-3111
M. W. 174.20096 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 11

SYNONYMS

IUPAC name
(2S)-2-amino-5-carbamimidamidopentanoic acid
IUPAC Traditional name
L-arginine
Brand Name
Argivene
R-Gene 10 (Pharmacia Corp.)
Levargin
Minophagen A
Argamine
Detoxargin
Synonyms
2-Amino-5-guanidinovaleric acid
Arginine
(S)-2-Amino-5-[(aminoiminomethyl)amino]pentanoic acid
L-(+)-Arginine
L-a-Amino-d-guanidinovaleric acid
L-Arg

DATABASE IDS

PubChem SID 46507180
CAS Number 74-79-3
PubChem CID 6322

PROPERTIES

Hydrophobicity(logP) -3.6
Solubility 182 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]

DETAILS

Description (English)
Item Information
Drug Groups approved; nutraceutical
Description An essential amino acid that is physiologically active in the L-form. [PubChem]
Indication Used for nutritional supplementation, also for treating dietary shortage or imbalance.
Pharmacology Studies have shown that is has improved immune responses to bacteria, viruses and tumor cells; promotes wound healing and regeneration of the liver; causes the release of growth hormones; considered crucial for optimal muscle growth and tissue repair.
Toxicity Oral supplementation with L-arginine at doses up to 15 grams daily are generally well tolerated. The most common adverse reactions of higher doses from 15 to 30 grams daily are nausea, abdominal cramps and diarrhea. Some may experience these symptoms at lower doses.
Affected Organisms
Humans and other mammals
Biotransformation Some metabolism of L-arginine takes place in the enterocytes. L-arginine not metabolized in the enterocytes enters the portal circulation from whence it is transported to the liver, where again some portion of the amino acid is metabolized.
Absorption Absorbed from the lumen of the small intestine into the enterocytes. Absorption is efficient and occurs by an active transport mechanism.
References
Morris SM Jr: Enzymes of arginine metabolism. J Nutr. 2004 Oct;134(10 Suppl):2743S-2747S; discussion 2765S-2767S. [Pubmed]
Schulman SP, Becker LC, Kass DA, Champion HC, Terrin ML, Forman S, Ernst KV, Kelemen MD, Townsend SN, Capriotti A, Hare JM, Gerstenblith G: L-arginine therapy in acute myocardial infarction: the Vascular Interaction With Age in Myocardial Infarction (VINTAGE MI) randomized clinical trial. JAMA. 2006 Jan 4;295(1):58-64. [Pubmed]
Alba-Roth J, Muller OA, Schopohl J, von Werder K: Arginine stimulates growth hormone secretion by suppressing endogenous somatostatin secretion. J Clin Endocrinol Metab. 1988 Dec;67(6):1186-9. [Pubmed]
External Links
Wikipedia
PDRhealth
Drugs.com

REFERENCES

  • Morris SM Jr: Enzymes of arginine metabolism. J Nutr. 2004 Oct;134(10 Suppl):2743S-2747S; discussion 2765S-2767S. Pubmed
  • Schulman SP, Becker LC, Kass DA, Champion HC, Terrin ML, Forman S, Ernst KV, Kelemen MD, Townsend SN, Capriotti A, Hare JM, Gerstenblith G: L-arginine therapy in acute myocardial infarction: the Vascular Interaction With Age in Myocardial Infarction (VINTAGE MI) randomized clinical trial. JAMA. 2006 Jan 4;295(1):58-64. Pubmed
  • Alba-Roth J, Muller OA, Schopohl J, von Werder K: Arginine stimulates growth hormone secretion by suppressing endogenous somatostatin secretion. J Clin Endocrinol Metab. 1988 Dec;67(6):1186-9. Pubmed