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Namespace Prefixes

PrefixIRI
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Statements

Subject Item
n2:DB00125
rdf:type
n3:Drug
n3:description
An essential amino acid that is physiologically active in the L-form. [PubChem]
n3:dosage
n9:271B47ED-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# Morris SM Jr: Enzymes of arginine metabolism. J Nutr. 2004 Oct;134(10 Suppl):2743S-2747S; discussion 2765S-2767S. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/15465778 # 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":http://www.ncbi.nlm.nih.gov/pubmed/16391217 # 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":http://www.ncbi.nlm.nih.gov/pubmed/2903866
n3:group
nutraceutical approved
n3:indication
Used for nutritional supplementation, also for treating dietary shortage or imbalance.
n3:manufacturer
n20:271B47E6-363D-11E5-9242-09173F13E4C5
owl:sameAs
n6:DB00125 n18:DB00125
dcterms:title
L-Arginine
adms:identifier
n11:C00062 n12:D02982 n13:721 n14:721 n16:DB00125 n17:21959 n19:16467 n22:0009-0436-24 n23:ARG n24:L-Arginine n25:PA448478
n3:mechanismOfAction
Many of supplemental L-arginine's activities, including its possible anti-atherogenic actions, may be accounted for by its role as the precursor to nitric oxide or NO. NO is produced by all tissues of the body and plays very important roles in the cardiovascular system, immune system and nervous system. NO is formed from L-arginine via the enzyme nitric oxide synthase or synthetase (NOS), and the effects of NO are mainly mediated by 3,'5' -cyclic guanylate or cyclic GMP. NO activates the enzyme guanylate cyclase, which catalyzes the synthesis of cyclic GMP from guanosine triphosphate or GTP. Cyclic GMP is converted to guanylic acid via the enzyme cyclic GMP phosphodiesterase. NOS is a heme-containing enzyme with some sequences similar to cytochrome P-450 reductase. Several isoforms of NOS exist, two of which are constitutive and one of which is inducible by immunological stimuli. The constitutive NOS found in the vascular endothelium is designated eNOS and that present in the brain, spinal cord and peripheral nervous system is designated nNOS. The form of NOS induced by immunological or inflammatory stimuli is known as iNOS. iNOS may be expressed constitutively in select tissues such as lung epithelium. All the nitric oxide synthases use NADPH (reduced nicotinamide adenine dinucleotide phosphate) and oxygen (O2) as cosubstrates, as well as the cofactors FAD (flavin adenine dinucleotide), FMN (flavin mononucleotide), tetrahydrobiopterin and heme. Interestingly, ascorbic acid appears to enhance NOS activity by increasing intracellular tetrahydrobiopterin. eNOS and nNOS synthesize NO in response to an increased concentration of calcium ions or in some cases in response to calcium-independent stimuli, such as shear stress. In vitro studies of NOS indicate that the Km of the enzyme for L-arginine is in the micromolar range. The concentration of L-arginine in endothelial cells, as well as in other cells, and in plasma is in the millimolar range. What this means is that, under physiological conditions, NOS is saturated with its L-arginine substrate. In other words, L-arginine would not be expected to be rate-limiting for the enzyme, and it would not appear that supraphysiological levels of L-arginine which could occur with oral supplementation of the amino acid^would make any difference with regard to NO production. The reaction would appear to have reached its maximum level. However, in vivo studies have demonstrated that, under certain conditions, e.g. hypercholesterolemia, supplemental L-arginine could enhance endothelial-dependent vasodilation and NO production.
n3:packager
n20:271B47E0-363D-11E5-9242-09173F13E4C5 n20:271B47E1-363D-11E5-9242-09173F13E4C5 n20:271B47DF-363D-11E5-9242-09173F13E4C5 n20:271B47E4-363D-11E5-9242-09173F13E4C5 n20:271B47E5-363D-11E5-9242-09173F13E4C5 n20:271B47E2-363D-11E5-9242-09173F13E4C5 n20:271B47E3-363D-11E5-9242-09173F13E4C5
n3:synonym
R L-Arginin L-Arg Arginine Arg (S)-2-Amino-5-guanidinovaleric acid L-Arginine (2S)-2-amino-5-(Carbamimidamido)pentanoic acid L-(+)-Arginine (S)-2-amino-5-guanidinopentanoic acid (2S)-2-amino-5-Guanidinopentanoic acid
n3: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.
n27:hasAHFSCode
n28:36-66-00
n3:salt
n3:synthesisReference
Kiyoshi Nakayama, Kazumi Araki, Hajime Yoshida, "Process for the production of L-arginine by fermentation." U.S. Patent US4086137, issued May, 1973.
n29:hasConcept
n30:M0001683
foaf:page
n8:l-arginine.html n26:lar_0024.shtml
n3:IUPAC-Name
n4:271B47F2-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B47F8-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B47F7-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B47F4-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B47F5-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B47F6-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B4808-363D-11E5-9242-09173F13E4C5 n4:271B47F0-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B480A-363D-11E5-9242-09173F13E4C5 n4:271B47F1-363D-11E5-9242-09173F13E4C5 n4:271B47EE-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B47EF-363D-11E5-9242-09173F13E4C5
n3:pKa
n4:271B480B-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Acceptor-Count
n4:271B47FE-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B47FF-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B47F9-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B47FA-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B47FC-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B47FB-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B47FD-363D-11E5-9242-09173F13E4C5
n3:absorption
Absorbed from the lumen of the small intestine into the enterocytes. Absorption is efficient and occurs by an active transport mechanism.
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
74-79-3
n3:category
n3:containedIn
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n3:Bioavailability
n4:271B4804-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B4806-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B4807-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n4:271B4809-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B4803-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B4802-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B4805-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B47F3-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B4800-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B4801-363D-11E5-9242-09173F13E4C5