CAS 74-79-3|CAS 7200-25-1|(2S)-2-amino-5-carbamimidamidopentanoic acid|L-Arginine|L-arginine|2-Amino-5-Guanidnovaleric Acid|L-ARGININE FREE BASE|(S)-2-氨基-5-胍基戊酸|L-Arginine|L-精氨酸|Arg|R|(S)-2...

L-Arginine2-Amino-5-Guanidnovaleric AcidL-ARGININE FREE BASE(S)-2-氨基-5-胍基戊酸L-ArginineL-精氨酸ArgR(S)-2-Amino-5-guanidinopentanoic acidArginine2-Amino-5-guanidinopentanoic acid(S)-2-Amino-5-[(aminoiminomethyl)amino]pentanoic acid2-Amino-5-guanidinovaleric acidArginineL-(+)-ArginineL-ArgL-a-Amino-d-guanidinovaleric acidL-2-Amino-5-guanidinopentanoic acidH-Arg-OH(S)-2-amino-5-guanidinopentanoic acidL-Arginin(2S)-2-amino-5-guanidinopentanoic acidL-Arginine(2S)-2-amino-5-(carbamimidamido)pentanoic acidRL-(+)-arginineArgL-ArgL-arginine(S)-2-Amino-5-guanidinovaleric acid

IUPAC Traditional name

L-arginine

Brand Name

ArgamineDetoxarginMinophagen AR-Gene 10 (Pharmacia Corp.)LevarginArgivene

International Nonproprietary Name (INN)

arginine

Names and Identifiers

Registration numbers

MDL Number

MFCD00002635

CAS Number

74-79-37200-25-1

EC Number

200-811-1230-571-3

PubChem SID

2489087046507180242780142489131624846956249018941609634748144863

PubChem CID

6322232

Beilstein Number

17254131725411, 1725412 R, 1725413 S

MeSH Name

DrugBank ID

Wikipedia Title

IUPHAR ligand ID

Gmelin ID

Unique Ingredient Identifier

Flavis Number

ATC CODE

KEGG ID

Merck Index

CHEBI ID

29016CHEBI:16467CHEBI:42927CHEBI:13077CHEBI:21235CHEBI:6185

FEMA ID

3819

Chemspider ID

227

CHEMBL

212301CHEMBL1485

PubMed Citation Links

2242806821814794108489232236173217168727113004971281282822652429164163652242581119030957174396668070089227094812261948022626826

Reaxys Registry

1725413

ACToR Database

25212-18-4142-49-417806-42-74455-52-1

BKMS React Database

9206814593536710268220829593958948139020622956393026532

BRENDA Database

3.2.1.66.3.4.54.2.2.12.1.3.63.1.1.432.4.2.312.3.1.354.3.3.73.4.11.22.6.1.132.3.2.22.5.1.663.4.11.33.3.2.63.4.14.5

MetaboLights Database

MTBLS601MTBLS123MTBLS3935MTBLS1145MTBLS145MTBLS4187MTBLS704MTBLS1925MTBLS3725MTBLS2224MTBLS706MTBLS4722MTBLS1693MTBLS2372MTBLS3927

SABIO-RK Database

5741460277261237812334975118857983123355731127610511305296911950

UniProt Database

Q5PAM4B0S733Q62504Q3JF27P78509Q8TDR0A1RP36A6UP37Q9PNC0Q9ZMB9A0B5P0Q896N5A1VEG5Q9PGZ9Q96T58

BRENDA Ligand Database

920682295639635897147123136824532102682948131063892082959505596159145021

SureChEMBL Database

MetaCyc Database

KNApSAcK Database

CompTox Database

Patent number

US2004097399US2005261312WO2005010160EP1182261US2007178435US2005027009US2007213399US2007254837EP1726303EP1671630GB1565032WO2006114706US2006142389US2007185200

PDBeChem Database

GNDARG

IntAct Database

EBI-6662325EBI-6662317EBI-12556402EBI-22119277EBI-6662218

BindingDB Database

21959

YMDB Database

YMDB00592

BioModels Database

BIOMD0000000579BIOMD0000001061BIOMD0000000496BIOMD0000000467BIOMD0000000497BIOMD0000000191

NMRShiftDB Database

30095880

KEGG DRUG Database

D02982

HMDB Database

HMDB0000517

EnzymePortal Database

O33289

ECMDB Database

ECMDB00517

Drug Central Database

1,549

ArrayExpress (Gene Expression Altlas)

E-GEOD-34874

Registration numbers

Properties

Pharmacology Properties

human ... NOS1(4842), NOS2(4843)rat ... Ppm1a(24666)

human ... NOS1(4842), NOS2(4843)

no known allergens

Properties

Related Proteins

No Data Available

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Related Proteins

Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB00125

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]

Molecule Details

References

PubChem Literature

From Data Sources

• 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

References

Bioactivity

PubChem BioAssay

Bioactivity

Molecule

ID:11