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Identification
NameL-Arginine
Accession NumberDB00125  (NUTR00014)
TypeSmall Molecule
GroupsApproved, Nutraceutical
Description

An essential amino acid that is physiologically active in the L-form. [PubChem]

Structure
Thumb
Synonyms
(2S)-2-amino-5-(Carbamimidamido)pentanoic acid
(2S)-2-amino-5-Guanidinopentanoic acid
(S)-2-amino-5-guanidinopentanoic acid
(S)-2-Amino-5-guanidinovaleric acid
Arg
Arginine
L-(+)-Arginine
L-Arg
L-Arginin
L-Arginine
R
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
L-arginine Hydrochloride Injectionliquid250 mgintravenousSandoz Canada Incorporated1973-12-31Not applicableCanada
R-geneinjection, solution10 g/100mLintravenousPharmacia and Upjohn Company1976-06-152016-04-23Us
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
R-Gene 10Pharmacia Corp.
Brand mixtures
NameLabellerIngredients
2.5% Travasol Amino Acid Injection With Electrolytes In 10% DextroseBaxter Corporation Clintec Nutrition Division
2.5% Travasol Amino Acid Injection With Electrolytes In 10% Dextrose ClinimixBaxter Corporation Clintec Nutrition Division
2.5% Travasol Amino Acid Injection Without Electrolytes In 10% Dextrose QuickmixBaxter Corporation Clintec Nutrition Division
2.5%travasol Amino Acid InJ.W.eleC.W.25%dexClintec Nutrition Company
2.75% Travas. Amino Acid InJ.W.elecw.25%dexClintec Nutrition Company
2.75% Travasol Amino Acid Injection With Electrolytes In 25% Dextrose QuickmixBaxter Corporation Clintec Nutrition Division
2.75% Travasol Amino Acid Injection With Electrolytes In 5% Dextrose QuickmixBaxter Corporation Clintec Nutrition Division
2.75%travasol Amino Acid InJ.W.eleC.W.5%dex.Clintec Nutrition Company
4.25% Amino Acid Injection Without Electrolytes In 20% Dextrose QuickmixBaxter Corporation Clintec Nutrition Division
4.25% Travasol Amino Acid Injection With Electrolytes In 10% DextroseBaxter Corporation Clintec Nutrition Division
4.25% Travasol Amino Acid Injection With Electrolytes In 20% DextroseBaxter Corporation Clintec Nutrition Division
4.25% Travasol Amino Acid Injection With Electrolytes In 20% Dextrose QuickmixBaxter Corporation Clintec Nutrition Division
4.25% Travasol Amino Acid Injection With Electrolytes In 25% DextroseBaxter Corporation Clintec Nutrition Division
4.25% Travasol Amino Acid Injection With Electrolytes In 5% Dextrose QuickmixBaxter Corporation Clintec Nutrition Division
4.25% Travasol Amino Acid Injection Without Electrlytes In 10% DextroseBaxter Corporation Clintec Nutrition Division
4.25% Travasol Amino Acid Injection Without Electrolytes In 20% DextroseBaxter Corporation Clintec Nutrition Division
4.25% Travasol Amino Acid Injection Without Electrolytes In 25% DextroseBaxter Corporation Clintec Nutrition Division
4.25% Travasol Amino Acid Without Electrolytes In 5% Dextrose QuickmixBaxter Corporation Clintec Nutrition Division
4.25%trav. Amino Acid InJ.W.O.elect.5%dext.Clintec Nutrition Company
4.25%travasol Amino Acid InJ.W.elecw.5%dex.Clintec Nutrition Company
5% Travasol Amino Acid Injection With Electrolytes In 20% DextroseBaxter Corporation Clintec Nutrition Division
5% Travasol Amino Acid Injection Without Electrolytes In 20% DextroseBaxter Corporation Clintec Nutrition Division
5% Travasol Amino Acid Injection Without Electrolytes In 25% DextroseBaxter Corporation Clintec Nutrition Division
AminosynHospira, Inc.
Aminosyn 10%Hospira Healthcare Corporation
Aminosyn 10% W ElectrolytesAbbott Laboratories, Limited
Aminosyn 3.5% MAbbott Laboratories, Limited
Aminosyn 5%Hospira Healthcare Corporation
Aminosyn 7%Hospira Healthcare Corporation
Aminosyn 8.5%Hospira Healthcare Corporation
Aminosyn 8.5% Injection With ElectrolytesHospira Healthcare Corporation
Aminosyn II 10%Hospira Healthcare Corporation
Aminosyn II 10% With ElectrolytesHospira Healthcare Corporation
Aminosyn II 15%Hospira Healthcare Corporation
Aminosyn II 5% InjAbbott Laboratories, Limited
Aminosyn II 7% InjectionHospira Healthcare Corporation
Aminosyn II 7% M In 10% Dextrose(dual Chamber)Hospira Healthcare Corporation
Aminosyn II 7% With 10% DextroseHospira Healthcare Corporation
Aminosyn II 7% With 50% DextroseHospira Healthcare Corporation
Aminosyn II 8.5% InjectionHospira Healthcare Corporation
Aminosyn II 8.5% M In 20% Dextrose (dual Chamber)Hospira Healthcare Corporation
Aminosyn II 8.5% With 50% DextroseHospira Healthcare Corporation
Aminosyn II In Dextrose InjectionHospira Healthcare Corporation
Aminosyn II With ElectrolytesHospira, Inc.
Aminosyn RF InjectionHospira Healthcare Corporation
Aminosyn Sulfite FreeHospira, Inc.
Aminosyn-PF 10%Hospira Healthcare Corporation
Aminosyn-PF 7%Hospira Healthcare Corporation
ClinimixBaxter Corporation
Clinimix 2.5% Travasol Aa Without Electrolytes In 10% Dextrose InjecBaxter Corporation Clintec Nutrition Division
Clinimix EBaxter Corporation
Freamine HbcB. Braun Medical Inc.
Freamine IIIB. Braun Medical Inc.
Hypertenevide-12.5Physician Therapeutics Llc
HypertenipinePhysician Therapeutics Llc
HypertensololPhysician Therapeutics Llc
Lytensopril-90Physician Therapeutics Llc
NovamineHospira, Inc.
Olimel 4.4%Baxter Corporation
Olimel 5.7%Baxter Corporation
Primene 10%-liq IVClintec Nutrition Company
Quick Mix 2.5% Travasol Aa With Electrolytes With 25% Dextrose InjecBaxter Corporation Clintec Nutrition Division
Renamin (amino Acids) InjectionBaxter Corporation
RimantalistPhysician Therapeutics Llc
TravasolBaxter Corporation
Travasol Amino Acid Inj 5.5%Baxter Corporation
Travasol Amino Acid Inj 8.5%Baxter Corporation
Travasol EBaxter Corporation
Travasol Inj Without Electrolytes 5.5%Baxter Corporation
Vamin 18 Electrolyte-freeFresenius Kabi Ab
Vamin NFresenius Kabi Ab
Salts
Name/CASStructureProperties
Arginine hydrochloride
ThumbNot applicableDBSALT001428
L-Arginine Hydrochloride
ThumbNot applicableDBSALT000869
Categories
UNII94ZLA3W45F
CAS number74-79-3
WeightAverage: 174.201
Monoisotopic: 174.111675712
Chemical FormulaC6H14N4O2
InChI KeyInChIKey=ODKSFYDXXFIFQN-BYPYZUCNSA-N
InChI
InChI=1S/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10)/t4-/m0/s1
IUPAC Name
(2S)-2-amino-5-carbamimidamidopentanoic acid
SMILES
N[C@@H](CCCNC(N)=N)C(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Guanidine
  • Carboximidamide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Imine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationUsed for nutritional supplementation, also for treating dietary shortage or imbalance.
PharmacodynamicsStudies 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.
Mechanism of actionMany 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.
Related Articles
AbsorptionAbsorbed from the lumen of the small intestine into the enterocytes. Absorption is efficient and occurs by an active transport mechanism.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

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.

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityOral 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
Pathways
PathwayCategorySMPDB ID
HypoacetylaspartiaDiseaseSMP00192
Non Ketotic HyperglycinemiaDiseaseSMP00223
ArgininemiaDiseaseSMP00357
Dimethylglycine Dehydrogenase DeficiencyDiseaseSMP00484
Argininosuccinic AciduriaDiseaseSMP00003
Prolidase Deficiency (PD)DiseaseSMP00207
Hyperglycinemia, non-ketoticDiseaseSMP00485
Citrullinemia Type IDiseaseSMP00001
Carbamoyl Phosphate Synthetase DeficiencyDiseaseSMP00002
Aspartate MetabolismMetabolicSMP00067
Ornithine Aminotransferase Deficiency (OAT Deficiency)DiseaseSMP00363
Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency)DiseaseSMP00188
Hyperprolinemia Type IIDiseaseSMP00360
Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency)DiseaseSMP00362
Creatine deficiency, guanidinoacetate methyltransferase deficiencyDiseaseSMP00504
Hyperornithinemia with gyrate atrophy (HOGA)DiseaseSMP00505
Hyperornithinemia-hyperammonemia-homocitrullinuria [HHH-syndrome]DiseaseSMP00506
L-arginine:glycine amidinotransferase deficiencyDiseaseSMP00507
3-Phosphoglycerate dehydrogenase deficiencyDiseaseSMP00721
Glycine and Serine MetabolismMetabolicSMP00004
Arginine and Proline MetabolismMetabolicSMP00020
Urea CycleMetabolicSMP00059
Canavan DiseaseDiseaseSMP00175
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)DiseaseSMP00179
Ornithine Transcarbamylase Deficiency (OTC Deficiency)DiseaseSMP00205
Prolinemia Type IIDiseaseSMP00208
Dimethylglycine Dehydrogenase DeficiencyDiseaseSMP00242
SarcosinemiaDiseaseSMP00244
Hyperprolinemia Type IDiseaseSMP00361
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8289
Blood Brain Barrier+0.6882
Caco-2 permeable-0.7316
P-glycoprotein substrateNon-substrate0.5564
P-glycoprotein inhibitor INon-inhibitor0.9814
P-glycoprotein inhibitor IINon-inhibitor0.8803
Renal organic cation transporterNon-inhibitor0.7475
CYP450 2C9 substrateNon-substrate0.7822
CYP450 2D6 substrateNon-substrate0.6787
CYP450 3A4 substrateNon-substrate0.8105
CYP450 1A2 substrateNon-inhibitor0.8555
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.7705
CYP450 3A4 inhibitorNon-inhibitor0.8925
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9945
Ames testAMES toxic0.7182
CarcinogenicityNon-carcinogens0.9229
BiodegradationReady biodegradable0.8394
Rat acute toxicity1.4851 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9533
hERG inhibition (predictor II)Non-inhibitor0.9683
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Pharmacia and upjohn co
Packagers
Dosage forms
FormRouteStrength
Liquidintravenous
Solutionintravenous
Injection, solutionintravenous
Liquidintravenous250 mg
Kit
Injection, solution, concentrateintravenous
Emulsionintravenous
Injection, solutionintravenous10 g/100mL
Prices
Unit descriptionCostUnit
Arginine 100% crystals0.51USD g
L-arginine mhc powder0.39USD g
Arginine-500 mg tablet0.12USD tablet
Arginine 500 mg tablet0.09USD tablet
L-arginine 1000 mg tablet0.07USD tablet
R-gene 10 vial0.04USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point244 dec °CPhysProp
water solubility1.82E+005 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-4.20HANSCH,C ET AL. (1995)
pKa2.24 (at 0 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility2.28 mg/mLALOGPS
logP-3.5ALOGPS
logP-3.2ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)2.41ChemAxon
pKa (Strongest Basic)12.41ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area125.22 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity53.92 m3·mol-1ChemAxon
Polarizability17.8 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (2.96 KB)
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-6z60000000-0191c1a63652c493660bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-zv60000000-eb6eb73302b678cf0a24View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-zt00000000-e47b41cff0e873f53932View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-7z80000000-8ae5af11398835d26bedView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-ez00000000-8c82418f7b35a97fb9b3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-z100000000-19b62da79866318c52ddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-z000000000-64b046d21bdcbb8d5923View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0z02000000-e07b937b6867d1f62293View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-1z00000000-87ab853583aab2973cfbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-8z00000000-28814246b728a51e761cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-8z00000000-cfe7e406be2172e94fbaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0z42100000-478a8345915bc15d85b5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-8z00000000-c930c47ecbe6975a00fcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-7z00000000-fa6be0f9ce4ee4c30738View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0z00000000-3425ee9829935182c0d5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0zgq9c5421-3d57d2304dcb33feab3fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-3z00000000-5b6dd6fb263ea09289fcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0z00000000-dfe35b3438d19320d8cbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0z00000000-f666ab7e5354bce67a2eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-1zsrjla842-046c4b70bd0ec351c41dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-z000000000-2f51e43e530976d63633View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0z00000000-b9ebb7ebccee1a313888View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0z00000000-5379b6fb6ea2313101f9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positivesplash10-0z00000000-02b2bc83599dc6944f2eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-rz00000000-b7cd48e0aca6a6256968View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-rz00000000-b7cd48e0aca6a6256968View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-sz00000000-4e69a6ce7b97433937eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0z00000000-835751d54af24bd337e7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0z00000000-2d2b5fd7617ccb227bb1View in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
Synthesis Reference

Kiyoshi Nakayama, Kazumi Araki, Hajime Yoshida, “Process for the production of L-arginine by fermentation.” U.S. Patent US4086137, issued May, 1973.

US4086137
General References
  1. Morris SM Jr: Enzymes of arginine metabolism. J Nutr. 2004 Oct;134(10 Suppl):2743S-2747S; discussion 2765S-2767S. [PubMed:15465778 ]
  2. 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:16391217 ]
  3. 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:2903866 ]
External Links
ATC CodesB05XB01
AHFS Codes
  • 36:66.00
PDB Entries
FDA labelNot Available
MSDSDownload (72.8 KB)
Interactions
Drug InteractionsNo interactions found.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
L-ornithine transmembrane transporter activity
Specific Function:
Mediates the uptake of the cationic amino acids arginine, lysine and ornithine in a sodium-independent manner.
Gene Name:
SLC7A3
Uniprot ID:
Q8WY07
Molecular Weight:
67168.31 Da
References
  1. Rotmann A, Simon A, Martine U, Habermeier A, Closs EI: Activation of classical protein kinase C decreases transport via systems y+ and y+L. Am J Physiol Cell Physiol. 2007 Jun;292(6):C2259-68. Epub 2007 Feb 28. [PubMed:17329401 ]
  2. Huang Y, Kang BN, Tian J, Liu Y, Luo HR, Hester L, Snyder SH: The cationic amino acid transporters CAT1 and CAT3 mediate NMDA receptor activation-dependent changes in elaboration of neuronal processes via the mammalian target of rapamycin mTOR pathway. J Neurosci. 2007 Jan 17;27(3):449-58. [PubMed:17234578 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Putrescine transmembrane transporter activity
Specific Function:
Antizyme inhibitor protein that positively regulates ornithine decarboxylase (ODC) activity and polyamine uptake by counteracting the negative effect of antizymes OAZ1, OAZ2 and OAZ3 on ODC1 activity (PubMed:17900240). Inhibits antizyme-dependent ODC1 degradation by binding to antizymes. Releases ODC1 from its inactive complex with antizymes, leading to formation of the catalytically active ODC...
Gene Name:
AZIN2
Uniprot ID:
Q96A70
Molecular Weight:
49979.185 Da
References
  1. Kotil K, Kuscuoglu U, Kirali M, Uzun H, Akcetin M, Bilge T: Investigation of the dose-dependent neuroprotective effects of agmatine in experimental spinal cord injury: a prospective randomized and placebo-control trial. J Neurosurg Spine. 2006 May;4(5):392-9. [PubMed:16703907 ]
  2. Regunathan S: Agmatine: biological role and therapeutic potentials in morphine analgesia and dependence. AAPS J. 2006 Jul 21;8(3):E479-84. [PubMed:17025265 ]
  3. Yang HQ, Gao HJ: [Physiological function of arginine and its metabolites in plants]. Zhi Wu Sheng Li Yu Fen Zi Sheng Wu Xue Xue Bao. 2007 Feb;33(1):1-8. [PubMed:17287563 ]
  4. Wu N, Su RB, Li J: Agmatine and imidazoline receptors: their role in opioid analgesia, tolerance and dependence. Cell Mol Neurobiol. 2008 Aug;28(5):629-41. Epub 2007 Jul 25. [PubMed:17653850 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Argininosuccinate lyase activity
Specific Function:
Not Available
Gene Name:
ASL
Uniprot ID:
P04424
Molecular Weight:
51657.505 Da
References
  1. Moradi H, Kwok V, Vaziri ND: Effect of chronic renal failure on arginase and argininosuccinate synthetase expression. Am J Nephrol. 2006;26(3):310-8. Epub 2006 Jun 29. [PubMed:16809898 ]
  2. Bizzoco E, Vannucchi MG, Faussone-Pellegrini MS: Transient ischemia increases neuronal nitric oxide synthase, argininosuccinate synthetase and argininosuccinate lyase co-expression in rat striatal neurons. Exp Neurol. 2007 Mar;204(1):252-9. Epub 2007 Jan 2. [PubMed:17198704 ]
  3. Mages W, Heinrich O, Treuner G, Vlcek D, Daubnerova I, Slaninova M: Complementation of the Chlamydomonas reinhardtii arg7-8 (arg2) point mutation by recombination with a truncated nonfunctional ARG7 gene. Protist. 2007 Oct;158(4):435-46. Epub 2007 Jul 3. [PubMed:17611150 ]
  4. Tischner R, Galli M, Heimer YM, Bielefeld S, Okamoto M, Mack A, Crawford NM: Interference with the citrulline-based nitric oxide synthase assay by argininosuccinate lyase activity in Arabidopsis extracts. FEBS J. 2007 Aug;274(16):4238-45. Epub 2007 Jul 25. [PubMed:17651442 ]
  5. Mori M: Regulation of nitric oxide synthesis and apoptosis by arginase and arginine recycling. J Nutr. 2007 Jun;137(6 Suppl 2):1616S-1620S. [PubMed:17513437 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Tetrahydrobiopterin binding
Specific Function:
Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such COX2. As component of the iNOS-S100A8/9 transnitrosylase complex involved in the selective inflammatory stimulus-dependent S-n...
Gene Name:
NOS2
Uniprot ID:
P35228
Molecular Weight:
131116.3 Da
References
  1. Cui YY, Tang CS, Geng B: [Restraint stress down-regulates L-Arg/NOS/NO pathway of platelet and aortic intima in rats]. Beijing Da Xue Xue Bao. 2006 Jun 18;38(3):231-5. [PubMed:16778961 ]
  2. Devan BD, Pistell PJ, Daffin LW Jr, Nelson CM, Duffy KB, Bowker JL, Bharati IS, Sierra-Mercado D, Spangler EL, Ingram DK: Sildenafil citrate attenuates a complex maze impairment induced by intracerebroventricular infusion of the NOS inhibitor Nomega-nitro-L-arginine methyl ester. Eur J Pharmacol. 2007 Jun 1;563(1-3):134-40. Epub 2007 Feb 17. [PubMed:17362916 ]
  3. Rotoli BM, Dall'asta V, Barilli A, D'Ippolito R, Tipa A, Olivieri D, Gazzola GC, Bussolati O: Alveolar macrophages from normal subjects lack the NOS-related system y+ for arginine transport. Am J Respir Cell Mol Biol. 2007 Jul;37(1):105-12. Epub 2007 Mar 15. [PubMed:17363779 ]
  4. Kagemann G, Sies H, Schnorr O: Limited availability of L-arginine increases DNA-binding activity of NF-kappaB and contributes to regulation of iNOS expression. J Mol Med (Berl). 2007 Jul;85(7):723-32. Epub 2007 Mar 6. [PubMed:17340133 ]
  5. Popovic PJ, Zeh HJ 3rd, Ochoa JB: Arginine and immunity. J Nutr. 2007 Jun;137(6 Suppl 2):1681S-1686S. [PubMed:17513447 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
L-ornithine transmembrane transporter activity
Specific Function:
High-affinity, low capacity permease involved in the transport of the cationic amino acids (arginine, lysine and ornithine) in non-hepatic tissues. May also function as an ecotropic retroviral leukemia receptor.
Gene Name:
SLC7A1
Uniprot ID:
P30825
Molecular Weight:
67637.62 Da
References
  1. Yang Z, Venardos K, Jones E, Morris BJ, Chin-Dusting J, Kaye DM: Identification of a novel polymorphism in the 3'UTR of the L-arginine transporter gene SLC7A1: contribution to hypertension and endothelial dysfunction. Circulation. 2007 Mar 13;115(10):1269-74. Epub 2007 Feb 26. [PubMed:17325243 ]
  2. Rotmann A, Simon A, Martine U, Habermeier A, Closs EI: Activation of classical protein kinase C decreases transport via systems y+ and y+L. Am J Physiol Cell Physiol. 2007 Jun;292(6):C2259-68. Epub 2007 Feb 28. [PubMed:17329401 ]
  3. Vasquez R, Farias M, Vega JL, Martin RS, Vecchiola A, Casanello P, Sobrevia L: D-glucose stimulation of L-arginine transport and nitric oxide synthesis results from activation of mitogen-activated protein kinases p42/44 and Smad2 requiring functional type II TGF-beta receptors in human umbilical vein endothelium. J Cell Physiol. 2007 Sep;212(3):626-32. [PubMed:17427197 ]
  4. Cerec V, Piquet-Pellorce C, Aly HA, Touzalin AM, Jegou B, Bauche F: Multiple pathways for cationic amino acid transport in rat seminiferous tubule cells. Biol Reprod. 2007 Feb;76(2):241-9. Epub 2006 Oct 25. [PubMed:17065601 ]
  5. Rotoli BM, Dall'asta V, Barilli A, D'Ippolito R, Tipa A, Olivieri D, Gazzola GC, Bussolati O: Alveolar macrophages from normal subjects lack the NOS-related system y+ for arginine transport. Am J Respir Cell Mol Biol. 2007 Jul;37(1):105-12. Epub 2007 Mar 15. [PubMed:17363779 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Metal ion binding
Specific Function:
May play a role in the regulation of extra-urea cycle arginine metabolism and also in down-regulation of nitric oxide synthesis. Extrahepatic arginase functions to regulate L-arginine bioavailability to NO synthase. Since NO synthase is found in the penile corpus cavernosum smooth muscle, the clitoral corpus cavernosum and the vagina, arginase II plays a role in both male and female sexual arou...
Gene Name:
ARG2
Uniprot ID:
P78540
Molecular Weight:
38577.515 Da
References
  1. Topal G, Brunet A, Walch L, Boucher JL, David-Dufilho M: Mitochondrial arginase II modulates nitric-oxide synthesis through nonfreely exchangeable L-arginine pools in human endothelial cells. J Pharmacol Exp Ther. 2006 Sep;318(3):1368-74. Epub 2006 Jun 26. [PubMed:16801455 ]
  2. Hood HM, Spevak CC, Sachs MS: Evolutionary changes in the fungal carbamoyl-phosphate synthetase small subunit gene and its associated upstream open reading frame. Fungal Genet Biol. 2007 Feb;44(2):93-104. Epub 2006 Sep 18. [PubMed:16979358 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
L-ornithine transmembrane transporter activity
Specific Function:
Involved in the transport of the cationic amino acids (arginine, lysine and ornithine).
Gene Name:
SLC7A4
Uniprot ID:
O43246
Molecular Weight:
68267.17 Da
References
  1. Rotmann A, Simon A, Martine U, Habermeier A, Closs EI: Activation of classical protein kinase C decreases transport via systems y+ and y+L. Am J Physiol Cell Physiol. 2007 Jun;292(6):C2259-68. Epub 2007 Feb 28. [PubMed:17329401 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Toxic substance binding
Specific Function:
Is indirectly involved in the control of blood pressure.
Gene Name:
ASS1
Uniprot ID:
P00966
Molecular Weight:
46530.055 Da
References
  1. Feun L, Savaraj N: Pegylated arginine deiminase: a novel anticancer enzyme agent. Expert Opin Investig Drugs. 2006 Jul;15(7):815-22. [PubMed:16787144 ]
  2. Moradi H, Kwok V, Vaziri ND: Effect of chronic renal failure on arginase and argininosuccinate synthetase expression. Am J Nephrol. 2006;26(3):310-8. Epub 2006 Jun 29. [PubMed:16809898 ]
  3. Cheng PN, Lam TL, Lam WM, Tsui SM, Cheng AW, Lo WH, Leung YC: Pegylated recombinant human arginase (rhArg-peg5,000mw) inhibits the in vitro and in vivo proliferation of human hepatocellular carcinoma through arginine depletion. Cancer Res. 2007 Jan 1;67(1):309-17. [PubMed:17210712 ]
  4. Szlosarek PW, Grimshaw MJ, Wilbanks GD, Hagemann T, Wilson JL, Burke F, Stamp G, Balkwill FR: Aberrant regulation of argininosuccinate synthetase by TNF-alpha in human epithelial ovarian cancer. Int J Cancer. 2007 Jul 1;121(1):6-11. [PubMed:17354225 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Tetrahydrobiopterin binding
Specific Function:
Produces nitric oxide (NO) which is implicated in vascular smooth muscle relaxation through a cGMP-mediated signal transduction pathway. NO mediates vascular endothelial growth factor (VEGF)-induced angiogenesis in coronary vessels and promotes blood clotting through the activation of platelets.Isoform eNOS13C: Lacks eNOS activity, dominant-negative form that may down-regulate eNOS activity by ...
Gene Name:
NOS3
Uniprot ID:
P29474
Molecular Weight:
133287.62 Da
References
  1. Akamine EH, Kawamoto EM, Scavone C, Nigro D, Carvalho MH, de Cassia A Tostes R, Britto LR, Fortes ZB: Correction of endothelial dysfunction in diabetic female rats by tetrahydrobiopterin and chronic insulin. J Vasc Res. 2006;43(4):309-20. Epub 2006 May 8. [PubMed:16682803 ]
  2. Gautier C, Mikula I, Nioche P, Martasek P, Raman CS, Slama-Schwok A: Dynamics of NO rebinding to the heme domain of NO synthase-like proteins from bacterial pathogens. Nitric Oxide. 2006 Dec;15(4):312-27. Epub 2006 Apr 5. [PubMed:16690332 ]
  3. Yang J, Ji R, Cheng Y, Sun JZ, Jennings LK, Zhang C: L-arginine chlorination results in the formation of a nonselective nitric-oxide synthase inhibitor. J Pharmacol Exp Ther. 2006 Sep;318(3):1044-9. Epub 2006 May 22. [PubMed:16717106 ]
  4. Ishikawa T, Harada T, Koi H, Kubota T, Azuma H, Aso T: Identification of arginase in human placental villi. Placenta. 2007 Feb-Mar;28(2-3):133-8. Epub 2006 May 23. [PubMed:16720041 ]
  5. Haruna Y, Morita Y, Komai N, Yada T, Sakuta T, Tomita N, Fox DA, Kashihara N: Endothelial dysfunction in rat adjuvant-induced arthritis: vascular superoxide production by NAD(P)H oxidase and uncoupled endothelial nitric oxide synthase. Arthritis Rheum. 2006 Jun;54(6):1847-55. [PubMed:16729278 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Symporter activity
Specific Function:
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3.
Gene Name:
SLC22A5
Uniprot ID:
O76082
Molecular Weight:
62751.08 Da
References
  1. Ohashi R, Tamai I, Yabuuchi H, Nezu JI, Oku A, Sai Y, Shimane M, Tsuji A: Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84. [PubMed:10525100 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Transporter activity
Specific Function:
Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells (By similarity).
Gene Name:
SLC16A10
Uniprot ID:
Q8TF71
Molecular Weight:
55492.07 Da
References
  1. Kim DK, Kanai Y, Chairoungdua A, Matsuo H, Cha SH, Endou H: Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters. J Biol Chem. 2001 May 18;276(20):17221-8. Epub 2001 Feb 20. [PubMed:11278508 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Symporter activity
Specific Function:
Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Relative uptake activity ratio of carnitine to TEA is 1.78. A key substrate of this transporter seems to be ergothioneine (ET).
Gene Name:
SLC22A4
Uniprot ID:
Q9H015
Molecular Weight:
62154.48 Da
References
  1. Yabuuchi H, Tamai I, Nezu J, Sakamoto K, Oku A, Shimane M, Sai Y, Tsuji A: Novel membrane transporter OCTN1 mediates multispecific, bidirectional, and pH-dependent transport of organic cations. J Pharmacol Exp Ther. 1999 May;289(2):768-73. [PubMed:10215651 ]
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Drug created on June 13, 2005 07:24 / Updated on November 30, 2015 12:10