Arginine

Overview

Description
A nutrient used to provide nutrition to some patients in hospitals or healthcare institutions.
Description
A nutrient used to provide nutrition to some patients in hospitals or healthcare institutions.
DrugBank ID
DB00125
Type
Small Molecule
US Approved
YES
Other Approved
YES
Clinical Trials
Phase 0
3
Phase 1
23
Phase 2
49
Phase 3
43
Phase 4
23

Identification

Summary

Arginine is an amino acid commonly found as a component of total parenteral nutrition.

Brand Names
Aminosyn II 7 %, Sulfite-free, Aminosyn-PF 7%, Clinimix 2.75/5, Clinimix E 2.75/5, Clinisol 15, Freamine 6.9, Freamine III 10, Hepatamine 8, Olimel, Periolimel, Plenamine, Premasol, Primene, Procalamine 3, Prosol, R-gene, Travasol 10, Trophamine 10 %
Generic Name
Arginine
DrugBank Accession Number
DB00125
Background

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

Type
Small Molecule
Groups
Investigational, Nutraceutical
Structure
Weight
Average: 174.201
Monoisotopic: 174.111675712
Chemical Formula
C6H14N4O2
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
  • Arginina
  • Arginine
  • L-(+)-Arginine
  • L-Arg
  • L-Arginin
  • L-arginine
  • R
External IDs
  • NSC-206269

Pharmacology

Indication

Used for nutritional supplementation, also for treating dietary shortage or imbalance.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Diagnostic agentAcromegaly••••••••••••
Diagnostic agentGigantism••••••••••••
Treatment ofHyperammonemia••• •••••
Diagnostic agentHypophysectomy••••••••••••
Used in combination to preventKidney damageCombination Product in combination with: Lysine (DB00123)•••••••••••••••••••••• ••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

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.

Mechanism of action

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.

TargetActionsOrganism
UCationic amino acid transporter 3Not AvailableHumans
UAntizyme inhibitor 2Not AvailableHumans
UArgininosuccinate lyaseNot AvailableHumans
UNitric oxide synthase, inducibleNot AvailableHumans
UHigh affinity cationic amino acid transporter 1Not AvailableHumans
UArginase-2, mitochondrialNot AvailableHumans
UCationic amino acid transporter 4Not AvailableHumans
UArgininosuccinate synthaseNot AvailableHumans
UNitric oxide synthase 3Not AvailableHumans
Absorption

Absorbed from the lumen of the small intestine into the enterocytes. Absorption is efficient and occurs by an active transport mechanism.

Volume of distribution

Not Available

Protein binding

Not 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 elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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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.

Pathways
PathwayCategory
Carbamoyl Phosphate Synthetase DeficiencyDisease
Argininosuccinic AciduriaDisease
Glycine and Serine MetabolismMetabolic
Arginine and Proline MetabolismMetabolic
Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency)Disease
Hyperprolinemia Type IIDisease
Hyperprolinemia Type IDisease
L-Arginine:Glycine Amidinotransferase DeficiencyDisease
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)Disease
Dimethylglycine Dehydrogenase DeficiencyDisease
Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency)Disease
Dimethylglycine Dehydrogenase DeficiencyDisease
Hyperglycinemia, Non-KetoticDisease
Creatine Deficiency, Guanidinoacetate Methyltransferase DeficiencyDisease
Hyperornithinemia with Gyrate Atrophy (HOGA)Disease
3-Phosphoglycerate Dehydrogenase DeficiencyDisease
Citrullinemia Type IDisease
Urea CycleMetabolic
Aspartate MetabolismMetabolic
Canavan DiseaseDisease
HypoacetylaspartiaDisease
Ornithine Transcarbamylase Deficiency (OTC Deficiency)Disease
Prolidase Deficiency (PD)Disease
Prolinemia Type IIDisease
Non-Ketotic HyperglycinemiaDisease
SarcosinemiaDisease
ArgininemiaDisease
Ornithine Aminotransferase Deficiency (OAT Deficiency)Disease
Hyperornithinemia-Hyperammonemia-Homocitrullinuria [HHH-syndrome]Disease
Nitric Oxide Signaling PathwaySignaling
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
No interactions found.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Arginine butyrateIK8S1P79MU80407-72-3Not applicable
Arginine hydrochlorideF7LTH1E20Y1119-34-2KWTQSFXGGICVPE-WCCKRBBISA-N
International/Other Brands
R-Gene 10 (Pharmacia Corp.)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
L-arginine Hydrochloride InjectionLiquid250 mg / mLIntravenousSandoz S.P.A.1973-12-31Not applicableCanada flag
R-GeneInjection, solution10 g/100mLIntravenousPharmacia & Upjohn Company LLC1976-06-15Not applicableUS flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
GNC L-Arginine 1000 CapletCapsule1000 mgOralGNC LIVEWELL MALAYSIA SDN. BHD.2020-09-08Not applicableMalaysia flag
GNC L-Arginine 500mg CapsuleCapsule500 mgOralGNC LIVEWELL MALAYSIA SDN. BHD.2020-09-08Not applicableMalaysia flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
2.5% Travasol Amino Acid Injection With Electrolytes In 10% DextroseArginine (290 mg / 100 mL) + Alanine (520 mg / 100 mL) + Dextrose, unspecified form (10 g / 100 mL) + Dipotassium phosphate (130.5 mg / 100 mL) + Glycine (260 mg / 100 mL) + Histidine (120 mg / 100 mL) + Isoleucine (150 mg / 100 mL) + Leucine (182.5 mg / 100 mL) + Lysine hydrochloride (145 mg / 100 mL) + Magnesium chloride (25.5 mg / 100 mL) + Methionine (100 mg / 100 mL) + Phenylalanine (140 mg / 100 mL) + Proline (170 mg / 100 mL) + Serine (125 mg / 100 mL) + Sodium acetate (170 mg / 100 mL) + Sodium chloride (29.3 mg / 100 mL) + Threonine (105 mg / 100 mL) + Tryptophan (45 mg / 100 mL) + Tyrosine (10 mg / 100 mL) + Valine (145 mg / 100 mL)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312015-08-05Canada flag
2.5% Travasol Amino Acid Injection With Electrolytes In 10% Dextrose ClinimixArginine (260 mg / 100 mL) + Alanine (520 mg / 100 mL) + Dextrose, unspecified form (10 g / 100 mL) + Dipotassium phosphate (130.5 mg / 100 mL) + Glycine (520 mg / 100 mL) + Histidine (110 mg / 100 mL) + Isoleucine (120 mg / 100 mL) + L-Leucine hydrochloride (155 mg / 100 mL) + Lysine hydrochloride (145 mg / 100 mL) + Magnesium chloride (25.5 mg / 100 mL) + Methionine (145 mg / 100 mL) + Phenylalanine hydrochloride (155 mg / 100 mL) + Proline (105 mg / 100 mL) + Sodium acetate (170 mg / 100 mL) + Sodium chloride (29.3 mg / 100 mL) + Threonine (105 mg / 100 mL) + Tryptophan (45 mg / 100 mL) + Tyrosine (10 mg / 100 mL) + Valine (115 mg / 100 mL)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1993-12-312015-08-05Canada flag
2.5% Travasol Amino Acid Injection Without Electrolytes In 10% Dextrose QuickmixArginine (260 mg / 100 mL) + Alanine (520 mg / 100 mL) + Dextrose, unspecified form (10 g / 100 mL) + Glycine (520 mg / 100 mL) + Histidine (110 mg / 100 mL) + Isoleucine (120 mg / 100 mL) + L-Leucine hydrochloride (155 mg / 100 mL) + Lysine hydrochloride (195 mg / 100 mL) + Methionine (195 mg / 100 mL) + Phenylalanine hydrochloride (155 mg / 100 mL) + Proline (105 mg / 100 mL) + Threonine (105 mg / 100 mL) + Tryptophan (45 mg / 100 mL) + Tyrosine (10 mg / 100 mL) + Valine (115 mg / 100 mL)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312007-08-02Canada flag
2.5%travasol Amino Acid InJ.W.eleC.W.25%dexArginine (290 mg / 100 mL) + Alanine (520 mg / 100 mL) + Dextrose, unspecified form (25 g / 100 mL) + Dipotassium phosphate (130.5 mg / 100 mL) + Glycine (260 mg / 100 mL) + Histidine (120 mg / 100 mL) + Isoleucine (150 mg / 100 mL) + Leucine (182.5 mg / 100 mL) + Lysine hydrochloride (145 mg / 100 mL) + Magnesium chloride (25.5 mg / 100 mL) + Methionine (100 mg / 100 mL) + Phenylalanine (140 mg / 100 mL) + Proline (170 mg / 100 mL) + Serine (125 mg / 100 mL) + Sodium acetate (170 mg / 100 mL) + Sodium chloride (29.3 mg / 100 mL) + Threonine (105 mg / 100 mL) + Tryptophan (45 mg / 100 mL) + Tyrosine (10 mg / 100 mL) + Valine (145 mg / 100 mL)LiquidIntravenousClintec Nutrition Company1996-07-301998-08-13Canada flag
2.75% Travas. Amino Acid InJ.W.elecw.25%dexArginine (316 mg / 100 mL) + Alanine (570 mg / 100 mL) + Dextrose, unspecified form (25 g / 100 mL) + Dipotassium phosphate (261 mg / 100 mL) + Glycine (283 mg / 100 mL) + Histidine (132 mg / 100 mL) + Isoleucine (165 mg / 100 mL) + Leucine (201 mg / 100 mL) + Lysine hydrochloride (159.5 mg / 100 mL) + Magnesium chloride (51 mg / 100 mL) + Methionine (110 mg / 100 mL) + Phenylalanine (154 mg / 100 mL) + Proline (187 mg / 100 mL) + Serine (137.5 mg / 100 mL) + Sodium acetate (215.5 mg / 100 mL) + Sodium chloride (112 mg / 100 mL) + Threonine (115.5 mg / 100 mL) + Tryptophan (49.5 mg / 100 mL) + Tyrosine (11 mg / 100 mL) + Valine (159.5 mg / 100 mL)LiquidIntravenousClintec Nutrition Company1996-07-301998-08-13Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ABOUND PORTAKAL AROMALI TOZ 24 GR 30 POSETArginine (7 g/1) + L-Glutamine (7 g/1)PowderOralABBOTT LABORATUARLARI İTHALAT İHRACAT VE TİC. LTD. ŞTİ.2013-01-292024-01-23Turkey flag
ClinimixArginine (3.17 g/1L) + Alanine (5.70 g/1L) + Calcium chloride dihydrate (0.33 g/1L) + D-glucose monohydrate (75.00 g/1L) + Dipotassium phosphate (2.61 g/1L) + Glycine (2.84 g/1L) + Histidine (1.32 g/1L) + Isoleucine (1.65 g/1L) + Leucine (2.01 g/1L) + Lysine (2.00 g/1L) + Magnesium chloride hexahydrate (0.51 g/1L) + Methionine (1.10 g/1L) + Phenylalanine (1.54 g/1L) + Proline (1.87 g/1L) + Serine (1.38 g/1L) + Sodium acetate trihydrate (2.16 g/1L) + Sodium chloride (1.12 g/1L) + Threonine (1.16 g/1L) + Tryptophan (0.50 g/1L) + Tyrosine (0.11 g/1L) + Valine (1.60 g/1L)SolutionIntravenousBaxter Healthcare Corporation2017-10-252019-11-30US flag
ClinimixArginine (3.17 g/1L) + Alanine (5.70 g/1L) + Calcium chloride dihydrate (0.33 g/1L) + D-glucose monohydrate (100.00 g/1L) + Dipotassium phosphate (2.61 g/1L) + Glycine (2.84 g/1L) + Histidine (1.32 g/1L) + Isoleucine (1.65 g/1L) + Leucine (2.01 g/1L) + Lysine (2.00 g/1L) + Magnesium chloride hexahydrate (0.51 g/1L) + Methionine (1.10 g/1L) + Phenylalanine (1.54 g/1L) + Proline (1.87 g/1L) + Serine (1.38 g/1L) + Sodium acetate trihydrate (2.16 g/1L) + Sodium chloride (1.12 g/1L) + Threonine (1.16 g/1L) + Tryptophan (0.50 g/1L) + Tyrosine (0.11 g/1L) + Valine (1.60 g/1L)SolutionIntravenousBaxter Healthcare Corporation2017-10-252019-11-30US flag
ClinimixArginine (9.78 g/2L) + Alanine (17.60 g/2L) + Calcium chloride dihydrate (0.66 g/2L) + D-glucose monohydrate (300.00 g/2L) + Dipotassium phosphate (5.22 g/2L) + Glycine (8.76 g/2L) + Histidine (4.08 g/2L) + Isoleucine (5.10 g/2L) + Leucine (6.20 g/2L) + Lysine (4.93 g/2L) + Magnesium chloride hexahydrate (1.02 g/2L) + Methionine (3.40 g/2L) + Phenylalanine (4.76 g/2L) + Proline (5.78 g/2L) + Serine (4.25 g/2L) + Sodium acetate trihydrate (5.94 g/2L) + Sodium chloride (1.54 g/2L) + Threonine (3.57 g/2L) + Tryptophan (1.53 g/2L) + Tyrosine (0.34 g/2L) + Valine (4.93 g/2L)SolutionIntravenousBaxter Healthcare Corporation2017-10-252019-11-30US flag
FREAMINE III %10 1000 ML(SETLI)Arginine (0.95 %) + Alanine (0.71 %) + Cysteine (0.016 %) + Glycine (1.4 %) + Histidine (0.28 %) + Isoleucine (0.69 %) + Leucine (0.91 %) + Lysine (0.73 %) + Methionine (0.53 %) + Phenylalanine (0.56 %) + Proline (1.12 %) + Serine (0.59 %) + Threonine (0.4 %) + Tryptophan (0.15 %) + Valine (0.66 %)SolutionIntravenousECZACIBAŞI-BAXTER HASTANE ÜRÜNLERİ SAN.VE TİC. A.Ş.2013-01-292024-01-23Turkey flag

Categories

ATC Codes
V03AF11 — Arginine and lysineB05XB01 — Arginine hydrochloride
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
L-alpha-amino acids
Alternative Parents
Fatty acids and conjugates / Guanidines / Amino acids / Propargyl-type 1,3-dipolar organic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Carboximidamides / Organopnictogen compounds / Organic oxides / Monoalkylamines
show 2 more
Substituents
Aliphatic acyclic compound / Amine / Amino acid / Carbonyl group / Carboximidamide / Carboxylic acid / Fatty acid / Guanidine / Hydrocarbon derivative / L-alpha-amino acid
show 11 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
proteinogenic amino acid, L-alpha-amino acid, arginine, glutamine family amino acid (CHEBI:16467) / Common amino acids (C00062)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
94ZLA3W45F
CAS number
74-79-3
InChI Key
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

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. [Article]
  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. [Article]
  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. [Article]
Human Metabolome Database
HMDB0000517
KEGG Drug
D02982
KEGG Compound
C00062
PubChem Compound
6322
PubChem Substance
46507180
ChemSpider
6082
BindingDB
181132
RxNav
1091
ChEBI
16467
ChEMBL
CHEMBL1485
ZINC
ZINC000001532525
PharmGKB
PA448478
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
ARG
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Arginine
MSDS
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Clinical Trials

Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package
PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
Not AvailableCompletedNot AvailableBeta-Thalassemia / Beta-Thalassemia Major / Hematologic Disease and Disorders / Iron Overload / Osteoporosis / Pulmonary Hypertension (PH) / Thalassemia1somestatusstop reasonjust information to hide
Not AvailableCompletedNot AvailableCitrulline / Gastrointestinal Failure / Intra Abdominal Pressure / Multi-organ Failure1somestatusstop reasonjust information to hide
Not AvailableCompletedBasic ScienceCardiovascular Disease (CVD)1somestatusstop reasonjust information to hide
Not AvailableCompletedBasic SciencePeripheral Arterial Disease (PAD)1somestatusstop reasonjust information to hide
Not AvailableCompletedSupportive CarePolycystic Ovarian Syndrome (PCOS)1somestatusstop reasonjust information to hide

Pharmacoeconomics

Manufacturers
  • Pharmacia and upjohn co
Packagers
  • 21st Century Healthcare Inc.
  • Amend
  • Hospira Inc.
  • Key Co.
  • Major Pharmaceuticals
  • Pharmacia Inc.
  • Professional Co.
Dosage Forms
FormRouteStrength
CapsuleOral
SolutionParenteral
PowderOral
SolutionIntravenous10.50 g/1000ml
InjectionIntravenous0.5 g/l
InjectionIntravenous0.25 g/1000ml
Solution, concentrateIntravenous
InjectionIntravenous0.52 g/l
Injection, solutionIntravenous
InjectionIntravenous11.000 g/1000ml
InjectionIntravenous5.5 g/1000ml
PowderNot applicable1 kg/1kg
GranuleOral
Tablet, coatedOral
LiquidCutaneous
CreamCutaneous
EmulsionIntravenous0.468 g
InjectionIntravenous16 g/1000ml
CapsuleOral1000 mg
CapsuleOral500 mg
EmulsionParenteral20.000 g
InjectionIntravenous1.6 g/l
TabletOral
LiquidIntravenous250 mg / mL
SprayCutaneous
KitOral
InjectionIntravenous0.37 g/l
Injection, solution, concentrateIntravenous
Injection, emulsionParenteral
EmulsionIntravenous0.466 g
Injection, emulsion; injection, solutionIntravenous
EmulsionParenteral
EmulsionIntravenous
Injection, emulsionIntravenous4.656 g/1000ml
Injection, emulsionIntravenous6.792 g/1000ml
SolutionIntraperitoneal
Injection, solutionIntraperitoneal
LiquidHemodialysis
SolutionIntraperitoneal0.184 g/l
Injection, emulsionIntravenous
SolutionOral
EmulsionIntravenous176 g/l
EmulsionIntravenous4 g
EmulsionIntravenous3 g
SolutionIntravenous
InjectionIntravenous4 g/l
InjectionIntravenous0.21 g/100ml
LiquidIntravenous
Injection, solutionIntravenous10 g/100mL
CapsuleVaginal
EmulsionIntravenous13.000 g
EmulsionParenteral42.00 g
Injection, emulsionIntravenous14 g/1000ml
InjectionIntravenous10.30 g/l
TabletOral
InjectionIntravenous
Solution
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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)244 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 FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
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)

Spectra

Mass Spec (NIST)
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Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-0a4i-1910000000-0191c1a63652c493660b
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-00di-9810000000-eb6eb73302b678cf0a24
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-00di-9700000000-e47b41cff0e873f53932
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-0a4i-1920000000-8ae5af11398835d26bed
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-00dl-9100000000-60db59de76b9a9b5bfc8
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0a4i-1910000000-0191c1a63652c493660b
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-9810000000-eb6eb73302b678cf0a24
GC-MS Spectrum - GC-MSGC-MSsplash10-00di-9700000000-e47b41cff0e873f53932
GC-MS Spectrum - GC-MSGC-MSsplash10-0a4i-1920000000-8ae5af11398835d26bed
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0udi-0900000000-afc3ca93f8fbf54ec9f4
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-00di-3900000000-8c82418f7b35a97fb9b3
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-00di-9000000000-19b62da79866318c52dd
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-00di-9000000000-64b046d21bdcbb8d5923
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-004i-0900000000-e07b937b6867d1f62293
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0a4i-0900000000-87ab853583aab2973cfb
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0a4i-2900000000-28814246b728a51e761c
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0a4i-2900000000-cfe7e406be2172e94fba
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-004i-0910000000-478a8345915bc15d85b5
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0a4i-2900000000-c930c47ecbe6975a00fc
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0a4i-2900000000-fa6be0f9ce4ee4c30738
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-004i-0900000000-3425ee9829935182c0d5
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0fk9-0946231100-3d57d2304dcb33feab3f
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-000i-0900000000-5b6dd6fb263ea09289fc
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-001i-0900000000-dfe35b3438d19320d8cb
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-00di-0900000000-f666ab7e5354bce67a2e
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-03kd-0977452210-046c4b70bd0ec351c41d
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-014i-9000000000-2f51e43e530976d63633
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-001i-0900000000-b9ebb7ebccee1a313888
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-00di-0900000000-5379b6fb6ea2313101f9
MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , PositiveLC-MS/MSsplash10-004i-0900000000-02b2bc83599dc6944f2e
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-00fr-7900000000-b7cd48e0aca6a6256968
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, PositiveLC-MS/MSsplash10-00fr-7900000000-b7cd48e0aca6a6256968
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-00fr-7900000000-4e69a6ce7b97433937ee
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-001i-0900000000-835751d54af24bd337e7
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-001i-0900000000-2d2b5fd7617ccb227bb1
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-001i-0900000000-dfe35b3438d19320d8cb
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-00di-0900000000-f666ab7e5354bce67a2e
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-001i-0900000000-b9ebb7ebccee1a313888
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-00di-0900000000-5379b6fb6ea2313101f9
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-001i-0900000000-835751d54af24bd337e7
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-001i-0900000000-2d2b5fd7617ccb227bb1
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-2900000000-28814246b728a51e761c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-2900000000-cfe7e406be2172e94fba
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-2900000000-c930c47ecbe6975a00fc
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-2900000000-1a13d259ec80cfb4cae3
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0900000000-3425ee9829935182c0d5
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00fr-7900000000-b7cd48e0aca6a6256968
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00fr-7900000000-b7cd48e0aca6a6256968
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00fr-7900000000-4e69a6ce7b97433937ee
MS/MS Spectrum - , positiveLC-MS/MSsplash10-02k9-4900000000-2fa515c22a40d21b8e10
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-1900000000-ab2b5c2c40bbf6b9b264
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9200000000-0d21425420fe93d3eec8
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0900000000-0c4db4147486764cd124
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-3b258f818397aa914cea
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9000000000-1be596e4a8b74335ff90
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-faa3c67873c43e76f2ee
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0900000000-0c4db4147486764cd124
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-1900000000-ab2b5c2c40bbf6b9b264
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-3b258f818397aa914cea
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9200000000-0d21425420fe93d3eec8
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-faa3c67873c43e76f2ee
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9000000000-1be596e4a8b74335ff90
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-145.7606786
predicted
DarkChem Lite v0.1.0
[M-H]-136.6401136
predicted
DarkChem Standard v0.1.0
[M-H]-145.9838786
predicted
DarkChem Lite v0.1.0
[M-H]-132.66614
predicted
DeepCCS 1.0 (2019)
[M-H]-145.7606786
predicted
DarkChem Lite v0.1.0
[M-H]-136.6401136
predicted
DarkChem Standard v0.1.0
[M-H]-145.9838786
predicted
DarkChem Lite v0.1.0
[M-H]-132.66614
predicted
DeepCCS 1.0 (2019)
[M+H]+147.1198786
predicted
DarkChem Lite v0.1.0
[M+H]+136.5889893
predicted
DarkChem Standard v0.1.0
[M+H]+147.0957786
predicted
DarkChem Lite v0.1.0
[M+H]+136.49348
predicted
DeepCCS 1.0 (2019)
[M+H]+147.1198786
predicted
DarkChem Lite v0.1.0
[M+H]+136.5889893
predicted
DarkChem Standard v0.1.0
[M+H]+147.0957786
predicted
DarkChem Lite v0.1.0
[M+H]+136.49348
predicted
DeepCCS 1.0 (2019)
[M+Na]+146.5321786
predicted
DarkChem Lite v0.1.0
[M+Na]+146.4709786
predicted
DarkChem Lite v0.1.0
[M+Na]+146.6673786
predicted
DarkChem Lite v0.1.0
[M+Na]+145.81657
predicted
DeepCCS 1.0 (2019)
[M+Na]+146.5321786
predicted
DarkChem Lite v0.1.0
[M+Na]+146.4709786
predicted
DarkChem Lite v0.1.0
[M+Na]+146.6673786
predicted
DarkChem Lite v0.1.0
[M+Na]+145.81657
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Uniporter that mediates the uptake of cationic L-amino acids such as L-arginine, L-lysine and L-ornithine (PubMed:11591158). The transport is sodium ions- and pH-independent, moderately trans-stimulated and is mediated by passive diffusion (PubMed:11591158)
Specific Function
amino acid transmembrane transporter activity
Gene Name
SLC7A3
Uniprot ID
Q8WY07
Uniprot Name
Cationic amino acid transporter 3
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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Antizyme inhibitor (AZI) protein that positively regulates ornithine decarboxylase (ODC) activity and polyamine uptake. AZI is an enzymatically inactive ODC homolog that counteracts the negative effect of ODC antizymes (AZs) OAZ1, OAZ2 and OAZ3 on ODC activity by competing with ODC for antizyme-binding (PubMed:17900240). Inhibits antizyme-dependent ODC degradation and releases ODC monomers from their inactive complex with antizymes, leading to formation of the catalytically active ODC homodimer and restoring polyamine production (PubMed:17900240). Participates in the morphological integrity of the trans-Golgi network (TGN) and functions as a regulator of intracellular secretory vesicle trafficking (PubMed:20188728)
Specific Function
arginine decarboxylase activity
Gene Name
AZIN2
Uniprot ID
Q96A70
Uniprot Name
Antizyme inhibitor 2
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. [Article]
  2. Regunathan S: Agmatine: biological role and therapeutic potentials in morphine analgesia and dependence. AAPS J. 2006 Jul 21;8(3):E479-84. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Catalyzes the reversible cleavage of L-argininosuccinate to fumarate and L-arginine, an intermediate step reaction in the urea cycle mostly providing for hepatic nitrogen detoxification into excretable urea as well as de novo L-arginine synthesis in nonhepatic tissues (PubMed:11747432, PubMed:11747433, PubMed:22081021, PubMed:2263616, PubMed:9045711). Essential regulator of intracellular and extracellular L-arginine pools. As part of citrulline-nitric oxide cycle, forms tissue-specific multiprotein complexes with argininosuccinate synthase ASS1, transport protein SLC7A1 and nitric oxide synthase NOS1, NOS2 or NOS3, allowing for cell-autonomous L-arginine synthesis while channeling extracellular L-arginine to nitric oxide synthesis pathway (PubMed:22081021)
Specific Function
argininosuccinate lyase activity
Gene Name
ASL
Uniprot ID
P04424
Uniprot Name
Argininosuccinate lyase
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body (PubMed:7504305, PubMed:7531687, PubMed:7544004, PubMed:7682706). In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such PTGS2/COX2 (By similarity). As component of the iNOS-S100A8/9 transnitrosylase complex involved in the selective inflammatory stimulus-dependent S-nitrosylation of GAPDH on 'Cys-247' implicated in regulation of the GAIT complex activity and probably multiple targets including ANXA5, EZR, MSN and VIM (PubMed:25417112). Involved in inflammation, enhances the synthesis of pro-inflammatory mediators such as IL6 and IL8 (PubMed:19688109)
Specific Function
arginine binding
Gene Name
NOS2
Uniprot ID
P35228
Uniprot Name
Nitric oxide synthase, inducible
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  5. Popovic PJ, Zeh HJ 3rd, Ochoa JB: Arginine and immunity. J Nutr. 2007 Jun;137(6 Suppl 2):1681S-1686S. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
High-affinity, low capacity permease involved in the transport of the cationic amino acids (arginine, lysine and ornithine) in non-hepatic tissues
Specific Function
amino acid transmembrane transporter activity
Gene Name
SLC7A1
Uniprot ID
P30825
Uniprot Name
High affinity cationic amino acid transporter 1
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General 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 nitric oxid synthase (NOS). Arginine metabolism is a critical regulator of innate and adaptive immune responses. Seems to be involved in negative regulation of the survival capacity of activated CD4(+) and CD8(+) T cells (PubMed:27745970). May suppress inflammation-related signaling in asthmatic airway epithelium (PubMed:27214549). May contribute to the immune evasion of H.pylori by restricting M1 macrophage activation and polyamine metabolism (By similarity). In fetal dendritic cells may play a role in promoting immune suppression and T cell TNF-alpha production during gestation (PubMed:28614294). Regulates RPS6KB1 signaling, which promotes endothelial cell senescence and inflammation and implicates NOS3/eNOS dysfunction (PubMed:22928666). Can inhibit endothelial autophagy independently of its enzymatic activity implicating mTORC2 signaling (PubMed:25484082). Involved in vascular smooth muscle cell senescence and apoptosis independently of its enzymatic activity (PubMed:23832324). Since NOS is found in the penile corpus cavernosum smooth muscle, the clitoral corpus cavernosum and the vagina, arginase-2 plays a role in both male and female sexual arousal (PubMed:12859189)
Specific Function
arginase activity
Gene Name
ARG2
Uniprot ID
P78540
Uniprot Name
Arginase-2, mitochondrial
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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Involved in the transport of the cationic amino acids (arginine, lysine and ornithine)
Specific Function
amino acid transmembrane transporter activity
Gene Name
SLC7A4
Uniprot ID
O43246
Uniprot Name
Cationic amino acid transporter 4
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
One of the enzymes of the urea cycle, the metabolic pathway transforming neurotoxic amonia produced by protein catabolism into inocuous urea in the liver of ureotelic animals. Catalyzes the formation of arginosuccinate from aspartate, citrulline and ATP and together with ASL it is responsible for the biosynthesis of arginine in most body tissues
Specific Function
amino acid binding
Gene Name
ASS1
Uniprot ID
P00966
Uniprot Name
Argininosuccinate synthase
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Produces nitric oxide (NO) which is implicated in vascular smooth muscle relaxation through a cGMP-mediated signal transduction pathway (PubMed:1378832). NO mediates vascular endothelial growth factor (VEGF)-induced angiogenesis in coronary vessels and promotes blood clotting through the activation of platelets
Specific Function
actin monomer binding
Gene Name
NOS3
Uniprot ID
P29474
Uniprot Name
Nitric oxide synthase 3
Molecular Weight
133273.59 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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General 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 (PubMed:10454528, PubMed:10525100, PubMed:10966938, PubMed:17509700, PubMed:20722056, PubMed:33124720). Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Relative uptake activity ratio of carnitine to TEA is 11.3 (PubMed:10454528, PubMed:10525100, PubMed:10966938). In intestinal epithelia, transports the quorum-sensing pentapeptide CSF (competence and sporulation factor) from Bacillus Subtilis wich induces cytoprotective heat shock proteins contributing to intestinal homeostasis (PubMed:18005709). May also contribute to regulate the transport of organic compounds in testis across the blood-testis-barrier (Probable)
Specific Function
(R)-carnitine transmembrane transporter activity
Gene Name
SLC22A5
Uniprot ID
O76082
Uniprot Name
Organic cation/carnitine transporter 2
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium- and proton-independent thyroid hormones and aromatic acids transporter (PubMed:11827462, PubMed:18337592, PubMed:28754537). Mediates both uptake and efflux of 3,5,3'-triiodothyronine (T3) and 3,5,3',5'-tetraiodothyronine (T4) with high affinity, suggesting a role in the homeostasis of thyroid hormone levels (PubMed:18337592). Responsible for low affinity bidirectional transport of the aromatic amino acids, such as phenylalanine, tyrosine, tryptophan and L-3,4-dihydroxyphenylalanine (L-dopa) (PubMed:11827462, PubMed:28754537). Plays an important role in homeostasis of aromatic amino acids (By similarity)
Specific Function
amino acid transmembrane transporter activity
Gene Name
SLC16A10
Uniprot ID
Q8TF71
Uniprot Name
Monocarboxylate transporter 10
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transporter that mediates the transport of endogenous and microbial zwitterions and organic cations (PubMed:10215651, PubMed:15107849, PubMed:15795384, PubMed:16729965, PubMed:20601551, PubMed:22206629, PubMed:22569296, PubMed:29530864). Functions as a Na(+)-dependent and pH-dependent high affinity microbial symporter of potent food-derived antioxidant ergothioeine (PubMed:15795384, PubMed:29530864, PubMed:33124720). Transports one sodium ion with one ergothioeine molecule (By similarity). Involved in the absorption of ergothioneine from the luminal/apical side of the small intestine and renal tubular cells, and into non-parenchymal liver cells, thereby contributing to maintain steady-state ergothioneine level in the body (PubMed:20601551). Also mediates the bidirectional transport of acetycholine, although the exact transport mechanism has not been fully identified yet (PubMed:22206629). Most likely exports anti-inflammatory acetylcholine in non-neuronal tissues, thereby contributing to the non-neuronal cholinergic system (PubMed:22206629, PubMed:22569296). Displays a general physiological role linked to better survival by controlling inflammation and oxidative stress, which may be related to ergothioneine and acetycholine transports (PubMed:15795384, PubMed:22206629). May also function as a low-affinity Na(+)-dependent transporter of L-carnitine through the mitochondrial membrane, thereby maintaining intracellular carnitine homeostasis (PubMed:10215651, PubMed:15107849, PubMed:16729965). May contribute to regulate the transport of cationic compounds in testis across the blood-testis-barrier (PubMed:35307651)
Specific Function
acetylcholine transmembrane transporter activity
Gene Name
SLC22A4
Uniprot ID
Q9H015
Uniprot Name
Solute carrier family 22 member 4
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. [Article]

Drug created at June 13, 2005 13:24 / Updated at November 06, 2024 19:56