Identification

Name
L-Arginine
Accession Number
DB00125  (NUTR00014)
Type
Small Molecule
Groups
Approved, Nutraceutical
Description

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

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
  • R
External IDs
NSC-206269
Product Ingredients
IngredientUNIICASInChI Key
L-Arginine HydrochlorideF7LTH1E20Y1119-34-2KWTQSFXGGICVPE-WCCKRBBISA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
L-arginine Hydrochloride InjectionLiquid250 mgIntravenousSandoz Canada Incorporated1973-12-31Not applicableCanada
R-GeneInjection, solution10 g/100mLIntravenousPharmacia & Upjohn Inc1976-06-15Not applicableUs
International/Other Brands
R-Gene 10 (Pharmacia Corp.)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
2.5% Travasol Amino Acid Injection With Electrolytes In 10% DextroseL-Arginine (290 mg) + Dipotassium phosphate (130.5 mg) + Glucose (10 g) + Glycine (260 mg) + Histidine (120 mg) + L-Alanine (520 mg) + L-Isoleucine (150 mg) + L-Leucine (182.5 mg) + L-Lysine (145 mg) + L-Methionine (100 mg) + L-Phenylalanine (140 mg) + L-Proline (170 mg) + L-Threonine (105 mg) + L-Tryptophan (45 mg) + L-Tyrosine (10 mg) + L-Valine (145 mg) + Magnesium chloride (25.5 mg) + Serine (125 mg) + Sodium Chloride (29.3 mg) + Sodium acetate (170 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312015-08-05Canada
2.5% Travasol Amino Acid Injection With Electrolytes In 10% Dextrose ClinimixL-Arginine (260 mg) + Dipotassium phosphate (130.5 mg) + Glucose (10 g) + Glycine (520 mg) + Histidine (110 mg) + L-Alanine (520 mg) + L-Isoleucine (120 mg) + L-Leucine hydrochloride (155 mg) + L-Lysine hydrochloride (145 mg) + L-Methionine (145 mg) + L-Phenylalanine hydrochloride (155 mg) + L-Proline (105 mg) + L-Threonine (105 mg) + L-Tryptophan (45 mg) + L-Tyrosine (10 mg) + L-Valine (115 mg) + Magnesium chloride (25.5 mg) + Sodium Chloride (29.3 mg) + Sodium acetate (170 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1993-12-312015-08-05Canada
2.5% Travasol Amino Acid Injection Without Electrolytes In 10% Dextrose QuickmixL-Arginine (260 mg) + Glucose (10 g) + Glycine (520 mg) + Histidine (110 mg) + L-Alanine (520 mg) + L-Isoleucine (120 mg) + L-Leucine hydrochloride (155 mg) + L-Lysine hydrochloride (195 mg) + L-Methionine (195 mg) + L-Phenylalanine hydrochloride (155 mg) + L-Proline (105 mg) + L-Threonine (105 mg) + L-Tryptophan (45 mg) + L-Tyrosine (10 mg) + L-Valine (115 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312007-08-02Canada
2.5%travasol Amino Acid InJ.W.eleC.W.25%dexL-Arginine (290 mg) + Dipotassium phosphate (130.5 mg) + Glucose (25 g) + Glycine (260 mg) + Histidine (120 mg) + L-Alanine (520 mg) + L-Isoleucine (150 mg) + L-Leucine (182.5 mg) + L-Lysine (145 mg) + L-Methionine (100 mg) + L-Phenylalanine (140 mg) + L-Proline (170 mg) + L-Threonine (105 mg) + L-Tryptophan (45 mg) + L-Tyrosine (10 mg) + L-Valine (145 mg) + Magnesium chloride (25.5 mg) + Serine (125 mg) + Sodium Chloride (29.3 mg) + Sodium acetate (170 mg)LiquidIntravenousClintec Nutrition Company1996-07-301998-08-13Canada
2.75% Travas. Amino Acid InJ.W.elecw.25%dexL-Arginine (316 mg) + Dipotassium phosphate (261 mg) + Glucose (25 g) + Glycine (283 mg) + Histidine (132 mg) + L-Alanine (570 mg) + L-Isoleucine (165 mg) + L-Leucine (201 mg) + L-Lysine (159.5 mg) + L-Methionine (110 mg) + L-Phenylalanine (154 mg) + L-Proline (187 mg) + L-Threonine (115.5 mg) + L-Tryptophan (49.5 mg) + L-Tyrosine (11 mg) + L-Valine (159.5 mg) + Magnesium chloride (51 mg) + Serine (137.5 mg) + Sodium Chloride (112 mg) + Sodium acetate (215.5 mg)LiquidIntravenousClintec Nutrition Company1996-07-301998-08-13Canada
2.75% Travasol Amino Acid Injection With Electrolytes In 25% Dextrose QuickmixL-Arginine (285 mg) + Dipotassium phosphate (261 mg) + Glucose (25 g) + Glycine (570 mg) + Histidine (120.5 mg) + L-Alanine (570 mg) + L-Isoleucine (131.5 mg) + L-Leucine hydrochloride (170 mg) + L-Lysine hydrochloride (159 mg) + L-Methionine (159 mg) + L-Phenylalanine hydrochloride (170 mg) + L-Proline (115 mg) + L-Threonine (115 mg) + L-Tryptophan (49.5 mg) + L-Tyrosine (11 mg) + L-Valine (126 mg) + Magnesium chloride (51 mg) + Sodium Chloride (112 mg) + Sodium acetate (215.5 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-02-022007-08-02Canada
2.75% Travasol Amino Acid Injection With Electrolytes In 5% Dextrose QuickmixL-Arginine (285 mg) + Dipotassium phosphate (215.5 mg) + Glucose (5 g) + Glycine (570 mg) + Histidine (120.5 mg) + L-Alanine (570 mg) + L-Isoleucine (131.5 mg) + L-Leucine hydrochloride (170 mg) + L-Lysine hydrochloride (159 mg) + L-Methionine (159 mg) + L-Phenylalanine hydrochloride (170 mg) + L-Proline (115 mg) + L-Threonine (115 mg) + L-Tryptophan (49.5 mg) + L-Tyrosine (11 mg) + L-Valine (126 mg) + Magnesium chloride (51 mg) + Sodium Chloride (112 mg) + Sodium acetate (256 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1993-12-312007-08-02Canada
2.75%travasol Amino Acid InJ.W.eleC.W.5%dex.L-Arginine (316 mg) + Dipotassium phosphate (261 mg) + Glucose (5 g) + Glycine (283 mg) + Histidine (132 mg) + L-Alanine (570 mg) + L-Isoleucine (165 mg) + L-Leucine (201 mg) + L-Lysine (159.5 mg) + L-Methionine (110 mg) + L-Phenylalanine (154 mg) + L-Proline (187 mg) + L-Threonine (115.5 mg) + L-Tryptophan (49.5 mg) + L-Tyrosine (11 mg) + L-Valine (159.5 mg) + Magnesium chloride (51 mg) + Serine (137.5 mg) + Sodium Chloride (112 mg) + Sodium acetate (215 mg)LiquidIntravenousClintec Nutrition Company1996-12-311999-08-10Canada
4.25% Amino Acid Injection Without Electrolytes In 20% Dextrose QuickmixL-Arginine (440 mg) + Glucose (20 g) + Glycine (880 mg) + Histidine (186 mg) + L-Alanine (880 mg) + L-Isoleucine (203 mg) + L-Leucine hydrochloride (263 mg) + L-Lysine hydrochloride (246 mg) + L-Methionine (246 mg) + L-Phenylalanine hydrochloride (263 mg) + L-Proline (178 mg) + L-Threonine (178 mg) + L-Tryptophan (76 mg) + L-Tyrosine (17 mg) + L-Valine (195 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312007-08-02Canada
4.25% Travasol Amino Acid Injection With Electrolytes In 10% DextroseL-Arginine (489 mg) + Dipotassium phosphate (261 mg) + Glucose (10 g) + Glycine (438 mg) + Histidine (204 mg) + L-Alanine (880 mg) + L-Isoleucine (255 mg) + L-Leucine (310 mg) + L-Lysine hydrochloride (246.5 mg) + L-Methionine (170 mg) + L-Phenylalanine (238 mg) + L-Proline (289 mg) + L-Threonine (178.5 mg) + L-Tryptophan (76.5 mg) + L-Tyrosine (17 mg) + L-Valine (246.5 mg) + Magnesium chloride (51 mg) + Serine (212.5 mg) + Sodium Chloride (77 mg) + Sodium acetate (297 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312015-08-05Canada
Categories
UNII
94ZLA3W45F
CAS number
74-79-3
Weight
Average: 174.201
Monoisotopic: 174.111675712
Chemical Formula
C6H14N4O2
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[[email protected]@H](CCCNC(N)=N)C(O)=O

Pharmacology

Indication

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

Structured Indications
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 AvailableHuman
UArginine decarboxylaseNot AvailableHuman
UArgininosuccinate lyaseNot AvailableHuman
UNitric oxide synthase, inducibleNot AvailableHuman
UHigh affinity cationic amino acid transporter 1Not AvailableHuman
UArginase-2, mitochondrialNot AvailableHuman
UCationic amino acid transporter 4Not AvailableHuman
UArgininosuccinate synthaseNot AvailableHuman
UNitric oxide synthase, endothelialNot AvailableHuman
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
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
Pathways
PathwayCategory
Argininosuccinic AciduriaDisease
Prolidase Deficiency (PD)Disease
Hyperglycinemia, non-ketoticDisease
HypoacetylaspartiaDisease
Non Ketotic HyperglycinemiaDisease
ArgininemiaDisease
Dimethylglycine Dehydrogenase DeficiencyDisease
Citrullinemia Type IDisease
Carbamoyl Phosphate Synthetase DeficiencyDisease
Aspartate MetabolismMetabolic
Ornithine Aminotransferase Deficiency (OAT Deficiency)Disease
Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency)Disease
Hyperprolinemia Type IIDisease
Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency)Disease
Creatine deficiency, guanidinoacetate methyltransferase deficiencyDisease
Hyperornithinemia with gyrate atrophy (HOGA)Disease
Hyperornithinemia-hyperammonemia-homocitrullinuria [HHH-syndrome]Disease
L-arginine:glycine amidinotransferase deficiencyDisease
3-Phosphoglycerate dehydrogenase deficiencyDisease
Glycine and Serine MetabolismMetabolic
Arginine and Proline MetabolismMetabolic
Urea CycleMetabolic
Canavan DiseaseDisease
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)Disease
Ornithine Transcarbamylase Deficiency (OTC Deficiency)Disease
Prolinemia Type IIDisease
Dimethylglycine Dehydrogenase DeficiencyDisease
SarcosinemiaDisease
Hyperprolinemia Type IDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
No interactions found.
Food Interactions
Not 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
Human Metabolome Database
HMDB00517
KEGG Drug
D02982
KEGG Compound
C00062
PubChem Compound
6322
PubChem Substance
46507180
ChemSpider
6082
BindingDB
21959
ChEBI
16467
ChEMBL
CHEMBL1485
PharmGKB
PA448478
IUPHAR
721
Guide to Pharmacology
GtP Drug Page
HET
ARG
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Arginine
ATC Codes
B05XB01 — Arginine hydrochloride
AHFS Codes
  • 36:66.00 — Pituitary Function
MSDS
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Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentEndothelial Dysfunction1
0CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Plasmodium Infections1
0Not Yet RecruitingTreatmentHypertensive Diseases / Renal Failure1
0RecruitingSupportive CareProtein Feeding in Post-traumatic Injury Patients1
1Active Not RecruitingNot AvailableHealthy Volunteers1
1Active Not RecruitingTreatmentMultiple Myeloma (MM) / Plasma Cell Neoplasms1
1CompletedNot AvailableBecker's Muscular Dystrophy (BMD) / Duchenne's Muscular Dystrophy (DMD) / Dystrophinopathies1
1CompletedNot AvailableHealthy Volunteers1
1CompletedNot AvailableTo Determine Bioequivalence Under Fasting Conditions1
1CompletedBasic ScienceAmphetamine-Related Disorders / Moods Disorders / Substance-Related Disorders1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedBasic SciencePatients With Chemotherapy Induced Anemia (CIA)1
1CompletedOtherTo Determine Bioequivalence Under Fed Conditions1
1CompletedTreatmentCentral nervous system neoplasms malignant NEC / Recurrent or Refractory Solid Tumors1
1CompletedTreatmentDuchenne's Muscular Dystrophy (DMD)1
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentHepatic Insufficiency1
1CompletedTreatmentJuvenile Myelomonocytic Leukemia Lymphoblastic / Leukemia Acute Myeloid Leukemia (AML) / Leukemia, Lymphocytic, Acute, T-Cell / Myelodysplastic Syndrome / T-cell Lymphoblastic Lymphoma1
1CompletedTreatmentLeukaemia, Acute / Lymphoma, Hodgkins / Non-Hodgkin's Lymphoma (NHL)1
1CompletedTreatmentLeukemias / Refractory Solid Tumors1
1CompletedTreatmentSickle Cell Disorders1
1Not Yet RecruitingBasic ScienceType 2 Diabetes Mellitus1
1RecruitingTreatmentClear Cell Carcinoma / Ewing's Sarcoma (ES) / Gastrointestinal Tumors / Germ Cell Tumors / Hepatic Tumors / Malignant Lymphomas / Melanoma / Neuroblastomas / Non-rhabdomyosarcoma / Renal Cell Adenocarcinoma / Rhabdoid Tumors / Rhabdomyosarcomas / Wilms' tumor1
1RecruitingTreatmentHigh-risk Tumor / Malignant Lymphomas / Neuroblastomas1
1RecruitingTreatmentTuberculosis1
1TerminatedTreatmentCancer, Ovarian / Fallopian Tube Cancer / Peritoneal Cavity Cancer1
1TerminatedTreatmentCardiac Transplant1
1WithdrawnTreatmentCervical Cancers1
1, 2CompletedTreatmentInfection, Human Immunodeficiency Virus I / Pf Subclinical Parasitemia1
1, 2CompletedTreatmentPrimary Biliary Cirrhosis (PBC)1
1, 2Enrolling by InvitationTreatmentSickle Cell Disorders1
1, 2RecruitingTreatmentGlioblastomas1
1, 2RecruitingTreatmentPeriodontitis1
1, 2TerminatedTreatmentGlioblastomas (GBM)1
1, 2Unknown StatusTreatmentMyalgic Encephalomyelitis (ME)1
2Active Not RecruitingBasic ScienceHormone Refractory Prostate Cancer / Metastatic Hormone Refractory Prostate Cancer1
2Active Not RecruitingTreatmentAdrenoleukodystrophy (ALD) / Alpha Mannosidosis / Aspartylglucosaminuria / Fucosidosis / Hunter Syndrome / Hurler's Syndrome / Krabbe's Disease / Metachromatic Leukodystrophy (MLD) / Mucopolysaccharidosis / Mucopolysaccharidosis VI / Peroxisomal Disorders / Sly Syndrome / Sphingolipidoses1
2Active Not RecruitingTreatmentAlzheimer's Disease (AD)1
2Active Not RecruitingTreatmentAsthma Bronchial / Inflammatory Reaction1
2Active Not RecruitingTreatmentCarcinoid Tumors / Medulloblastomas / Neuroblastomas / Neuroendocrine Tumors1
2Active Not RecruitingTreatmentDesmoplastic Small Round Cell Tumor (DSRCT) / Ewing Sarcoma of Bone or Soft Tissue / Localized Ewing Sarcoma/Peripheral Primitive Neuroectodermal Tumor / Metastatic Ewing Sarcoma/Peripheral Primitive Neuroectodermal Tumor1
2Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2Active Not RecruitingTreatmentMantle Cell Lymphoma (MCL)1
2Active Not RecruitingTreatmentMultiple Myeloma (MM)1
2CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis1
2CompletedBasic ScienceCervical Ripening / Induction of Labour1
2CompletedPreventionBloodloss / Surgical Procedures, Operative1
2CompletedPreventionOral Mucositis1
2CompletedTreatmentAcute Lymphoblastic Leukaemias (ALL) / Lymphoma, Lymphoblastic1
2CompletedTreatmentAge Related Macular Degeneration (ARMD)1
2CompletedTreatmentAmino Acid Metabolism, Inborn Errors / Argininosuccinic Aciduria / Deficiencies in enzymes of the urea cycle1
2CompletedTreatmentAsthma Bronchial1
2CompletedTreatmentB-cell Chronic Lymphocytic Leukemia CLL1
2CompletedTreatmentCancer, Breast2
2CompletedTreatmentCancer, Ovarian / Cervical Cancers / Endometrial Cancers / Fallopian Tube Cancer / Sarcomas / Thromboembolism / Vaginal Cancers / Vulvar Cancers1
2CompletedTreatmentBone destruction / Cancer, Ovarian / Leukemias / Malignant Lymphomas / Myelodysplastic Syndromes1
2CompletedTreatmentCardiac Arrest1
2CompletedTreatmentCervical Ripening / Induction of Labour1
2CompletedTreatmentChronic Hepatitis C Infection2
2CompletedTreatmentCystic Fibrosis (CF)1
2CompletedTreatmentEndometrial Cancers1
2CompletedTreatmentFollicular Lymphoma (FL)1
2CompletedTreatmentGlaucoma1
2CompletedTreatmentGlaucoma / Ocular Hypertension1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentHypercholesterolaemia / One to five years postmenopausal1
2CompletedTreatmentInfection, Human Immunodeficiency Virus I1
2CompletedTreatmentInfertilities1
2CompletedTreatmentLeukemia Acute Myeloid Leukemia (AML)1
2CompletedTreatmentLeukemia, Plasma Cell / Multiple Myeloma (MM)1
2CompletedTreatmentLung Cancer Small Cell Lung Cancer (SCLC)1
2CompletedTreatmentMELAS Syndrome1
2CompletedTreatmentMalignant Lymphomas1
2CompletedTreatmentMalignant Melanoma1
2CompletedTreatmentParkinson's Disease (PD)1
2CompletedTreatmentPersistent Atrial Fibrillation1
2CompletedTreatmentPharmacodynamics / Pharmacokinetics / Tolerability / Tuberculous Meningitis1
2CompletedTreatmentPhiladelphia Positive Acute Lymphoblastic Leukemia1
2CompletedTreatmentPneumonia / Sickle Cell Disorders1
2CompletedTreatmentProstate Cancer / Prostatic Adenocarcinoma / Prostatic Neoplasms1
2CompletedTreatmentSickle Cell Disorders1
2CompletedTreatmentTraumatic Brain Injury (TBI)1
2CompletedTreatmentVaso-occlusive Pain Episodes1
2Not Yet RecruitingPreventionHigh Risk Pregnancies1
2RecruitingSupportive CareProstate Cancer1
2RecruitingTreatmentEpidermolysis Bullosa1
2RecruitingTreatmentLeukemias / Malignant Lymphomas1
2RecruitingTreatmentMedulloblastomas1
2RecruitingTreatmentMedulloblastomas / Meningiomas / Neuroblastomas / Neuroendocrine Tumors1
2RecruitingTreatmentNeuroblastomas1
2RecruitingTreatmentPrimary Central Nervous System Lymphoma (PCNSL)1
2RecruitingTreatmentRecurrent B-Cell Childhood Acute Lymphoblastic Leukemia / Recurrent Childhood B-Lymphoblastic Lymphoma1
2RecruitingTreatmentRetinoblastoma1
2RecruitingTreatmentRhabdomyosarcomas1
2RecruitingTreatmentSickle Cell Disorders1
2RecruitingTreatmentSickle Cell Disorders / Vaso-occlusive Pain Episodes1
2RecruitingTreatmentStage II Childhood Hodgkin Lymphoma / Stage III Childhood Hodgkin Lymphoma / Stage IV Childhood Hodgkin Lymphoma1
2SuspendedTreatmentSevere Falciparum Malaria1
2TerminatedSupportive CareHodgkins Disease (HD) / Leukemia Acute Myeloid Leukemia (AML) / Multiple Myeloma (MM) / Myeloproliferative Disorders / Non-Hodgkin's Lymphoma (NHL)1
2TerminatedTreatmentAcute Lymphoblastic Leukaemias (ALL)1
2TerminatedTreatmentAcute Lymphoblastic Leukaemias (ALL) / Acute Myelocytic Leukemia / Chronic Myelocytic Leukemia / Granulocytic Sarcoma / Hodgkin's or Non-Hodgkin's Lymphoma / Juvenile Myelomonocytic Leukemia / Myelodysplastic Syndrome1
2TerminatedTreatmentCastration Resistant Prostate Cancer (CRPC) / Prostate Cancer / Prostatic Neoplasms1
2TerminatedTreatmentHaematological Malignancies1
2TerminatedTreatmentHead and Neck Carcinoma1
2TerminatedTreatmentHistiocytosis, Langerhans-Cell1
2TerminatedTreatmentLeukemias / Malignant Lymphomas1
2TerminatedTreatmentMyelodysplastic Syndromes1
2TerminatedTreatmentPain / Pain, Chronic / Pain, Neuropathic / Postoperative pain1
2Unknown StatusTreatmentCervical Dystonia1
2Unknown StatusTreatmentContraception1
2Unknown StatusTreatmentDental Decay1
2Unknown StatusTreatmentPost-Traumatic Stress Disorder (PTSD)1
2Unknown StatusTreatmentShock, Septic1
2WithdrawnTreatmentAlcoholic Hepatitis (AH)1
2WithdrawnTreatmentCancer, Breast1
2WithdrawnTreatmentMedulloblastomas / Meningiomas / Neuroblastomas / Neuroendrocrine Tumors1
2, 3Active Not RecruitingTreatmentAcute Kidney Injury (AKI)1
2, 3CompletedPreventionNEC / Sepsis1
2, 3CompletedTreatmentDisseminated Sclerosis / Optic Neuritis1
2, 3CompletedTreatmentHuman Immunodeficiency Virus (HIV)1
2, 3CompletedTreatmentHypertension,Essential1
2, 3RecruitingTreatmentCirculatory Perfusion Disorder / Congenital Heart Disease (CHD) / Single-ventricle1
2, 3RecruitingTreatmentHairy Cell Leukemia (HCL)1
2, 3RecruitingTreatmentHuman Immunodeficiency Virus (HIV) / Pediatric AIDS1
2, 3RecruitingTreatmentPleural Effusions / Single-ventricle1
2, 3RecruitingTreatmentType 2 Diabetes Mellitus1
2, 3TerminatedTreatmentBladder Cancers1
2, 3TerminatedTreatmentStroke, Ischemic / Transient Ischaemic Attack (TIA)1
2, 3Unknown StatusBasic ScienceSDF-1 is an Important Cytokine for Neovascularization. Cleavage of SDF-1 is Reduced by DPPIV Inhibitors1
2, 3Unknown StatusTreatmentCongestive Heart Failure (CHF) / Kidney Failure,Chronic1
2, 3Unknown StatusTreatmentNeuromuscular Blockade / Obesity, Morbid1
3Active Not RecruitingPreventionAcute Otitis Media1
3Active Not RecruitingTreatmentBrain and Central Nervous System Tumors1
3CompletedDiagnosticDiagnosis of Adult Growth Hormone Deficiency (AGDH)1
3CompletedEducational/Counseling/TrainingProphylaxis of preeclampsia1
3CompletedPreventionAortic Aneurism / Myocardial Infarction (MI) / Peripheral Vascular Disease (PVD)1
3CompletedPreventionCardiovascular Disease (CVD)1
3CompletedPreventionCerebral Infarctions1
3CompletedPreventionEndothelial Dysfunction / Impaired Glucose Tolerance (IGT) / Insulin Resistance / Metabolic Syndromes1
3CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections / Malaria in Pregnancy1
3CompletedTreatmentAdhd1
3CompletedTreatmentAlzheimer's Disease (AD)1
3CompletedTreatmentAutosomal Dominant Polycystic Kidney Disease (ADPKD)1
3CompletedTreatmentCervical Ripening / Induction of Labour1
3CompletedTreatmentCervical Ripening / Induction of Labour / Reducing Time to Vaginal Delivery1
3CompletedTreatmentChronic Lung Diseases1
3CompletedTreatmentCritical Illness1
3CompletedTreatmentEpilepsies1
3CompletedTreatmentFibromyalgia1
3CompletedTreatmentHCV Infections / Infection, Human Immunodeficiency Virus I1
3CompletedTreatmentHerpes Labialis1
3CompletedTreatmentHigh Blood Pressure (Hypertension)1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections3
3CompletedTreatmentHypertension in Pregnancy2
3CompletedTreatmentInfant, Low Birth Weight / Infant, Small for Gestational Age / Infants, Premature / Newborn Infants / Sepsis1
3CompletedTreatmentInfection, Human Immunodeficiency Virus I2
3CompletedTreatmentLymphoma, Large-Cell, Diffuse1
3CompletedTreatmentPulmonary Arterial Hypertension (PAH)1
3CompletedTreatmentSickle Cell Disorders1
3CompletedTreatmentSmear Positive Pulmonary Tuberculosis1
3CompletedTreatmentUrinary Bladder, Overactive1
3RecruitingTreatmentAcute Lymphoblastic Leukaemias (ALL)1
3RecruitingTreatmentAcute Promyelocytic Leukemia (APL)1
3RecruitingTreatmentAnemias / Chronic Arthritis / Haemorrhage / Ischaemic Heart Diseases / Nonvalvular Atrial Fibrillation1
3RecruitingTreatmentDentin Sensitivity1
3RecruitingTreatmentFollicular Lymphoma (FL)1
3RecruitingTreatmentFollicular Lymphoma (FL) / Immunocytomas / Lymphocytic Lymphomas / Mantle-Cell Lymphomas / Marginal Zone Lymphomas / Non-Hodgkin's Lymphoma (NHL)1
3RecruitingTreatmentHCC2
3RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
3RecruitingTreatmentInsertion of Intrauterine Contraception1
3RecruitingTreatmentOveractive Bladder1
3RecruitingTreatmentSevere Seborrheic Dermatitis1
3TerminatedTreatmentNon Small Cell Lung Carcinoma (NSCLC)1
3TerminatedTreatmentOtitis Externa1
3TerminatedTreatmentTraumatic Brain Injury (TBI)1
3Unknown StatusTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
3Unknown StatusTreatmentAdipose Tissue, Brown / Glucose tolerance impaired / Nitric Oxide1
3Unknown StatusTreatmentChronic Hepatitis C Infection / Human Immunodeficiency Virus (HIV) Infections2
3WithdrawnTreatmentChronic Obstructive Pulmonary Disease (COPD) / Dyspnea1
4Active Not RecruitingBasic ScienceDiabetes, Diabetes Mellitus Type 11
4Active Not RecruitingTreatmentHiv-positive / Malnourished1
4Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4Active Not RecruitingTreatmentTooth Bleaching / Tooth Sensitivity1
4CompletedDiagnosticSchizophrenic Disorders1
4CompletedPreventionMitochondrial Dysfunction / Severe Lower Limb Ischemia / Skeletal Muscle Ischemia1
4CompletedPreventionPost-gastrointestinal bypass surgery1
4CompletedTreatmentAnxiety-comorbidity to Schizophrenia / Schizophrenic Disorders1
4CompletedTreatmentChronic Infection With HIV / HCV Coinfection1
4CompletedTreatmentCritically Ill1
4CompletedTreatmentErectile Dysfunction (ED)1
4CompletedTreatmentGestational Diabetes Mellitus (GDM)1
4CompletedTreatmentHigh Blood Pressure (Hypertension)1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections6
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Lipoatrophy1
4CompletedTreatmentLeukemia, Lymphocytic / Malignant Lymphomas / Myelodysplastic Syndromes / Myeloproliferative Disorders / Plasma Cell Myeloma1
4CompletedTreatmentBone destruction / Osteopenia / Primary Hyperparathyroidism1
4CompletedTreatmentPain, Neuropathic1
4CompletedTreatmentPulmonary Hypertension (PH)1
4Not Yet RecruitingPreventionHepatocellular,Carcinoma1
4RecruitingPreventionHIV/AIDS and Infections1
4RecruitingTreatmentAcquired Immune Deficiency Syndrome Virus1
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
4TerminatedTreatmentHigh Blood Pressure (Hypertension) / Type 2 Diabetes Mellitus1
4Unknown StatusSupportive CareBrain Dead Organ Donors1
4Unknown StatusTreatmentDepression/Anxiety / Impaired Cognition / Infection, Human Immunodeficiency Virus I / Poor Quality Sleep / Quality of Life1
4Unknown StatusTreatmentMajor Depressive Disorder (MDD)1
4Unknown StatusTreatmentPlasmodium Infections1
4WithdrawnTreatmentAtopic Dermatitis (AD)1
Not AvailableActive Not RecruitingNot AvailableAge Related Macular Degeneration (ARMD)1
Not AvailableCompletedNot AvailableAcute iron intoxication / Beta-Thalassemia / Bone destruction / Hematologic Diseases / Pulmonary Hypertension (PH) / Thalassaemic disorders / Thalassemia Major (TM)1
Not AvailableCompletedNot AvailableHeart Rate Variability / High Blood Pressure (Hypertension) / Tachycardia1
Not AvailableCompletedNot AvailableIschemia, Brain / Ischemic Attack1
Not AvailableCompletedNot AvailableMyelodysplastic Syndromes1
Not AvailableCompletedNot AvailableType 2 Diabetes Mellitus1
Not AvailableCompletedBasic ScienceCardiovascular Disease (CVD)1
Not AvailableCompletedPreventionCardiovascular Disease (CVD)1
Not AvailableCompletedPreventionHuman Immunodeficiency Virus (HIV)1
Not AvailableCompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedSupportive CarePain1
Not AvailableCompletedTreatmentCardiovascular Disease (CVD) / Peripheral Vascular Disease (PVD)1
Not AvailableCompletedTreatmentGraft Versus Host Disease (GVHD) / Mucositis1
Not AvailableCompletedTreatmentKeratoconjunctivitis Sicca1
Not AvailableCompletedTreatmentMyocardial Infarction (MI)1
Not AvailableCompletedTreatmentPhysiology, Ocular / Regional Blood Flow1
Not AvailableCompletedTreatmentSchizophrenic Disorders2
Not AvailableRecruitingNot AvailableAortic Valve Stenosis / Hypertension,Essential / Impaired Renal Function / Secondary Hypertension1
Not AvailableRecruitingDiagnosticGliomas1
Not AvailableRecruitingTreatmentIntrauterine Growth Restriction Asymmetrical1
Not AvailableTerminatedNot AvailableCystic Fibrosis Pulmonary Exacerbation1
Not AvailableTerminatedNot AvailableGrowth Hormone Deficiency (GHD)1
Not AvailableTerminatedDiagnosticDiabetes Mellitus (DM)1
Not AvailableTerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableUnknown StatusTreatmentAIDS/HIV PROBLEM1
Not AvailableUnknown StatusTreatmentHeart Failure, Unspecified / Hypogonadism1

Pharmacoeconomics

Manufacturers
  • Pharmacia and upjohn co
Packagers
Dosage forms
FormRouteStrength
Injection, solutionIntravenous
LiquidIntravenous250 mg
Kit
Injection, solution, concentrateIntravenous
EmulsionIntravenous
LiquidIntravenous
Injection, solutionIntravenous10 g/100mL
InjectionIntravenous
SolutionIntravenous
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)
Download (2.96 KB)
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-MSNot Available
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
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
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

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
L-alpha-amino acid / Fatty acid / Guanidine / Amino acid / Carboxylic acid / Monocarboxylic acid or derivatives / Carboximidamide / Propargyl-type 1,3-dipolar organic compound / Organic 1,3-dipolar compound / Amine
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)

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
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. [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 activi...
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. [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
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. [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 ...
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. [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 leuk...
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. [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 bioavailabili...
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. [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
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. [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
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. [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)-induce...
Gene Name
NOS3
Uniprot ID
P29474
Uniprot Name
Nitric oxide synthase, endothelial
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 cat...
Gene Name
SLC22A5
Uniprot ID
O76082
Uniprot Name
Solute carrier family 22 member 5
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
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. [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...
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. [PubMed:10215651]

Drug created on June 13, 2005 07:24 / Updated on December 10, 2017 17:18