Arginine
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Also known as ArgininaL-arginineNSC-206269L-ArgSID11110746SID11113629SID50104526SID90341198SID170465748L-Arginine HCl
Summary
Arginine (CHEMBL1485) is an approved small-molecule nutraceutical targeting GPRC6A; indicated across 36 conditions including preeclampsia and hepatocellular carcinoma.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- Targets: 1 (GPRC6A)
- Indications: 36 conditions
- Clinical trials: 136
- Chemistry: 174.2 Da · C6H14N4O2
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL1485 |
| Name | Arginine |
| Type | Small molecule |
| Max phase | 3 |
| FDA approved | yes |
| PubChem CID | 6322 |
| ChEBI | CHEBI:16467 |
| Molecular formula | C6H14N4O2 |
| Molecular weight | 174.2 |
| InChIKey | ODKSFYDXXFIFQN-BYPYZUCNSA-N |
SMILES: C(C[C@@H](C(=O)O)N)CN=C(N)N
IUPAC name: (2S)-2-amino-5-(diaminomethylideneamino)pentanoic acid
ChEBI definition: An L-α-amino acid that is the L-isomer of arginine.
Pharmacological roles (ChEBI): nutraceutical, biomarker, micronutrient.
Other ChEBI roles (chemical / environmental): Escherichia coli metabolite, mouse metabolite.
Also known as: Arginina, Arginine, L-arginine, NSC-206269, L-Arginine, L-Arg, SID11110746, SID11113629, SID50104526, SID90341198, l-arginine, SID170465748
Patent coverage: 288,579 distinct patent families (895,147 SureChEMBL compound mentions), from 4 matched compound structure(s). One matched structure accounts for 888,611 (99%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.
Targets
Targets
Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).
| Gene | Target | Action | pAffinity | Cancer dependency | UniProt |
|---|---|---|---|---|---|
| GPRC6A | GPRC6 | Full agonist | 4.4 | 0% | Q5T6X5 |
Broader ChEMBL bioactivity targets: 10 (assay-derived). Sample: 4’-phosphopantetheinyl transferase ffp, Thyrotropin receptor, Alpha-galactosidase A, Muscarinic acetylcholine receptor M1, Nuclear factor NF-kappa-B p105 subunit, Cytochrome P450 1A2, Cytochrome P450 2C19, Lethal factor, Nitric oxide synthase, inducible, DNA repair nuclease/redox regulator APEX1.
Bioactivity
ChEMBL activities: 9 potent at pChembl ≥ 5 of 13 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| NFKB1 | 6.6 | Potency | 251.2 | nM | CHEMBL_ACT_3671930 |
| NFKB1 | 6.6 | Potency | 251.2 | nM | CHEMBL_ACT_4585212 |
| P08482 | 6.4 | Potency | 398.1 | nM | CHEMBL_ACT_4803536 |
| GLA | 5.3 | Potency | 5012 | nM | CHEMBL_ACT_4849103 |
| TSHR | 5.2 | Potency | 6310 | nM | CHEMBL_ACT_3915455 |
| NOS2 | 5.16 | Kd | 7000 | nM | CHEMBL_ACT_2101100 |
| NOS2 | 5.16 | Kd | 7000 | nM | CHEMBL_ACT_2414017 |
| CYP2C19 | 5 | Potency | 10000 | nM | CHEMBL_ACT_4016397 |
| CYP2C19 | 5 | AC50 | 10000 | nM | CHEMBL_ACT_6008812 |
Target pathways
Aggregated over 1 target gene(s): GPRC6A.
Top Reactome pathways
2 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| G alpha (q) signalling events | 1 | GPRC6A |
| Class C/3 (Metabotropic glutamate/pheromone receptors) | 1 | GPRC6A |
Dominant GO biological processes
| GO term | Targets |
|---|---|
| adenylate cyclase-activating G protein-coupled receptor signaling pathway | 1 |
| calcium-mediated signaling | 1 |
| positive regulation of insulin secretion involved in cellular response to glucose stimulus | 1 |
| response to amino acid | 1 |
| regulation of testosterone biosynthetic process | 1 |
| signal transduction | 1 |
| G protein-coupled receptor signaling pathway | 1 |
Indications & clinical
Indications
36 indications (0 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).
| Indication | Trial phase | MONDO | EFO |
|---|---|---|---|
| preeclampsia | 3 | MONDO:0005081 | EFO:0000668 |
| hepatocellular carcinoma | 3 | MONDO:0007256 | EFO:0000182 |
| cardiovascular disorder | 3 | MONDO:0004995 | EFO:0000319 |
| dental caries | 3 | MONDO:0005276 | EFO:0003819 |
| pulmonary tuberculosis | 3 | MONDO:0006052 | EFO:1000049 |
| glucose intolerance | 3 | MONDO:0001076 | HP:0001952 |
| severe acute respiratory syndrome | 3 | MONDO:0005091 | MONDO:0100096 |
| periodontitis | 3 | MONDO:0005076 | EFO:0000649 |
| allergic disease | 3 | MONDO:0005271 | MONDO:0005271 |
| sickle cell disease | 3 | MONDO:0011382 | MONDO:0011382 |
| polycystic ovary syndrome | 3 | MONDO:0008487 | EFO:0000660 |
| heart failure | 3 | MONDO:0005252 | EFO:0003144 |
| pituitary dwarfism | 3 | MONDO:0006909 | EFO:1001109 |
| alcoholic hepatitis | 2 | MONDO:0001505 | EFO:1001345 |
| congenital heart disease | 2 | MONDO:0005453 | EFO:0005207 |
| MELAS syndrome | 2 | MONDO:0010789 | Orphanet:550 |
| peripheral arterial disease | 2 | MONDO:0005386 | EFO:0004265 |
| rheumatoid arthritis | 2 | MONDO:0008383 | EFO:0000685 |
| essential hypertension | 2 | MONDO:0001134 | MONDO:0001134 |
| Alzheimer disease | 2 | MONDO:0004975 | MONDO:0004975 |
| asthma | 2 | MONDO:0004979 | MONDO:0004979 |
| argininosuccinic aciduria | 2 | MONDO:0008815 | MONDO:0008815 |
| cystic fibrosis | 2 | MONDO:0009061 | MONDO:0009061 |
| glioblastoma | 1 | MONDO:0018177 | EFO:0000519 |
| hypertensive disorder | 1 | MONDO:0005044 | EFO:0000537 |
| Plasmodium falciparum malaria | 1 | MONDO:0005920 | EFO:0007444 |
| coronary artery disorder | 1 | MONDO:0005010 | EFO:0001645 |
| type 2 diabetes mellitus | 1 | MONDO:0005148 | MONDO:0005148 |
| Duchenne muscular dystrophy | 1 | MONDO:0010679 | MONDO:0010679 |
| neuroendocrine neoplasm | 1 | MONDO:0019496 | EFO:1001901 |
| kidney disorder | 0 | MONDO:0005240 | EFO:0003086 |
5 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 136.
Phase distribution
| Phase | Trials |
|---|---|
| Not specified | 56 |
| PHASE2 | 24 |
| PHASE4 | 17 |
| PHASE3 | 16 |
| PHASE1 | 10 |
| PHASE2/PHASE3 | 5 |
| EARLY_PHASE1 | 5 |
| PHASE1/PHASE2 | 3 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT03982160 | PHASE4 | RECRUITING | L-arginine to Reduce Sympathetic Nerve Activity in CKD Patients |
| NCT00569465 | PHASE4 | TERMINATED | N-Acetylcysteine and Arginine Administration in Diabetic Patients |
| NCT00720902 | PHASE4 | TERMINATED | Adult Growth Hormone Deficiency and Cardiovascular Risk |
| NCT00777075 | PHASE4 | COMPLETED | L-Arginine and Erectile Dysfunction |
| NCT00856817 | PHASE4 | TERMINATED | Heme Oxygenase (HO) Activity and Adenosine Induced Vasodilation |
| NCT00902616 | PHASE4 | COMPLETED | Effect of Arginine on Microcirculation in Patients With Diabetes |
| NCT01038622 | PHASE4 | COMPLETED | Directed Immuno Nutrition by L-arginine for Critically Ill Patients |
| NCT01682889 | PHASE4 | COMPLETED | The Effect of High Dose Arginine Infusion on Hemodynamic and Peripheral Microcirculation |
| NCT01855334 | PHASE4 | WITHDRAWN | L-Arginine and Spironolactone Trial in Dialysis-Dependent ESRD |
| NCT02455960 | PHASE4 | UNKNOWN | Protective Effects of Oral L-Arginine CI-AKI |
| NCT02894723 | PHASE4 | UNKNOWN | L-arginine Treatment in Mild Hypertension |
| NCT03402191 | PHASE4 | UNKNOWN | L-arginine Versus Sildenafil in Children With Beta Thalassemia Associated With Pulmonary Hypertension |
| NCT04524442 | PHASE4 | COMPLETED | Post-Authorization Safety Study (PASS) of LysaKare® in Adult Gastroenteropancreatic Neuroendocrine Tumor (GEP-NET) Patients |
| NCT04765644 | PHASE4 | COMPLETED | Arginine Supplementation to Improve Cardiovascular and Endothelial Function After NSAID Treatment |
| NCT04935814 | PHASE4 | COMPLETED | Cardiac Output Response to Vasopressin Infusion In Abdominal Surgery Patients Under Mechanical Ventilation |
| NCT05029778 | PHASE4 | UNKNOWN | Arginine + Citrulline as a Supplement for Weight Gain in Fetus With a Decrease in Their Growth Curve |
| NCT06947265 | PHASE4 | COMPLETED | Safety And Efficacy Of L-Arginine Monotherapy Versus Tadalafil Monotherapy Versus Their Combination In Men With Erectile Dysfunction; A Prospective Randomized Study |
| NCT06405243 | PHASE3 | NOT_YET_RECRUITING | Myoinositol, L-arginine and Chromium With Letrozole for Ovulation Induction in Polycystic Ovarian Syndrome Patients |
| NCT00134420 | PHASE3 | COMPLETED | Growth Hormone and Chromosome 18q- and Abnormal Growth |
| NCT00137124 | PHASE2/PHASE3 | COMPLETED | L-Arginine Metabolism in Essential Hypertension |
| NCT00157521 | PHASE3 | COMPLETED | L-Arginine in Pre-Eclampsia |
| NCT00408577 | PHASE3 | COMPLETED | Prevention of Cardiac and Vascular Events in Patients With NGT/IGT. |
| NCT00448747 | PHASE3 | COMPLETED | Investigation of a New, Oral Growth Hormone Secretagogue, AEZS-130 as a Growth Hormone Stimulation Test. |
| NCT00571766 | PHASE3 | COMPLETED | Effects of Oral L-Arginine on Chronic Hypertension in Pregnancy |
| NCT00677339 | PHASE3 | COMPLETED | L-arginine and Vitamin D Adjunctive Therapy in Pulmonary Tuberculosis (TB) |
| NCT00917449 | PHASE3 | COMPLETED | Prevention of Type 2 Diabetes Mellitus by L-Arginine in Patients With Metabolic Syndrome |
| NCT00974714 | PHASE3 | COMPLETED | L-arginine Effects on Chronic Hypertension in Pregnancy |
| NCT01072188 | PHASE3 | COMPLETED | Clinical Efficacy of 10% Arginine Bicarbonate Prophylaxis Paste |
| NCT01142219 | PHASE3 | COMPLETED | L-Arginine and Sickle Cell Disease |
| NCT01263041 | PHASE2/PHASE3 | COMPLETED | Effect of L-arginine and Glutamine on Preterm |
| NCT02291458 | PHASE3 | UNKNOWN | L-arginine and Brown Adipose Tissue |
| NCT03088345 | PHASE2/PHASE3 | COMPLETED | Early Use of Vasopressin in Post-Fontan Management |
| NCT03640949 | PHASE2/PHASE3 | COMPLETED | Vasopressin and Methylprednisolone for In-Hospital Cardiac Arrest |
| NCT04631536 | PHASE3 | UNKNOWN | Managing Endothelial Dysfunction in COVID-19 : A Randomized Controlled Trial at LAUMC |
| NCT04786873 | PHASE3 | COMPLETED | A Research Study of How Well Macimorelin Works to Find Out if Children Have a Lack of Growth Hormone and How Safe it is |
| NCT05281562 | PHASE2/PHASE3 | TERMINATED | Immunonutrition for Diabetic Foot Ulcers |
| NCT05470998 | PHASE3 | COMPLETED | L-Arginine in Children Having Sickle Cell Disease With Increased Tricuspid Regurgitant Jet Velocity |
| NCT06044194 | PHASE3 | UNKNOWN | Evaluation of the Effect of Liposomal L-Arg and Vit C Integration on Mitochondrial Function in Patients With Heart Failure |
| NCT02447874 | PHASE1/PHASE2 | RECRUITING | Arginine Therapy for the Treatment of Pain in Children With Sickle Cell Disease |
| NCT07338682 | PHASE2 | RECRUITING | Evaluation of the Effect of L-Arginine on the Cognitive Function in Geriatric Patients |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.
Related molecules
Related molecules
No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).