Glutamine
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Also known as EndariFEMA NO. 3684GlutaminaL-glutamineLevoglutamideNSC-27421NutrestoreSID26747519SID50106343SID90341595polyglutamine(L)-glutamineGLUTAMINE-(L)
Summary
Glutamine (CHEMBL930) is an approved small-molecule EC 1.14.13.39 (nitric oxide synthase) inhibitor (ATC A16AA03) targeting SLC38A3; indicated across 43 conditions including sickle cell disease and short bowel syndrome.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: A16AA03
- Targets: 1 (SLC38A3)
- Indications: 43 conditions
- Clinical trials: 109
- Chemistry: 146.14 Da · C5H10N2O3
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL930 |
| Name | Glutamine |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | yes |
| PubChem CID | 5961 |
| ChEBI | CHEBI:18050 |
| ATC | A16AA03 |
| Molecular formula | C5H10N2O3 |
| Molecular weight | 146.14 |
| InChIKey | ZDXPYRJPNDTMRX-VKHMYHEASA-N |
SMILES: C(CC(=O)N)[C@@H](C(=O)O)N
IUPAC name: (2S)-2,5-diamino-5-oxopentanoic acid
ChEBI definition: An optically active form of glutamine having L-configuration.
Pharmacological roles (ChEBI): EC 1.14.13.39 (nitric oxide synthase) inhibitor, nutraceutical, micronutrient.
Other ChEBI roles (chemical / environmental): human metabolite, Saccharomyces cerevisiae metabolite, Escherichia coli metabolite, mouse metabolite.
Also known as: Endari, FEMA NO. 3684, Glutamina, Glutamine, L-glutamine, Levoglutamide, NSC-27421, Nutrestore, L-Glutamine, SID26747519, SID50106343, SID90341595
Patent coverage: 232,178 distinct patent families (737,979 SureChEMBL compound mentions), from 1 matched compound structure(s). 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 |
|---|---|---|---|---|---|
| SLC38A3 | Sodium-coupled neutral amino acid transporter 3 | 0% | Q99624 |
Broader ChEMBL bioactivity targets: 4 (assay-derived). Sample: RecQ-like DNA helicase BLM, Peripheral myelin protein 22, Histone-lysine N-methyltransferase 2A, Polyunsaturated fatty acid lipoxygenase ALOX15.
Bioactivity
ChEMBL activities: 2 potent at pChembl ≥ 5 of 5 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| BLM | 8.55 | Potency | 2.8 | nM | CHEMBL_ACT_4753920 |
| BLM | 8.55 | Potency | 2.8 | nM | CHEMBL_ACT_4945850 |
Target pathways
Aggregated over 1 target gene(s): SLC38A3.
Top Reactome pathways
4 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| Amino acid transport across the plasma membrane | 1 | SLC38A3 |
| Transport of small molecules | 1 | SLC38A3 |
| R-HSA-425393 | 1 | SLC38A3 |
| SLC-mediated transmembrane transport | 1 | SLC38A3 |
Dominant GO biological processes
| GO term | Targets |
|---|---|
| amino acid transmembrane transport | 1 |
| amino acid transport | 1 |
| asparagine transport | 1 |
| L-glutamine transport | 1 |
| female pregnancy | 1 |
| response to acidic pH | 1 |
| L-glutamine secretion | 1 |
| L-alanine transport | 1 |
| histidine transport | 1 |
| positive regulation of transcription by RNA polymerase II | 1 |
| cellular response to potassium ion starvation | 1 |
| intracellular amino acid homeostasis | 1 |
| transport across blood-brain barrier | 1 |
| L-histidine transport | 1 |
| L-glutamine import across plasma membrane | 1 |
Indications & clinical
Indications
43 indications (2 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 |
|---|---|---|---|
| sickle cell disease | 4 | MONDO:0011382 | MONDO:0011382 |
| short bowel syndrome | 4 | MONDO:0015183 | EFO:0700081 |
| peripheral neuropathy | 3 | MONDO:0005244 | EFO:0003100 |
| fetal growth restriction | 3 | MONDO:0005030 | EFO:0000495 |
| neoplasm | 3 | MONDO:0005070 | EFO:0000616 |
| colorectal neoplasm | 3 | MONDO:0005335 | EFO:0004142 |
| stomatitis | 3 | MONDO:0004842 | EFO:1001904 |
| mucositis | 3 | MONDO:0020579 | EFO:1001898 |
| diarrheal disease | 3 | MONDO:0001673 | MONDO:0001673 |
| coronary artery disorder | 3 | MONDO:0005010 | EFO:0001645 |
| multiple organ dysfunction syndrome | 3 | MONDO:0043726 | EFO:1001373 |
| severe acute respiratory syndrome | 3 | MONDO:0005091 | MONDO:0100096 |
| Duchenne muscular dystrophy | 3 | MONDO:0010679 | MONDO:0010679 |
| colorectal adenocarcinoma | 3 | MONDO:0005008 | EFO:0000365 |
| irritable bowel syndrome | 2 | MONDO:0005052 | EFO:0000555 |
| injury | 2 | MONDO:0021178 | EFO:0000546 |
| lymphoma | 2 | MONDO:0005062 | EFO:0000574 |
| periodontitis | 2 | MONDO:0005076 | EFO:0000649 |
| plasma cell myeloma | 2 | MONDO:0009693 | EFO:0001378 |
| heart failure | 2 | MONDO:0005252 | EFO:0003144 |
| thalassemia | 2 | MONDO:0000984 | EFO:1001996 |
| Clostridium infectious disease | 2 | MONDO:0024388 | EFO:0009130 |
| breast neoplasm | 2 | MONDO:0021100 | MONDO:0007254 |
| generalized anxiety disorder | 2 | MONDO:0001942 | EFO:1001892 |
| cystic fibrosis | 2 | MONDO:0009061 | MONDO:0009061 |
| nosocomial infection | 2 | MONDO:0043544 | MONDO:0043544 |
| herpes simplex infectious disease | 2 | MONDO:0004609 | EFO:1002022 |
| herpes labialis | 2 | MONDO:0043653 | MONDO:0043653 |
| Crohn disease | 1 | MONDO:0005011 | EFO:0000384 |
| chronic kidney disease | 1 | MONDO:0005300 | EFO:0003884 |
| diabetes mellitus | 1 | MONDO:0005015 | EFO:0000400 |
| type 2 diabetes mellitus | 1 | MONDO:0005148 | MONDO:0005148 |
| propionic acidemia | 1 | MONDO:0011628 | MONDO:0011628 |
| dyspepsia | 1 | MONDO:0002268 | EFO:0008533 |
| pancreatic ductal adenocarcinoma | 1 | MONDO:0005184 | MONDO:0005184 |
| head and neck squamous cell carcinoma | 0 | MONDO:0010150 | EFO:0000181 |
| head and neck cancer | 0 | MONDO:0005627 | EFO:0006859 |
6 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 109.
Phase distribution
| Phase | Trials |
|---|---|
| Not specified | 34 |
| PHASE2 | 23 |
| PHASE3 | 17 |
| PHASE4 | 12 |
| PHASE1 | 9 |
| PHASE2/PHASE3 | 6 |
| PHASE1/PHASE2 | 6 |
| EARLY_PHASE1 | 2 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT00204958 | PHASE4 | COMPLETED | Glutamine Popsicles in Bone Marrow Transplant (BMT)/Hematopoietic Stem Cell Transplant (HSCT) Patients |
| NCT00213668 | PHASE4 | COMPLETED | Effect of Glutamine on Gastric Emptying and Length of Parenteral Nutrition in Premature Neonates |
| NCT00772824 | PHASE4 | COMPLETED | Study of the Effect of Glutamine Supplementation on Chemotherapy Induced Toxicities in Breast Cancer Patients |
| NCT00828399 | PHASE4 | COMPLETED | Prevention of Acute Radiation Enteritis With Glutamine |
| NCT00875797 | PHASE4 | TERMINATED | Enteral Versus Parenteral Glutamine Supplement |
| NCT00922714 | PHASE4 | TERMINATED | Scandinavian Intensive Care Unit (ICU) Glutamine Study |
| NCT00943020 | PHASE4 | COMPLETED | Effects of Glutamine on Gastric Emptying |
| NCT01552291 | PHASE4 | COMPLETED | The Impact of Preoperative Oral Glutamine Intake on the Immunocompetence and Outcomes of Malnourished Patients Undergoing Major Abdominal Surgery Due to Malignancies |
| NCT03782155 | PHASE4 | UNKNOWN | Effect of Supplementation With HMB and Glutamine in Wound Healing on Bloody Areas |
| NCT03867214 | PHASE4 | UNKNOWN | Effects of Oral Care With Glutamine on Oral Health, Oral Flora and Incidence of Pneumonia After Neurosurgery With Microbiome Analysis |
| NCT04684381 | PHASE4 | COMPLETED | Pharmacokinetics and Safety of Endari (L-glutamine) in Sickle Cell Disease Patients |
| NCT05371184 | PHASE4 | COMPLETED | Glutamine Role in Preventing Vaso-occlusive Crisis Among SCD Patients |
| NCT00003170 | PHASE3 | COMPLETED | Glutamine in Preventing Acute Diarrhea in Patients With Pelvic Cancer |
| NCT00005775 | PHASE3 | COMPLETED | Glutamine Supplementation to Prevent Death or Infection in Extremely Premature Infants |
| NCT00006994 | PHASE3 | TERMINATED | S9908: Glutamine in Treating Mucositis Caused by Radiation Therapy in Patients With Newly Diagnosed Cancer of the Mouth or Throat |
| NCT00016653 | PHASE2/PHASE3 | COMPLETED | Creatine and Glutamine in Steroid-Naive Duchenne Muscular Dystrophy |
| NCT00018109 | PHASE3 | COMPLETED | A Multicenter Randomized Placebo-Controlled Double-Blind Study to Assess Efficacy and Safety of Glutamine and Creatine Monohydrate in Duchenne Muscular Dystrophy (DMD) |
| NCT00133406 | PHASE3 | UNKNOWN | Long-term Impact and Intervention for Diarrhea in Brazil |
| NCT00195013 | PHASE3 | COMPLETED | Randomized Placebo-Controlled Trial of Glutamine for Breast Cancer Patients With Peripheral Neuropathy |
| NCT00318331 | PHASE2/PHASE3 | TERMINATED | Enteral Glutamine in Critical Illness |
| NCT00395161 | PHASE3 | TERMINATED | The CRISIS Prevention Study |
| NCT00455247 | PHASE3 | COMPLETED | Efficacy of an Oral Formula in Prevention of Anti-cancer Therapy Side Effects |
| NCT00985205 | PHASE3 | UNKNOWN | The RE-ENERGIZE Study: RandomizEd Trial of ENtERal Glutamine to minimIZE Thermal Injury |
| NCT01087658 | PHASE3 | COMPLETED | Oral Glutamine in the Prevention of Oxaliplatin-induced Neurotoxicity |
| NCT01179217 | PHASE3 | COMPLETED | A Phase III Safety and Efficacy Study of L-Glutamine to Treat Sickle Cell Disease or Sickle βo-thalassemia |
| NCT01263041 | PHASE2/PHASE3 | COMPLETED | Effect of L-arginine and Glutamine on Preterm |
| NCT01534663 | PHASE2/PHASE3 | COMPLETED | Supplementation of Glutamine and Fish Oil Versus Placebo in Patients With Heart Failure |
| NCT01952847 | PHASE3 | TERMINATED | Randomized Trial of Glutamine in Patients With Mucositis or Esophagitis |
| NCT02024191 | PHASE3 | UNKNOWN | The Role of Glutamine for Preventing Oxaliplatin-Induced Peripheral Neuropathy |
| NCT02282839 | PHASE3 | UNKNOWN | Oral Glutamine and Mucositis of Head and Neck Cancer Patients Undergoing Radiation |
| NCT04019184 | PHASE3 | COMPLETED | Reduction of Occurence of Acute Kidney Injury (AKI) Through Administration of Glutamine |
| NCT04710290 | PHASE2/PHASE3 | UNKNOWN | A Cohort Study of Beta-Glucan or Beta-Glucan Compound in Metastatic Cancers |
| NCT04909905 | PHASE3 | COMPLETED | Glutamine Supplementation and Short-term Mortality in Covid-19 |
| NCT06031012 | PHASE3 | COMPLETED | Glutamine Combined With Thalidomide in Preventing Radiation-induced Oral Mucositis |
| NCT07210450 | PHASE2/PHASE3 | COMPLETED | Effect of L-Glutamine on Pulmonary Artery Pressure in Patients With Non-Transfusion-Dependent Thalassemia |
| NCT06617182 | PHASE2 | RECRUITING | Efficacy and Safety of Thalidomide Combined With Glutamine in the Treatment of Radiation Intestinal Injury. |
| NCT07053761 | PHASE2 | NOT_YET_RECRUITING | A Randomized Controlled Trial of Five - Flavor Sophora Flavescens Enteric - Coated Capsules for Radiation - Induced Proctitis After Pelvic Radiotherapy |
| NCT00003898 | PHASE2 | COMPLETED | Glutamine in Treating Side Effects in Children Who Are Undergoing Stem Cell Transplantation |
| NCT00010634 | PHASE2 | COMPLETED | Complementary Naturopathic Medicine for Periodontitis |
| NCT00125788 | PHASE2 | COMPLETED | L-Glutamine Therapy for Sickle Cell Anemia and Sickle ß0 Thalassemia |
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).
Related Atlas pages
- Genes: SLC38A3
- Diseases: sickle cell disease, short bowel syndrome, peripheral neuropathy, fetal growth restriction, neoplasm, colorectal neoplasm, stomatitis, mucositis, diarrheal disease, coronary artery disorder, multiple organ dysfunction syndrome, severe acute respiratory syndrome, Duchenne muscular dystrophy, colorectal adenocarcinoma