l-glutamine
Approved
Jun 10, 2004
Glutamine is a non-essential amino acid present abundantly throughout the body and is involved in many metabolic processes. It is synthesized from glutamic acid and ammonia. It is the principal carrier of nitrogen in the body and is an important energy source for many cells. Supplemental L-glutamine's possible immunomodulatory role may be accounted for in a number of ways. L-glutamine appears to play a major role in protecting the integrity of the gastrointestinal tract and, in particular, the large intestine. During catabolic states, the integrity of the intestinal mucosa may be compromised with consequent increased intestinal permeability and translocation of Gram-negative bacteria from the large intestine into the body. The demand for L-glutamine by the intestine, as well as by cells such as lymphocytes, appears to be much greater than that supplied by skeletal muscle, the major storage tissue for L-glutamine. L-glutamine is the preferred respiratory fuel for enterocytes, colonocytes and lymphocytes. Therefore, supplying supplemental L-glutamine under these conditions may do a number of things. For one, it may reverse the catabolic state by sparing skeletal muscle L-glutamine. It also may inhibit translocation of Gram-negative bacteria from the large intestine. L-glutamine helps maintain secretory IgA, which functions primarily by preventing the attachment of bacteria to mucosal cells. L-glutamine appears to be required to support the proliferation of mitogen-stimulated lymphocytes, as well as the production of interleukin-2 (IL-2) and interferon-gamma (IFN-gamma). It is also required for the maintenance of lymphokine-activated killer cells (LAK). L-glutamine can enhance phagocytosis by neutrophils and monocytes. It can lead to an increased synthesis of glutathione in the intestine, which may also play a role in maintaining the integrity of the intestinal mucosa by ameliorating oxidative stress. The exact mechanism of the possible immunomodulatory action of supplemental L-glutamine, however, remains unclear. It is conceivable that the major effect of L-glutamine occurs at the level of the intestine. Perhaps enteral L-glutamine acts directly on intestine-associated lymphoid tissue and stimulates overall immune function by that mechanism, without passing beyond the splanchnic bed. Glutamine is used for nutritional supplementation, also for treating dietary shortage or imbalance. — NCATS
Clinical trial activity
143 trials · 165 clinical orgs · 6 marketing orgs
Earliest trial started Feb 1, 1998 (NCT00003170)
Timeline
1990s
2000s
- Jan 1, 2004
Earliest Phase 1 Sponsor(trial)
- Jun 10, 2004
Earliest FDA Approval
- Jun 10, 2004
Emmaus Medical — NDA Secondary Org
2020s
- Jan 10, 2023
Novitium Pharma — Marketing Organization
- Jan 10, 2023
Ani Pharmaceuticals — Marketing Organization
- May 14, 2026
STIRA — Marketing Organization
- May 26, 2026
Annora Pharma — Marketing Organization
Indications
Approved for
Studied for
- Anemia, Sickle Cell · Phase 4
- Anxiety Disorders · Phase 2
- Aortic Valve Stenosis · Phase 4
- beta-Thalassemia · Phase 3
- Bifidobacterium · Phase 2/Phase 3
- Blood Pressure · Phase 2/Phase 3
- Blood Transfusion · Phase 2/Phase 3
- Bone Marrow Transplantation · Phase 4
- Brain Injuries, Traumatic · Phase 4
- Breast Neoplasms · Phase 4
- Burns · Phase 3
- Carcinoma, Non-Small-Cell Lung · Phase 3
- Cardiopulmonary Bypass · Phase 4
- Cardiovascular Diseases · Phase 2
- Colorectal Neoplasms · Phase 4
- Coronary Artery Bypass · Phase 3
- Coronary Artery Disease · Phase 3
- Coronary Disease · Phase 2
- COVID-19 · Phase 3
- Critical Illness · Phase 4
- Crohn Disease · Phase 1
- Cystic Fibrosis · Phase 2
- Diabetes Mellitus · Phase 4
- Diabetes Mellitus, Type 2 · Phase 1
- Diarrhea · Phase 3
- Digestive System Neoplasms · Phase 3
- Diverticulosis, Colonic · Phase 1
- Drug-Related Side Effects and Adverse Reactions · Phase 3
- Drug Therapy · Phase 2/Phase 3
- Dyspepsia · Phase 1/Phase 2
- Eczema · Early Phase 1
- Endothelial Cells · Phase 2
- Enteral Nutrition · Phase 4
- Enteritis · Phase 4
- Enterocolitis, Necrotizing · Phase 2/Phase 3
- Gastrointestinal Microbiome · Phase 2/Phase 3
- Glutamine · Phase 2/Phase 3
- Head and Neck Neoplasms · Phase 3
- Healthy Volunteers · Phase 1
- Heart Failure · Phase 3
- Hematopoietic Stem Cell Transplantation · Phase 4
- Herpes Labialis · Phase 2
- HIV · Phase 1/Phase 2
- Hypertension, Pulmonary · Phase 2
- Hypertrophy, Left Ventricular · Phase 4
- Immune System Diseases · Phase 2
- Infant, Low Birth Weight · Phase 3
- Infant, Newborn · Phase 3
- Infant, Premature · Phase 3
- Infant, Small for Gestational Age · Phase 3
- Infections · Phase 3
- Inflammation · Phase 4
- Intensive Care Units · Phase 4
- Intestinal Neoplasms · Phase 4
- Irritable Bowel Syndrome · Phase 2
- Kidney Diseases · Phase 2
- Kidney Neoplasms · Phase 3
- Leukemia · Phase 3
- Leukemia, Lymphocytic, Chronic, B-Cell · Early Phase 1
- Leukemia, Plasma Cell · Phase 2
- Lymphangioleiomyomatosis · Phase 1
- Lymphoma · Phase 3
- Malnutrition · Phase 4
- Mitochondrial Diseases · Phase 2
- mTOR Associated Protein, LST8 Homolog · Early Phase 1
- Mucositis · Phase 3
- Multiple Myeloma · Phase 2
- Multiple Organ Failure · Phase 4
- Muscular Dystrophy, Duchenne · Phase 3
- Myocardial Infarction · Phase 3
- Myocardial Ischemia · Phase 4
- Neoplasm Metastasis · Phase 2
- Neoplasms · Phase 3
- Pain · Phase 3
- Pancreatic Neoplasms · Phase 1
- Periodontitis · Phase 2
- Peripheral Nervous System Diseases · Phase 3
- Pharmacokinetics · Phase 4
- Plasmacytoma · Phase 2
- Postoperative Complications · Phase 3
- Probiotics · Phase 2/Phase 3
- Proctitis · Phase 2/Phase 3
- Propionic Acidemia · Phase 1
- Prostatic Neoplasms · Phase 2
- Respiratory Aspiration · Phase 2
- Respiratory Insufficiency · Phase 2/Phase 3
- Rheumatic Heart Disease · Phase 2
- Sarcoma · Phase 3
- Sarcopenia · Phase 2
- Sepsis · Phase 3
- Shock · Phase 1
- Simplexvirus · Phase 2
- Squamous Cell Carcinoma of Head and Neck · Early Phase 1
- Starvation · Phase 4
- Stomatitis · Phase 3
- Thalassemia · Phase 2/Phase 3
- Traumatology · Phase 2
- Urological Manifestations · Phase 4
- Wound Healing · Phase 4
- Wounds and Injuries · Phase 1
Mechanism of action
- Unspecified targetOTHER
Unknown
L-glutamine may improve the NAD redox potential in sickle RBCs through increasing the availability of reduced glutathione
Approval history
- approvedJun 10, 2004
Chemistry & pharmacology
SMILES
N[C@@H](CCC(N)=O)C(O)=O- Mol. weight
- 146.1445 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
- Availability
- Prescription Only
Oral
No
Parenteral
No
Topical
No
Sources
- WikipediaGlutamic acid ↗
- NCATS0RH81L854J ↗
- ChEMBLCHEMBL930 ↗
- ChEMBLCHEMBL1255943 ↗
- WikipediaGlutamine ↗
Also known as
- (2s)-2,5-diamino-5-oxopentanoic acid
- (2s)-2,5-diamino-5-oxopentanoic acid
- (2s)-2-amino-4-carbamoylbutanoic acid
- (2s)-2-amino-4-carbamoylbutanoic acid
- glutamate
- glutamate
- glutamate
- glutamate
- glutamate
- glutamate
- glutamate
- glutamic acid 5-amide
- glutamic acid 5-amide
- glutamic acid amide
- glutamic acid amide
- glutamic acid amide
- glutamic acid hcl
- glutamine
- glutamine
- glutamine
- glutamine
- glutamine
- glutamine
- glutaminic acid
- glutaminol
- l-2-aminoglutaramic acid
- l-2-aminoglutaramic acid
- l-2-aminoglutaramidic acid
- levoglutamide
- levoglutamide
- levoglutamide
- levoglutamide
- l-glutamic acid γ-amide
- l-glutamic acid γ-amide
- l-glutamin
- l-glutamin
- l-glutamine
- l-glutamine
- l-glutamine
- l-glutamine
- l-glutamine
- l-glutamine
- l-glutamine
- l-glutamine
- l-glutamine
- l-(+)-glutamine
- l-(+)-glutamine
- l-(+)-glutamine
- l-glutaminsäure-5-amid
- l-glutaminsäure-5-amid
- nutrestore
- nutrestore
- nutrestore
- q
- q
- (s)-2,5-diamino-5-oxopentanoic acid
- (s)-2,5-diamino-5-oxopentanoic acid
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT07287592 | Phase 3 | Dec 30, 2025 | Ain Shams University |
| NCT07053761 | Phase 2 | Jun 30, 2025 | Peking University |
| NCT07020754 | Phase 2 | Apr 1, 2025 | Ain Shams University |
| NCT06617182 | Phase 2 | Sep 30, 2024 | People's Liberation Army of China |
| NCT05972291 | N/A | Oct 16, 2023 | Department of Veteran Affairs |
| NCT06031012 | Phase 3 | Sep 15, 2023 | Air Force Military Medical University, China |
| NCT07210450 | Phase 2/Phase 3 (Phase 3) | Aug 15, 2023 | Mazandaran University of Medical Sciences |
| NCT05808010 | N/A | Jun 7, 2023 | Shandong Provincial Hospital |
| NCT06764420 | N/A | May 20, 2023 | Ain Shams University |
| NCT06027242 | N/A | Feb 21, 2023 | National Taiwan University |
| NCT05655819 | Phase 1/Phase 2 (Phase 2) | Jan 31, 2023 | Mayo Clinic |
| NCT05569993 | Early Phase 1 (Phase 1) | Oct 30, 2022 | Assiut University |
| NCT05322135 | Early Phase 1 (Phase 1) | Sep 14, 2022 | University of Texas at Houston |
| NCT05406882 | Phase 2/Phase 3 (Phase 3) | Apr 15, 2022 | Sichuan University |
| NCT05852990 | Phase 3 | Mar 1, 2022 | Government of Mexico |
| NCT05371184 | Phase 4 | Jan 4, 2022 | Ain Shams University |
| NCT05856188 | N/A | Jan 1, 2022 | Ain Shams University |
| NCT04785989 | Early Phase 1 (Phase 1) | Dec 31, 2021 | University of Wisconsin |
| NCT05255328 | N/A | Jul 1, 2021 | Universidad Complutense de Madrid |
| NCT05092113 | Phase 3 | Jun 30, 2021 | Sichuan University, West China Hospital |
Organizations
Research & Development (165)
Marketing (6)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Ani Pharmaceuticals | For profit | MKTG | Jan 10, 2023 |
| Annora Pharma | For profit | MKTG | May 26, 2026 |
| Cato Research | For profit | NDA | — |
| Emmaus Medical | For profit | NDA2 | Jun 10, 2004 |
| Novitium Pharma | For profit | MKTG | Jan 10, 2023 |
| STIRA | For profit | MKTG | May 14, 2026 |