l-glutamine

Small moleculeapprovedOrphan Drug FDA

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

Phase 1
20
Phase 2
58
Phase 3
32
Phase 4
16

Earliest trial started Feb 1, 1998 (NCT00003170)

Timeline

1990s

  1. Mar 6, 1995

    Orphan Drug Designation

  2. Jan 1, 1998

    Earliest Phase 3 Sponsor(trial)

  3. Jan 1, 1999

    Earliest Phase 2 Sponsor(trial)

2000s

  1. Jan 1, 2004

    Earliest Phase 1 Sponsor(trial)

  2. Jun 10, 2004

    Earliest FDA Approval

  3. Jun 10, 2004

    Emmaus Medical — NDA Secondary Org

2020s

  1. Jan 10, 2023

    Novitium Pharma — Marketing Organization

  2. Jan 10, 2023

    Ani Pharmaceuticals — Marketing Organization

  3. May 14, 2026

    STIRA — Marketing Organization

  4. May 26, 2026

    Annora Pharma — Marketing Organization

Indications

Studied for

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

Loading structure…

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

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 IDPhaseStart dateSponsor(s)
NCT07287592Phase 3Dec 30, 2025Ain Shams University
NCT07053761Phase 2Jun 30, 2025Peking University
NCT07020754Phase 2Apr 1, 2025Ain Shams University
NCT06617182Phase 2Sep 30, 2024People's Liberation Army of China
NCT05972291N/AOct 16, 2023Department of Veteran Affairs
NCT06031012Phase 3Sep 15, 2023Air Force Military Medical University, China
NCT07210450Phase 2/Phase 3 (Phase 3)Aug 15, 2023Mazandaran University of Medical Sciences
NCT05808010N/AJun 7, 2023Shandong Provincial Hospital
NCT06764420N/AMay 20, 2023Ain Shams University
NCT06027242N/AFeb 21, 2023National Taiwan University
NCT05655819Phase 1/Phase 2 (Phase 2)Jan 31, 2023Mayo Clinic
NCT05569993Early Phase 1 (Phase 1)Oct 30, 2022Assiut University
NCT05322135Early Phase 1 (Phase 1)Sep 14, 2022University of Texas at Houston
NCT05406882Phase 2/Phase 3 (Phase 3)Apr 15, 2022Sichuan University
NCT05852990Phase 3Mar 1, 2022Government of Mexico
NCT05371184Phase 4Jan 4, 2022Ain Shams University
NCT05856188N/AJan 1, 2022Ain Shams University
NCT04785989Early Phase 1 (Phase 1)Dec 31, 2021University of Wisconsin
NCT05255328N/AJul 1, 2021Universidad Complutense de Madrid
NCT05092113Phase 3Jun 30, 2021Sichuan University, West China Hospital
Showing 20 of 143 trials
Page 1 / 8

Organizations

Research & Development (165)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
University of Texas at HoustonAcademic/Hospital10931999
Emmaus MedicalFor profit8452003
National Cancer Institute (NCI)Government7231998
Ain Shams UniversityAcademic/Hospital6642011
Emory UniversityAcademic/Hospital6231999
Mayo ClinicAcademic/Hospital5331998
National Institutes of Health (NIH)Government5042005
National Institute of Diabetes and Digestive and Kidney Diseases (NIDDK)Government4032008
Thomas Jefferson UniversityAcademic/Hospital4322006
FreseniusFor profit3022004
National Center for Research Resources (NCRR)Government3221999
National Institute of Allergy and Infectious Diseases (NIAID)Government3232006
Rouen Normandy UniversityAcademic/Hospital3332002
Sichuan UniversityAcademic/Hospital3112021
Universidad Complutense de MadridAcademic/Hospital3222011
University of AlbertaAcademic/Hospital3122002
University of WisconsinAcademic/Hospital3322003
Vanderbilt UniversityAcademic/Hospital3122013
Assiut UniversityAcademic/Hospital2222021
Case Western Reserve UniversityAcademic/Hospital2121999
165 organizations
Page 1 / 9

Marketing (6)

OrganizationOrg typeRelationshipDate
Ani PharmaceuticalsFor profitMKTGJan 10, 2023
Annora PharmaFor profitMKTGMay 26, 2026
Cato ResearchFor profitNDA
Emmaus MedicalFor profitNDA2Jun 10, 2004
Novitium PharmaFor profitMKTGJan 10, 2023
STIRAFor profitMKTGMay 14, 2026