citrulline

Small moleculeexperimental

Citrulline (name derived from citrullus, the Latin word for watermelon, from which it was first isolated) is an amino acid. It is made from ornithine and carbamoyl phosphate in one of the central reactions in the urea cycle. It is also produced from arginine as a by-product of the reaction catalyzed by nitric oxide synthase (NOS) family. Citrulline supplements have been claimed to promote energy levels, stimulate the immune system and help detoxify ammonia (a cell toxin). Citrulline is not involved in protein synthesis. Several pharmacokinetic studies have confirmed that citrulline is efficiently absorbed when administered orally. Oral citrulline could be used to deliver arginine to the systemic circulation or as a protein anabolic agent in specific clinical situations (for example in case of malnourishment), because recent data have suggested that citrulline, although not a component of proteins, stimulates protein synthesis in skeletal muscle through the mammalian target of rapamycin signaling pathway. Citrulline is converted to L-arginine by argininosuccinate synthase. L-arginine is in turn responsible for citrulline's therapeutic effects. Many of L-arginine's activities, including its possible anti-atherogenic actions, may be accounted for by its role as the precursor to nitric oxide (NO). — NCATS

Clinical trial activity

85 trials · 72 clinical orgs · 0 marketing orgs

Phase 1
25
Phase 2
24
Phase 3
10
Phase 4
1

Earliest trial started Oct 1, 2001 (NCT00223730)

Timeline

2000s

  1. Jan 1, 2001

    Earliest Phase 2 Sponsor(trial)

  2. Jan 1, 2003

    Earliest Phase 1 Sponsor(trial)

  3. Jan 1, 2006

    Earliest Phase 3 Sponsor(trial)

Indications

Approved for

Studied for

Mechanism of action

  • Unspecified targetSupplementation

    supplementation

Chemistry & pharmacology

Loading structure…

SMILES

N[C@@H](CCCNC(N)=O)C(O)=O
Mol. weight
175.1857 g/mol

Oral

No

Parenteral

No

Topical

No

Sources

Also known as

  • 2-amino-5-ureidovaleric acid
  • 2-amino-5-ureidovaleric acid
  • 9.5 s alpha(1)-glycoprotein alpha(1)-glycoprotein
  • alpha-amino-delta-ureidovaleric acid
  • alpha-amino-delta-ureidovaleric acid
  • cirulline
  • cit
  • cit
  • cit
  • citrulline
  • citrulline
  • citrulline
  • citrulline
  • citrulline
  • citrulline malate
  • citrulline malate
  • delta-ureidonorvaline
  • delta-ureidonorvaline
  • l-2-amino-5-ureidovaleric acid
  • l-2-amino-5-ureidovaleric acid
  • l-citrulline
  • l-citrulline
  • l-citrulline
  • l-citrulline
  • l-citrulline malate
  • n(5)-(aminocarbonyl)-l-ornithine
  • n(5)-(aminocarbonyl)-l-ornithine
  • n5-(aminocarbonyl)ornithine
  • n5-(aminocarbonyl)ornithine
  • n5-carbamoyl-l-ornithine
  • n5-carbamoyl-l-ornithine
  • n5-carbamoylornithine
  • n5-carbamoylornithine
  • n(delta)-carbamylornithine
  • n(delta)-carbamylornithine
  • (s)-2-amino-5-ureidopentanoic acid
  • (s)-2-amino-5-ureidopentanoic acid
  • serum p-component
  • sigma-ureidonorvaline
  • α-amino-δ-ureidovaleric acid
  • α-amino-δ-ureidovaleric acid
  • δ-ureidonorvaline
  • δ-ureidonorvaline

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT06989567Phase 3Jul 25, 2025Asklepion
NCT06426147N/AJan 1, 2025University of Barcelona
NCT06635902Phase 2Nov 30, 2024Georgetown University, National Heart, Lung, and Blood Institute (NHLBI)
NCT05259904Phase 2Apr 30, 2024Department of Defense, University of Colorado, Denver
NCT06212765Phase 3Jan 25, 2024University of Grenoble
NCT05934318N/ASep 30, 2023Kenya Medical Research Institute, Telethon Kids Institute, University of Liverpool, University of Toronto
NCT06025383N/AJul 20, 2023Texas Tech University
NCT05722860Phase 1May 3, 2023University of Oklahoma
NCT06016478N/AMay 1, 2023Texas Tech University
NCT05778266N/AMar 14, 2023Universidad de Guanajuato
NCT05636397N/AFeb 28, 2023University of Toronto
NCT06025357N/AJan 1, 2023Texas Tech University
NCT05974813N/AJan 1, 2023European University Cyprus
NCT05525871N/AAug 15, 2022Universidad Católica San Antonio de Murcia
NCT05253209Phase 3Jun 29, 2022Asklepion, Indiana University
NCT05183893N/AFeb 15, 2022University of Granada
NCT05029778Phase 4Oct 20, 2021University of Guadalajara
NCT04513288N/ASep 1, 2021University of Rennes
NCT04979793Phase 1Jul 28, 2021University of Texas, Galveston
NCT04770155Early Phase 1 (Phase 1)May 27, 2021University of Mississippi
Showing 20 of 85 trials
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Organizations

Research & Development (72)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
AsklepionFor profit7722006
Texas Tech UniversityAcademic/Hospital7712015
University of MississippiAcademic/Hospital5422010
University of PittsburghAcademic/Hospital5332006
Vanderbilt UniversityAcademic/Hospital5432001
Florida State UniversityAcademic/Hospital4422011
National Institutes of Health (NIH)Government4022010
University of GrenobleAcademic/Hospital4422015
Baylor UniversityAcademic/Hospital3322009
Maastricht UniversityAcademic/Hospital3322010
National Heart, Lung, and Blood Institute (NHLBI)Government3012003
Shahid Beheshti University of Medical SciencesAcademic/Hospital3122012
University of BaselAcademic/Hospital3022013
University of BernAcademic/Hospital3222013
University of Colorado, DenverAcademic/Hospital3322017
University of NantesAcademic/Hospital3322008
University of RennesAcademic/Hospital3312016
AngiogenixFor profit2222006
Kyowa Hakko KogyoFor profit2012009
Masih Daneshvari HospitalAcademic/Hospital2212012
72 organizations
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