U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C6H13N3O3
Molecular Weight 175.186
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CITRULLINE

SMILES

C(C[C@@]([H])(C(=O)O)N)CNC(=N)O

InChI

InChIKey=RHGKLRLOHDJJDR-BYPYZUCNSA-N
InChI=1S/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12)/t4-/m0/s1

HIDE SMILES / InChI
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).

Approval Year

PubMed

PubMed

TitleDatePubMed
Postabsorptive plasma citrulline concentration is a marker of absorptive enterocyte mass and intestinal failure in humans.
2000 Dec
Extracting biological information from DNA arrays: an unexpected link between arginine and methionine metabolism in Bacillus subtilis.
2001
Is the balance between nitric oxide and superoxide altered in spontaneously hypertensive rats with endothelial dysfunction?
2001
Effects of dietary L-arginine on structure and function of flow-restricted vein grafts.
2001 Apr
Time course of inducible nitric oxide synthase activity following endotoxin administration in dogs.
2001 Apr
Ornithine transcarbamylase deficiency unmasked because of gastrointestinal bleeding.
2001 Apr
Effect of arginine on cyclosporine-induced systemic hypertension after cardiac transplantation in the young.
2001 Apr 1
Nitric oxide and nitric oxide synthase in Huntington's disease.
2001 Apr 15
Inducible nitric oxide synthase in rat neutrophils: role of insulin.
2001 Aug 1
Characterization of a putative nitric oxide synthase in the neuromuscular system of the parasitic nematode, Ascaris suum.
2001 Feb
Nitric oxide generation by hemocytes of the mussel Mytilus galloprovincialis.
2001 Feb
Immunohistochemical localization of nitric oxide synthase and soluble guanylyl cyclase in the ventral cochlear nucleus of the rat.
2001 Feb 26
Temporal expression of nitric oxide synthase isoforms in healing Achilles tendon.
2001 Jan
Ornithine transcarbamylase deficiency and pancreatitis.
2001 Jan
Use of anti-citrullinated peptide and anti-RA33 antibodies in distinguishing erosive arthritis in patients with systemic lupus erythematosus and rheumatoid arthritis.
2001 Jan
Nerve injury induces a rapid efflux of nitric oxide (NO) detected with a novel NO microsensor.
2001 Jan 1
A kinetic simulation model that describes catalysis and regulation in nitric-oxide synthase.
2001 Jan 12
Kinetic mechanism of antiports catalyzed by reconstituted ornithine/citrulline carrier from rat liver mitochondria.
2001 Jan 19
Role of nitric oxide synthase in the light-induced development of sporangiophores in Phycomyces blakesleeanus.
2001 Jul
Neuroprotective effect of sigma(1)-receptor ligand 4-phenyl-1-(4-phenylbutyl) piperidine (PPBP) is linked to reduced neuronal nitric oxide production.
2001 Jul
Phenanthraquinone inhibits eNOS activity and suppresses vasorelaxation.
2001 Jul
Arginine metabolism and the synthesis of nitric oxide in the nervous system.
2001 Jul
Decreased pulmonary and tracheal smooth muscle expression and activity of type 1 nitric oxide synthase (nNOS) after ovalbumin immunization and multiple aerosol challenge in guinea pigs.
2001 Jul 1
Development of specific CXCR4 inhibitors possessing high selectivity indexes as well as complete stability in serum based on an anti-HIV peptide T140.
2001 Jul 23
Metabolic effects of arginine addition to the enteral feeding of critically ill patients.
2001 Jul-Aug
Endothelial cell dysfunction in a model of oxidative stress.
2001 Jul-Aug
Involvement of cyclic guanosine 3',5'-monophosphate in nitric oxide-induced glucagon secretion from pancreatic alpha cells.
2001 Jun
Coinduction of endothelial nitric oxide synthase and arginine recycling enzymes in aorta of diabetic rats.
2001 Jun
Radiochemical nitric oxide synthase activity determination in rat brain with fast and accurate HPLC analysis.
2001 Jun
Co-induction of argininosuccinate synthetase, cationic amino acid transporter-2, and nitric oxide synthase in activated murine microglial cells.
2001 Jun 20
Indomethacin prevents the induction of inducible nitric oxide synthase in murine peritoneal macrophages and decreases their nitric oxide production.
2001 Mar 9
Extremely short small bowel induces focal tubulointerstitial fibrosis.
2001 May
Patents
Name Type Language
CITRULLINE
INCI   MART.   MI   VANDF   WHO-DD  
INCI  
Official Name English
CITRULLINE [MI]
Common Name English
CITRULLINE [WHO-DD]
Common Name English
CITRULLINE, L-
Systematic Name English
CITRULLINE [VANDF]
Common Name English
L-CITRULLINE
Systematic Name English
L-CITRULLINE [USP-RS]
Common Name English
CITRULLINE [MART.]
Common Name English
N(SUP 5)-(AMINOCARBONYL)-L-ORNITHINE
Systematic Name English
NSC-27425
Code English
CITRULLINE [INCI]
Common Name English
Classification Tree Code System Code
LOINC 56676-0
Created by admin on Fri Jun 25 21:32:57 UTC 2021 , Edited by admin on Fri Jun 25 21:32:57 UTC 2021
LOINC 53399-2
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LOINC 25877-2
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LOINC 2131-1
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FDA ORPHAN DRUG 779420
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LOINC 30161-4
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LOINC 53236-6
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FDA ORPHAN DRUG 544216
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LOINC 13723-2
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LOINC 32235-4
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LOINC 22654-8
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LOINC 49629-9
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LOINC 9511-7
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DSLD 701 (Number of products:222)
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LOINC 22722-3
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LOINC 53157-4
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LOINC 22694-4
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LOINC 13392-6
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EU-Orphan Drug EU/3/17/1965
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LOINC 6876-7
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LOINC 20640-9
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LOINC 2129-5
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NCI_THESAURUS C29596
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LOINC 54092-2
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LOINC 25878-0
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LOINC 15143-1
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LOINC 27056-1
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DSLD 2792 (Number of products:612)
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LOINC 53506-2
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LOINC 75215-4
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LOINC 15135-7
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LOINC 2130-3
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LOINC 26745-0
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LOINC 44307-7
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LOINC 42892-0
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LOINC 25376-5
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LOINC 32234-7
Created by admin on Fri Jun 25 21:32:57 UTC 2021 , Edited by admin on Fri Jun 25 21:32:57 UTC 2021
FDA ORPHAN DRUG 769820
Created by admin on Fri Jun 25 21:32:57 UTC 2021 , Edited by admin on Fri Jun 25 21:32:57 UTC 2021
Code System Code Type Description
WIKIPEDIA
CITRULLINE
Created by admin on Fri Jun 25 21:32:57 UTC 2021 , Edited by admin on Fri Jun 25 21:32:57 UTC 2021
PRIMARY
NCI_THESAURUS
C53406
Created by admin on Fri Jun 25 21:32:57 UTC 2021 , Edited by admin on Fri Jun 25 21:32:57 UTC 2021
PRIMARY
MESH
D002956
Created by admin on Fri Jun 25 21:32:57 UTC 2021 , Edited by admin on Fri Jun 25 21:32:57 UTC 2021
PRIMARY
CAS
372-75-8
Created by admin on Fri Jun 25 21:32:57 UTC 2021 , Edited by admin on Fri Jun 25 21:32:57 UTC 2021
PRIMARY
RXCUI
2567
Created by admin on Fri Jun 25 21:32:57 UTC 2021 , Edited by admin on Fri Jun 25 21:32:57 UTC 2021
PRIMARY RxNorm
PUBCHEM
9750
Created by admin on Fri Jun 25 21:32:57 UTC 2021 , Edited by admin on Fri Jun 25 21:32:57 UTC 2021
PRIMARY
MERCK INDEX
M3600
Created by admin on Fri Jun 25 21:32:57 UTC 2021 , Edited by admin on Fri Jun 25 21:32:57 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
206-759-6
Created by admin on Fri Jun 25 21:32:57 UTC 2021 , Edited by admin on Fri Jun 25 21:32:57 UTC 2021
PRIMARY
DRUG CENTRAL
3103
Created by admin on Fri Jun 25 21:32:57 UTC 2021 , Edited by admin on Fri Jun 25 21:32:57 UTC 2021
PRIMARY
DRUG BANK
DB00155
Created by admin on Fri Jun 25 21:32:57 UTC 2021 , Edited by admin on Fri Jun 25 21:32:57 UTC 2021
PRIMARY
FDA UNII
29VT07BGDA
Created by admin on Fri Jun 25 21:32:57 UTC 2021 , Edited by admin on Fri Jun 25 21:32:57 UTC 2021
PRIMARY
USP_CATALOG
1133842
Created by admin on Fri Jun 25 21:32:57 UTC 2021 , Edited by admin on Fri Jun 25 21:32:57 UTC 2021
PRIMARY USP-RS
EVMPD
SUB13384MIG
Created by admin on Fri Jun 25 21:32:57 UTC 2021 , Edited by admin on Fri Jun 25 21:32:57 UTC 2021
PRIMARY