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

Details

Stereochemistry ABSOLUTE
Molecular Formula C6H13N3O3
Molecular Weight 175.1857
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CITRULLINE

SMILES

N[C@@H](CCCNC(N)=O)C(O)=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
Metabolic effects of intraportal nutrition in humans.
2001 Apr
Selective inhibition of human inducible nitric oxide synthase by S-alkyl-L-isothiocitrulline-containing dipeptides.
2001 Apr
Caveolar localization of arginine regeneration enzymes, argininosuccinate synthase, and lyase, with endothelial nitric oxide synthase.
2001 Apr
Ornithine transcarbamylase deficiency unmasked because of gastrointestinal bleeding.
2001 Apr
Formation of a protonated trihydrobiopterin radical cation in the first reaction cycle of neuronal and endothelial nitric oxide synthase detected by electron paramagnetic resonance spectroscopy.
2001 Feb
Characterization of a putative nitric oxide synthase in the neuromuscular system of the parasitic nematode, Ascaris suum.
2001 Feb
Effects of oral L-arginine on plasma nitrate and blood pressure in cortisol-treated humans.
2001 Feb
Nitric oxide generation by hemocytes of the mussel Mytilus galloprovincialis.
2001 Feb
Antineutrophil cytoplasm antibody-induced neutrophil nitric oxide production is nitric oxide synthase independent.
2001 Feb
Protein deimination in the rat brain after kainate administration: citrulline-containing proteins as a novel marker of neurodegeneration.
2001 Feb 16
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
Metabolic flux measurements across portal drained viscera, liver, kidney and hindquarter in mice.
2001 Jan
Nerve injury induces a rapid efflux of nitric oxide (NO) detected with a novel NO microsensor.
2001 Jan 1
Kinetic mechanism of antiports catalyzed by reconstituted ornithine/citrulline carrier from rat liver mitochondria.
2001 Jan 19
Expression, but not activity, of neuronal nitric oxide synthase is regionally increased in the alcoholic brain.
2001 Jan-Feb
New data and concepts on glutamine and glucose metabolism in the gut.
2001 Jul
A Chinese adult onset type II citrullinaemia patient with 851del4/1638ins23 mutations in the SLC25A13 gene.
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
IgG reactivity against citrullinated myelin basic protein in multiple sclerosis.
2001 Jul 2
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
Co-induction of argininosuccinate synthetase, cationic amino acid transporter-2, and nitric oxide synthase in activated murine microglial cells.
2001 Jun 20
Nitric oxide synthase isoforms during fracture healing.
2001 Mar
Effect of vitamin C on the availability of tetrahydrobiopterin in human endothelial cells.
2001 Mar
Simultaneous detection of NOS-3 protein expression and nitric oxide production using a flow cytometer.
2001 Mar
Nitric oxide synthases in pregnant rat uterus.
2001 Mar
Ace-inhibition with quinapril modulates the nitric oxide pathway in normotensive rats.
2001 Mar
Carbamoylation of glomerular and tubular proteins in patients with kidney failure: a potential mechanism of ongoing renal damage.
2001 Mar 24
Cigarette smoke-induced endothelium dysfunction: role of superoxide anion.
2001 May
Peroxynitrite inhibits inducible (type 2) nitric oxide synthase in murine lung epithelial cells in vitro.
2001 May 1
Increased expression of arginase II in human diabetic corpus cavernosum: in diabetic-associated erectile dysfunction.
2001 May 18
Helicobacter pylori lipopolysaccharide-provoked injury to rat gastroduodenal microvasculature involves inducible nitric oxide synthase.
2001 May 25
A pediatric patient with classical citrullinemia who underwent living-related partial liver transplantation.
2001 May 27
Patents
Name Type Language
CITRULLINE
INCI   MART.   MI   VANDF   WHO-DD  
INCI  
Official Name English
CITRULLINE [MI]
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
Citrulline [WHO-DD]
Common Name English
Classification Tree Code System Code
LOINC 56676-0
Created by admin on Wed Jul 05 22:49:41 UTC 2023 , Edited by admin on Wed Jul 05 22:49:41 UTC 2023
LOINC 53399-2
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LOINC 25877-2
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LOINC 2131-1
Created by admin on Wed Jul 05 22:49:41 UTC 2023 , Edited by admin on Wed Jul 05 22:49:41 UTC 2023
FDA ORPHAN DRUG 779420
Created by admin on Wed Jul 05 22:49:41 UTC 2023 , Edited by admin on Wed Jul 05 22:49:41 UTC 2023
LOINC 30161-4
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LOINC 53236-6
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FDA ORPHAN DRUG 544216
Created by admin on Wed Jul 05 22:49:41 UTC 2023 , Edited by admin on Wed Jul 05 22:49:41 UTC 2023
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)
Created by admin on Wed Jul 05 22:49:41 UTC 2023 , Edited by admin on Wed Jul 05 22:49:41 UTC 2023
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 Wed Jul 05 22:49:41 UTC 2023 , Edited by admin on Wed Jul 05 22:49:41 UTC 2023
FDA ORPHAN DRUG 769820
Created by admin on Wed Jul 05 22:49:41 UTC 2023 , Edited by admin on Wed Jul 05 22:49:41 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID80883373
Created by admin on Wed Jul 05 22:49:41 UTC 2023 , Edited by admin on Wed Jul 05 22:49:41 UTC 2023
PRIMARY
RS_ITEM_NUM
1133842
Created by admin on Wed Jul 05 22:49:41 UTC 2023 , Edited by admin on Wed Jul 05 22:49:41 UTC 2023
PRIMARY
WIKIPEDIA
CITRULLINE
Created by admin on Wed Jul 05 22:49:41 UTC 2023 , Edited by admin on Wed Jul 05 22:49:41 UTC 2023
PRIMARY
CHEBI
16349
Created by admin on Wed Jul 05 22:49:41 UTC 2023 , Edited by admin on Wed Jul 05 22:49:41 UTC 2023
PRIMARY
NCI_THESAURUS
C53406
Created by admin on Wed Jul 05 22:49:41 UTC 2023 , Edited by admin on Wed Jul 05 22:49:41 UTC 2023
PRIMARY
MESH
D002956
Created by admin on Wed Jul 05 22:49:41 UTC 2023 , Edited by admin on Wed Jul 05 22:49:41 UTC 2023
PRIMARY
CAS
372-75-8
Created by admin on Wed Jul 05 22:49:41 UTC 2023 , Edited by admin on Wed Jul 05 22:49:41 UTC 2023
PRIMARY
CHEBI
57743
Created by admin on Wed Jul 05 22:49:41 UTC 2023 , Edited by admin on Wed Jul 05 22:49:41 UTC 2023
PRIMARY
RXCUI
2567
Created by admin on Wed Jul 05 22:49:41 UTC 2023 , Edited by admin on Wed Jul 05 22:49:41 UTC 2023
PRIMARY RxNorm
DAILYMED
29VT07BGDA
Created by admin on Wed Jul 05 22:49:41 UTC 2023 , Edited by admin on Wed Jul 05 22:49:41 UTC 2023
PRIMARY
SMS_ID
100000080134
Created by admin on Wed Jul 05 22:49:41 UTC 2023 , Edited by admin on Wed Jul 05 22:49:41 UTC 2023
PRIMARY
PUBCHEM
9750
Created by admin on Wed Jul 05 22:49:41 UTC 2023 , Edited by admin on Wed Jul 05 22:49:41 UTC 2023
PRIMARY
MERCK INDEX
M3600
Created by admin on Wed Jul 05 22:49:41 UTC 2023 , Edited by admin on Wed Jul 05 22:49:41 UTC 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
206-759-6
Created by admin on Wed Jul 05 22:49:41 UTC 2023 , Edited by admin on Wed Jul 05 22:49:41 UTC 2023
PRIMARY
NSC
27425
Created by admin on Wed Jul 05 22:49:41 UTC 2023 , Edited by admin on Wed Jul 05 22:49:41 UTC 2023
PRIMARY
DRUG CENTRAL
3103
Created by admin on Wed Jul 05 22:49:41 UTC 2023 , Edited by admin on Wed Jul 05 22:49:41 UTC 2023
PRIMARY
DRUG BANK
DB00155
Created by admin on Wed Jul 05 22:49:41 UTC 2023 , Edited by admin on Wed Jul 05 22:49:41 UTC 2023
PRIMARY
FDA UNII
29VT07BGDA
Created by admin on Wed Jul 05 22:49:41 UTC 2023 , Edited by admin on Wed Jul 05 22:49:41 UTC 2023
PRIMARY
CHEBI
18211
Created by admin on Wed Jul 05 22:49:41 UTC 2023 , Edited by admin on Wed Jul 05 22:49:41 UTC 2023
PRIMARY
EVMPD
SUB13384MIG
Created by admin on Wed Jul 05 22:49:41 UTC 2023 , Edited by admin on Wed Jul 05 22:49:41 UTC 2023
PRIMARY