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

Molecular Formula C6H13N3O3
Molecular Weight 175.1857
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Inducible nitric oxide synthase in rat neutrophils: role of insulin.
2001-08-01
Development of specific CXCR4 inhibitors possessing high selectivity indexes as well as complete stability in serum based on an anti-HIV peptide T140.
2001-07-23
Metabolic effects of arginine addition to the enteral feeding of critically ill patients.
2001-07-04
Endothelial cell dysfunction in a model of oxidative stress.
2001-07-04
IgG reactivity against citrullinated myelin basic protein in multiple sclerosis.
2001-07-02
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.
2001-07-01
New data and concepts on glutamine and glucose metabolism in the gut.
2001-07
Role of nitric oxide synthase in the light-induced development of sporangiophores in Phycomyces blakesleeanus.
2001-07
Neuroprotective effect of sigma(1)-receptor ligand 4-phenyl-1-(4-phenylbutyl) piperidine (PPBP) is linked to reduced neuronal nitric oxide production.
2001-07
A Chinese adult onset type II citrullinaemia patient with 851del4/1638ins23 mutations in the SLC25A13 gene.
2001-07
Expression control and specificity of the basic amino acid exporter LysE of Corynebacterium glutamicum.
2001-07
Ornithine aminotransferase messenger RNA expression and enzymatic activity in fetal porcine intestine.
2001-07
Phenanthraquinone inhibits eNOS activity and suppresses vasorelaxation.
2001-07
Co-induction of argininosuccinate synthetase, cationic amino acid transporter-2, and nitric oxide synthase in activated murine microglial cells.
2001-06-20
Neonatal pulmonary hypertension--urea-cycle intermediates, nitric oxide production, and carbamoyl-phosphate synthetase function.
2001-06-14
Amino acid concentrations in fluids from the bovine oviduct and uterus and in KSOM-based culture media.
2001-06-01
Methohexital affects neutrophil (PMN) dynamic free amino acid pool and immune functions in vitro.
2001-06
HHH syndrome associated with callosal agenesis and disordered neuronal migration.
2001-06
Involvement of cyclic guanosine 3',5'-monophosphate in nitric oxide-induced glucagon secretion from pancreatic alpha cells.
2001-06
Coinduction of endothelial nitric oxide synthase and arginine recycling enzymes in aorta of diabetic rats.
2001-06
Diagnostic accuracy of the anti-citrulline antibody assay for rheumatoid arthritis.
2001-06
Nitric oxide synthase in porcine heart mitochondria: evidence for low physiological activity.
2001-06
Radiochemical nitric oxide synthase activity determination in rat brain with fast and accurate HPLC analysis.
2001-06
Gastrectomized patients are in a state of chronic protein malnutrition analyses of 23 amino acids.
2001-05-31
A pediatric patient with classical citrullinemia who underwent living-related partial liver transplantation.
2001-05-27
Helicobacter pylori lipopolysaccharide-provoked injury to rat gastroduodenal microvasculature involves inducible nitric oxide synthase.
2001-05-25
Increased expression of arginase II in human diabetic corpus cavernosum: in diabetic-associated erectile dysfunction.
2001-05-18
Convenient method for the determination of arginine and its related compounds in rumen fluid by reversed-phase high-performance liquid chromatography.
2001-05-05
Peroxynitrite inhibits inducible (type 2) nitric oxide synthase in murine lung epithelial cells in vitro.
2001-05-01
Extremely short small bowel induces focal tubulointerstitial fibrosis.
2001-05
Cigarette smoke-induced endothelium dysfunction: role of superoxide anion.
2001-05
Control of electron transfer in neuronal NO synthase.
2001-05
Retinoic acid attenuates inducible nitric oxide synthase (NOS2) activation in cultured rat cardiac myocytes and microvascular endothelial cells.
2001-05
Ceramide reduces endothelium-dependent vasodilation by increasing superoxide production in small bovine coronary arteries.
2001-04-27
Vaginocervical stimulation-induced release of classical neurotransmitters and nitric oxide in the nucleus of the solitary tract varies as a function of the oestrus cycle.
2001-04-20
Cholinergic-nitrergic transmitter mechanisms in the cerebral circulation.
2001-04-15
Depletion of energy metabolites following acetylcholinesterase inhibitor-induced status epilepticus: protection by antioxidants.
2001-04
Angiotensin-converting enzyme inhibitors and AT1-receptor antagonist restore nitric oxide synthase (NOS) activity and neuronal NOS expression in the adrenal glands of spontaneously hypertensive rats.
2001-04
Metabolic effects of intraportal nutrition in humans.
2001-04
Endothelial nitric oxide synthase (eNOS) expression and localization in healthy and diabetic rat hearts.
2001-04
Selective inhibition of human inducible nitric oxide synthase by S-alkyl-L-isothiocitrulline-containing dipeptides.
2001-04
Effects of dietary L-arginine on structure and function of flow-restricted vein grafts.
2001-04
Time course of inducible nitric oxide synthase activity following endotoxin administration in dogs.
2001-04
Carbamoylation of glomerular and tubular proteins in patients with kidney failure: a potential mechanism of ongoing renal damage.
2001-03-24
Neurotransmitter sampling and storage for capillary electrophoresis analysis.
2001-02
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.
2001-02
Temporal expression of nitric oxide synthase isoforms in healing Achilles tendon.
2001-01
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
Plant amino acid research in retrospect: from Chinball to Singh.
2001
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:53:40 GMT 2025
Edited
by admin
on Mon Mar 31 17:53:40 GMT 2025
Record UNII
29VT07BGDA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CITRULLINE
INCI   MART.   MI   VANDF   WHO-DD  
INCI  
Official Name English
NSC-27425
Preferred Name English
L-2-AMINO-5-(CARBAMOYLAMINO)PENTANOIC ACID
Systematic 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
Citrulline [WHO-DD]
Common Name English
Classification Tree Code System Code
LOINC 56676-0
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FDA ORPHAN DRUG 779420
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LOINC 30161-4
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FDA ORPHAN DRUG 544216
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DSLD 701 (Number of products:222)
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EU-Orphan Drug EU/3/17/1965
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LOINC 2129-5
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NCI_THESAURUS C29596
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DSLD 2792 (Number of products:612)
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LOINC 32234-7
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FDA ORPHAN DRUG 769820
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Code System Code Type Description
EPA CompTox
DTXSID80883373
Created by admin on Mon Mar 31 17:53:40 GMT 2025 , Edited by admin on Mon Mar 31 17:53:40 GMT 2025
PRIMARY
RS_ITEM_NUM
1133842
Created by admin on Mon Mar 31 17:53:40 GMT 2025 , Edited by admin on Mon Mar 31 17:53:40 GMT 2025
PRIMARY
WIKIPEDIA
CITRULLINE
Created by admin on Mon Mar 31 17:53:40 GMT 2025 , Edited by admin on Mon Mar 31 17:53:40 GMT 2025
PRIMARY
CHEBI
16349
Created by admin on Mon Mar 31 17:53:40 GMT 2025 , Edited by admin on Mon Mar 31 17:53:40 GMT 2025
PRIMARY
NCI_THESAURUS
C53406
Created by admin on Mon Mar 31 17:53:40 GMT 2025 , Edited by admin on Mon Mar 31 17:53:40 GMT 2025
PRIMARY
MESH
D002956
Created by admin on Mon Mar 31 17:53:40 GMT 2025 , Edited by admin on Mon Mar 31 17:53:40 GMT 2025
PRIMARY
CAS
372-75-8
Created by admin on Mon Mar 31 17:53:40 GMT 2025 , Edited by admin on Mon Mar 31 17:53:40 GMT 2025
PRIMARY
CHEBI
57743
Created by admin on Mon Mar 31 17:53:40 GMT 2025 , Edited by admin on Mon Mar 31 17:53:40 GMT 2025
PRIMARY
RXCUI
2567
Created by admin on Mon Mar 31 17:53:40 GMT 2025 , Edited by admin on Mon Mar 31 17:53:40 GMT 2025
PRIMARY RxNorm
DAILYMED
29VT07BGDA
Created by admin on Mon Mar 31 17:53:40 GMT 2025 , Edited by admin on Mon Mar 31 17:53:40 GMT 2025
PRIMARY
SMS_ID
100000080134
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PRIMARY
PUBCHEM
9750
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PRIMARY
MERCK INDEX
m3600
Created by admin on Mon Mar 31 17:53:40 GMT 2025 , Edited by admin on Mon Mar 31 17:53:40 GMT 2025
PRIMARY Merck Index
ECHA (EC/EINECS)
206-759-6
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PRIMARY
NSC
27425
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PRIMARY
DRUG CENTRAL
3103
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PRIMARY
DRUG BANK
DB00155
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PRIMARY
FDA UNII
29VT07BGDA
Created by admin on Mon Mar 31 17:53:40 GMT 2025 , Edited by admin on Mon Mar 31 17:53:40 GMT 2025
PRIMARY
CHEBI
18211
Created by admin on Mon Mar 31 17:53:40 GMT 2025 , Edited by admin on Mon Mar 31 17:53:40 GMT 2025
PRIMARY
EVMPD
SUB13384MIG
Created by admin on Mon Mar 31 17:53:40 GMT 2025 , Edited by admin on Mon Mar 31 17:53:40 GMT 2025
PRIMARY
Related Record Type Details
ACTIVE MOIETY