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
Extracting biological information from DNA arrays: an unexpected link between arginine and methionine metabolism in Bacillus subtilis.
2001
Depletion of energy metabolites following acetylcholinesterase inhibitor-induced status epilepticus: protection by antioxidants.
2001 Apr
Metabolic effects of intraportal nutrition in humans.
2001 Apr
Endothelial nitric oxide synthase (eNOS) expression and localization in healthy and diabetic rat hearts.
2001 Apr
Time course of inducible nitric oxide synthase activity following endotoxin administration in dogs.
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
Role of nitric oxide in renal tubular apoptosis of unilateral ureteral obstruction.
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
The binding of oxidized low density lipoprotein (ox-LDL) to ox-LDL receptor-1 reduces the intracellular concentration of nitric oxide in endothelial cells through an increased production of superoxide.
2001 Apr 27
Hypochlorite-modified low density lipoprotein inhibits nitric oxide synthesis in endothelial cells via an intracellular dislocalization of endothelial nitric-oxide synthase.
2001 Apr 27
Neurotransmitter sampling and storage for capillary electrophoresis analysis.
2001 Feb
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
[The immunologic homunculus in rheumatoid arthritis. A new viewpoint of immunopathogenesis in rheumatoid arthritis and therapeutic consequences].
2001 Feb
Superoxide inhibits neuronal nitric oxide synthase influences on afferent arterioles in spontaneously hypertensive rats.
2001 Feb
Effects of oral L-arginine on plasma nitrate and blood pressure in cortisol-treated humans.
2001 Feb
Temporal expression of nitric oxide synthase isoforms in healing Achilles tendon.
2001 Jan
Secretion of anti-citrulline-containing peptide antibody by B lymphocytes in rheumatoid arthritis.
2001 Jan
Metabolic flux measurements across portal drained viscera, liver, kidney and hindquarter in mice.
2001 Jan
Role of nitric oxide synthase in the light-induced development of sporangiophores in Phycomyces blakesleeanus.
2001 Jul
Expression control and specificity of the basic amino acid exporter LysE of Corynebacterium glutamicum.
2001 Jul
Ornithine aminotransferase messenger RNA expression and enzymatic activity in fetal porcine intestine.
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
IgG reactivity against citrullinated myelin basic protein in multiple sclerosis.
2001 Jul 2
Endothelial cell dysfunction in a model of oxidative stress.
2001 Jul-Aug
HHH syndrome associated with callosal agenesis and disordered neuronal migration.
2001 Jun
Diagnostic accuracy of the anti-citrulline antibody assay for rheumatoid arthritis.
2001 Jun
Radiochemical nitric oxide synthase activity determination in rat brain with fast and accurate HPLC analysis.
2001 Jun
Amino acid concentrations in fluids from the bovine oviduct and uterus and in KSOM-based culture media.
2001 Jun 1
Neonatal pulmonary hypertension--urea-cycle intermediates, nitric oxide production, and carbamoyl-phosphate synthetase function.
2001 Jun 14
Co-induction of argininosuccinate synthetase, cationic amino acid transporter-2, and nitric oxide synthase in activated murine microglial cells.
2001 Jun 20
Short-term oral administration of L-arginine improves hemodynamics and exercise capacity in patients with precapillary pulmonary hypertension.
2001 Mar
Nitric oxide synthase isoforms during fracture healing.
2001 Mar
Effect of vitamin C on the availability of tetrahydrobiopterin in human endothelial cells.
2001 Mar
Regulation of NO synthase isoforms in the peritoneum: implications for ultrafiltration failure in peritoneal dialysis.
2001 Mar
Simultaneous detection of NOS-3 protein expression and nitric oxide production using a flow cytometer.
2001 Mar
In vivo confocal Raman microspectroscopy of the skin: noninvasive determination of molecular concentration profiles.
2001 Mar
Nitric oxide synthases in pregnant rat uterus.
2001 Mar
Arginase I expression and activity in human mononuclear cells after injury.
2001 Mar
Neural network partitioning by NO and cGMP.
2001 Mar 1
The major synovial targets of the rheumatoid arthritis-specific antifilaggrin autoantibodies are deiminated forms of the alpha- and beta-chains of fibrin.
2001 Mar 15
Carbamoylation of glomerular and tubular proteins in patients with kidney failure: a potential mechanism of ongoing renal damage.
2001 Mar 24
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
Cigarette smoke-induced endothelium dysfunction: role of superoxide anion.
2001 May
Retinoic acid attenuates inducible nitric oxide synthase (NOS2) activation in cultured rat cardiac myocytes and microvascular endothelial cells.
2001 May
Convenient method for the determination of arginine and its related compounds in rumen fluid by reversed-phase high-performance liquid chromatography.
2001 May 5
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
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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