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
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
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
Title | Date | PubMed |
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Metabolic effects of intraportal nutrition in humans. | 2001 Apr |
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Selective inhibition of human inducible nitric oxide synthase by S-alkyl-L-isothiocitrulline-containing dipeptides. | 2001 Apr |
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Caveolar localization of arginine regeneration enzymes, argininosuccinate synthase, and lyase, with endothelial nitric oxide synthase. | 2001 Apr |
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Ornithine transcarbamylase deficiency unmasked because of gastrointestinal bleeding. | 2001 Apr |
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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 |
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Characterization of a putative nitric oxide synthase in the neuromuscular system of the parasitic nematode, Ascaris suum. | 2001 Feb |
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Effects of oral L-arginine on plasma nitrate and blood pressure in cortisol-treated humans. | 2001 Feb |
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Nitric oxide generation by hemocytes of the mussel Mytilus galloprovincialis. | 2001 Feb |
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Antineutrophil cytoplasm antibody-induced neutrophil nitric oxide production is nitric oxide synthase independent. | 2001 Feb |
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Protein deimination in the rat brain after kainate administration: citrulline-containing proteins as a novel marker of neurodegeneration. | 2001 Feb 16 |
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Immunohistochemical localization of nitric oxide synthase and soluble guanylyl cyclase in the ventral cochlear nucleus of the rat. | 2001 Feb 26 |
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Temporal expression of nitric oxide synthase isoforms in healing Achilles tendon. | 2001 Jan |
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Metabolic flux measurements across portal drained viscera, liver, kidney and hindquarter in mice. | 2001 Jan |
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Nerve injury induces a rapid efflux of nitric oxide (NO) detected with a novel NO microsensor. | 2001 Jan 1 |
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Kinetic mechanism of antiports catalyzed by reconstituted ornithine/citrulline carrier from rat liver mitochondria. | 2001 Jan 19 |
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Expression, but not activity, of neuronal nitric oxide synthase is regionally increased in the alcoholic brain. | 2001 Jan-Feb |
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New data and concepts on glutamine and glucose metabolism in the gut. | 2001 Jul |
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A Chinese adult onset type II citrullinaemia patient with 851del4/1638ins23 mutations in the SLC25A13 gene. | 2001 Jul |
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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 |
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IgG reactivity against citrullinated myelin basic protein in multiple sclerosis. | 2001 Jul 2 |
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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 |
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Metabolic effects of arginine addition to the enteral feeding of critically ill patients. | 2001 Jul-Aug |
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Endothelial cell dysfunction in a model of oxidative stress. | 2001 Jul-Aug |
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Co-induction of argininosuccinate synthetase, cationic amino acid transporter-2, and nitric oxide synthase in activated murine microglial cells. | 2001 Jun 20 |
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Nitric oxide synthase isoforms during fracture healing. | 2001 Mar |
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Effect of vitamin C on the availability of tetrahydrobiopterin in human endothelial cells. | 2001 Mar |
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Simultaneous detection of NOS-3 protein expression and nitric oxide production using a flow cytometer. | 2001 Mar |
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Nitric oxide synthases in pregnant rat uterus. | 2001 Mar |
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Ace-inhibition with quinapril modulates the nitric oxide pathway in normotensive rats. | 2001 Mar |
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Carbamoylation of glomerular and tubular proteins in patients with kidney failure: a potential mechanism of ongoing renal damage. | 2001 Mar 24 |
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Cigarette smoke-induced endothelium dysfunction: role of superoxide anion. | 2001 May |
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Peroxynitrite inhibits inducible (type 2) nitric oxide synthase in murine lung epithelial cells in vitro. | 2001 May 1 |
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Increased expression of arginase II in human diabetic corpus cavernosum: in diabetic-associated erectile dysfunction. | 2001 May 18 |
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Helicobacter pylori lipopolysaccharide-provoked injury to rat gastroduodenal microvasculature involves inducible nitric oxide synthase. | 2001 May 25 |
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A pediatric patient with classical citrullinemia who underwent living-related partial liver transplantation. | 2001 May 27 |
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ACTIVE MOIETY