DGIdb - L-CITRULLINE Drug Record

L-CITRULLINE chembl:CHEMBL444814

Alternate Names:

L-CITRULLINE
Δ-UREIDONORVALINE
ALPHA-AMINO-DELTA-UREIDOVALERIC ACID
2-AMINO-5-UREIDOVALERIC ACID
N5-(AMINOCARBONYL)ORNITHINE
CITRULLINE
DELTA-UREIDONORVALINE
N5-CARBAMOYL-L-ORNITHINE
N(5)-(AMINOCARBONYL)-L-ORNITHINE
Α-AMINO-Δ-UREIDOVALERIC ACID
N5-CARBAMOYLORNITHINE
(S)-2-AMINO-5-UREIDOPENTANOIC ACID
L-2-AMINO-5-UREIDOVALERIC ACID
CIT
N(DELTA)-CARBAMYLORNITHINE
rxcui:2567
chembl:CHEMBL444814
chemidplus:372-75-8
drugbank:00155
pubchem.compound:9750

Drug Info:

Drug Groups	investigational
Drug Categories	oat1/slc22a6 substrates
Drug Categories	oat3/slc22a8 substrates

(0 More Sources)

Publications:

Perry et al., 2000, Cu2+ and Zn2+ inhibit nitric-oxide synthase through an interaction with the reductase domain., J. Biol. Chem.
Kominami et al., 1999, EPR studies on the photo-induced intermediates of ferric NO complexes of rat neuronal nitric oxide synthase trapped at low temperature., J. Biochem.
Giraldi-Guimarães et al., 1999, Nitric oxide synthase expression in the opossum superior colliculus: a histochemical, immunohistochemical and biochemical study., Brain Behav. Evol.
Adak et al., 2000, Arginine conversion to nitroxide by tetrahydrobiopterin-free neuronal nitric-oxide synthase. Implications for mechanism., J. Biol. Chem.
Yu et al., 2000, Decrease of neuronal nitric oxide synthase in the cerebellum of aged rats., Neurosci. Lett.
Mishima et al., 2004, Expression of DDAH1 in chick and rat embryos., Brain Res. Dev. Brain Res.
Arrigoni et al., 2003, Metabolism of asymmetric dimethylarginines is regulated in the lung developmentally and with pulmonary hypertension induced by hypobaric hypoxia., Circulation
Tran et al., 2000, Chromosomal localization, gene structure, and expression pattern of DDAH1: comparison with DDAH2 and implications for evolutionary origins., Genomics
McDuffie et al., 1999, 5-hydroxytryptamine evokes endothelial nitric oxide synthase activation in bovine aortic endothelial cell cultures., Proc. Soc. Exp. Biol. Med.
Hayakawa et al., 1999, Relationship between hypercholesterolaemia, endothelial dysfunction and hypertension., J. Hypertens.
Trovati et al., 1999, Human vascular smooth muscle cells express a constitutive nitric oxide synthase that insulin rapidly activates, thus increasing guanosine 3':5'-cyclic monophosphate and adenosine 3':5'-cyclic monophosphate concentrations., Diabetologia
Abu-Soud et al., 2000, Electron transfer, oxygen binding, and nitric oxide feedback inhibition in endothelial nitric-oxide synthase., J. Biol. Chem.
Tan et al., 1999, Estrogen receptor-alpha gene transfer into bovine aortic endothelial cells induces eNOS gene expression and inhibits cell migration., Cardiovasc. Res.
Dong et al., 2005, Regulation of the expression of peptidylarginine deiminase type II gene (PADI2) in human keratinocytes involves Sp1 and Sp3 transcription factors., J. Invest. Dermatol.
Yi et al., Fire ant venom alkaloid, isosolenopsin A, a potent and selective inhibitor of neuronal nitric oxide synthase., Int. J. Toxicol.
Keilhoff et al., 2000, Citrulline immunohistochemistry for demonstration of NOS activity in vivo and in vitro., Nitric Oxide
Knowles et al., 1998, Measurement of NOS activity by conversion of radiolabeled arginine to citrulline using ion-exchange separation., Methods Mol. Biol.
Cunningham et al., 1998, Radiochemical measurement of NOS activity by conversion of [14C]L-arginine to citrulline using HPLC separation., Methods Mol. Biol.
Conrad et al., 2002, Citrulline is not the major product using the standard "NOS activity" assay on renal cortical homogenates., Am. J. Physiol. Regul. Integr. Comp. Physiol.
Iida et al., 2004, Identification of 45 novel SNPs in the 83-kb region containing peptidylarginine deiminase types 1 and 3 loci on chromosomal band 1p36.13., J. Hum. Genet.
Kanno et al., 2000, Human peptidylarginine deiminase type III: molecular cloning and nucleotide sequence of the cDNA, properties of the recombinant enzyme, and immunohistochemical localization in human skin., J. Invest. Dermatol.
Dong et al., 2006, NF-Y and Sp1/Sp3 are involved in the transcriptional regulation of the peptidylarginine deiminase type III gene (PADI3) in human keratinocytes., Biochem. J.
Morizono et al., 2006, Acetylornithine transcarbamylase: a novel enzyme in arginine biosynthesis., J. Bacteriol.
Quintero et al., 2000, Arginine catabolism in the cyanobacterium Synechocystis sp. Strain PCC 6803 involves the urea cycle and arginase pathway., J. Bacteriol.
Takahashi et al., 2006, A case of adult-onset type II citrullinemia--deterioration of clinical course after infusion of hyperosmotic and high sugar solutions., Med. Sci. Monit.
Zhang et al., 2000, Stable expression of varied levels of inducible nitric oxide synthase in primary cultures of endothelial cells., Anal. Biochem.
Braissant et al., 1999, Hyperammonemia: regulation of argininosuccinate synthetase and argininosuccinate lyase genes in aggregating cell cultures of fetal rat brain., Neurosci. Lett.
Husson et al., 2003, Argininosuccinate synthetase from the urea cycle to the citrulline-NO cycle., Eur. J. Biochem.
Zandvliet et al., Transient hyperammonemia due to urea cycle enzyme deficiency in Irish wolfhounds., J. Vet. Intern. Med.
Zhang et al., 2000, Coinduction of inducible nitric oxide synthase and arginine recycling enzymes in cytokine-stimulated PC12 cells and high output production of nitric oxide., Brain Res. Mol. Brain Res.
Van Geldre et al., 2002, L-citrulline recycling by argininosuccinate synthetase and lyase in rat gastric fundus., Eur. J. Pharmacol.
Braissant et al., 1999, L-arginine uptake, the citrulline-NO cycle and arginase II in the rat brain: an in situ hybridization study., Brain Res. Mol. Brain Res.
Hammermann et al., 1998, Inability of rat alveolar macrophages to recycle L-citrulline to L-arginine despite induction of argininosuccinate synthetase mRNA and protein, and inhibition of nitric oxide synthesis by exogenous L-citrulline., Naunyn Schmiedebergs Arch. Pharmacol.
Esposito G et al., 2007, Peptidylarginine deiminase (PAD) 6 is essential for oocyte cytoskeletal sheet formation and female fertility., Mol Cell Endocrinol
Snow AJ et al., 2008, Phosphorylation-dependent interaction of tyrosine 3-monooxygenase/tryptophan 5-monooxygenase activation protein (YWHA) with PADI6 following oocyte maturation in mice., Biol Reprod
Overington et al., 2006, How many drug targets are there?, Nat Rev Drug Discov
Imming et al., 2006, Drugs, their targets and the nature and number of drug targets., Nat Rev Drug Discov
Tain et al., 2007, Determination of dimethylarginine dimethylaminohydrolase activity in the kidney., Kidney Int.
Yamamoto et al., 2005, Genome-wide single nucleotide polymorphism analyses of rheumatoid arthritis., J. Autoimmun.
Wang et al., 2004, Human PAD4 regulates histone arginine methylation levels via demethylimination., Science
Chang et al., 2006, Expression of peptidylarginine deiminase type 4 (PAD4) in various tumors., Mol. Carcinog.
Wysocka et al., 2006, Histone arginine methylation and its dynamic regulation., Front. Biosci.
Okazaki et al., 2006, Identification of citrullinated eukaryotic translation initiation factor 4G1 as novel autoantigen in rheumatoid arthritis., Biochem. Biophys. Res. Commun.

L-CITRULLINE PADI6

Interaction Score: 21.85

Interaction Types & Directionality:

product of

Interaction Info:

PMIDs:
17587491 18463355 17139284 17016423

Sources:
DrugBank
L-CITRULLINE DDAH2

Interaction Score: 13.11

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
17653133 10950934

Sources:
DrugBank
L-CITRULLINE ASS1

Interaction Score: 8.01

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
16449956 11067741 10353334 12709047 17427379 11072090 10944418 12445581 10407171 9879717

Sources:
DrugBank
L-CITRULLINE PADI3

Interaction Score: 5.83

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
11069618 16671893 15150696

Sources:
DrugBank
L-CITRULLINE PADI4

Interaction Score: 3.75

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
16271291 15345777 16355400 16146736 16412378

Sources:
DrugBank
L-CITRULLINE DDAH1

Interaction Score: 3.5

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
14766200 12615801 10950934

Sources:
DrugBank
L-CITRULLINE OTC

Interaction Score: 3.28

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
16585758 10648527

Sources:
DrugBank
L-CITRULLINE PADI1

Interaction Score: 2.91

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
15150696

Sources:
DrugBank
L-CITRULLINE PADI2

Interaction Score: 2.18

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
15854045

Sources:
DrugBank
L-CITRULLINE GPRC6A

Interaction Score: 0.55

Interaction Types & Directionality:

agonist (activating)

Interaction Info:

Specific Action of the Ligand Full agonist

Endogenous Drug? True

PMIDs:
None found

Sources:
GuideToPharmacology
L-CITRULLINE NOS2

Interaction Score: 0.49

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
12745988 10944418 10906994 10906995 11742852

Sources:
DrugBank
L-CITRULLINE NOS3

Interaction Score: 0.49

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
10460702 10403604 10440125 10749853 10690351

Sources:
DrugBank
L-CITRULLINE NOS1

Interaction Score: 0.43

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
10799481 10502685 10681601 10945985 10962148

Sources:
DrugBank

DrugBank: DB00155

Version: 5.1.7

Alternate Names:

CITRULLINE DrugBank Drug Name

372-75-8 CAS Number

Lipovite Drug Brand

Drug Info:

Drug Type small molecule

Drug Groups approved

Drug Groups investigational

Publications:

Zhang et al., 2000, Stable expression of varied levels of inducible nitric oxide synthase in primary cultures of endothelial cells., Anal. Biochem.

Braissant et al., 1999, Hyperammonemia: regulation of argininosuccinate synthetase and argininosuccinate lyase genes in aggregating cell cultures of fetal rat brain., Neurosci. Lett.

Zhang et al., 2000, Coinduction of inducible nitric oxide synthase and arginine recycling enzymes in cytokine-stimulated PC12 cells and high output production of nitric oxide., Brain Res. Mol. Brain Res.

GuideToPharmacology: 135650512
- Version: 29-September-2020
Alternate Names:

L-CITRULLINE GuideToPharmacology Ligand Name

Drug Info:

Publications:
ChemblDrugs: chembl:CHEMBL444814
- Version: ChEMBL_27
Alternate Names:

Drug Info:

Publications:

Specific Action of the Ligand	Full agonist
Endogenous Drug?	True

CITRULLINE	DrugBank Drug Name
372-75-8	CAS Number
Lipovite	Drug Brand

Drug Type	small molecule
Drug Groups	approved
Drug Groups	investigational

L-CITRULLINE Drug Record

L-CITRULLINE chembl:CHEMBL444814

Alternate Names:

Drug Info:

Publications:

Interaction Types & Directionality: product of

Interaction Info:

PMIDs: 17587491 18463355 17139284 17016423

Sources: DrugBank

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: 17653133 10950934

Sources: DrugBank

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: 16449956 11067741 10353334 12709047 17427379 11072090 10944418 12445581 10407171 9879717

Sources: DrugBank

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: 11069618 16671893 15150696

Sources: DrugBank

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: 16271291 15345777 16355400 16146736 16412378

Sources: DrugBank

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: 14766200 12615801 10950934

Sources: DrugBank

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: 16585758 10648527

Sources: DrugBank

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: 15150696

Sources: DrugBank

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: 15854045

Sources: DrugBank

Interaction Types & Directionality: agonist (activating)

Interaction Info: Specific Action of the Ligand Full agonist Endogenous Drug? True

PMIDs: None found

Sources: GuideToPharmacology

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: 12745988 10944418 10906994 10906995 11742852

Sources: DrugBank

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: 10460702 10403604 10440125 10749853 10690351

Sources: DrugBank

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: 10799481 10502685 10681601 10945985 10962148

Sources: DrugBank

DrugBank: DB00155

Alternate Names: CITRULLINE DrugBank Drug Name 372-75-8 CAS Number Lipovite Drug Brand

Drug Info: Drug Type small molecule Drug Groups approved Drug Groups investigational

GuideToPharmacology: 135650512

Alternate Names: L-CITRULLINE GuideToPharmacology Ligand Name

Drug Info:

Publications:

ChemblDrugs: chembl:CHEMBL444814

Alternate Names:

Drug Info:

Publications:

Interaction Types & Directionality:

product of

PMIDs:
17587491 18463355 17139284 17016423

Sources:
DrugBank

Interaction Types & Directionality:

n/a

PMIDs:
17653133 10950934

Sources:
DrugBank

Interaction Types & Directionality:

n/a

PMIDs:
16449956 11067741 10353334 12709047 17427379 11072090 10944418 12445581 10407171 9879717

Sources:
DrugBank

Interaction Types & Directionality:

n/a

PMIDs:
11069618 16671893 15150696

Sources:
DrugBank

Interaction Types & Directionality:

n/a

PMIDs:
16271291 15345777 16355400 16146736 16412378

Sources:
DrugBank

Interaction Types & Directionality:

n/a

PMIDs:
14766200 12615801 10950934

Sources:
DrugBank

Interaction Types & Directionality:

n/a

PMIDs:
16585758 10648527

Sources:
DrugBank

Interaction Types & Directionality:

n/a

PMIDs:
15150696

Sources:
DrugBank

Interaction Types & Directionality:

n/a

PMIDs:
15854045

Sources:
DrugBank

Interaction Types & Directionality:

agonist (activating)

Interaction Info:

Specific Action of the Ligand Full agonist

Endogenous Drug? True

PMIDs:
None found

Sources:
GuideToPharmacology

Interaction Types & Directionality:

n/a

PMIDs:
12745988 10944418 10906994 10906995 11742852

Sources:
DrugBank

Interaction Types & Directionality:

n/a

PMIDs:
10460702 10403604 10440125 10749853 10690351

Sources:
DrugBank

Interaction Types & Directionality:

n/a

PMIDs:
10799481 10502685 10681601 10945985 10962148

Sources:
DrugBank

Alternate Names:

CITRULLINE DrugBank Drug Name

372-75-8 CAS Number

Lipovite Drug Brand

Drug Info:

Drug Type small molecule

Drug Groups approved

Drug Groups investigational

Alternate Names:

L-CITRULLINE GuideToPharmacology Ligand Name