NITROARGININE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C6H13N5O4
Molecular Weight	219.1985
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

N[C@@H](CCCNC(=N)N[N+]([O-])=O)C(O)=O

InChI

InChIKey=MRAUNPAHJZDYCK-BYPYZUCNSA-N

InChI=1S/C6H13N5O4/c7-4(5(12)13)2-1-3-9-6(8)10-11(14)15/h4H,1-3,7H2,(H,12,13)(H3,8,9,10)/t4-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.drugbank.ca/drugs/DB04223 | https://www.ncbi.nlm.nih.gov/pubmed/29139306 | https://www.ncbi.nlm.nih.gov/pubmed/7689333 |https://www.ncbi.nlm.nih.gov/mesh/68019331 | https://www.ncbi.nlm.nih.gov/pubmed/29087727

L-NAME is a non-selective inhibitor of nitric oxide synthase. It is used in experimental models of hypertension.

Approval Year

Targets

Primary Target	Pharmacology	Potency
Nitric-oxide synthase, brain 24 Target ID: CHEMBL3568 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1710109	Inhibitor 8297
Nitric oxide synthase, inducible 50 Target ID: CHEMBL4481 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8619882	Inhibitor 8297
Nitric-oxide synthase, endothelial 19 Target ID: CHEMBL4803 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8619882	Inhibitor 8297
Nitric-oxide synthase, endothelial 19 Target ID: CHEMBL4803 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7689333	Inhibitor 8297	39.0 nM [Ki]
Nitric oxide synthase, inducible 50 Target ID: P35228\|\|\|Q9UD42 Gene ID: 4843.0 Gene Symbol: NOS2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/11040050	Inhibitor 8297	4.44 null [pIC50]

PubMed

Title	Date	PubMed
[Effect of nitric oxide synthase inhibitor L-NNA on the activities of antioxidant enzymes and lipid peroxidation in blood and tissues of rats with different resistance to hypoxia].	2001	11392115
[Intermittent hypoxic training with exogenous nitric oxide improves rat liver mitochondrial oxidation and phosphorylation during acute hypoxia].	2001	11296563
Nitric oxide in the afferent synaptic transmission of the axolotl vestibular system.	2001	11246160
Cerebral hyperemia and nitric oxide synthase in rats with ammonia-induced brain edema.	2001 Apr	11394654
Role of nitric oxide in the secondary expansion of a cortical brain lesion from cold injury.	2001 Apr	11336443
Signal transduction pathways involved in kinin B(2) receptor-mediated vasodilation in the rat isolated perfused kidney.	2001 Apr	11309245
Effects of bradykinin on renal nerve stimulation-induced antidiuresis and norepinephrine overflow in anesthetized dogs.	2001 Apr	11300659
NMDA-induced phosphorylation of the microtubule-associated protein MAP-2 is mediated by activation of nitric oxide synthase and MAP kinase.	2001 Apr	11298788
Endothelin-1 induces vasoconstriction on portal-systemic collaterals of portal hypertensive rats.	2001 Apr	11283844
Effect of age on electrical field stimulation (EFS)-induced endothelium-dependent vasodilation in male and female rats.	2001 Apr	11282086
Expression of vascular endothelial growth factor and its receptors is increased, but microvascular relaxation is impaired in patients after acute myocardial ischemia.	2001 Apr	11279416
Ocular blood flow and retinal metabolism in abyssinian cats with hereditary retinal degeneration.	2001 Apr	11274083
Contributions of prostacyclin and nitric oxide to carbon monoxide-induced cerebrovascular dilation in piglets.	2001 Apr	11247758
Role of inducible nitric oxide synthase in the pulmonary vascular response to birth-related stimuli in the ovine fetus.	2001 Apr 13	11304495
Role of endothelial nitric oxide in shear stress-induced vasodilation of human microvasculature: diminished activity in hypertensive and hypercholesterolemic patients.	2001 Apr 3	11282906
The dual effect of a nitric oxide donor in nociception.	2001 Apr 6	11282353
No parallel relationship between nitric oxide production and wet dog shakes susceptible to nitric oxide synthase inhibitors following systemic administration of paraquat in rats.	2001 Feb	11305780
Short term hypercholesterolemia alters N(G)-nitro-L-arginine- and indomethacin-resistant endothelium-dependent relaxation by acetylcholine in rabbit renal artery.	2001 Feb	11286404
Glucocorticoids inhibit tetrahydrobiopterin-dependent endothelial function.	2001 Jan	11368234
Relative significance of the nitric oxide (NO)/cGMP pathway and K+ channel activation in endothelium-dependent vasodilation in the femoral artery of developing piglets.	2001 Jan	11350260
Differing effects of two nitric oxide synthase inhibitors on experimental colitis.	2001 Jan-Feb	11268945
Arachidonate dilates basilar artery by lipoxygenase-dependent mechanism and activation of K(+) channels.	2001 Jul	11404300
The influence of nitric oxide synthase 1 on blood flow and interstitial nitric oxide in the kidney.	2001 Jul	11404282
The vascular activity of some isoflavone metabolites: implications for a cardioprotective role.	2001 Jun	11399677
Low-dose nitric oxide inhibition produces a negative sodium balance in conscious dogs.	2001 Jun	11373336
Phytoestrogens restore nitric oxide-mediated relaxation in isolated pulmonary arteries from chronically hypoxic rats.	2001 Jun	11356918
Simulated microgravity enhances vasoconstrictor responsiveness of rat basilar artery.	2001 Jun	11356795
Nitric oxide inhibition abolishes sleep-wake differences in cerebral circulation.	2001 Jun	11356615
Immunostimulation of rat primary astrocytes decreases intracellular ATP level.	2001 Jun 1	11384613
Wogonin, baicalin, and baicalein inhibition of inducible nitric oxide synthase and cyclooxygenase-2 gene expressions induced by nitric oxide synthase inhibitors and lipopolysaccharide.	2001 Jun 1	11331078
The role of nitric oxide in development of topographic precision in the retinotectal projection of chick.	2001 Jun 15	11404417
The cerebrovascular response to elevated potassium--role of nitric oxide in the in vitro model of isolated rat middle cerebral arteries.	2001 Jun 22	11403958
The influence of nitric oxide donors on the responses to nitrergic nerve stimulation in the mouse duodenum.	2001 Jun 8	11399268
Involvement of cyclooxygenase-derived prostaglandin E2 and nitric oxide in the protection of rat pancreas afforded by low dose of lipopolysaccharide.	2001 Mar	11321505
The role of nitric oxide and the renin-angiotensin system in salt-restricted Dahl rats.	2001 Mar	11281241
Diabetes potentiates acetylcholine-induced relaxation in rabbit renal arteries.	2001 Mar	11275003
Marked variation in responses to long-term nitric oxide inhibition during pregnancy in outbred rats from two different colonies.	2001 Mar	11262473
Tecto-isthmo-optic transmission in pigeons is mediated by glutamate and nitric oxide.	2001 Mar 1	11306192
Protein and DNA oxidation in spinal injury: neurofilaments--an oxidation target.	2001 Mar 15	11295359
Angiotensin type 1 receptor antagonism and ACE inhibition produce similar renoprotection in N(omega)-nitro-L>-arginine methyl ester/spontaneously hypertensive rats.	2001 May	11358938
Nitric oxide deficiency contributes to impairment of airway relaxation in cystic fibrosis mice.	2001 May	11350833
Role of nitric oxide (NO) in pulmonary dysfunction associated with experimental cirrhosis.	2001 May	11311311
Pregnancy enhances G protein activation and nitric oxide release from uterine arteries.	2001 May	11299208
Responsiveness of canine bronchial vasculature to excitatory stimuli and to cooling.	2001 May	11290517
Lead-cadmium interaction effect on the responsiveness of rat mesenteric vessels to norepinephrine and angiotensin II.	2001 May 21	11369112
Failure of L-nitroarginine to inhibit the activity of aortic inducible nitric oxide synthase.	2001 May-Jun	11399899
Epoxygenase metabolites contribute to nitric oxide-independent afferent arteriolar vasodilation in response to bradykinin.	2001 May-Jun	11399897
Nonvasomotor influence of sodium nitroprusside on arteriolar remote response to methacholine.	2001 May-Jun	11399894
K(Ca) channel-opening activity of Ginkgo Biloba extracts and ginsenosides in cultured endothelial cells.	2001 May-Jun	11380519
Defective hippocampal mossy fiber long-term potentiation in endothelial nitric oxide synthase knockout mice.	2001 Sep 1	11391779

Patents

Sample Use Guides

In Vivo Use Guide

Rats: Nitroarginine inhibits NO synthase activity in the brain after i.p. administration of 5 or 50 mg/kg.

Route of Administration: Intraperitoneal

In Vitro Use Guide

The vasodilator responses evoked by low doses of 5-HT (5 x 10(-10)-10(-8) mol) were almost abolished by Nitroarginine (L-NOARG) (at 10(-4) M). The vasodilator response evoked by substance P (5 x 10(-12)-5 x 10(-9) mol) was reduced in the presence of L-NOARG ( 3 x 10(-5) M). The response to substance P was almost abolished by L-NOARG (at 10(-4) M).

Name

Type

Language

NITROARGININE

Systematic Name

English

N.OMEGA.-NITRO-L-ARGININE

Systematic Name

English

(+)-NG-NITROARGININE

Common Name

English

NG-NITRO-L-ARGININE

Common Name

English

NSC-53662

Code

English

L-NG-NITROARGININE

Common Name

English

L-ARGININE, .OMEGA.-NITRO-

Systematic Name

English

L-ORNITHINE, N5-(IMINO(NITROAMINO)METHYL)-

Systematic Name

English

L-ARGININE, NG-NITRO-

Systematic Name

English

ORNITHINE, N5-(NITROAMIDINO)-, L-

Systematic Name

English

.OMEGA.-NITROARGININE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1742