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
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
Nitroarginine (LNNA), an analog of L-arginine, is a competitive inhibitor of nitric oxide synthase which has been shown to prevent glutamate toxicity. Nitroarginine has been experimentally tested for its ability to prevent ammonia toxicity and ammonia-induced alterations in brain energy and ammonia metabolites. The Kd value (k(off)/k(on)) of bovine brain cNOS for LNNA was 15 nM. In contrast to the potent and slow onset of LNNA inhibition of brain cNOS, LNNA inhibition of inducible mouse macrophage NOS (iNOS) was weaker (Ki = 4.4 uM) and rapidly reversible. Thus, LNNA was a 300-fold more potent inhibitor of bovine brain cNOS than mouse macrophage iNOS. By inhibiting nitric oxide synthase LNNA causes the selective reduction of blood flow to tumor cells. Despite the potential of LNNA to function as an adjuvant in cancer therapies, its poor solubility and stability have hindered the development of an injectable formulation of LNNA that is suitable for human administration.
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9860150/ |
1 mg/kg/h single, intravenous dose: 1 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
N.OMEGA.-NITRO-L-ARGININE METHYL ESTER plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
6.2 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9860150/ |
1 mg/kg/h single, intravenous dose: 1 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
NITROARGININE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
12.8 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9860150/ |
1 mg/kg/h single, intravenous dose: 1 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
N.OMEGA.-NITRO-L-ARGININE METHYL ESTER plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
208 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9860150/ |
1 mg/kg/h single, intravenous dose: 1 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
NITROARGININE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
0.32 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9860150/ |
1 mg/kg/h single, intravenous dose: 1 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
N.OMEGA.-NITRO-L-ARGININE METHYL ESTER plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
22.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9860150/ |
1 mg/kg/h single, intravenous dose: 1 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
NITROARGININE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effect of 20-HETE inhibition on L-NAME-induced hypertension in rats. | 2018 |
|
| Defective hippocampal mossy fiber long-term potentiation in endothelial nitric oxide synthase knockout mice. | 2001-09-01 |
|
| Arachidonate dilates basilar artery by lipoxygenase-dependent mechanism and activation of K(+) channels. | 2001-07 |
|
| The influence of nitric oxide synthase 1 on blood flow and interstitial nitric oxide in the kidney. | 2001-07 |
|
| The cerebrovascular response to elevated potassium--role of nitric oxide in the in vitro model of isolated rat middle cerebral arteries. | 2001-06-22 |
|
| Failure of L-nitroarginine to inhibit the activity of aortic inducible nitric oxide synthase. | 2001-06-16 |
|
| Epoxygenase metabolites contribute to nitric oxide-independent afferent arteriolar vasodilation in response to bradykinin. | 2001-06-16 |
|
| Nonvasomotor influence of sodium nitroprusside on arteriolar remote response to methacholine. | 2001-06-16 |
|
| The role of nitric oxide in development of topographic precision in the retinotectal projection of chick. | 2001-06-15 |
|
| The influence of nitric oxide donors on the responses to nitrergic nerve stimulation in the mouse duodenum. | 2001-06-08 |
|
| Immunostimulation of rat primary astrocytes decreases intracellular ATP level. | 2001-06-01 |
|
| Wogonin, baicalin, and baicalein inhibition of inducible nitric oxide synthase and cyclooxygenase-2 gene expressions induced by nitric oxide synthase inhibitors and lipopolysaccharide. | 2001-06-01 |
|
| The vascular activity of some isoflavone metabolites: implications for a cardioprotective role. | 2001-06 |
|
| Low-dose nitric oxide inhibition produces a negative sodium balance in conscious dogs. | 2001-06 |
|
| Phytoestrogens restore nitric oxide-mediated relaxation in isolated pulmonary arteries from chronically hypoxic rats. | 2001-06 |
|
| Simulated microgravity enhances vasoconstrictor responsiveness of rat basilar artery. | 2001-06 |
|
| Nitric oxide inhibition abolishes sleep-wake differences in cerebral circulation. | 2001-06 |
|
| K(Ca) channel-opening activity of Ginkgo Biloba extracts and ginsenosides in cultured endothelial cells. | 2001-05-31 |
|
| Lead-cadmium interaction effect on the responsiveness of rat mesenteric vessels to norepinephrine and angiotensin II. | 2001-05-21 |
|
| Angiotensin type 1 receptor antagonism and ACE inhibition produce similar renoprotection in N(omega)-nitro-L>-arginine methyl ester/spontaneously hypertensive rats. | 2001-05 |
|
| Nitric oxide deficiency contributes to impairment of airway relaxation in cystic fibrosis mice. | 2001-05 |
|
| Role of nitric oxide (NO) in pulmonary dysfunction associated with experimental cirrhosis. | 2001-05 |
|
| Pregnancy enhances G protein activation and nitric oxide release from uterine arteries. | 2001-05 |
|
| Responsiveness of canine bronchial vasculature to excitatory stimuli and to cooling. | 2001-05 |
|
| Role of inducible nitric oxide synthase in the pulmonary vascular response to birth-related stimuli in the ovine fetus. | 2001-04-13 |
|
| The dual effect of a nitric oxide donor in nociception. | 2001-04-06 |
|
| Role of endothelial nitric oxide in shear stress-induced vasodilation of human microvasculature: diminished activity in hypertensive and hypercholesterolemic patients. | 2001-04-03 |
|
| Cerebral hyperemia and nitric oxide synthase in rats with ammonia-induced brain edema. | 2001-04 |
|
| Role of nitric oxide in the secondary expansion of a cortical brain lesion from cold injury. | 2001-04 |
|
| Signal transduction pathways involved in kinin B(2) receptor-mediated vasodilation in the rat isolated perfused kidney. | 2001-04 |
|
| Effects of bradykinin on renal nerve stimulation-induced antidiuresis and norepinephrine overflow in anesthetized dogs. | 2001-04 |
|
| NMDA-induced phosphorylation of the microtubule-associated protein MAP-2 is mediated by activation of nitric oxide synthase and MAP kinase. | 2001-04 |
|
| Endothelin-1 induces vasoconstriction on portal-systemic collaterals of portal hypertensive rats. | 2001-04 |
|
| Effect of age on electrical field stimulation (EFS)-induced endothelium-dependent vasodilation in male and female rats. | 2001-04 |
|
| Expression of vascular endothelial growth factor and its receptors is increased, but microvascular relaxation is impaired in patients after acute myocardial ischemia. | 2001-04 |
|
| Protein and DNA oxidation in spinal injury: neurofilaments--an oxidation target. | 2001-03-15 |
|
| Tecto-isthmo-optic transmission in pigeons is mediated by glutamate and nitric oxide. | 2001-03-01 |
|
| Involvement of cyclooxygenase-derived prostaglandin E2 and nitric oxide in the protection of rat pancreas afforded by low dose of lipopolysaccharide. | 2001-03 |
|
| The role of nitric oxide and the renin-angiotensin system in salt-restricted Dahl rats. | 2001-03 |
|
| Diabetes potentiates acetylcholine-induced relaxation in rabbit renal arteries. | 2001-03 |
|
| No parallel relationship between nitric oxide production and wet dog shakes susceptible to nitric oxide synthase inhibitors following systemic administration of paraquat in rats. | 2001-02 |
|
| Short term hypercholesterolemia alters N(G)-nitro-L-arginine- and indomethacin-resistant endothelium-dependent relaxation by acetylcholine in rabbit renal artery. | 2001-02 |
|
| Glucocorticoids inhibit tetrahydrobiopterin-dependent endothelial function. | 2001-01 |
|
| Relative significance of the nitric oxide (NO)/cGMP pathway and K+ channel activation in endothelium-dependent vasodilation in the femoral artery of developing piglets. | 2001-01 |
|
| [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 |
|
| [Intermittent hypoxic training with exogenous nitric oxide improves rat liver mitochondrial oxidation and phosphorylation during acute hypoxia]. | 2001 |
|
| The inhibitory potency and selectivity of arginine substrate site nitric-oxide synthase inhibitors is solely determined by their affinity toward the different isoenzymes. | 2000-11 |
|
| Selective inhibition of constitutive nitric oxide synthase by L-NG-nitroarginine. | 1993-08-24 |
|
| Characterization of three inhibitors of endothelial nitric oxide synthase in vitro and in vivo. | 1990-11 |
|
| L-NG-nitro-arginine and its methyl ester are potent inhibitors of non-adrenergic, non-cholinergic transmission in the rat anococcygeus. | 1990-08 |
Patents
Sample Use Guides
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
Curator's Comment: The effect of L-NG-nitroarginine (L-NOARG) on vasodilatation induced by ATP, substance P, 5-hydroxytryptamine (5-HT), bradykinin and sodium nitroprusside (SNP) was examined in the guinea-pig coronary bed, by use of a Langendorff technique.
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).
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C1742
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| Code System | Code | Type | Description | ||
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DTXSID2042696
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2149-70-4
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DB04223
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440005
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C96232
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PRIMARY | NCIT | ||
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7O8V7H6P2J
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218-418-9
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Nitroarginine
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53662
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ACTIVE MOIETY
PRODRUG (METABOLITE ACTIVE)
