NAV

Nitroarginine

Identification

Generic Name
Nitroarginine
DrugBank Accession Number
DB04223
Background

An inhibitor of nitric oxide synthetase 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. (Neurochem Res 1995:200(4):451-6)

Type
Small Molecule
Groups
Experimental, Investigational
Structure
3D
Similar Structures
Weight
Average: 219.1985
Monoisotopic: 219.096753929
Chemical Formula
C6H13N5O4
Synonyms
  • L-NNA
  • N(gamma)-nitro-L-arginine
  • Ngamma-Nitro-L-arginine
  • omega-Nitroarginine
External IDs
  • NSC-53662
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UNitric oxide synthase, endothelialNot AvailableHumans
UNitric oxide synthase, brainNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
L-alpha-amino acids
Alternative Parents
Nitro fatty acids / Nitroguanidines / Nitramines / Amino acids / Propargyl-type 1,3-dipolar organic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Carboximidamides / Organopnictogen compounds / Organic zwitterions
show 4 more
Substituents
Aliphatic acyclic compound / Allyl-type 1,3-dipolar organic compound / Amine / Amino acid / Carbonyl group / Carboximidamide / Carboxylic acid / Fatty acid / Fatty acyl / Guanidine
show 18 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
guanidines, non-proteinogenic L-alpha-amino acid, L-arginine derivative, N-nitro compound (CHEBI:27960)
Affected organisms
Not Available

Chemical Identifiers

UNII
7O8V7H6P2J
CAS number
2149-70-4
InChI Key
MRAUNPAHJZDYCK-BYPYZUCNSA-N
InChI
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
IUPAC Name
(2S)-2-amino-5-(N'-nitrocarbamimidamido)pentanoic acid
SMILES
N[C@@H](CCCNC(=N)N[N+]([O-])=O)C(O)=O

References

General References
Not Available
KEGG Compound
C03417
PubChem Compound
440005
PubChem Substance
46508354
ChemSpider
389023
BindingDB
50225106
ChEBI
27960
ChEMBL
CHEMBL227744
ZINC
ZINC000019796052
PDBe Ligand
NRG
Wikipedia
Nitroarginine
PDB Entries
1ed5 / 1k2r / 3idm / 4uqr / 8nse

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.874 mg/mLALOGPS
logP-2.8ALOGPS
logP-3.8Chemaxon
logS-2.4ALOGPS
pKa (Strongest Acidic)1.9Chemaxon
pKa (Strongest Basic)9.22Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area154.37 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity59.91 m3·mol-1Chemaxon
Polarizability20.19 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.8729
Blood Brain Barrier+0.5504
Caco-2 permeable-0.6463
P-glycoprotein substrateNon-substrate0.5623
P-glycoprotein inhibitor INon-inhibitor0.9627
P-glycoprotein inhibitor IINon-inhibitor0.9694
Renal organic cation transporterNon-inhibitor0.9008
CYP450 2C9 substrateNon-substrate0.8412
CYP450 2D6 substrateNon-substrate0.8015
CYP450 3A4 substrateNon-substrate0.7115
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9308
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.897
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9946
Ames testAMES toxic0.8475
CarcinogenicityNon-carcinogens0.7987
BiodegradationReady biodegradable0.8664
Rat acute toxicity2.3722 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8183
hERG inhibition (predictor II)Non-inhibitor0.9218
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-00di-9300000000-95f7951b9081bdfa98f6
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-156.9670803
predicted
DarkChem Lite v0.1.0
[M-H]-149.23561
predicted
DeepCCS 1.0 (2019)
[M+H]+157.0616803
predicted
DarkChem Lite v0.1.0
[M+H]+151.48006
predicted
DeepCCS 1.0 (2019)
[M+Na]+156.7704803
predicted
DarkChem Lite v0.1.0
[M+Na]+157.5732
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Nitric oxide synthase, endothelial
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Tetrahydrobiopterin binding
Specific Function
Produces nitric oxide (NO) which is implicated in vascular smooth muscle relaxation through a cGMP-mediated signal transduction pathway. NO mediates vascular endothelial growth factor (VEGF)-induce...
Gene Name
NOS3
Uniprot ID
P29474
Uniprot Name
Nitric oxide synthase, endothelial
Molecular Weight
133287.62 Da
References
  1. Raman CS, Li H, Martasek P, Southan G, Masters BS, Poulos TL: Crystal structure of nitric oxide synthase bound to nitro indazole reveals a novel inactivation mechanism. Biochemistry. 2001 Nov 13;40(45):13448-55. [Article]
  2. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Details2. Nitric oxide synthase, brain
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Tetrahydrobiopterin binding
Specific Function
Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In the brain and peripheral nervous system, NO displays many properties of a neurotransmitter. P...
Gene Name
NOS1
Uniprot ID
P29475
Uniprot Name
Nitric oxide synthase, brain
Molecular Weight
160969.095 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 28, 2022 01:17