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
Structure for Nitroarginine (DB04223)
- 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
Pharmacology
- Indication
Not Available
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UNitric oxide synthase, endothelial Not Available Humans UNitric oxide synthase, brain Not Available Humans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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
- External Links
- 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
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
Property Value Source Water Solubility 0.874 mg/mL ALOGPS logP -2.8 ALOGPS logP -3.8 Chemaxon logS -2.4 ALOGPS pKa (Strongest Acidic) 1.9 Chemaxon pKa (Strongest Basic) 9.22 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 154.37 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 59.91 m3·mol-1 Chemaxon Polarizability 20.19 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.8729 Blood Brain Barrier + 0.5504 Caco-2 permeable - 0.6463 P-glycoprotein substrate Non-substrate 0.5623 P-glycoprotein inhibitor I Non-inhibitor 0.9627 P-glycoprotein inhibitor II Non-inhibitor 0.9694 Renal organic cation transporter Non-inhibitor 0.9008 CYP450 2C9 substrate Non-substrate 0.8412 CYP450 2D6 substrate Non-substrate 0.8015 CYP450 3A4 substrate Non-substrate 0.7115 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.9308 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.897 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9946 Ames test AMES toxic 0.8475 Carcinogenicity Non-carcinogens 0.7987 Biodegradation Ready biodegradable 0.8664 Rat acute toxicity 2.3722 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8183 hERG inhibition (predictor II) Non-inhibitor 0.9218
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- 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
- 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]
- 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]
- 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
- 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