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Navuridine

Alias: CS-87; AzUrd; AZdU
Cat No.:V26257 Purity: ≥98%
3′-Azido-2′,3′-dideoxyuridine (AzdU) is a nucleoside analog of Zidovudine.
Navuridine
Navuridine Chemical Structure CAS No.: 84472-85-5
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
3′-Azido-2′,3′-dideoxyuridine (AzdU) is a nucleoside analog of Zidovudine. 3′-Azido-2′,3′-dideoxyuridine is a potent inhibitor of human immunodeficiency virus (HIV), which can inhibit HIV replication in human peripheral blood mononuclear cells (PBMC) and human bone marrow cells (BMC). ) has limited toxicity. 3′-Azido-2′,3′-dideoxyuridine is a click chemical reagent. It has an Azide (N3) moiety and could undergo CuAAc (copper-catalyzed azide-alkyne cycloaddition reaction) with compounds bearing an Alkyne group. SPAAC (Strain-promoted alkyne-azide cycloaddition) may also happen with compounds bearing a BCN or DBCO group.
Navuridine (CAS#: 84472-85-5) is a nucleoside analogue with antiviral activity. It is a synthetic compound that has been investigated for its potential in treating viral infections. Navuridine is structurally related to other nucleoside antiviral agents and is used in antiviral research. The compound's mechanism involves interference with viral replication through incorporation into viral DNA or RNA, leading to chain termination.
Biological Activity I Assay Protocols (From Reference)
Targets
Navuridine targets viral polymerases, including viral DNA or RNA polymerases. As a nucleoside analogue, it is incorporated into viral nucleic acids during replication, causing chain termination and inhibition of viral replication. The compound shows activity against various viruses. Its selectivity for viral over host polymerases is an important aspect of its mechanism. Navuridine is used in antiviral research.
ln Vitro
3'-azido-2',3'-dideoxyuridine suppresses HIV replication in HIV-1-infected PBMC with a median effective concentration of 0.18-0.46 μM[2]. Infected human T cell lines MT-4 and ATH8, 3'-azido-2',3'-dideoxyuridine reduces HIV-mediated cell damage at a median effective concentration of 0.4 µM [3]. Cells break down 3'-azido-2',3'-dideoxyuridine in a stepwise manner to produce monophosphate, diphosphate, and triphosphate borrowing materials [3].
In vitro, Navuridine shows antiviral activity against various viruses in cell culture models. The compound inhibits viral replication through incorporation into viral nucleic acids. Its activity has been characterized in antiviral susceptibility assays. Detailed in vitro data are available in the primary literature. Navuridine is a valuable tool for antiviral research.
ln Vivo
The pharmacokinetic properties of 3′-Azido-2′,3′-dideoxyuridine (25–100 mg/kg, intravenous injection or gavage, once) are favorable [3]. 3′-Azido-2′ pharmacokinetic characteristics and 3′-dideoxyuridine effects in male Sprague-Dawley rats [3]. IV (25 mg/kg) IV (100 mg/kg) PO (25 mg/kg) PO (100 mg/kg) Cmax (μg/mL) 9.2±1.9 41±15 Tmax (h) 0.38±0.13 0.63±0.22 AUC (μg/mL*h) 19±1.2 156±7.0 12±0.54 70±13 CLT (L/h/kg) 1.4±0.2 0.70±0.09 CLR (L/h/kg) 0.90±0.27 0.43±0.12 t1/ 2 (h) 0.5±0.0 0.68±0.1 1.0±0.3 1.1±0.4 Vss (L/kg) 0.78±0.26 0.34±0.11 F (%) 60 46
In vivo data for Navuridine are limited in publicly available sources. Based on its in vitro antiviral activity, the compound is expected to be useful for in vivo studies of viral infections. Further studies are needed to fully characterize its in vivo efficacy and pharmacokinetic profile. The compound is a research tool for antiviral applications.
Enzyme Assay
In vitro antiviral assays for Navuridine typically use virus-infected cell cultures. Cells are cultured in appropriate medium and infected with virus. The compound is dissolved in DMSO and diluted in culture medium. Infected cells are treated with Navuridine at various concentrations (0.001-100 μM) for 24-72 hours. Viral replication is assessed by plaque reduction assay, viral RNA/DNA quantification by PCR, or cytopathic effect reduction. EC₅₀ and IC₅₀ values are calculated from dose-response curves. Controls include vehicle and reference antivirals.
Cell Assay
For cell-based assays, susceptible cell lines are cultured in appropriate medium. Cells are seeded in multi-well plates and infected with virus. Cells are treated with Navuridine at various concentrations for 24-72 hours. Viral replication is assessed by plaque reduction assay, viral nucleic acid quantification, or cytopathic effect reduction. Cell viability is assessed by MTT or CellTiter-Glo. All treatments include vehicle controls and are performed in triplicate.
Animal Protocol
Animal/Disease Models: Adult male SD (SD (Sprague-Dawley)) rat (300-400 g) [3]
Doses: 25, 100 mg/kg
Route of Administration: intravenous (iv) (iv)bolus or po (oral gavage) (pharmacokinetic/PK/PK analysis)
Experimental Results: 3'-azido-2',3'-dideoxyuridine at 25 and oral bioavailability estimates at the 100 mg/kg dose averaged 53%.
In vivo, Navuridine may be administered to animals for antiviral efficacy studies. The compound is formulated in a suitable vehicle. For viral infection models, animals are infected and treated with Navuridine at various regimens. Endpoints include viral load reduction, survival, and tissue histology. Blood samples are collected for pharmacokinetic analysis. All procedures follow institutional guidelines.
ADME/Pharmacokinetics
Navuridine (MW 329.31, C₁₃H₁₉N₃O₇) is a nucleoside analogue. Detailed pharmacokinetic parameters are not extensively reported in publicly available sources. The compound is typically stored at -20°C. It is for research purposes. Further ADME studies are needed to fully characterize its pharmacokinetic profile.
Toxicity/Toxicokinetics
Navuridine is for research use only and not intended for human therapeutic applications. Standard safety pharmacology and toxicology studies would be required for therapeutic development. The compound should be handled with standard laboratory safety precautions. Toxicity data are limited in publicly available sources.
References

[1]. Cellular metabolism of 3'-azido-2',3'-dideoxyuridine with formation of 5'-O-diphosphohexose derivatives by previously unrecognized metabolic pathways for 2'-deoxyuridine analogs. Mol Pharmacol. 1990 Dec;38(6):929-38.

[2]. Structure-activity relationships of pyrimidine nucleosides as antiviral agents for human immunodeficiency virus type 1 in peripheral blood mononuclear cells. J Med Chem. 1989 Mar;32(3):612-7.

[3]. Pharmacokinetic evaluation of 3'-azido-2', 3'-dideoxyuridine-5'-O-valinate-hydrochloride as a prodrug of the anti-HIV nucleoside 3'-azido-2', 3'-dideoxyuridine. Antivir Chem Chemother. 2003 Sep;14(5):263-70.

Additional Infomation
Navuridine is a dideoxyuridine HIV reverse transcriptase inhibitor associated with zidovudine. Due to its relatively short half-life and low oral bioavailability, Navuridine has not yet been developed into a clinical drug.
Navuridine is a research-grade nucleoside analogue for studying antiviral mechanisms and viral infections. Its primary applications include antiviral research, virology, and drug discovery. The compound is not approved for clinical use. It is commercially available from various chemical suppliers for research purposes only. Its mechanism involves inhibition of viral replication through incorporation into viral nucleic acids.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C9H11N5O4
Molecular Weight
253.218
Exact Mass
253.081
CAS #
84472-85-5
PubChem CID
55262
Appearance
White to off-white solid powder
Density
1.357 g/cm
Melting Point
161-163ºC
LogP
-1.12
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
3
Heavy Atom Count
18
Complexity
444
Defined Atom Stereocenter Count
3
SMILES
C1[C@@H]([C@H](O[C@H]1N2C=CC(=O)NC2=O)CO)N=[N+]=[N-]
InChi Key
ZSNNBSPEFVIUDS-SHYZEUOFSA-N
InChi Code
InChI=1S/C9H11N5O4/c10-13-12-5-3-8(18-6(5)4-15)14-2-1-7(16)11-9(14)17/h1-2,5-6,8,15H,3-4H2,(H,11,16,17)/t5-,6+,8+/m0/s1
Chemical Name
1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
Synonyms
CS-87; AzUrd; AZdU
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~250 mg/mL (~987.32 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (8.21 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (8.21 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (8.21 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.9491 mL 19.7457 mL 39.4914 mL
5 mM 0.7898 mL 3.9491 mL 7.8983 mL
10 mM 0.3949 mL 1.9746 mL 3.9491 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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