Floxuridine

Alias: 5-Fluorouracil 2''-deoxyriboside; NSC27640;NSC 27640;5-fluorodeoxyuridine; Deoxyfluorouridine; FDUR; NSC-27640; FdUrD; floxuridin; fluorodeoxyuridine; fluorouridine deoxyribose; fluoruridine deoxyribose; FUDF; 5FUDR; FDUR; FUdR; WR138720
Cat No.:V1448 Purity: ≥98%
Floxuridine (5-fluorodeoxyuridine; Deoxyfluorouridine, FDUR, NSC-27640; FdUrD; fluorodeoxyuridine; fluorouridine deoxyribose; FUDF; 5FUDR; FUdR; WR138720) is an antimetabolite anticancer drug approved for the treatment of colon carcinoma and colorectal cancer that has metastasized to the liver.
Floxuridine Chemical Structure CAS No.: 50-91-9
Product category: DNA(RNA) Synthesis
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Floxuridine (5-fluorodeoxyuridine; Deoxyfluorouridine, FDUR, NSC-27640; FdUrD; fluorodeoxyuridine; fluorouridine deoxyribose; FUDF; 5FUDR; FUdR; WR138720) is an antimetabolite anticancer drug approved for the treatment of colon carcinoma and colorectal cancer that has metastasized to the liver.

Biological Activity I Assay Protocols (From Reference)
Targets
DNA synthesis; Bacterial; HSV; CMV
ln Vitro

Floxuridine surpasses the corresponding 5'-O-mono amino acid ester prodrugs in its affinity for PEPT1. Human T-lymphoblast leukemia cells are inhibited in their growth by the synergistic combination of leucovorin and fluorouracil[1]. The absorption of [(3)H]-inosine and [(3)H]-adenosine is considerably inhibited by floxuridine (60–70% of control); however, the potency of its amino acid ester prodrugs, such as Lys, Asp, Phe, and Val esters, is significantly reduced (10–30% of control).[3] After 36 days, floxuridine inhibits cell proliferation by over 50% when compared to untreated control cells; however, the number of cells increases fourfold when compared to the initial density. In vitro, floxuridine has long-lasting effects on human Tenon's capsule fibroblast proliferation. [4] Because of its short half life, steep dose response curve, high total body clearance, and high hepatic extraction, floxuridine (FUDR) is a great drug for hepatic artery infusion (HAI). [5]

ln Vivo

Cell Assay
Cell Line: Ovarian cancer cells
Concentration: 0-25 μM
Incubation Time: 4, 8, 24 hours
Result: Was potentiated the sensitivity by PARP inhibitors.
Animal Protocol
C57BL/6 mice injected with S. aureus
0.5-1.25 mg/kg
once per day for 7 days or single dose
References

[1]. Mol Pharm . 2008 Sep-Oct;5(5):717-27.

[2]. Cancer Treat Rep . 1987 Apr;71(4):381-9.

[3]. Biol Pharm Bull . 2006 Feb;29(2):247-52.

[4]. Arch Ophthalmol . 1992 Aug;110(8):1150-4.

[5]. Mol Cancer Ther . 2009 May;8(5):1015-25.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C9H11FN2O5
Molecular Weight
246.19
Exact Mass
246.07
Elemental Analysis
C, 43.91; H, 4.50; F, 7.72; N, 11.38; O, 32.49
CAS #
50-91-9
Related CAS #
50-91-9
Appearance
White powder
SMILES
C1[C@@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)F)CO)O
InChi Key
ODKNJVUHOIMIIZ-RRKCRQDMSA-N
InChi Code
InChI=1S/C9H11FN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1
Chemical Name
5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
Synonyms
5-Fluorouracil 2''-deoxyriboside; NSC27640;NSC 27640;5-fluorodeoxyuridine; Deoxyfluorouridine; FDUR; NSC-27640; FdUrD; floxuridin; fluorodeoxyuridine; fluorouridine deoxyribose; fluoruridine deoxyribose; FUDF; 5FUDR; FDUR; FUdR; WR138720
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: 49~125 mg/mL (199.0~507.7 mM)
Water: ~49 mg/mL (~199.0 mM)
Ethanol: ~49 mg/mL (~199.0 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (8.45 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 (8.45 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 (8.45 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.


Solubility in Formulation 4: 100 mg/mL (406.19 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.0619 mL 20.3095 mL 40.6190 mL
5 mM 0.8124 mL 4.0619 mL 8.1238 mL
10 mM 0.4062 mL 2.0310 mL 4.0619 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
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
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:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
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.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT00492999 Active
Recruiting
Drug: floxuridine
Drug: fluorouracil
Colorectal Cancer
Metastatic Cancer
Memorial Sloan Kettering
Cancer Center
May 2007 Phase 2
NCT00410956 Active
Recruiting
Drug: floxuridine
Drug: dexamethasone
Liver Cancer Memorial Sloan Kettering Cancer
Center
May 2007 Phase 2
NCT01862315 Active
Recruiting
Drug: Floxuridine (FUDR)
Drug: dexamethasone
Cholangiolar Carcinoma
Cholangiocellular Carcinoma
Memorial Sloan Kettering Cancer
Center
May 2013 Phase 2
NCT00059930 Active
Recruiting
Drug: floxuridine
Drug: fluorouracil
Colorectal Cancer
Metastatic Cancer
Memorial Sloan Kettering Cancer
Center
January 2003 Phase 1
NCT03693807 Active
Recruiting
Drug: Floxuridine (FUDR)
Drug: Gemcitabine
Febrile Neutropenia
Cholangiocarcinoma
Memorial Sloan Kettering Cancer
Center
October 18, 2018 Phase 2
Biological Data
  • The metabolic pathway of floxuridine and floxuridine prodrugs with enzymes. Mol Pharm . 2008 Sep-Oct;5(5):717-27.
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