Floxuridine

Floxuridine Basic information
Product Name:Floxuridine
Synonyms:Floxuridine (250 mg);5-F-2'--dU;Floxuridine API;1-(2-Deoxy-beta-D-ribofuranosyl)-5-fluorouracil 5-Fluoro-2'-deoxy-beta-uridine Floxuridine FUDR;2'-deoxy-5-fluorouridine 5'-phosphate;5-fluoro-1-[(2S,4R,5S)-4-hydroxy-5-(hydroxyMethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyriMidine-2,4-dione;Floxuridine (Fludara);5-Fluoro-1-((2R,4S,5R)-4-hydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione
CAS:50-91-9
MF:C9H11FN2O5
MW:246.19
EINECS:200-072-5
Product Categories:Intermediates & Fine Chemicals;Pharmaceuticals;Pyrimidine series;Biochemistry;Chemical Reagents for Pharmacology Research;Nucleosides and their analogs;FINE Chemical & INTERMEDIATES;Pyridines, Pyrimidines, Purines and Pteredines;Nucleosides, Nucleotides & Related Reagents;Bases & Related Reagents;Carbohydrates & Derivatives;Nucleotides;PAH;50-91-9
Mol File:50-91-9.mol
Floxuridine Structure
Floxuridine Chemical Properties
Melting point 148 °C(lit.)
alpha 35.9 º (c=1, water)
Boiling point 150 °C
density 1.3751 (estimate)
storage temp. room temp
solubility Soluble to 100 mM in water and to 100 mM in DMSO
pkapKa 7.44 (Uncertain)
form Powder
color White to almost white
Water Solubility soluble
Merck 14,4112
BRN 2645818
Stability:Stable. Incompatible with strong oxidizing agents.
InChIKeyODKNJVUHOIMIIZ-GFCOJPQKSA-N
CAS DataBase Reference50-91-9(CAS DataBase Reference)
NIST Chemistry ReferenceUridine, 2'-deoxy-5-fluoro-(50-91-9)
EPA Substance Registry SystemFloxuridine (50-91-9)
Safety Information
Hazard Codes Xn,T,Xi
Risk Statements 22-68-36/37/38-40-20/21/22
Safety Statements 22-36-36/37/39-26
RIDADR UN 2811 6.1/PG 3
WGK Germany 3
RTECS YU7525000
10-23
Hazard Note Toxic
HazardClass 6.1
PackingGroup III
HS Code 29349990
Hazardous Substances Data50-91-9(Hazardous Substances Data)
ToxicityLD50 oral in rat: 215mg/kg
MSDS Information
ProviderLanguage
Fluorodeoxyuridine English
SigmaAldrich English
ACROS English
ALFA English
Floxuridine Usage And Synthesis
DescriptionFloxuridine is a nucleoside analog that inhibits the enzyme ribonucleotide reductase, which is involved in the synthesis of DNA. Floxuridine has been shown to inhibit the growth of cancer cells and induce apoptosis in vivo. Floxuridine has also been shown to inhibit tumor growth in animal models by inhibiting the production of reactive oxygen species and upregulating tumor suppressor genes, such as p53. This drug also has inhibitory effects on enzymes that are involved in cell proliferation, such as protein kinase C and tyrosine kinases.
Chemical PropertiesWhite Solid
OriginatorFUDR,Roche,US ,1971
UsesFloxuridine USP is used in Palliative treatment of gastrointestinal adenocarcinoma with liver metastases.
UsesAntiviral; antineoplastic.
Usesrenal function diagnosis
DefinitionChEBI: A pyrimidine 2'-deoxyribonucleoside compound having 5-fluorouracil as the nucleobase; used to treat hepatic metastases of gastrointestinal adenocarcinomas and for palliation in malignant neoplasms of the liver and gastrointestinal tract.
Manufacturing ProcessCells of Streptococcus fecalis (ATCC-8043) were grown in the AOAC folic acid assay medium [Lepper, Official and Tentative Methods of the Association of Official Agricultural Chemists, Washington, D.C., 7th edition, 784 (1950)], supplemented with 2 mg per liter of thymine; following the teachings of Prusoff, Proc. Soc. Exp. Biol. & Med. 85, 564 (1954). After 20 hours of incubation at 37°C, the cells were harvested by centrifugation. The collected cells were washed three times with four volumes of potassium phosphate buffer solution (M/15 aqueous KH2PO4 solution, adjusted to pH 8.0 by addition of 2 N aqueous KOH) and the wet cells were weighed. The cells were finally suspended in the above potassium phosphate buffer solution and ground in a glass tissue homogenizer.
An amount of enzyme preparation equivalent to 900 mg of wet cells was made up to 25 ml with the above potassium phosphate buffer solution. 150 mg (1.15 mmol) of 5-fluorouracil and 1.0 gram of thymidine (4.12 mmol) were dissolved in 15 ml of the above potassium phosphate buffer solution. The mixture was incubated at 37°C for 18 hours. After this time, enzyme action was stopped by the addition of four volumes of acetone and one volume of peroxide-free diethyl ether. The precipitated solids were removed by filtration, and the filtrate was evaporated under nitrogen at reduced pressure until substantially all volatile organic solvent had been removed. About 20 ml of aqueous solution, essentially free of organic solvent, remained. This solution was diluted to 100 ml with distilled water.
Ten microliters of this solution were submitted to descending chromatography on a paper buffered with 0.2 N KH2PO4 (pH 7.8), using a solvent mixture of tertiary amyl alcohol:water:n-butyl ether (80:13:7 by volume). A spot visible under ultraviolet light and having Rf = 0.55 was leached with 0.1 N HCl and assayed for deoxyribose by the method of Stumpf, J. Biol. Chem. 169, 367 (1947). This analysis indicated the presence of a minimum of 85.5 mg (0.35 mmol) of 2'-deoxy-5-fluorouridine in the protein-free reaction mixture according to US Patent 2,885,396. An alternate route from 5-fluorouracil via the mercury derivative, through toluoyl deoxyuridines and then toluoyl removal to give floxuridine is described in US Patent 3,041,335.


Brand nameFudr (Mayne).
Therapeutic FunctionAntiviral, Cancer chemotherapy
General DescriptionThe drug is available as a 500-mg vial of lyophilized powder.The drug is used to treat metastatic GI adenocarcinoma.The mechanism of action of this fluoropyrimidine deoxynucleosideanalog involves metabolic conversion to 5-fluorouracil(5-FU) metabolites resulting in inhibition of TSthus disrupting DNA synthesis, function, and repair.Resistance can occur because of increased expression of TS,decreased levels of reduced folate 5,10-methylenetetrahydrofolate,increased activity of DNA repair enzymes, and increasedexpression of dihydropyrimidine dehydrogenase(the major catabolic enzyme). The drug is poorly absorbedfrom the GI tract and is extensive metabolized to 5-FU and5-FU metabolites. Dihydropyrimidine dehydrogenase is themain enzyme responsible for 5-FU catabolism, and it ispresent in liver, GI mucosa, white blood cells, and kidney.The drug interaction and toxicity profiles are equivalent tothose of 5-FU.
General DescriptionInhibits DNA synthesis.
Health HazardACUTE/CHRONIC HAZARDS: Floxuridine is highly toxic by ingestion.
Fire HazardFlash point data for Floxuridine are not available, but Floxuridine is probably combustible.
Biochem/physiol ActionsAntineoplastic drug that acts as a potent inhibitor of thymidylate synthetase Resistance to FUdR can develop in cancer cell cultures, among other means, by low-level Mycoplasma infection.
Safety ProfilePoison by ingestion. Moderately toxic by intraperitoneal route. An experimental teratogen. Other experimental reproductive effects. Human systemic effects: hypermotitity, diarrhea, nausea, vomiting and other gastrointestinal effects, allergic dermatitis, and bone marrow changes. Human mutation data reported. When heated to decomposition it emits very toxic fumes of Fand NOx.
SynthesisFluoxuridine, 5-fluoro-1-(2-deoxyribofuranosyl)-pyrimidin-2,4-(1H,3H)- dione (30.1.3.5), is a pyrimidine nucleotide made by reacting fluorouracil (30.1.3.3) with 2-deoxyribofuranosylbromide in the presence of silver or mercury salts.

Synthesis_50-91-9

Floxuridine Preparation Products And Raw materials
Raw materials5-Fluorouracil-->Thymidine
Fluorine Deoxynucleotide 5-FLUORO 2'-DEOXYURIDINE 5'-MONOPHOSPHATE, DIAMMONIUM SALT, [6-3H]- 5-FLUOROURIDINE-[6-3H] 3',5'-DI-O-BENZOYL-5-FLUORO-2'-O-METHYLURIDINE 5'-O-(4,4'-DIMETHOXYTRITYL)-5-FLUORODEOXYURIDINE-3'-(2-CYANOETHYL-N,N-DIISOPROPYL)PHOSPHORAMIDITE Floxuridine 2'-Deoxyuridine Hexaflumuron 2'-DEOXY-5-FLUOROURIDINE, [3H]- 5-FLUOROURIDINE T 506 Chlorfluazuron 5-fluorouridine 5'-triphosphate 5-FLUOROURIDINE 5'-MONOPHOSPHATE, DIAMMONIUM SALT 5-FLUOROURIDINE, [2-14C]- 5-Fluorouridine 3',5'-DI-O-ACETYL-5-FLUORO-2'-O-METHYLURIDINE

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