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Floxuridine

Floxuridine Structure
Floxuridine
  • CAS No.50-91-9
  • Chemical Name:Floxuridine
  • CBNumber:CB3210097
  • Molecular Formula:C9H11FN2O5
  • Formula Weight:246.19
  • MOL File:50-91-9.mol
Floxuridine Property
  • Melting point: :148 °C(lit.)
  • Boiling point: :150 °C
  • alpha  :35.9 º (c=1, water)
  • Density  :1.3751 (estimate)
  • storage temp.  :room temp
  • pka :pKa 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.
  • InChIKey :ODKNJVUHOIMIIZ-GFCOJPQKSA-N
  • CAS DataBase Reference :50-91-9(CAS DataBase Reference)
  • FDA UNII :039LU44I5M
  • NCI Dictionary of Cancer Terms :floxuridine
  • NCI Drug Dictionary :floxuridine
  • NIST Chemistry Reference :Uridine, 2'-deoxy-5-fluoro-(50-91-9)
  • EPA Substance Registry System :Floxuridine (50-91-9)
Safety
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordDanger
  • Hazard statements H302-H341-H360-H301
  • Precautionary statements P264-P270-P301+P310+P330-P405-P501-P201-P280-P301+P312a-P308+P313-P501a
Floxuridine Price More Price(14)
  • Brand: Sigma-Aldrich
  • Product number: 343333
  • Product name : 5-Fluoro-2?-deoxyuridine
  • Purity: 
  • Packaging: 50mg
  • Price: $119.32
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: PHR2589
  • Product name : Floxuridine
  • Purity: 
  • Packaging: 500MG
  • Price: $149
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: 1271008
  • Product name : Floxuridine
  • Purity: United States Pharmacopeia (USP) Reference Standard
  • Packaging: 250mg
  • Price: $366
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: TCI Chemical
  • Product number: D2235
  • Product name : 2'-Deoxy-5-fluorouridine
  • Purity: >98.0%(HPLC)(T)
  • Packaging: 1g
  • Price: $327
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: TCI Chemical
  • Product number: D2235
  • Product name : 2'-Deoxy-5-fluorouridine
  • Purity: >98.0%(HPLC)(T)
  • Packaging: 100mg
  • Price: $63
  • Updated: 2021/03/22
  • Buy: Buy

Floxuridine Chemical Properties,Usage,Production

  • Chemical Properties White Solid
  • Originator FUDR,Roche,US ,1971
  • Uses Floxuridine USP is used in Palliative treatment of gastrointestinal adenocarcinoma with liver metastases.
  • Uses Antiviral; antineoplastic.
  • Uses renal function diagnosis
  • Definition ChEBI: 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 Process Cells 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 name Fudr (Mayne).
  • Therapeutic Function Antiviral, Cancer chemotherapy
  • General Description The 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 Description Inhibits DNA synthesis.
  • Health Hazard ACUTE/CHRONIC HAZARDS: Floxuridine is highly toxic by ingestion.
  • Fire Hazard Flash point data for Floxuridine are not available, but Floxuridine is probably combustible.
  • Safety Profile Poison 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.
  • Chemical Synthesis Fluoxuridine, 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.

Floxuridine Preparation Products And Raw materials
Raw materials
Preparation Products
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50-91-9, FloxuridineRelated Search:
  • 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
  • Fluoro-2′-deoxyuri
  • 5-fluoro-1-(4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
  • 5-fluoro-1-(4-hydroxy-5-methylol-tetrahydrofuran-2-yl)pyrimidine-2,4-quinone
  • 5-fluoro-1-[4-hydroxy-5-(hydroxymethyl)-2-tetrahydrofuranyl]pyrimidine-2,4-dione
  • 5-fluoro-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
  • 5-fluoro-1-[4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4(1H,3H)-dione
  • 5-fluoro-1-[4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione
  • 5-Fluoro-2'-de
  • 5-FDU, 1-(2-Deoxy-beta-D-ribofuranosyl)-5-fluorouracil
  • 5-Fluoro-2&priMe
  • Floxuridine, >=98%
  • 5-F-2'-deoxyuridine
  • (+)-5-FLUORO-2''-DEOXYURIDINE 98.5+%
  • 1-beta-d-2’-deoxyribofuranosyl-5-flurouracil
  • 1beta-D-2'-Deoxyribofuranosyl-5-fluorouracil
  • 2’-deoxy-5-fluoro-uridin
  • 5-fluor-1-(beta-2’-deoxyribofuranosyl)pyrimidin-2,4(1h,3h)-dion
  • 5-Fluor-1-(beta-2'-deoxyribofuranosyl)pyrimidin-2,4(1H,3H)-dion
  • 5-Fluoro-2'-deoxyiridine
  • 5-Fluorouracil 2'-deoxyriboside
  • 5-Fluorouracil deoxyriboside
  • 5-fluorouracil2’-deoxyriboside
  • 5-fluorouracildeoxyriboside
  • 5-FUDR
  • (+)-5-FLUORODEOXYURIDINE
  • 5-FLUORODEOXYURIDINE
  • 5-FDU
  • 5-FLOXURIDINE
  • 5-FLUORO-1-((2R,4S,5R)-4-HYDROXY-5-HYDROXYMETHYL-TETRAHYDRO-FURAN-2-YL)-1H-PYRIMIDINE-2,4-DIONE
  • 5-FLUORO-2'-DEOXY-BETA-URIDINE
  • (+)-5-FLUORO-2'-DEOXYURIDINE
  • 5-FLUORO-2'-DEOXYURIDINE
  • 5-FLUORO-2-DEOXYURIDINE
  • 2-DEOXY-5'-FLUOROURIDINE
  • 1-(2-DEOXY-BETA-D-RIBOFURANOSYL)-5-FLUOROURACIL
  • FDURD
  • fluorodeoxyuridine
  • fluoruridine deoxyribose
  • FLOXURIDINE
  • FUDR
  • Fluoxuridine
  • 2'-DFUR
  • Deoxyfluorouridine,98%
  • 5-Fluoro-2'-deoxyuridine (FUDR)
  • (+)-5-FLUORODEOXYURIDINE, 98+%
  • 5-FLURO-2’-DEOXYURIDINE
  • Floxuridine(5-Fudr)
  • 5-Fluoro-2'-deoxyuridine,98+%
  • (+)-5-Fluoro-2'-deoxyuridine, 99+%
  • 1-(2-Deoxy-b-D-ribofuranosyl)-5-fluorouracil