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Floxuridine

Basic information Safety Supplier Related

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
  • Nucleosides, Nucleotides & Related Reagents
  • PAH
  • Bases & Related Reagents
  • Carbohydrates & Derivatives
  • Nucleotides
  • Pyridines, Pyrimidines, Purines and Pteredines
  • FINE Chemical & INTERMEDIATES
Mol File:
50-91-9.mol
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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. 
2-8°C
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)
NIST Chemistry Reference
Uridine, 2'-deoxy-5-fluoro-(50-91-9)
EPA Substance Registry System
Floxuridine (50-91-9)
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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 Data
50-91-9(Hazardous Substances Data)
Toxicity
LD50 oral in rat: 215mg/kg

MSDS

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Floxuridine Usage And Synthesis

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.

Floxuridine Preparation Products And Raw materials

Raw materials

FloxuridineSupplier

Hongene Biotech Corporation Gold
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021-64757213-
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Kuer Chemical Technology (Beijing) Co., Ltd. Gold
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4008369963
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kuer@kuerhuaxue.com
TOKYO CHEMICAL INDUSTRY CO., LTD. Gold
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03-3668-0489
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Sales-JP@TCIchemicals.com
J & K SCIENTIFIC LTD.
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010-82848833- ;010-82848833-
Email
jkinfo@jkchemical.com;market6@jkchemical.com
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
21-61259100-
Email
sh@meryer.com