ChemicalBook > CAS DataBase List > Floxuridine

Floxuridine

Product Name
Floxuridine
CAS No.
50-91-9
Chemical Name
Floxuridine
Synonyms
FUDR;5-FUDR;FDUR;5-FLUORODEOXYURIDINE;5-FLUORO-2-DEOXYURIDINE;5-Fluoro-1-((2R,4S,5R)-4-hydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione;Floxuridin;Floxuridine (250 mg);FUD;5-FDU
CBNumber
CB3210097
Molecular Formula
C9H11FN2O5
Formula Weight
246.19
MOL File
50-91-9.mol
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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
solubility 
Soluble to 100 mM in water and to 100 mM in DMSO
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

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
F 
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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHR2589
Product name
Floxuridine
Packaging
500MG
Price
$200
Updated
2024/03/01
Sigma-Aldrich
Product number
343333
Product name
5-Fluoro-2?-deoxyuridine
Packaging
50mg
Price
$155
Updated
2024/03/01
Sigma-Aldrich
Product number
1271008
Product name
Floxuridine
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
250mg
Price
$436
Updated
2024/03/01
TCI Chemical
Product number
D2235
Product name
2'-Deoxy-5-fluorouridine
Purity
>98.0%(HPLC)(T)
Packaging
1g
Price
$406
Updated
2024/03/01
TCI Chemical
Product number
D2235
Product name
2'-Deoxy-5-fluorouridine
Purity
>98.0%(HPLC)(T)
Packaging
100mg
Price
$78
Updated
2024/03/01
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Floxuridine Chemical Properties,Usage,Production

Description

Floxuridine 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 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.

Biochem/physiol Actions

Antineoplastic 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 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.

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

glycoside 5-Fluorouracil

Preparation Products

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Floxuridine Suppliers

Americas 1 Belgium 1 Brazil 1 Canada 3 China 289 Europe 3 France 2 Germany 5 India 21 Japan 4 Slovakia 1 South Korea 2 Switzerland 2 The Netherlands 1 Ukraine 2 United Kingdom 22 United States 77 Global 437
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View Lastest Price from Floxuridine manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Floxuridine 50-91-9
Price
US $0.00/KG
Min. Order
1KG
Purity
98.0%
Supply Ability
500kg/month
Release date
2023-01-09
Hebei Weibang Biotechnology Co., Ltd
Product
Floxuridine 50-91-9
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
500000kg
Release date
2024-11-05
Hebei Chuanghai Biotechnology Co,.LTD
Product
5-fluoro-2'-deoxyuridine 50-91-9
Price
US $5.70/kg
Min. Order
10kg
Purity
99%
Supply Ability
10000kg
Release date
2024-08-21

50-91-9, FloxuridineRelated Search:

5-Fluorouridine Chlorfluazuron Hexaflumuron 2'-Deoxyuridine Fluorine Uridine 5-Fluorouridine Doxifluridine 5-Fluorouracil Uracil 3',5'-DI-O-BENZOYL-5-FLUORO-2'-O-METHYLURIDINE 2'-DEOXY-5-FLUOROURIDINE, [3H]- T 506 3',5'-DI-O-ACETYL-5-FLUORO-2'-O-METHYLURIDINE 5'-O-(4,4'-DIMETHOXYTRITYL)-5-FLUORODEOXYURIDINE-3'-(2-CYANOETHYL-N,N-DIISOPROPYL)PHOSPHORAMIDITE 5-fluorouridine 5'-triphosphate 3',5'-DI-O-ACETYL-5-FLUORO-2'-DEOXYURIDINE 5-FLUORO-2'-DEOXYURIDINE 5'-MONOPHOSPHATE SODIUM SALT

  • 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