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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;FDURD
CBNumber:
CB3210097
Molecular Formula:
C9H11FN2O5
Molecular Weight:
246.19
MDL Number:
MFCD00006530
MOL File:
50-91-9.mol
MSDS File:
SDS
Last updated:2023-10-11 17:37:18

Floxuridine Properties

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)
NCI Dictionary of Cancer Terms floxuridine
FDA UNII 039LU44I5M
NIST Chemistry Reference Uridine, 2'-deoxy-5-fluoro-(50-91-9)
NCI Drug Dictionary floxuridine
ATC code L01BC09
EPA Substance Registry System Floxuridine (50-91-9)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS06
Signal word  Danger
Hazard statements  H301
Precautionary statements  P264-P270-P301+P310-P405-P501
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
Toxicity LD50 oral in rat: 215mg/kg
NFPA 704
1
3 1

Floxuridine price More Price(55)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich PHR2589 Floxuridine 50-91-9 500MG $200 2024-03-01 Buy
Sigma-Aldrich 343333 5-Fluoro-2?-deoxyuridine 50-91-9 50mg $155 2024-03-01 Buy
Sigma-Aldrich 1271008 Floxuridine United States Pharmacopeia (USP) Reference Standard 50-91-9 250mg $436 2024-03-01 Buy
TCI Chemical D2235 2'-Deoxy-5-fluorouridine >98.0%(HPLC)(T) 50-91-9 1g $406 2024-03-01 Buy
TCI Chemical D2235 2'-Deoxy-5-fluorouridine >98.0%(HPLC)(T) 50-91-9 100mg $78 2024-03-01 Buy
Product number Packaging Price Buy
PHR2589 500MG $200 Buy
343333 50mg $155 Buy
1271008 250mg $436 Buy
D2235 1g $406 Buy
D2235 100mg $78 Buy

Floxuridine Chemical Properties,Uses,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

renal function diagnosis

Uses

Antiviral; antineoplastic.

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.

Synthesis_50-91-9

1582-79-2
50-91-9
Synthesis of Floxuridine from 3,5-Di-O-p-chlorobenzoyl Floxuridine

Floxuridine Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 431)Suppliers
Supplier Tel Email Country ProdList Advantage
Beijing Ribio Biotech Co.,Ltd
010-62664360 +8613328773880 wucy@ribio.com.cn China 117 58
TOKYO CHEMICAL INDUSTRY CO., LTD.
03-36680489 Sales-JP@TCIchemicals.com Japan 28398 80
Hebei Mojin Biotechnology Co., Ltd
+86-13288715578 +86-13231137666 sales@hbmojin.com China 12409 58
Capot Chemical Co.,Ltd.
571-85586718 +8613336195806 sales@capotchem.com China 29797 60
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21703 55
Hangzhou FandaChem Co.,Ltd.
008657128800458; +8615858145714 fandachem@gmail.com China 9359 55
career henan chemical co
+86-0371-86658258 sales@coreychem.com China 29919 58
SHANDONG ZHI SHANG CHEMICAL CO.LTD
+86 18953170293 sales@sdzschem.com China 2931 58
Jinan Carbotang Biotech Co.,Ltd.
+8615866703830 figo.gao@foxmail.com China 8136 58
Yunbio Tech Co.,Ltd.
+86-010-60605551 +86-18046518538 yunbiochem@126.com China 321 58

View Lastest Price from Floxuridine manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Floxuridine pictures 2023-10-11 Floxuridine
50-91-9
US $0.00 / KG 1KG 99% 50000KG/month Hebei Mojin Biotechnology Co., Ltd
Floxuridine pictures 2023-09-06 Floxuridine
50-91-9
US $0.00-0.00 / KG 1KG 99% 500000kg Hebei Guanlang Biotechnology Co., Ltd.
5-fluoro-2'-deoxyuridine pictures 2023-03-06 5-fluoro-2'-deoxyuridine
50-91-9
US $5.70 / g/Bag 10g 99% 10000kg Hebei Guanlang Biotechnology Co,.LTD
  • Floxuridine pictures
  • Floxuridine
    50-91-9
  • US $0.00 / KG
  • 99%
  • Hebei Mojin Biotechnology Co., Ltd
  • Floxuridine pictures
  • Floxuridine
    50-91-9
  • US $0.00-0.00 / KG
  • 99%
  • Hebei Guanlang Biotechnology Co., Ltd.
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 2-DEOXY-5'-FLUOROURIDINE 1-(2-DEOXY-BETA-D-RIBOFURANOSYL)-5-FLUOROURACIL FDURD fluorodeoxyuridine fluoruridine deoxyribose FLOXURIDINE 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 FUD 2'-Deoxy-5-fluoro-D-uridine 5-Fluoro-2'-deoxyuridine 98% beta-5-fluoro-2’-deoxyuridine beta-5-Fluoro-2'-deoxyuridine Deoxyfluorouridine Nsc 27640 NSC-26740 nsc27640 nsc-27640 Ro 5-0360 ro5-0360 Uridine, 2'-deoxy-5'-fluoro- FLOSCHRYSANTHEMI.P.E 2''-DEOXY-5-FLUOROURIDINE (FLOXURIDINE) FLOXURIDINE (2''-DEOXY-5-FLUOROURIDINE) 2'-DEOXY-5-FLUOROURIDINE 1-(2-Deoxy--D-ribofuranosyl)-5-fluorouracil 5-FLURO-2-DEOXYURIDINE extrapure 2μ-Deoxy-5-fluorouridine, Floxuridine, FUDR 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) 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