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Merck
CN

V900394

5-Fluorouracil

Vetec™, reagent grade, ≥99%

Synonym(s):

2,4-Dihydroxy-5-fluoropyrimidine, 5-FU, 5-Fluoro-2,4(1H,3H)-pyrimidinedione

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About This Item

Empirical Formula (Hill Notation):
C4H3FN2O2
CAS Number:
51-21-8
Molecular Weight:
130.08
EC Number:
200-085-6
UNSPSC Code:
12171500
PubChem Substance ID:
329829803
Beilstein/REAXYS Number:
127172
MDL number:
MFCD00006018

Key Documents

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Product Name

5-Fluorouracil, Vetec™, reagent grade, ≥99%

InChI key

GHASVSINZRGABV-UHFFFAOYSA-N

InChI

1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)

SMILES string

FC1=CNC(=O)NC1=O

grade

reagent grade

product line

Vetec™

assay

≥99%

form

powder

mp

282-286 °C (dec.) (lit.)

solubility

1 M NH4OH: 50 mg/mL, clear, colorless to faintly yellow

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

room temp

Gene Information

human ... TYMS(7298)

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Application

5-Fluorouracil (5-FU) can be used as a precursor for the preparation of 5-FU derivatives such as 1-acyloxyalkyl-5-fluorouracil, 3-acyloxyalkyl-5-fluorouracil, 1, 3-bis (acyloxyalkyl)-5-fluorouracil, and 1-hexylcarbamoyl-5-fluorouracil (HCFU), as potent antitumor agents. It can be also used in the synthesis of 5-5FU/diazeniumdiolate conjugate, which exhibits a greater cytotoxic effect than fluorouracil on cancer cells.

Biochem/physiol Actions

5-Fluorouracil (5-FU) is a potent antitumor agent that affects pyrimidine synthesis by inhibiting thymidylate synthetase, thus depleting intracellular dTTP pools. It is metabolized to ribonucleotides and deoxyribonucleotides, which can be incorporated into RNA and DNA. Treatment of cells with 5-FU leads to an accumulation of cells in S-phase and has been shown to induce p53 dependent apoptosis.

Legal Information

Vetec is a trademark of Merck KGaA, Darmstadt, Germany

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

hcodes

H301,H351

Hazard Classifications

Acute Tox. 3 Oral - Carc. 2

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

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Certificates of Analysis (COA)

Lot/Batch Number
WXBD5262V
WXBD7919V
WXBD3710V
WXBD1215V
WXBC7976V

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Molecular Mechanisms Of Drug Action (1994)
Handbook of Reagents for Organic Synthesis, Sulfur-Containing Reagents (2004)
Synthesis and cytotoxicity of 5-fluorouracil/diazeniumdiolate conjugates
Cai TB, et al.
Bioorganic & Medicinal Chemistry, 11(23), 4971-4975 (2003)
5-Fluorouracil derivatives. IV. Synthesis of antitumor-active acyloxyalkyl-5-fluorouracils
OZAKI S, et al.
Chemical & Pharmaceutical Bulletin, 32(2), 733-738 (1984)
Cellular response to 5-fluorouracil (5-FU) in 5-FU-resistant colon cancer cell lines during treatment and recovery.
De Angelis P M, et al.
Molecular Cancer, 5(1), 20-20 (2006)
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