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V900394

Sigma-Aldrich

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
Beilstein:
127172
EC Number:
200-085-6
MDL number:
MFCD00006018
UNSPSC Code:
12171500
PubChem Substance ID:
329829803

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

SMILES string

FC1=CNC(=O)NC1=O

InChI

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

InChI key

GHASVSINZRGABV-UHFFFAOYSA-N

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

Signal Word

Danger

Hazard Statements

H301 - H351

Hazard Classifications

Acute Tox. 3 Oral - Carc. 2

Storage Class Code

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

WGK

WGK 3

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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5-fluorouracil activation of p53 involves an MDM2-ribosomal protein interaction.
Sun X X, et al.
The Journal of Biological Chemistry, 282(11), 8052-8059 (2007)
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)
5-Fluorouracil derivatives. I. The synthesis of 1-carbamoyl-5-fluorouracils
Ozaki S, et al.
Bulletin of the Chemical Society of Japan, 50(9), 2406-2412 (1977)
Handbook of Reagents for Organic Synthesis, Sulfur-Containing Reagents (2004)
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