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:
Molecular Weight:
130.08
EC Number:
200-085-6
UNSPSC Code:
12171500
PubChem Substance ID:
Beilstein/REAXYS Number:
127172
MDL number:
Assay:
≥99%
Form:
powder
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)
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
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signalword
Danger
hcodes
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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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)
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)
Handbook of Reagents for Organic Synthesis, Sulfur-Containing Reagents (2004)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| V900394-1G | 04061826117187 |
| V900394-5G | 04061832346632 |