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F6627 Sigma

5-Fluorouracil

≥99% (HPLC), powder

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

  • CAS Number 51-21-8

  • Empirical Formula (Hill Notation) C4H3FN2O2

  • Molecular Weight 130.08

  •  Beilstein Registry Number 127172

  •  EC Number 200-085-6

  •  MDL number MFCD00006018

  •  PubChem Substance ID 24278439

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Properties

Related Categories Antitumor Agents, Apoptosis and Cell Cycle, Cancer Research, Cell Biology, Cell Cycle Proteins, Antibodies and Reagents,
InChI Key   GHASVSINZRGABV-UHFFFAOYSA-N
assay   ≥99% (HPLC)
form   powder
color   white
mp   282-286 °C (dec.) (lit.)
solubility   1 M NH4OH: soluble
  DMSO/DMF: soluble
  methanol: soluble
Gene Information   human ... TYMS(7298)

Description

Packaging

1, 5, 10 g in glass bottle

Application

5-Fluorouracil has been used to induce apoptosis in cells. It has been used as a chemosensitizing agent.

Biochem/physiol Actions

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.

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
3

Frequently Asked Questions

Which document(s) contains shelf-life or expiration date information for a given product?
If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.
How do I get lot-specific information or a Certificate of Analysis?
The lot specific COA document can be found by entering the lot number above under the "Documents" section.
How do I find price and availability?
There are several ways to find pricing and availability for our products.Once you log onto our website, you will find the price and availability displayed on the product detail page.You can contact any of our Customer Sales and Service offices to receive a quote. USA customers: 1-800-325-3010 orview local office numbers.
What is the Department of Transportation shipping information for this product?
Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
Is Product F6627, 5-Fluorouracil, sterile?
No. No sterility or endotoxin testing has been performed. Solutions of the product can be sterile filtered before use.
Products F6627 and 47576 are stated to have 99% purity.What are the differences between the two 5-fluorouracil products?
The purity of Product No. F6627 is determined by TLC (thin layer chromatography).The purity of deleted product 47576 was determined by HPLC (high performance liquid chromatography).
I see that Product F6627, 5-Fluorouracil, is soluble at a concentration of 50 mg/mL in 1M ammonium hydroxide. Do you have any information regarding the solubility in water?
Although product F6627 is not tested for solubility in water, there should be some limited solubility. Product 47576 from Fluka has been tested at 10 mg/mL in water, although heat had to be applied. Upon cooling it might be possible to observe some precipitation. No testing in water is performed at Sigma on a lot to lot basis. The product is more soluble at higher alkaline pH.
Why does the 5-Fluorouracil have no effect on my cell line, even at micromolar concentrations that should be more than high enough?
Some cells, and in particular cancer cells, may be resistant to 5-fluorouracil. Please see this paper Huanwen, W., et al., Molecular Cancer, 8, 125 (2009)which addresses this observation, as well as references 16 and 30 in this publication.If the cells are treated with the closely related gemcitabine (Sigma-Aldrich Product G6423), and cell growth is not inhibited by that drug either, you will have shown that the "problem" is with the cell line, and not with the drug(s).
My question is not addressed here, how can I contact Technical Service for assistance?
Ask a Scientist here.
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Protocols & Articles

Articles

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Keywords: Apoptosis, Autophagy, Cancer, Degradations, Metabolites, transformation

DNA Damage and Repair

Damage to cellular DNA is involved in mutagenesis and the development of cancer. The DNA in a human cell undergoes several thousand to a million damaging events per day, generated by both external (e...
Keywords: AGE, Alkylations, Apoptosis, Biochemistry, Cancer, Carcinogens, Catalysis, Clinical, DNA replication, Deaminations, Degradations, Eliminations, Environmental, Enzymology, Gene expression, Genetic, Infrared spectroscopy, Metabolites, Methylations, Mutagens, Oncology, Oxidations, Polymorphisms, Rearrangements, Recombination, Substitutions, Transcription, transformation

Nucleotide Synthesis in Cancer Cells

Neoplastic cells are highly dependent on the de novo synthesis of nucleotides to maintain sufficient pools to support DNA replication and the production of RNA. The metabolic pathways supporting nucl...
Keywords: Biofiles, Cancer, Catalysis, Citric Acid Cycle, DNA replication, Gene expression, Glycolysis, Metabolic Pathways, Metabolism, Metabolites, Nucleotide Synthesis, PAGE, Pentose phosphate pathway, Pyrimidine synthesis, Support

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Peer-Reviewed Papers
15

References

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