5-Fluorouracil

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Cat.No. 3257 - 5-Fluorouracil | C4H3FN2O2 | CAS No. 51-21-8
Description: Thymidylate synthetase inhibitor
Alternative Names: 5-FU
Chemical Name: 5-Fluoro-2,4-(1H,3H)-pyrimidinedione
Purity: ≥99% (HPLC)
Datasheet
Citations (2)
Reviews
Literature
Pathways

Biological Activity

Anticancer agent. Metabolized to form fluorodeoxyuridine monophosphate (FdUMP), fluorodeoxyuridine triphosphate (FdUTP) and fluorouridine (FUTP). FdUMP inhibits thymidylate synthase, causing a reduction in dTMP synthesis. FUTP and FdUTP are misincorporated into RNA and DNA respectively.

Technical Data

M. Wt 130.08
Formula C4H3FN2O2
Storage Store at +4°C
Purity ≥99% (HPLC)
CAS Number 51-21-8
PubChem ID 3385
InChI Key GHASVSINZRGABV-UHFFFAOYSA-N
Smiles O=C1C(F)=CNC(N1)=O

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 13.01 100
ethanol 1.3 10

Preparing Stock Solutions

The following data is based on the product molecular weight 130.08. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 7.69 mL 38.44 mL 76.88 mL
5 mM 1.54 mL 7.69 mL 15.38 mL
10 mM 0.77 mL 3.84 mL 7.69 mL
50 mM 0.15 mL 0.77 mL 1.54 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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References

References are publications that support the biological activity of the product.

Ghoshal and Jacob (1997) An alternative molecular mechanism of action of 5-fluorouracil, a potent anticancer drug. Biochem.Pharmacol. 53 1569 PMID: 9264308

Peters et al (2002) Induction of thymidylate synthase as a 5-fluorouracil resistance mechanism. Biochim.Biophys.Acta. 1587 194 PMID: 12084461

Longley et al (2003) 5-Fluorouracil: mechanisms of action and clinical strategies. Nat.Rev.Cancer 3 330 PMID: 12724731


If you know of a relevant reference for 5-Fluorouracil, please let us know.

View Related Products by Product Action

View all Thymidylate Synthetase Inhibitors

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⚠ WARNING: This product can expose you to chemicals including Fluorouracil, which is known to the State of California to cause reproductive toxicity with developmental effects. For more information, go to www.P65Warnings.ca.gov

2 Citations for 5-Fluorouracil

Citations are publications that use Tocris products. Selected citations for 5-Fluorouracil include:

Robinson et al (2013) RB1 status in triple negative breast cancer cells dictates response to radiation treatment and selective therapeutic drugs. PLoS One 8 e78641 PMID: 24265703

Fukushima et al (2015) Atonal homolog 1 protein stabilized by tumor necrosis factor α induces high malignant potential in colon cancer cell line. Cancer Sci 106 1000 PMID: 26017781


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Literature in this Area

Tocris offers the following scientific literature in this area to showcase our products. We invite you to request* or download your copy today!

*Please note that Tocris will only send literature to established scientific business / institute addresses.


Cancer Metabolism

Cancer Metabolism Poster

Adapted from the 2015 Cancer Product Guide, Edition 3, this poster summarizes the main targets for cancer metabolism researchers. Genetic changes and epigenetic modifications in cancer cells alter the regulation of cellular metabolic pathways. These distinct metabolic circuits could provide viable cancer therapeutic targets.

Cell Cycle & DNA Damage Repair

Cell Cycle & DNA Damage Repair Poster

In normal cells, each stage of the cell cycle is tightly regulated, however in cancer cells many genes and proteins that are involved in the regulation of the cell cycle are mutated or over expressed. Adapted from the 2015 Cancer Product Guide, Edition 3, this poster summarizes the stages of the cell cycle and DNA repair. It also highlights strategies for enhancing replicative stress in cancer cells to force mitotic catastrophe and cell death.

Pathways for 5-Fluorouracil

Apoptosis

Apoptosis Signaling Pathway

Apoptosis is a physiological process for cell death that is critical during aging and development. It may also be referred to as cell 'suicide'. Apoptosis can be triggered by events both inside and outside of the cell.
p53

p53 Signaling Pathway

p53 signaling plays an important role in the co-ordination of the cellular response different types of stress such as DNA damage and hypoxia. The downstream signals lead to apoptosis, senescence and cell cycle arrest.