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F6627

Sigma-Aldrich

5-Fluorouracil

≥99% purity (HPLC), powder

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
Beilstein:
127172
EC Number:
MDL number:
UNSPSC Code:
12171500
PubChem Substance ID:
NACRES:
NA.47

product name

5-Fluorouracil, ≥99% (HPLC), powder

Quality Level

Assay

≥99% (HPLC)

form

powder

color

white

mp

282-286 °C (dec.) (lit.)

solubility

1 M NH4OH: soluble
DMSO/DMF: soluble
methanol: soluble

εmax

7.07 at 265 nm in 0.1 M HCl

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 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.

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Oral - Carc. 2

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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  1. 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.

  2. 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.

  3. 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 or view local office numbers.

  4. 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. 

  5. 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.

  6. 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).

  7. 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 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.

  8. 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).

  9. Do you have 5-FU (5-Fluorouracil) for injection? If not, how can I prepare it from the powder?

    Sigma-Aldrich lists several fluorouracil products, but we do not offer Fluorouracil for injection. Our 5-Fluorouracil (5-FU) products cannot be given to human patients. (Note that although Product F8423 meets USP testing specifications, it is not a pharmaceutical grade or PharmaGrade product.)Having said that, a solution for injection into research animals could be prepared the same way as the Fluorouracil Injection, USP is. According to the drugs.com, "Fluorouracil Injection, USP, an antineoplastic anti-metabolite, is a colorless to yellow aqueous sterile, nonpyrogenic injectable solution for intravenous administration. Each mL contains: 50 mg fluorouracil; pH is adjusted to 8.6 to 9.4 with sodium hydroxide".

  10. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Handbook of Drug Nutrient Interactions Nutrition and Health (2004)
Overexpression of microRNA-125b sensitizes human hepatocellular carcinoma cells to 5-fluorouracil through inhibition of glycolysis by targeting hexokinase II.
Jiang JX
Molecular Medicine Reports, 10, 995-995 (2014)
Coulson CJ
Molecular Mechanisms Of Drug Action (1994)
Curcumin promotes apoptosis, increases chemosensitivity, and inhibits nuclear factor kappaB in esophageal adenocarcinoma.
Hartojo W
Translational Oncology, 3, 99-99 (2010)
Joe S Matarlo et al.
Cell chemical biology, 26(8), 1133-1142 (2019-06-04)
Identification of RNA-interacting pharmacophores could provide chemical probes and, potentially, small molecules for RNA-based therapeutics. Using a high-throughput differential scanning fluorimetry assay, we identified small-molecule natural products with the capacity to bind the discrete stem-looped structure of pre-miR-21. The most

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