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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:
51-21-8
Molecular Weight:
130.08
Beilstein:
127172
EC Number:
200-085-6
MDL number:
MFCD00006018
UNSPSC Code:
12171500
PubChem Substance ID:
24278439
NACRES:
NA.47
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Product Name

5-Fluorouracil, ≥99% (HPLC), powder

Quality Level

200

Assay

≥99% (HPLC)

form

powder

technique(s)

titration: suitable

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.[1][2] It has been used as a chemosensitizing agent.[3]

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.[4][5] 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
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

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Certificates of Analysis (COA)

Lot/Batch Number
WXBD7919V
WXBF4258V
WXBF1881V
WXBD6882V
MKCK9623

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Coulson CJ
Molecular Mechanisms Of Drug Action (1994)
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)
Handbook of Drug Nutrient Interactions Nutrition and Health (2004)
Curcumin promotes apoptosis, increases chemosensitivity, and inhibits nuclear factor kappaB in esophageal adenocarcinoma.
Hartojo W
Translational Oncology, 3, 99-99 (2010)
CCL2/CCR2 chemokine signaling coordinates survival and motility of breast cancer cells through Smad3 protein- and p42/44 mitogen-activated protein kinase (MAPK)-dependent mechanisms.
Fang WB et al.
The Journal of Biological Chemistry, 287, 36593-36593 (2012)
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Questions

1–7 of 7 Questions  

  1. I see that there is limited solubility of the product in water, and that heat had to be applied. Which is the maximum heat that can be applied?

    1 answer

    1. There is no solubility testing for F6627 in water during quality control testing. The product is tested at 50 mg/ml in 1 M Ammonium Hydroxide. Product 343922 is tested for solubility at 5mg/ml in DMF and DMSO. The product is also tested at 1 mg/ml in hot water. Hot can be up to about 95°C. It should be noted that no solution stability studies have been performed on solutions heated to 95°C.
      The Product Information Sheet for F6627 lists solution stability at 37°C for 7 days only. Solutions at 25°C are stable for several weeks. Solutions stored at 0-4°C are stable for at least 4 months. The product information for 343922 states stock solutions are stable up to 3 months at -20°C. Solubility in aqueous solutions increases with pH. The trend in storage temperatures shows decreased solution stability with increasing temperature.

      Different sources will give widely varying solubility information for 5 Fluorouracil. The solubility guarantee for F6627 is listed on the Specification Sheet/Certificate of Analysis as 50mg/ml in 1M NaOH. The guarantees for 343922 are DMF (5 mg/ml), DMSO (5 mg/ml), Methanol (1 mg/ml), or hot H?O (1 mg/ml). Claims made by other suppliers are not guaranteed.

      Helpful?

  2. Is Product F6627, 5-Fluorouracil, sterile?

    1 answer

    1. No. No sterility or endotoxin testing has been performed. Solutions of the product can be sterile filtered before use.

      Helpful?

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

    1 answer

    1. 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".

      Helpful?

  4. Products F6627 and 47576 are stated to have 99% purity.  What are the differences between the two 5-fluorouracil products?

    1 answer

    1. 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).

      Helpful?

  5. 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?

    1 answer

    1. 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.

      Helpful?

  6. Why does the 5-Fluorouracil have no effect on my cell line, even at micromolar concentrations that should be more than high enough?

    1 answer

    1. 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).

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  7. What is the Department of Transportation shipping information for this product?

    1 answer

    1. 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.

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