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Merck

F6627

Sigma-Aldrich

5-Fluorouracil

≥99% purity (HPLC), powder

Synonym(e):

2,4-Dihydroxy-5-Fluoropyrimidin, 5-FU, 5-Fluor-2,4(1H,3H)-pyrimidindion

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1 G
CHF 47.90
5 G
CHF 166.00
10 G
CHF 306.00

CHF 47.90


Voraussichtliches Versanddatum22. März 2025


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1 G
CHF 47.90
5 G
CHF 166.00
10 G
CHF 306.00

About This Item

Empirische Formel (Hill-System):
C4H3FN2O2
CAS-Nummer:
Molekulargewicht:
130.08
Beilstein:
127172
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12171500
PubChem Substanz-ID:
NACRES:
NA.47

CHF 47.90


Voraussichtliches Versanddatum22. März 2025


Bulk-Bestellung anfordern

Produktbezeichnung

5-Fluorouracil, ≥99% (HPLC), powder

Qualitätsniveau

Assay

≥99% (HPLC)

Form

powder

Methode(n)

titration: suitable

Farbe

white

mp (Schmelzpunkt)

282-286 °C (dec.) (lit.)

Löslichkeit

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

εmax

7.07 at 265 nm in 0.1 M HCl

Anwendung(en)

diagnostic assay manufacturing
hematology
histology

Lagertemp.

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)

InChIKey

GHASVSINZRGABV-UHFFFAOYSA-N

Angaben zum Gen

human ... TYMS(7298)

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Anwendung

5-Fluorouracil wurde für die Induzierung der Apoptose in Zellen verwendet.[1][2] Es wird als chemosensibilisierendes Mittel verwendet.[3]

Biochem./physiol. Wirkung

Ein potenter Antitumor-Wirkstoff, der die Pyrimidinsynthese durch Hemmung der Thymidylatsynthetase beeinflusst und dadurch intrazelluläre dTTP-Pools abbaut. Er wird zu Ribonukleotiden und Desoxyribonukleotiden metabolisiert, die in die RNA und DNA integriert werden können.[4][5] Die Behandlung von Zellen mit 5-FU führt zu einer Ansammlung von Zellen in der S-Phase und induziert nachweislich eine p53-abhängige Apoptose.

Piktogramme

Skull and crossbonesHealth hazard

Signalwort

Danger

H-Sätze

Gefahreneinstufungen

Acute Tox. 3 Oral - Carc. 2

Lagerklassenschlüssel

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3


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In der Dokumentenbibliothek finden Sie die Dokumentation zu den Produkten, die Sie kürzlich erworben haben.

Die Dokumentenbibliothek aufrufen

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)
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)
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)

Artikel

We presents an article on Autophagy in Cancer Promotes Therapeutic Resistance

DNA damage and repair mechanism is vital for maintaining DNA integrity. Damage to cellular DNA is involved in mutagenesis, the development of cancer among others.

Questions

1–6 of 6 Questions  
  1. 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?

  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. 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?

  4. 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.

      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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