Merck
CN

F6627

Sigma-Aldrich

5-氟脲嘧啶

≥99% (HPLC), powder

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别名:
2,4-二羟基-5-氟嘧啶, 5-FU, 5-氟-2,4(1H,3H)-嘧啶二酮
经验公式(希尔记法):
C4H3FN2O2
CAS号:
分子量:
130.08
Beilstein:
127172
EC 号:
MDL编号:
PubChem化学物质编号:
NACRES:
NA.47

质量水平

检测方案

≥99% (HPLC)

形式

powder

颜色

white

mp

282-286 °C (dec.) (lit.)

溶解性

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

储存温度

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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应用

5-氟尿嘧啶被用于诱导细胞凋亡。它被用作化学增敏剂。

生化/生理作用

一种有效的抗肿瘤药物,通过抑制胸苷酯合成酶来影响嘧啶的合成,从而耗尽细胞内的dTTP池。其代谢产物为核糖核酸和脱氧核糖核酸,可与RNA和DNA结合。用5-FU处理细胞可导致细胞在S-期积累,并已被证明其可诱导p53依赖的凋亡。

象形图

Skull and crossbonesHealth hazard

警示用语:

Danger

危险声明

危险分类

Acute Tox. 3 Oral - Carc. 2

储存分类代码

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

WGK

WGK 3


分析证书(COA)

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T1503
货号
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包装规格/数量

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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)
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)
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)

商品

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.

DNA损伤和修复机制对于维持DNA完整性至关重要。细胞DNA的损伤与突变、癌症发展等有关。

我们的科学家团队拥有各种研究领域经验,包括生命科学、材料科学、化学合成、色谱、分析及许多其他领域.

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