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Fluorouracil (Adrucil)

In stock
Catalog No.
A4071
Antitumor agent;inhibitor of thymidylate synthase
Grouped product items
SizePriceStock Qty
10mM (in 1mL DMSO)
$50.00
In stock
100mg
$105.00
In stock
200mg
$34.00
In stock
500mg
$290.00
In stock

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Background

Fluorouracil (Adrucil), a heterocyclic aromatic organic compound, is a potent anticancer agent widely used for the treatment of solid tumors, including breast cancer, ovarian cancer, head and neck cancer, and colon cancer. As an analogue of uracil, fluorouracil has a fluorine atom replacing the hydrogen atom at the C-5 position. Due to its similar chemical structure to DNA and RNA, fluorouracil and metabolites exert strong anticancer activities through incorporation into DNA and RNA and inhibition of thymidylate synthase (TS). Fluorouracil is metabolized into fluorodeoxyuridine monophosphate (FdUMP), which inhibits TS by forming a stable complex with it and subsequently suppresses the production of deoxythymidine monophosphate (dTMP), an essential enzyme involved in DNA replication and repair, leading to cytotoxicity and cell death.

Reference

Ning Zhang, Ying Yin, Shen-Jie Xu and Wei-Shan Chen. 5-Fluorouracil: mechanisms of resistance and reversal strategies.  Molecules 2008, 13, 1551-1569

Michael D. Wyatt and David M. Wilson III. Participation of DNA repair in the response to 5-fluorouracil. Cell Mol Life Sci. 2009; 66(5): 788-799

Product Citation

Chemical Properties

Physical AppearanceA solid
StorageStore at -20°C
M.Wt130.1
Cas No.51-21-8
FormulaC4H3FN2O2
Synonyms5-Fluorouracil,5-FU, Efudex, Adrucil, Carac
Solubility≥6.5 mg/mL in DMSO, <2.51 mg/mL in EtOH, ≥10.04 mg/mL in H2O with ultrasonic and warming
Chemical Name5-fluoro-1H-pyrimidine-2,4-dione
SDFDownload SDF
Canonical SMILESC1=C(C(=O)NC(=O)N1)F
Shipping ConditionEvaluation sample solution : ship with blue ice.All other available size: ship with RT , or blue ice upon request
General tipsFor obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.

Protocol

Cell experiment [1]:

Cell lines

Human colon carcinoma cell line HT-29

Preparation method

The solubility of this compound in DMSO is >10 mM. General tips for obtaining a higher concentration: Please warm the tube at 37℃ for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20℃ for several months.

Reaction Conditions

0.01 ~ 10 μM; 7 days

Applications

In human colon carcinoma cell line HT-29, Fluorouracil suppressed cell viability, with the IC50 value of 2.5 μM.

Animal experiment [2]:

Animal models

C56B1/6 mice bearing Colon 38 tumor

Dosage form

100 mg/kg; i.p.; weekly

Applications

Fluorouracil (100mg/kg) significantly suppressed tumor growth of murine colon carcinoma Colon 38 with tumor-doubling time (TD), growth-delay factor (GDF), and T/C of 26.5 days, 4.4, and 14%.

Other notes

Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal.

References:

[1]. Schwartz EL, Baptiste N, Wadler S, Makower D. Thymidine phosphorylase mediates the sensitivity of human colon carcinoma cells to 5-fluorouracil. J Biol Chem. 1995 Aug 11;270(32):19073-7.

[2]. Van Laar JA, Rustum YM, Van der Wilt CL, Smid K, Kuiper CM, Pinedo HM, Peters GJ. Tumor size and origin determine the antitumor activity of cisplatin or 5-fluorouracil and its modulation by leucovorin in murine colon carcinomas. Cancer Chemother Pharmacol. 1996;39(1-2):79-89.

Quality Control

Chemical structure

Fluorouracil (Adrucil)

Related Biological Data

Fluorouracil (Adrucil)

Related Biological Data

Fluorouracil (Adrucil)

Related Biological Data

Fluorouracil (Adrucil)

Related Biological Data

Fluorouracil (Adrucil)