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Merck

F6627

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
NACRES:
NA.47
PubChem Substance ID:
24278439
UNSPSC Code:
12171500
EC Number:
200-085-6
MDL number:
MFCD00006018
Beilstein/REAXYS Number:
127172

Key Documents

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Product Name

5-Fluorouracil, ≥99% (HPLC), powder

InChI key

GHASVSINZRGABV-UHFFFAOYSA-N

InChI

1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)

SMILES string

FC1=CNC(=O)NC1=O

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

Quality Level

200

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
GHS06,GHS08

signalword

Danger

hcodes

H301,H351

Hazard Classifications

Acute Tox. 3 Oral - Carc. 2

Storage Class

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
WXBD6882V
MKCK9623
WXBD5262V
WXBD3710V
MKCH3192

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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)
Curcumin promotes apoptosis, increases chemosensitivity, and inhibits nuclear factor kappaB in esophageal adenocarcinoma.
Hartojo W
Translational Oncology, 3, 99-99 (2010)
Handbook of Drug Nutrient Interactions Nutrition and Health (2004)
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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