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F0503

Sigma-Aldrich

5-Fluoro-2′-deoxyuridine

thymidylate synthase inhibitor

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Synonym(s):
floxuridine, 2′-Deoxy-5-fluorouridine, FUDR, Floxuridine
Empirical Formula (Hill Notation):
C9H11FN2O5
CAS Number:
50-91-9
Molecular Weight:
246.19
Beilstein:
90221
EC Number:
200-072-5
MDL number:
MFCD00006530
UNSPSC Code:
12352202
PubChem Substance ID:
24894724
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

200

Assay

≥99% (HPLC)

form

powder

mp

148 °C (lit.)

solubility

water: 50 mg/mL, clear, colorless to faintly yellow

storage temp.

room temp

SMILES string

OC[C@H]1O[C@H](C[C@@H]1O)N2C=C(F)C(=O)NC2=O

InChI

1S/C9H11FN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1

InChI key

ODKNJVUHOIMIIZ-RRKCRQDMSA-N

Gene Information

human ... TYMS(7298)
mouse ... Tyms(22171)

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General description

5-Fluoro-2′-deoxyuridine, also called floxuridine elicits DNA-directed cytotoxicity in cancer cells. Floxuridine is effective for treating liver cancer and eliminating virulence of Staphylococcus aureus. Dipeptide prodrugs combination of floxuridine with gemcitabine are more cell permeable and display enhanced anti-proliferative activity. Floxuridine is effective on solid tumours and advanced stage cancers.

Application

5-Fluoro-2′-deoxyuridine has been used as a mitotic inhibitor in schwann cell proliferation, glia proliferation and nonneuronal cells in dorsal root ganglion cultures.

Biochem/physiol Actions

Antineoplastic drug that acts as a potent inhibitor of thymidylate synthetase Resistance to FUdR can develop in cancer cell cultures, among other means, by low-level Mycoplasma infection.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P301 + P330 + P331 + P310

Hazard Classifications

Acute Tox. 3 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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J A van Laar et al.
European journal of cancer (Oxford, England : 1990), 34(3), 296-306 (1998-06-26)
Despite more than 30 years of intensive studies on new drugs against advanced colorectal cancer, the fluoropyrimidines remain the drugs of choice for systemic treatment and for hepatic artery infusion (HAI). This overview describes new developments in advanced colorectal cancer
The Dipeptide Monoester Prodrugs of Floxuridine and Gemcitabine?Feasibility of Orally Administrable Nucleoside Analogs
Tsume Y, et al.
Pharmaceuticals (Basel, Switzerland), 7(2), 169-191 (2014)
Iron deficiency impairs developing hippocampal neuron gene expression, energy metabolism, and dendrite complexity
Bastian TW, et al.
Developmental Neuroscience, 38(4), 264-276 (2016)
Enhanced absorption and growth inhibition with amino acid monoester prodrugs of floxuridine by targeting hPEPT1 transporters
Tsume Y, et al.
Molecules (Basel), 13(7), 1441-1454 (2008)
Diana Andrea Fernandes de Abreu et al.
PLoS genetics, 10(3), e1004225-e1004225 (2014-03-29)
Insulin-like peptides (ILPs) play highly conserved roles in development and physiology. Most animal genomes encode multiple ILPs. Here we identify mechanisms for how the forty Caenorhabditis elegans ILPs coordinate diverse processes, including development, reproduction, longevity and several specific stress responses.
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