F0503

5-Fluoro-2′-deoxyuridine

Name: 5-Fluoro-2′-deoxyuridine
Brand: SIGMA

thymidylate synthase inhibitor

Synonym(s):

floxuridine, 2′-Deoxy-5-fluorouridine, FUDR, Floxuridine

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About This Item

Empirical Formula (Hill Notation):

C₉H₁₁FN₂O₅

CAS Number:

50-91-9

Molecular Weight:

246.19

UNSPSC Code:

12352202

NACRES:

NA.77

PubChem Substance ID:

24894724

EC Number:

200-072-5

Beilstein/REAXYS Number:

90221

MDL number:

MFCD00006530

Product Name

5-Fluoro-2′-deoxyuridine, thymidylate synthase inhibitor

InChI key

ODKNJVUHOIMIIZ-RRKCRQDMSA-N

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

SMILES string

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

biological source

synthetic (organic)

assay

≥99% (HPLC)

form

powder

mp

148 °C (lit.)

solubility

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

storage temp.

room temp

Quality Level

200

Gene Information

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

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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.

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.

pictograms

GHS06

signalword

Danger

hcodes

H301

pcodes

P301 + P330 + P331 + P310

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

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

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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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)

Comparison of 5-fluoro-2'-deoxyuridine with 5-fluorouracil and their role in the treatment of colorectal cancer.

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

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)

An insulin-to-insulin regulatory network orchestrates phenotypic specificity in development and physiology.

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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