Merck
All Photos(4)

F0503

Sigma-Aldrich

5-Fluoro-2′-deoxyuridine

thymidylate synthase inhibitor

Synonym(s):
floxuridine, 2′-Deoxy-5-fluorouridine, FUDR, Floxuridine
Empirical Formula (Hill Notation):
C9H11FN2O5
CAS Number:
Molecular Weight:
246.19
Beilstein:
90221
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

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.[1] Floxuridine is effective for treating liver cancer[2] and eliminating virulence of Staphylococcus aureus.[3] Dipeptide prodrugs combination of floxuridine with gemcitabine are more cell permeable and display enhanced anti-proliferative activity.[4] Floxuridine is effective on solid tumours and advanced stage cancers.[5]

Application

5-Fluoro-2′-deoxyuridine has been used as a mitotic inhibitor in schwann cell proliferation[6], glia proliferation[7][8] and nonneuronal cells in dorsal root ganglion cultures.[9]

Packaging

100, 250 mg in poly bottle
1 g in poly bottle

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

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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