F0503

5-Fluoro-2′-deoxyuridine

thymidylate synthase inhibitor

• 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

Properties

• 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
• 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)

Description

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.

Safety Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H301
• Precautionary Statements: P301 + P330 + P331 + P310
• Hazard Classifications: Acute Tox. 3 Oral
• Storage Class Code: 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
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves