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
• NACRES: NA.77
• PubChem Substance ID: 24894724
• EC Number: 200-072-5
• Beilstein/REAXYS Number: 90221
• MDL number: MFCD00006530
• UNSPSC Code: 12352208

Properties

• biological source: synthetic (organic)
• Quality Segment: 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)

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
• 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