An active metabolite of 5-fluorouracil
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Floxuridine

Item No. 14154

Technical Information
Formal Name
2'-deoxy-5-fluoro-uridine
CAS Number
50-91-9
Synonyms
  • 5-FDU
  • FdUrd
  • 5-Fluorodeoxyuridine
  • 5-FUDR
  • NSC 26740
  • NSC 27640
Molecular Formula
C9H11FN2O5
Formula Weight
Purity
≥98%
A crystalline solid
DMF: 16 mg/mlDMSO: 10 mg/mlPBS (pH 7.2): 5 mg/ml
λmax
269 nm
SMILES
OC[C@@H]1[C@@H](O)C[C@H](N2C=C(F)C(NC2=O)=O)O1
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Floxuridine is an active metabolite of the fluorodeoxyuridylate (FdUMP) prodrug 5-fluorouracil (5-FU; Item No. 14416).1 It is formed from 5-FU by thymidine phosphorylase, which is then phosphorylated by thymidine kinase to form FdUMP. Floxuridine (1 µM) induces DNA double-strand breaks in thymidylate synthase-deficient FM3A murine breast cancer cells, as well as increases dATP levels and decreases dTTP and dGTP levels in FM3A F28-7 murine breast cancer cells expressing wild-type thymidylate synthase.2 It inhibits the proliferation of L1210 leukemia and HeLa cancer cells (IC50s = 1.1 and 9.4 nM, respectively).1 Floxuridine (200 mg/kg, i.p.) reduces tumor growth by 86.3% in a S180 murine sarcoma model.3 Formulations containing floxuridine have previously been used in the treatment of metastatic gastrointestinal adenocarcinoma.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Tzioumaki, N., Manta, S., Tsoukala, E., et alSynthesis and biological evaluation of unsaturated keto and exomethylene D-arabinopyranonucleoside analogs: Novel 5-fluorouracil analogs that target thymidylate synthase. Eur. J. Med. Chem. 46(4), 993-1005 (2011).

    2. Yoshioka, A., Tanaka, S., Hiraoka, O., et alDeoxyribonucleoside triphosphate imbalance. 5-Fluorodeoxyuridine-induced DNA double strand breaks in mouse FM3A cells and the mechanism of cell death. The Journal of Biological Chemisty 262(17), 8235-8241 (1987).

    3. Bollag, W., and Hartmann, H.R. Tumor inhibitory effects of a new fluorouracil derivative: 5'-Deoxy-5-fluorouridine. Eur. J. Cancer 16(4), 427-432 (1980).