An antimetabolite, a DNA methylation and dCK inhibitor, and a prodrug form of 5-FU
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2'-Deoxy-5-fluorocytidine

Item No. 37477

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2'-deoxy-5-fluoro-cytidine
CAS Number
10356-76-0
Synonyms
  • 2'-DFCR
  • 5-Fluoro-2′-deoxycytidine
  • NSC 48006
  • Ro 5-1090
Molecular Formula
C9H12FN3O4
Formula Weight
245.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlEthanol: 5 mg/mlPBS (pH 7.2): 5 mg/ml
SMILES
OC[C@@H]1[C@@H](O)C[C@@](N2C=C(F)C(N)=NC2=O)([H])O1
InChi Code
InChI=1S/C9H12FN3O4/c10-4-2-13(9(16)12-8(4)11)7-1-5(15)6(3-14)17-7/h2,5-7,14-15H,1,3H2,(H2,11,12,16)/t5-,6+,7+/m0/s1
InChi Key
IDYKCXHJJGMAEV-RRKCRQDMSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    250 mg

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    Product Description

    2'-Deoxy-5-fluorocytidine is an antimetabolite, an inhibitor of DNA methylation and deoxycytidine kinase, and a prodrug form of the FdUMP prodrug 5-fluorouracil (Item No. 14416).1,2,3,4 Incorporation of 2'-deoxy-5-fluorocytidine into a synthetic DNA polymer inhibits methylation of DNA in a cell-free assay, and 2'-deoxy-5-fluorocytidine-containing oligonucleotides form a covalent complex with DNA methyltransferase 3a (Dnmt3a).1,2 2'-Deoxy-5-fluorocytidine inhibits deoxycytidine kinase (dCK; IC50 = 120 nM).3 It reduces the cytopathic effects of the influenza H5N1 strain Vietnam/1203/2004 in MDCK cells (IC50 = 0.19 µM).5 2'-Deoxy-5-fluorocytidine (12 mg/kg) in combination with the cytidine deaminase inhibitor tetrahydrouridine (Item No. 16402) inhibits tumor growth in an ascitic mammary adenocarcinoma 755 murine model.4 It induces embryonic lethality and skeletal malformations in a dose-dependent manner when administered to pregnant mice.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Osterman, D.G., DePillis, G.D., Wu, J.C., et al. 5-Fluorocytosine in DNA is a mechanism-based inhibitor of HhaI methylase. Biochemistry 27(14), 5204-5210 (1988).

    2. Reither, S., Li, F., Gowher, H., et al. Catalytic mechanism of DNA-(cytosine-C5)-methyltransferases revisited: Covalent intermediate formation is not essential for methyl group transfer by the murine Dnmt3a enzyme. J. Mol. Biol. 329(4), 675-684 (2003).

    3. Tarver, J.E., Jessop, T.C., Carlsen, M., et al. 5-Fluorocytosine derivatives as inhibitors of deoxycytidine kinase. Bioorg. Med. Chem. Lett. 19(23), 6780-6783 (2009).

    4. Boothman, D.A., Briggle, T.V., and Greer, S. Protective, tumor-selective dual pathway activation of 5-fluoro-2'-deoxycytidine provided by tetrahydrouridine in mice bearing mammary adenocarcinoma-755. Cancer Res. 47(9), 2344-2353 (1987).

    5. Kumaki, Y., Day, C.W., Smee, D.F., et al. In vitro and in vivo efficacy of fluorodeoxycytidine analogs against highly pathogenic avian influenza H5N1, seasonal, and pandemic H1N1 virus infections. Antiviral Res. 92(2), 329-340 (2011).

    6. Kleinbrecht, J. The embryotoxic effects of 5-fluoro-2'-deoxyuridine in mice. Teratology 3(4), 315-318 (1970).