A fluorinated derivative of 2'-deoxycytidine
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2'-Fluoro-2'-deoxy-arabino-Cytidine

Item No. 39935

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-amino-1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-2(1H)-pyrimidinone
CAS Number
56632-83-8
Synonyms
  • 2'-Ara-FdC
  • FAC
Molecular Formula
C9H12FN3O4
Formula Weight
245.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: SolubleMethanol: Soluble
SMILES
F[C@@H]([C@@H]1O)[C@H](N(C=CC(N)=N2)C2=O)O[C@@H]1CO
InChi Code
InChI=1S/C9H12FN3O4/c10-6-7(15)4(3-14)17-8(6)13-2-1-5(11)12-9(13)16/h1-2,4,6-8,14-15H,3H2,(H2,11,12,16)/t4-,6+,7-,8-/m1/s1
InChi Key
NVZFZMCNALTPBY-PXBUCIJWSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $31

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    10 mg

    $59

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    25 mg

    $139

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    50 mg

    $216

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    Product Description

    2'-Fluoro-2'-deoxy-arabino-cytidine is a fluorinated derivative of the deoxyribonucleoside 2'-deoxycytidine (Item Nos. 34708 | 30125).1 It is cytotoxic to CCRF-HSB-2 T lymphoblast, COLO 320DM colon, and MKN28 gastric cancer cells (IC50s = 0.15, 0.19, and 29 µg/ml, respectively). 2'-Fluoro-2'-deoxy-arabino-cytidine inhibits HIV-1 replication in HIV-1-infected C8166 cells (IC50 = 0.7 µM), as well as herpes simplex virus 1 (HSV-1) and HSV-2 replication in HSV-1- or HSV-2-infected Vero cells (IC50s = 0.12 and 0.3 µM, respectively).2,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Miura, S., Yoshimura, Y., Endo, M., et al. Antitumor activity of a novel orally effective nucleoside, 1-(2-deoxy-2-fluoro-4-thio-β-D-arabinofuranosyl)cytosine. Cancer Lett. 129(1), 103-110 (1998).

    2. Martin, J.A., Bushnell, D.J., Duncan, I.B., et al. Synthesis and antiviral activity of monofluoro and difluoro analogues of pyrimidine deoxyribonucleosides against human immunodeficiency virus (HIV-1). J. Med. Chem. 33(8), 2137-2145 (1990).

    3. Watanabe, K.A., Su, T.-L., Klein, R.S., et al. Nucleosides. 123. Synthesis of antiviral nucleosides: 5-substituted 1-(2-deoxy-2-halogeno-β-D-arabinofuranosyl)cytosines and -uracils. Some structure-activity relationships. J. Med. Chem. 26(2), 152-156 (1983).