An intermediate active metabolite of fludarabine
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Isomer(s)
356993'-Deoxy-3'-fluoroguanosine
Pro-drug Form(s)
14251Fludarabine Phosphate
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Fludarabine

Item No. 14128

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9-β-D-arabinofuranosyl-2-fluoro-9H-purin-6-amine
CAS Number
21679-14-1
Synonyms
  • 2-fluoro-ara-A
  • NSC 118218
Molecular Formula
C10H12FN5O4
Formula Weight
285.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 3.3 mg/mlDMSO: 11 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.50 mg/ml
λmax
261 nm
SMILES
O[C@@H]1[C@@H](CO)O[C@@H](N2C(N=C(F)N=C3N)=C3N=C2)[C@H]1O
InChi Code
InChI=1S/C10H12FN5O4/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)/t3-,5-,6+,9-/m1/s1
InChi Key
HBUBKKRHXORPQB-FJFJXFQQSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    5 mg

    $36

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    10 mg

    $61

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    25 mg

    $128

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    50 mg

    $169

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    Product Description

    Fludarabine is an intermediate active metabolite of the prodrug fludarabine phosphate (Item No. 14251).1 It is produced by the dephosphorylation of fludarabine phosphate in vivo and re-phosphorylation intracellularly to 2-fluoro-ara-ATP, another active metabolite. Fludarabine inhibits the proliferation of RPMI-8226, MM.1S, and MM.1R multiple myeloma cells (IC50s = 1.54, 13.48, and 33.79 µM, respectively).2 It increases Bax levels and decreases BH3-interacting domain (Bid), X-linked inhibitor of apoptosis (XIAP), and survivin levels, indicating the induction of apoptosis, in RPMI-8226 cells when used at a concentration of 2 µg/ml. Fludarabine is also an inhibitor of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) RNA-dependent RNA polymerase (RdRp; EC50 = 1.06 µM).3 It completely inhibits DNA synthesis in an SA-NH murine sarcoma model when administered at a dose of 200 mg/kg.4 Fludarabine reduces tumor growth in an RPMI-8226 mouse xenograft model when administered at a dose of 40 mg/kg.2 It also reduces tumor growth in an L1210 murine leukemia model.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Mittelman, A., Savona, S., Puccio, C., et al. Phase II trial of fludarabine phosphate (F-Ara-AMP) in patients with advanced head and neck cancer. Invest. New Drugs 8, S65-S67 (1990).

    2. Meng, H., Yang, C., Ni, W., et al. Antitumor activity of fludarabine against human multiple myeloma in vitro and in vivo. Eur. J. Haematol. 79(6), 486-493 (2007).

    3. Zhao, J., Liu, Q., Yi, D., et al. 5-Iodotubercidin inhibits SARS-CoV-2 RNA synthesis. Antiviral Res. 198, 105254 (2022).

    4. Gregoire, V., Van, N.T., Stephens, C., et al. The role of fludarabine-induced apoptosis and cell cycle synchronization in enhanced murine tumor radiation response in vivo. Cancer Res. 54(23), 6201-6209 (1994).

    5. Brockman, R.W., Cheng, Y.-C., Schabel, F.M.J., et al. Metabolism and chemotherapeutic activity of 9-β-D-arabinofuranosyl-2-fluoroadenine against murine leukemia L1210 and evidence for its phosphorylation by deoxycytidine kinase. Cancer Res. 40(10), 3610-3615 (1980).