A prodrug form of fludarabine and 2-fluoro-ara-ATP
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Active Metabolite(s)
14128Fludarabine
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Fludarabine Phosphate

Item No. 14251

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-fluoro-9-(5-O-phosphono-β-D-arabinofuranosyl)-9H-purin-6-amine
CAS Number
75607-67-9
Synonyms
  • 2F-ara-AMP
  • 2-fluoro-ara-AMP
  • 2-fluoroadenine Arabinoside-5-phosphate
  • FAMP
  • NSC 312887
  • NSC 328002
Molecular Formula
C10H13FN5O7P
Formula Weight
365.2
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 3 mg/ml
λmax
261 nm
SMILES
OP(OC[C@@H]1[C@@H](O)[C@H](O)[C@H](N2C=NC3=C2N=C(F)N=C3N)O1)(O)=O
InChi Code
InChI=1S/C10H13FN5O7P/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(18)5(17)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,17-18H,1H2,(H2,12,14,15)(H2,19,20,21)/t3-,5-,6+,9-/m1/s1
InChi Key
GIUYCYHIANZCFB-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

    $74

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    10 mg

    $124

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    50 mg

    $367

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    250 mg

    $722

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    Cayman Chemical
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    Product Description

    Fludarabine phosphate is a prodrug form of fludarabine (Item No. 14128) and 2-fluoro-ara-ATP.1 It is dephosphorylated in vivo to fludarabine and re-phosphorylated intracellularly to the active form, 2-fluoro-ara-ATP, which inhibits DNA synthesis.2,3 Fludarabine phosphate reduces viability of, and induces apoptosis in, N-Myc-overexpressing LASCPC-01 neuroendocrine prostate cancer cells (IC50 = 17.67 µM).1 It also reduces N-Myc protein levels when used at a concentration of 25 µM for at least 48 hours but does not reduce the levels of N-Myc mRNA. Fludarabine phosphate (120 mg/kg per day) reduces tumor volume in N-Myc-overexpressing 22Rv1-N-Myc and LASCPC-01, but not non-N-Myc-overexpressing 22Rv1, mouse xenograft models. Fludarabine phosphate is also an inhibitor of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) RNA-dependent RNA polymerase (RdRp; EC50 = 0.93 µM).4 Formulations containing fludarabine phosphate have been used in the treatment of B cell chronic lymphocytic leukemia (CLL).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Elhasasna, H., Khan, R., Bhanumathy, K.K., et al. A drug repurposing screen identifies fludarabine phosphate as a potential therapeutic agent for N-MYC overexpressing neuroendocrine prostate cancers. Cells 11(14), 2246 (2022).

    2. 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).

    3. Plunkett, W., Chubb, S., Alexander, L., et al. Comparison of the toxicity and metabolism of 9-β-D-arabinofuranosyl-2-fluoroadenine and 9-β-D-arabinofuranosyladenine in human lymphoblastoid cells. Cancer Res. 40(7), 2349-2355 (1980).

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