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Fludarabine phosphate

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Fludarabine phosphate Basic information
Fludarabine phosphate Chemical Properties
  • Melting point:203°C(dec.)(lit.)
  • alpha [α]D20 +10~+14゜(c=0.5,H2O)
  • Boiling point:864.2±75.0 °C(Predicted)
  • Density 2.39±0.1 g/cm3(Predicted)
  • RTECS UO7440900
  • storage temp. 2-8°C
  • solubility DMSO: soluble1mg/mL
  • pka1.86±0.10(Predicted)
  • form Powder
  • color white
  • Water Solubility Soluble in DMSO or water at 5mg/ml
  • Merck 14,4126
  • InChIKeyGIUYCYHIANZCFB-GFRUICAKSA-N
  • CAS DataBase Reference75607-67-9(CAS DataBase Reference)
Safety Information
  • WGK Germany 3
  • HS Code 2934990002
Fludarabine phosphate Usage And Synthesis
  • DescriptionFludarabine phosphate is an antimetabolite indicated for the treatment of B cell lymphocytic leukemia. It is reportedly effective in patients refractory to other therapies. Fludarabine phosphate acts by inhibiting primer RNA synthesis. Its side effects include bone marrow suppression, anemia, thrombocytopenia and neutropenia.
  • Chemical PropertiesWhite or almost white, crystalline powder, hygroscopic.
  • OriginatorSouthern Research Institute (U.S.A.)
  • Usesanticonvulsant
  • DefinitionChEBI: A purine arabinonucleoside monophosphate having 2-fluoroadenine as the nucleobase. A prodrug, it is rapidly dephosphorylated to 2-fluoro-ara-A and then phosphorylated intracellularly by deoxycytidine kinase to the active triphosphate, 2-fluoro-ara-ATP. Onc incorporated into DNA, 2-fluoro-ara-ATP functions as a DNA chain terminator. It is used for the treatment of adult patients with B-cell chronic lymphocytic leukemia (CLL) who have not responded to, or whose disease has progressed during, treatment with at least one standard alkylating-agent containing regimenas.
  • brand nameFludara (Berlex).
  • PharmacologyFludarabine phosphate is rapidly dephosphorylated to 2-fluoro-ara-A and then phosphorylated intracellularly by deoxycytidine kinase to the active triphosphate, 2-fluoro-ara-ATP. This metabolite appears to act by inhibiting DNA polymerase alpha, ribonucleotide reductase and DNA primase, thus inhibiting DNA synthesis. The mechanism of action of this antimetabolite is not completely characterized and may be multi-faceted.
    Phase I studies in humans have demonstrated that fludarabine phosphate is rapidly converted to the active metabolite, 2-fluoro-ara-A, within minutes after intravenous infusion.
    Consequently, clinical pharmacology studies have focused on 2-fluoro-ara-A pharmacokinetics. After the five daily doses of 25 mg 2-fluoro-ara-AMP/m2 to cancer patients infused over 30 minutes, 2-fluoro-ara-A concentrations show a moderate accumulation. During a 5-day treatment schedule, 2-fluoro-ara-A plasma trough levels increased by a factor of about 2. The terminal half-life of 2-fluoro-ara-A was estimated as approximately 20 hours. In vitro, plasma protein binding of fludarabine ranged between 19% and 29%.
  • Clinical UseFludarabine phosphate (Fludara ® ), is a fluorinated nucleotide analog of the antiviral agent vidarabine, 9-β-D-arabinofuranosyladenine(ara-A), which differs only by the presence of a fluorine atom at position 2 of the purine moiety and a phosphate group at position 5 of the arabinose moiety (Plunkett et al., 1993). These structural modifications result in increased aqueous solubility and resistance to enzymatic degradation by adenosine deaminases compared to vidarabine (Brockman et al., 1977; Plunkett et al., 1990). Fludarabine phosphate is indicated for the treatment of patients with B-cell chronic lymphocytic leukemia (CLL) who have not responded to or whose disease has progressed during treatment with at least one standard alkylating agent containing regimen (Boogaerts et al., 2001; Rossi et al., 2004).
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