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Product Details:

  • Product Name: Gemcitabine
  • CAS #: 95058-81-4
  • Mode of Action:

    Gemcitabine inhibits thymidylate synthetase, leading to inhibition of DNA synthesis and cell death. Gemcitabine is a prodrug so activity occurs as a result of intracellular conversion to two active metabolites, gemcitabine diphosphate and gemcitabine triphosphate by deoxycitidine kinase. Gemcitabine diphosphate also inhibits ribonucleotide reductase, the enzyme responsible for catalyzing synthesis of deoxynucleoside triphosphates required for DNA synthesis. Finally, Gemcitabine triphosphate (diflurorodeoxycytidine triphosphate) competes with endogenous deoxynucleoside triphosphates for incorporation into DNA.Gemcitabine offers potent antitumor activity both in vitro and in vivo tumor models. 

  • Pharmacodynamics:

    Gemcitabine is an antineoplastic anti-metabolite. Anti-metabolites masquerade as purine or pyrimidine - which become the building blocks of DNA. They prevent these substances becoming incorporated in to DNA during the "S" phase (or DNA synthesis phase of the cell cycle), stopping normal development and division. Gemcitabine blocks an enzyme which converts the cytosine nucleotide into the deoxy derivative. In addition, DNA synthesis is further inhibited because Gemcitabine blocks the incorporation of the thymidine nucleotide into the DNA strand. It demonstrates dose-dependent synergistic activity with cisplatin in vitro. In vivo, gemcitabine showed activity in combination with cisplatin against the LX-1 and CALU-6 human lung xenografts, but minimal activity was seen with the NCI-H460 or NCI-H520 xenografts. Gemcitabine was synergistic with cisplatin in the Lewis lung murine xenograft. Sequential exposure to gemcitabine 4 hours before cisplatin produced the greatest interaction.

  • Metabolism:

    Transformed via nucleoside kinases to two active metabolites, gemcitabine diphosphate and gemcitabine triphosphate. Can also undergo deamination via cytidine deaminase to an inactive uracil metabolite (dFdU). Within one week roughly 92 percent to 98 percent of the Gemcitabine dosage is recovered, almost entirely in the urine.

  • Toxicity:

    Few toxicity concerns have emerged from studies of Gemcitabine. Though rare, pulmonary toxicities are possible with Gemcitabine use, however symptoms are telling and come with rapid onset. Commonly occurring side effects, documented in over 30 percent of patients include fever, flu-like symptoms, vomiting, nausea, extreme fatigue and low blood counts.

  • IUPAC: 4-amino-1-(2-deoxy-2, 2-difluoro-β-D-erythro-pentofuranosyl)pyrimidin-2(1H)-on
  • ATC: L01BC05
  • PubChem: 60750
  • DrugBank: APRD00201
  • Formula: C9-H11-F2-N3-O4
  • Molecular Mass: 263.1989
  • Synonyms: 2',2'-Difluorodeoxycytidine, 2'-Deoxy-2',2'-difluorocytidine, CCRIS 8984, DDFC, DFdC, DFdCyd, Folfugem, Gamcitabine, Gemcel, Gemcitabina, Gemcitabina [INN-Spanish], Gemcitabine, Gemcitabinum, Gemcitabinum [INN-Latin], GemLip, HSDB 7567, LY 188011, LY188011, NSC 613327, UNII-B76N6SBZ8R, Zefei,
  • SMILES: c1cn(c(=O)nc1N)[C@H]2C([C@@H]([C@H](O2)CO)O)(F)F
  • AHFS Code: 10:00.0
  • InChl: 1S/C9H11F2N3O4/c10-9(11)6(16)4(3-15)18-7(9)14-2-1-5(12)13-8(14)17/h1-2,4,6-7,15-16H,3H2,(H2,12,13,17)/t4-,6-,7-/m1/s1
  • General Reference:
    1. N Engl J Med 2010; 362:1273-1281April 8, 2010DOI: 10.1056/NEJMoa0908721
    2. The Lancet Oncology, 2015.
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