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Product Details:

  • Product Name: Capecitabine
  • CAS #: 154361-50-9
  • Mode of Action:

    Capecitabine is a prodrug that is selectively tumour-activated to its cytotoxic moiety, fluorouracil, by thymidine phosphorylase, an enzyme found in higher concentrations in many tumors compared to normal tissues or plasma. Fluorouracil is further metabolized to two active metabolites, 5-fluoro-2'-deoxyuridine 5'-monophosphate (FdUMP) and 5-fluorouridine triphosphate (FUTP), within normal and tumour cells. These metabolites cause cell injury by two different mechanisms. First, FdUMP and the folate cofactor, N5-10-methylenetetrahydrofolate, bind to thymidylate synthase (TS) to form a covalently bound ternary complex. This binding inhibits the formation of thymidylate from 2'-deaxyuridylate. Thymidylate is the necessary precursor of thymidine triphosphate, which is essential for the synthesis of DNA, therefore a deficiency of this compound can inhibit cell division. Secondly, nuclear transcriptional enzymes can mistakenly incorporate FUTP in place of uridine triphosphate (UTP) during the synthesis of RNA. This metabolic error can interfere with RNA processing and protein synthesis through the production of fraudulent RNA.

  • Pharmacodynamics:

    Capecitabine is a fluoropyrimidine carbamate with antineoplastic activity indicated for the treatment of metastatic breast cancer and colon cancer. It is an orally administered systemic prodrug that has little pharmacologic activity until it is converted to fluorouracil by enzymes that are expressed in higher concentrations in many tumors. Fluorouracil it then metabolized both normal and tumor cells to 5-fluoro-2_-deoxyuridine 5_-monophosphate (FdUMP) and 5-fluorouridine triphosphate (FUTP).

  • Metabolism:

    Metabolized by thymidine phosphorylase to fluoruracil.

  • IUPAC: pentyl N-{1-[(2R, 3R, 4S, 5R)-3, 4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxo-1, 2-dihydropyrimidin-4-yl}carbamate
  • ATC: L01BC06
  • PubChem: 60953
  • DrugBank: DB01101 (APRD00203)
  • Formula: C19H15NO6
  • Molecular Mass: 359.3501
  • Synonyms: R340
  • SMILES: CCCCCOC(=O)NC1=NC(=O)N(C=C1F)[C@@H]1O[C@H](C)[C@@H](O)[C@H]1O
  • AHFS Code: 10:00.0
  • General Reference:

    1. Walko CM, Lindley C: Capecitabine: a review. Clin Ther. 2005 Jan;27(1):23-44. Pubmed
    2. Wagstaff AJ, Ibbotson T, Goa KL: Capecitabine: a review of its pharmacology and therapeutic efficacy in the management of advanced breast cancer. Drugs. 2003;63(2):217-36. Pubmed
    3. Koukourakis GV, Kouloulias V, Koukourakis MJ, Zacharias GA, Zabatis H, Kouvaris J: Efficacy of the oral fluorouracil pro-drug capecitabine in cancer treatment: a review. Molecules. 2008 Aug 27;13(8):1897-922. Pubmed
    4. Twelves C: Vision of the future: capecitabine. Oncologist. 2001;6 Suppl 4:35-9. Pubmed
    5. Milano G, Ferrero JM, Francois E: Comparative pharmacology of oral fluoropyrimidines: a focus on pharmacokinetics, pharmacodynamics and pharmacomodulation. Br J Cancer. 2004 Aug 16;91(4):613-7. Pubmed
    6. de Bono JS, Twelves CJ: The oral fluorinated pyrimidines. Invest New Drugs. 2001;19(1):41-59. Pubmed

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LGM Pharma Acquires CDMO

On July 27, 2020, LGM Pharma announced its acquisition of the formulation development and drug product contract manufacturing business of Nexgen Pharma, Inc. As a result, you will notice our new logo and visuals throughout the website. We’re working on updates to reflect the exciting, expanded CDMO capabilities and services we now can offer you.

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