Epirubicin

Epirubicin is an anthracycline drug used for chemotherapy. It can be used in combination with other medications to treat breast cancer in patients who have had surgery to remove the tumor. It is marketed by Pfizer under the trade name Ellence in the US and Pharmorubicin or Epirubicin Ebewe elsewhere.

Epirubicin
Clinical data
Trade namesEllence
AHFS/Drugs.comMonograph
MedlinePlusa603003
Pregnancy
category
  • AU: D
  • US: D (Evidence of risk)
    Routes of
    administration    		Intravenous
    ATC code
    Legal status
    Legal status
    Pharmacokinetic data
    BioavailabilityNA
    Protein binding77%
    MetabolismHepatic glucuronidation and oxidation
    ExcretionBiliary and renal
    Identifiers
    CAS Number
    PubChem CID
    DrugBank
    ChemSpider
    UNII
    KEGG
    ChEBI
    ChEMBL
    CompTox Dashboard (EPA)
    Chemical and physical data
    FormulaC27H29NO11
    Molar mass543.525 g·mol−1
    3D model (JSmol)
      (verify)

    Similarly to other anthracyclines, epirubicin acts by intercalating DNA strands. Intercalation results in complex formation which inhibits DNA and RNA synthesis. It also triggers DNA cleavage by topoisomerase II, resulting in mechanisms that lead to cell death. Binding to cell membranes and plasma proteins may be involved in the compound's cytotoxic effects. Epirubicin also generates free radicals that cause cell and DNA damage.

    Epirubicin is favoured over doxorubicin, the most popular anthracycline, in some chemotherapy regimens as it appears to cause fewer side-effects. Epirubicin has a different spatial orientation of the hydroxyl group at the 4' carbon of the sugar - it has the opposite chirality - which may account for its faster elimination and reduced toxicity. Epirubicin is primarily used against breast and ovarian cancer, gastric cancer, lung cancer and lymphomas.

    Development history

    The first trial of epirubicin in humans was published in 1980.[1] Upjohn applied for approval by the U.S. Food and Drug Administration (FDA) in node-positive breast cancer in 1984, but was turned down because of lack of data.[2] In 1999 Pharmacia (who had by then merged with Upjohn) received FDA approval for the use of epirubicin as a component of adjuvant therapy in node-positive patients.

    Patent protection for epirubicin expired in August 2007.

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    References
    1. Bonfante V, Bonadonna G, Villani F, Martini A (1980). "Preliminary clinical experience with 4-epidoxorubicin in advanced human neoplasia". Recent Results in Cancer Research. Fortschritte der Krebsforschung. Progres dans les Recherches Sur le Cancer. Recent Results in Cancer Research. 74: 192–9. doi:10.1007/978-3-642-81488-4_24. ISBN 978-3-642-81490-7. PMID 6934564.
    2. "Oncology Approval: epirubicin hydrochloride (Ellence)". On Target. Target Health Inc. September 15, 1999. Archived from the original on 2008-05-10. Retrieved 2007-08-04.
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