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Epirubicin

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Epirubicin
File:Epirubicin.png
File:Epirubicin ball-and-stick.png
Systematic (IUPAC) name
(8R,10S)-10-((2S,4S,5R,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione
Clinical data
Trade names Ellence
AHFS/Drugs.com monograph
MedlinePlus a603003
  • ℞-only (U.S.), POM (UK)
Intravenous
Pharmacokinetic data
Bioavailability NA
Protein binding 77%
Metabolism Hepatic glucuronidation and oxidation
Excretion Biliary and renal
Identifiers
56420-45-2 7pxY
L01DB03
PubChem CID 41867
DrugBank DB00445 7pxY
ChemSpider 38201 7pxY
UNII 3Z8479ZZ5X 7pxY
KEGG D07901 7pxY
ChEBI CHEBI:47898 7pxY
ChEMBL CHEMBL417 7pxY
Chemical data
Formula C27H29NO11
543.519 g/mol
 14pxY (what is this?)  (verify)

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.

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] It appears to have been licensed for use in Europe from around this time however.[3] 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.

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 74: 192–9. PMID 6934564. PM6934564. 
  2. ^ "On Target". 
  3. ^ According to the proprietary database iddb.com

External links