Epirubicin



Epirubicin
Systematic (IUPAC) name
10-(4-amino-5-hydroxy-6-methyl-oxan-2-yl) oxy-6,8,11-trihydroxy-8-(2-hydroxyacetyl)- 1-methoxy-9,10-dihydro-7H-tetracene-5,12-dione
Identifiers
CAS number 56420-45-2
ATC code L01DB03
PubChem 41867
DrugBank APRD00361
Chemical data
O11 
mol
Pharmacokinetic data
Bioavailability NA
Protein binding 77%
oxidation
Half life  ?
Excretion Biliary and renal
Therapeutic considerations
Pregnancy cat.

D (Au, U.S.)

Legal status

℞-only (U.S.), POM (UK)

Routes Intravenous

Epirubicin is an Pfizer under the trade name Ellence in the US and Pharmorubicin or Epirubicin "Ebewe" elsewhere.

Similarly to other anthracyclines, epirubicin acts by DNA strands. Intercalation results in complex formation which inhibits DNA and RNA synthesis. It also triggers DNA cleavage by free radicals that cause cell and DNA damage.

Epirubicin is favoured over 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, 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 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 (1980). "Preliminary clinical experience with 4-epidoxorubicin in advanced human neoplasia". Recent results in cancer research 74: 192–9. PM6934564.
  2. ^ On Target.
  3. ^ According to the proprietary database iddb.com
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This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Epirubicin". A list of authors is available in Wikipedia.