Epirubicin

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Epirubicin
Epirubicin2DACS.svg
Epirubicin ball-and-stick.png
Names
Trade namesEllence, Pharmorubicin, Epirubicin Ebewe, others
  • (8S,10S)-10-{[(2R,4S,5R,6S)-4-Amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
Clinical data
Pregnancy
category
  • AU: D
  • US: D (Evidence of risk)
Routes of
use
Intravenous
External links
AHFS/Drugs.comMonograph
US NLMEpirubicin
MedlinePlusa603003
Legal
Legal status
Pharmacokinetics
BioavailabilityNA
Protein binding77%
MetabolismHepatic glucuronidation and oxidation
ExcretionBiliary and renal
Chemical and physical data
FormulaC27H29NO11
Molar mass543.525 g·mol−1
3D model (JSmol)
  • O=C2c1c(O)c5c(c(O)c1C(=O)c3cccc(OC)c23)C[C@@](O)(C(=O)CO)C[C@@H]5O[C@@H]4O[C@H]([C@H](O)[C@@H](N)C4)C
  • InChI=1S/C27H29NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,17-,22-,27-/m0/s1 checkY
  • Key:AOJJSUZBOXZQNB-VTZDEGQISA-N checkY
  (verify)

Epirubicin, sold under the brand name Ellence among others, is a medication used to treat breast cancer, ovarian cancer, gastric cancer, lung cancer and lymphomas.


It is an anthracycline. 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.


Side effects

Anthracyclines (including Epirubicin) have been shown to have cardiotoxic properties.[1]

History

The first trial of epirubicin in humans was published in 1980.[2] 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.[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. Mecinaj A, Gulati G, Heck SL, Holte E, Fagerland MW, Larsen AI, Blix ES, Geisler J, Wethal T, Omland T. Rationale and design of the PRevention of cArdiac Dysfunction during Adjuvant breast cancer therapy (PRADA II) trial: a randomized, placebo-controlled, multicenter trial. Cardiooncology. 2021 Sep 27;7(1):33. doi: 10.1186/s40959-021-00115-w. PMID: 34579775; PMCID: PMC8474901.
  2. 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.
  3. "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.

External links

Identifiers: