Article: 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
Formula	C27H29NO11
Mol. weight	543.519 g/mol
Pharmacokinetic data
Bioavailability	NA
Protein binding	77%
Metabolism	Hepatic glucuronidation and 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 (marketed by Pfizer under the trade name Ellence®) is an anthracycline drug used for chemotherapy. Similarly to other anthracyclines, it 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 less 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 ovarium cancer, gastric cancer, lung cancer, and lymphomas.