Epirubicin

AU:D L01DB03(WHO) UK:POM(Prescription only)US:℞-only (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 56420-45-2Y 41867 DB00445Y 38201Y 3Z8479ZZ5X D07901Y CHEBI:47898Y ChEMBL417Y DTXSID0022987 Interactive image 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/s1YKey:AOJJSUZBOXZQNB-VTZDEGQISA-NY Epirubicinis ananthracyclinedrugused forchemotherapy.​‍​​​​​‍​‍‍‍‍​‍‍ It can be used in combination with other medications to treatbreast cancerin patients who have had surgery to remove the tumor. It is marketed byPfizerunder the trade nameEllencein the US andPharmorubicinorEpirubicin Ebeweelsewhere. Similarly to other anthracyclines, epirubicin acts byintercalatingDNAstrands. Intercalation results in complex formation which inhibits DNA and RNA synthesis. It also triggers DNA cleavage bytopoisomerase 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 generatesfree radicalsthat cause cell and DNA damage. Epirubicin is favoured overdoxorubicin, the most popular anthracycline, in somechemotherapy regimensas 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.