Compound: Epirubicin
SMILES: O=C1c2c(O)c3c(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@@H]4O[C@H]([C@H](O)[C@H](C4)N)C)c(c2C(=O)c5c1c(OC)ccc5)O
InChIKey: AOJJSUZBOXZQNB-VTZDEGQISA-N
Synonyms: Epirubicin, 56420-45-2, Epiadriamycin, Epidoxorubicin, 4'-Epiadriamycin, Epirubicine, Epirubicina, Ridorubicin, Epirubicinum, Pidorubicina, Pidorubicine, Pidorubicinum, 4'-epidoxorubicin, Farmorubicin, Epirubicinum [Latin], Pidorubicin, IMI 28, NSC-256942, 4'-epi-Doxorubicin, NSC 256942, 3Z8479ZZ5X, DTXSID0022987, CHEBI:47898, NSC256942, Epirubicinum (Latin), (7S,9S)-7-[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione, (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, 4' Epi Adriamycin, 4'-Epi-DXR, Farmorubicine, EPIcell, 4' Epiadriamycin, EPI cell, 4' Epidoxorubicin, (7S,9S)-7-((2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl)oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione, (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, Epi DX, 4' Epi Doxorubicin, RefChem:55117, 4'-epi DX, 4' Epi DXR, DTXCID202987, L01DB03, 5,12-Naphthacenedione, 10-((3-amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S-cis)-, (1S,3S)-3-GLYCOLOYL-1,2,3,4,6,11-HEXAHYDRO-3,5,12-TRIHYDROXY-10-METHOXY-6,11-DIOXO-1-NAPHTHACENYL 3-AMINO-2,3,6-TRIDEOXY-alpha-L-ARABINO-HEXOPYRANOSIDE, (8S-cis)-10-((3-Amino-2,3,6-trideoxy-beta-L-arabino-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione, 3-Glycoloyl-1,2,3,4,6,11-hexahydro-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1-naphthacenyl-3-amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranoside, Pharmorubicin, 4-Epidoxorubicin, Epirubicin free base, Epirubicin (INN), (8S,10S)-10-(((2R,4S,5R,6S)-4-Amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione, Epi-DX, Epirubicine [French], Epirubicina [Spanish], 5,12-Naphthacenedione,10-[(3-amino-2,3,6-trideoxy-a-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S,10S)-, Epirubicine [INN-French], Epirubicinum [INN-Latin], Epirubicina [INN-Spanish], Pidorubicine [INN-French], Pidorubicinum [INN-Latin], Pidorubicina [INN-Spanish], EPIRUBICIN [INN], Epirubicin [INN:BAN], (1S,3S)-3,5,12-trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranoside, WP 697, Farmorubicin (TN), CCRIS 2261, HSDB 6962, BRN 1445813, Epi-doxorubicin, UNII-3Z8479ZZ5X, DM6, Acid, 8, EPIRUBICIN [MI], 56420-45-2 (FREE BASE), EPIRUBICIN [HSDB], EPIRUBICIN [VANDF], CHEMBL417, SCHEMBL8582, EPIRUBICIN [WHO-DD], orb1740387, SCHEMBL29350836, SCHEMBL29711855, BDBM43839, Doxorubicin-13CD3 (discontinued), DM2, EBC-27300, DB00445, NCGC00263918-04, NCGC00263918-06, NCGC00263918-08, (1S,3S)-3,5,12-trihydroxy-3-(hydroxyacetyl)-10-(methyloxy)-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranoside, (7S,9R)-7-[(2S,4S,5R,6S)-4-Amino-5-hydroxy-6-methyl-oxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione, (7S,9S)-7-[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione, 10-((3-amino-2,3,6-trideoxy-beta-L-arabino-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-(8S-cis)-5,12-naphthacenedione, 5,12-Naphthacenedione, 10-((3-amino-2,3,6-trideoxy-beta-L-arabino-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S-cis)-, BP-43652, HY-13624, SBI-0206890.P001, NS00069619, D07901, AB00698552-11, AB00698552-13, AB00698552-14, AB00698552_15, AB00698552_16, EN300-7410311, Q425122, BRD-K04548931-003-13-2, BRD-K04548931-003-16-5, (1S,3S)-3-GLYCOLOYL-1,2,3,4,6,11-HEXAHYDRO-3,5,12-TRIHYDROXY-10-METHOXY-6,11-DIOXO-1-NAPHTHACENYL 3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-ARABINO-HEXOPYRANOSIDE, 5,12-NAPHTHACENEDIONE, 10-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-ARABINO-HEXOPYRANOSYL)OXY)-7,8,9,10-TETRAHYDRO-6,8,11-TRIHYDROXY-8-(HYDROXYACETYL)-1-METHOXY-, (8S-CIS)-, 5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-.alpha.-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-, (8S,10S)-
Theoretical properties:
molecular_formula: C27H29NO11
molecular_weight: 543.5 g/mol
exact_mass: 543.17406074 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 6
hydrogen_bond_acceptor_count: 12
rotatable_bond_count: 5
heavy_atom_count: 39
topological_polar_surface_area: 206 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: 4'-epidoxorubicin is an anthracycline that is the 4'-epi-isomer of doxorubicin. It has a role as an antimicrobial agent, an antineoplastic agent and an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor. It is a primary alpha-hydroxy ketone, a tertiary alpha-hydroxy ketone, a member of p-quinones, a deoxy hexoside, an aminoglycoside, an anthracycline, an anthracycline antibiotic and a monosaccharide derivative. It is functionally related to a doxorubicin. It is a conjugate base of a 4'-epidoxorubicinium.
chebi: An anthracycline that is the 4'-epi-isomer of doxorubicin.
chembl: EPIRUBICIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: 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.