Compound: Amrubicin
SMILES: O=C1c2c(O)c3c(C[C@@](N)(C(=O)C)C[C@@H]3O[C@@H]4OC[C@@H](O)[C@H](C4)O)c(c2C(=O)c5c1cccc5)O
InChIKey: VJZITPJGSQKZMX-XDPRQOKASA-N
Synonyms: Amrubicin, 110267-81-7, amrubicina, amrubicine, amrubicinum, 93N13LB4Z2, CHEBI:135779, DTXSID30869526, RefChem:557927, DTXCID00817498, L01DB10, (+)-(7S,9S)-9-Acetyl-9-amino-7-((2-deoxy-beta-D-erythro-pentopyranosyl)oxy)-6,11-dihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione, (7S,9S)-9-acetyl-9-amino-7-(((2S,4S,5R)-4,5-dihydroxyoxan-2-yl)oxy)-6,11-dihydroxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione, Amrubicin(SM-5887), Amrubicin [INN], (+-)-(7S,9S)-9-Acetyl-9-amino-7-((2-deoxy-beta-D-erythro-pentopyranosyl)oxy)-7,8,9,10-tetrahydro-6,11-dihydroxy-5,12-naphthacenedione, (7S,9S)-9-acetyl-9-amino-7-[(2S,4S,5R)-4,5-dihydroxyoxan-2-yl]oxy-6,11-dihydroxy-8,10-dihydro-7H-tetracene-5,12-dione, (7S,9S)-9-acetyl-9-amino-7-(((2S,4S,5R)-4,5-dihydroxytetrahydro-2H-pyran-2-yl)oxy)-6,11-dihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione, C25H25NO9, Amrubicin [USAN:INN], UNII-93N13LB4Z2, Amrubicin maleate, (7S,9S)-9-acetyl-9-amino-7-{[(2S,4S,5R)-4,5-dihydroxytetrahydro-2H-pyran-2-yl]oxy}-6,11-dihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione, AMRUBICIN [MI], Amrubicin (USAN/INN), AMRUBICIN [USAN], AMRUBICIN [MART.], AMRUBICIN [WHO-DD], SCHEMBL9140, orb1704691, CHEMBL1186894, EX-A161, VJZITPJGSQKZMX-XDPRQOKASA-N, HY-B0067, AKOS030526071, AA16085, DB06263, AC-31129, NS00069182, D08854, W-60403, Q4748723, BRD-K13843533-001-01-7, BRD-K13843533-001-02-5, (+)-(7S,9S)-9-acetyl-9-amino-7-[(2-deoxy--D-erythro-pentopyranosyl)oxy]-7,8,9,10-tetrahydro-6,11-dihydroxy-5,12-naphthacenedione hydrochloride, (1S,3S)-3-acetyl-3-amino-5,12-dihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 2-deoxy-beta-D-erythro-pentopyranoside, (7S,9S)-9-acetyl-9-amino-7-[(2S,4S,5R)-4,5-dihydroxytetrahydropyran-2-yl]oxy-6,11-dihydroxy-8,10-dihydro-7H-tetracene-5,12-dione, 5,12-Naphthacenedione, 9-acetyl-9-amino-7-((2-deoxy-beta-D-erythro-pentopyranosyl)oxy)-7,8,9,10-tetrahydro-6,11-dihydroxy-, (7S,9S)-, 913076-54-7
Theoretical properties:
molecular_formula: C25H25NO9
molecular_weight: 483.5 g/mol
exact_mass: 483.15293138 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 5
hydrogen_bond_acceptor_count: 10
rotatable_bond_count: 3
heavy_atom_count: 35
topological_polar_surface_area: 177 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 172-174
solubility: not soluble in water, but soluble in DMSO
Descriptions:
pubchem: Amrubicin is a synthetic anthracycline antibiotic with molecular formula C25H25NO9. A specific inhibitor of topoisomerase II, it is used (particularly as the hydrochloride salt) in the treatment of cancer, especially lung cancer, where it is a prodrug for the active metabolite, ambrucinol. It has a role as a topoisomerase II inhibitor, an antineoplastic agent and a prodrug. It is a quinone, an anthracycline antibiotic, a primary amino compound, a member of tetracenes and a methyl ketone.
chebi: A synthetic anthracycline antibiotic with molecular formula C<small><sub>25</sub></small>H<small><sub>25</sub></small>NO<small><sub>9</sub></small>. A specific inhibitor of topoisomerase II, it is used (particularly as the hydrochloride salt) in the treatment of cancer, especially lung cancer, where it is a prodrug for the active metabolite, ambrucinol.
chembl: AMRUBICIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
wikipedia: Amrubicin (INN; previously known as SM-5887) is an anthracycline used in the treatment of lung cancer. It is marketed in Japan since 2002 by Sumitomo under the brand name Calsed.
Amrubicin acts by inhibiting topoisomerase II, and has been compared in clinical trials with topotecan, a Topoisomerase I inhibitor.
It has also been studied for the treatment of bladder carcinoma and gastric cancer.
Amrubicin was the first anthracycline derivative created by de novo synthesis and was first published in 1989 by scientists from Sumitomo.