Compound: IDARUBICIN
SMILES: O=C1c2c(O)c3c(C[C@@](O)(C(=O)C)C[C@@H]3O[C@@H]4O[C@H]([C@@H](O)[C@H](C4)N)C)c(c2C(=O)c5c1cccc5)O
InChIKey: XDXDZDZNSLXDNA-TZNDIEGXSA-N
Synonyms: IDARUBICIN, 58957-92-9, 4-Demethoxydaunorubicin, 4-Demethoxydaunomycin, Idarubicina, Idarubicine, Idarubicinum, Zavedos, ZRP63D75JW, NSC 256439, DTXSID7023142, CHEBI:42068, (7S,9S)-9-acetyl-7-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione, 5,12-Naphthacenedione, 9-acetyl-7-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,9,11-trihydroxy-, (7S-cis)-, (1S,3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydronaphthacen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside, 4-Desmethoxydaunorubicin, 4 Demethoxydaunorubicin, (7S,9S)-9-acetyl-7-(((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl)oxy)-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione, 4 Desmethoxydaunorubicin, RefChem:56926, 4-DMDR, DTXCID503142, L01DB06, (7S-cis)-9-Acetyl-7-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,9,11-trihydroxy-5,12-naphthacenedione, (1S,3S)-3-Acetyl-1,2,3,4,6,11-hexahydro-3,5,12-trihydroxy-6,11-dioxo-1-naphthacenyl-3-amino-2,3,6-trideoxy-alpha-L-hexopyranoside, Idarubicine [INN-French], Idarubicinum [INN-Latin], Idarubicina [INN-Spanish], Idarubicin (INN), (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione, (1S,3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside, IDARUBICIN [INN], Idarubicin [INN:BAN], (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione, DM5, MLS001401448, Daunomycin, 4-demethoxy-, Zavedos (TN), CCRIS 5083, C26H27NO9, NCGC00093976-03, SMR000466355, UNII-ZRP63D75JW, 4-DMD, Idarubicin?, SR-01000075934, IDARUBICIN [MI], (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride, IDARUBICIN [VANDF], I 1656, SCHEMBL3750, CHEMBL1117, IDARUBICIN [WHO-DD], Lopac0_000600, KBioSS_002388, Idarubicin hydrochloride, solid, cid_636362, GTPL7083, orb1689953, 4-DEMETHOXY-DAUNORUBICIN, SCHEMBL29367751, SCHEMBL29381904, BDBM58490, HMS2089D05, HMS3261H22, Tox21_500600, EBC-27233, HY-17381A, AKOS015895563, AC-9384, CCG-204689, DB01177, LP00600, SDCCGSBI-0050582.P002, NCGC00093976-01, NCGC00093976-02, NCGC00093976-04, NCGC00093976-05, NCGC00093976-12, NCGC00093976-18, NCGC00261285-01, 5,12-Naphthacenedione, 7,8,9,10-tetrahydro-9-acetyl-7-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-6,9,11-trihydroxy-, (7S-cis)-, CS-0007534, EU-0100600, D08062, H58679, AB00698511-06, AB00698511-08, AB00698511-09, AB00698511-10, AB00698511_11, EN300-7479233, Q1063862, SR-01000075934-1, BRD-K69650333-001-01-1, BRD-K69650333-001-02-9, BRD-K69650333-003-13-2, BRD-K69650333-003-14-0, Idarubicin, United States Pharmacopeia (USP) Reference Standard, (1S,3S)-3-ACETYL-1,2,3,4,6,11-HEXAHYDRO-3,5,12-TRIHYDROXY-6,11-DIOXO-1-NAPHTHACENYL 3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSIDE, (7S,9S)-7-[(2R,4S,5S,6S)-4-azanyl-6-methyl-5-oxidanyl-oxan-2-yl]oxy-9-ethanoyl-6,9,11-tris(oxidanyl)-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride, (7S,9S)-9-Acetyl-7-(((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,9,11-trihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione, (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-quinone;hydrochloride, (7S,9S)-9-acetyl-7-[[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-2-oxanyl]oxy]-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride, 5,12-Naphthacenedione, 7,8,9,10-tetrahydro-9-acetyl-7-((3-amino-2,3,6-trideoxy-.alpha.-L-lyxo-hexopyranosyl)oxy)-6,9,11-trihydroxy-, (7S-cis)-, 5,12-NAPHTHACENEDIONE, 9-ACETYL-7-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-7,8,9,10-TETRAHYDRO-6,9,11-TRIHYDROXY-, (7S,9S)-, 5,12-Naphthacenedione,9-acetyl-7-[(3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,9,11-trihydroxy-, (7S,9S)-
Theoretical properties:
molecular_formula: C26H27NO9
molecular_weight: 497.5 g/mol
exact_mass: 497.16858144 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 5
hydrogen_bond_acceptor_count: 10
rotatable_bond_count: 3
heavy_atom_count: 36
topological_polar_surface_area: 177 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
solubility: 7.72e-01 g/L
Descriptions:
pubchem: Idarubicin is a deoxy hexoside, an anthracycline antibiotic and a monosaccharide derivative. It derives from a hydride of a tetracene.
chembl: IDARUBICIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Idarubicin  or 4-demethoxydaunorubicin is an anthracycline antileukemic drug. It inserts itself into DNA and prevents DNA unwinding by interfering with the enzyme topoisomerase II. It is an analog of daunorubicin, but the absence of a methoxy group increases its fat solubility and cellular uptake.
Similar to other anthracyclines, it also induces histone eviction from chromatin.
It belongs to the family of drugs called antitumor antibiotics.
It is currently combined with cytosine arabinoside as a first line treatment of acute myeloid leukemia.
It is used for treatment of acute lymphoblastic leukemia and chronic myelogenous leukemia in blast crisis.
It is distributed under the trade names Zavedos (UK) and Idamycin (USA).