4-demethoxydaunorubicin

Idarubicin

Clinical data
AHFS/Drugs.com	Monograph
MedlinePlus	a691004
Pregnancy category	US: D (Evidence of risk)
ATC code	L01DB06 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Protein binding	97%
Biological half-life	22 hours
Identifiers
IUPAC name (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-trideoxo-α-L-lyxo-hexopyranoside
Synonyms	9-acetyl-7-(4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl)oxy-6,9,11-trihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione
CAS Number	58957-92-9 Y
PubChem CID	42890
IUPHAR/BPS	7083
DrugBank	DB01177 Y
ChemSpider	39117 Y
UNII	ZRP63D75JW
KEGG	D08062 Y
ChEBI	CHEBI:42068 Y
ChEMBL	CHEMBL1117 Y
Chemical and physical data
Formula	C26H27NO9
Molar mass	497.494 g/mol
3D model (JSmol)	Interactive image
SMILES O=C2c1c(O)c5c(c(O)c1C(=O)c3ccccc23)C[C@@](O)(C(=O)C)C[C@@H]5O[C@@H]4O[C@H]([C@@H](O)[C@@H](N)C4)C
InChI InChI=1S/C26H27NO9/c1-10-21(29)15(27)7-17(35-10)36-16-9-26(34,11(2)28)8-14-18(16)25(33)20-19(24(14)32)22(30)12-5-3-4-6-13(12)23(20)31/h3-6,10,15-17,21,29,32-34H,7-9,27H2,1-2H3/t10-,15-,16-,17-,21+,26-/m0/s1 Y Key:XDXDZDZNSLXDNA-TZNDIEGXSA-N Y

Idarubicin /ˌaɪdəˈruːbᵻsɪn/ 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 distributed under the trade names Zavedos (UK) and Idamycin (USA).