Idarubicin

Idarubicin

Clinical data
Other names	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
ATC code	L01DB06 (WHO)
Pharmacokinetic data
Protein binding	97%
Elimination 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
CAS Number	58957-92-9
PubChem CID	42890
DrugBank	APRD00126
ChemSpider	39117 Y
UNII	ZRP63D75JW
KEGG	D08062 Y
ChEBI	CHEBI:42068
ChEMBL	ChEMBL1117 Y
CompTox Dashboard (EPA)	DTXSID7023142
Chemical and physical data
Formula	C26H27NO9
Molar mass	497.494 g/mol g·mol−1
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
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Idarubicin (Template:Pron-en) or 4-demethoxydaunorubicin is an anthracycline antileukemic drug. It inserts itself into DNA and prevents DNA from 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.

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).