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
AHFS/Drugs.com	Monograph
MedlinePlus	a691004
ATC code	L01DB06 (WHO)
Legal status
Legal status	US: ℞-only
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 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
E number	{{#property:P628}}
CompTox Dashboard (EPA)	{{#property:P3117}}
ECHA InfoCard	{{#property:P2566}}
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[[email protected]@](O)(C(=O)C)C[[email protected]@H]5O[[email protected]@H]4O[[email protected]]([[email protected]@H](O)[[email protected]@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 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).

Side effects

Diarrhea, stomach cramps, nausea and vomiting are common among patients treated with idarubicin.

External links

• Idarubicin bound to proteins in the PDB

Latest research - Idarubicin

• Most recent articles
• Most cited
• Ongoing trials