Idarubicin

Idarubicin

Systematic (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
Clinical data
AHFS/Drugs.com	monograph
MedlinePlus	a691004
Pregnancy category	US: D (Evidence of risk)
Legal status	US: ℞-only
Pharmacokinetic data
Protein binding	97%
Biological half-life	22 hours
Identifiers
CAS Number	58957-92-9 Y
ATC code	L01DB06 (WHO)
PubChem	CID: 42890
IUPHAR/BPS	7083
DrugBank	DB01177 Y
ChemSpider	39117 Y
UNII	ZRP63D75JW Y
KEGG	D08062 Y
ChEBI	CHEBI:42068 Y
ChEMBL	CHEMBL1117 Y
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
Chemical data
Formula	C26H27NO9
Molecular mass	497.494 g/mol
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 /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).

External links

• Idarubicin bound to proteins in the PDB