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 cat.	D (US)
Legal status	℞-only (US)
Pharmacokinetic data
Protein binding	97%
Half-life	22 hours
Identifiers
CAS number	58957-92-9 Y
ATC code	L01DB06
PubChem	CID 42890
DrugBank	DB01177
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
Mol. 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
Y (what is this?)  (verify)

Idarubicin (pron.: /ˌaɪdəˈruːbɨsɪn/) 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).

External links

• Idarubicin bound to proteins in the PDB