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 ;
PubChem CID	42890;
DrugBank	DB01177 ;
ChemSpider	39117 ;
UNII	ZRP63D75JW;
KEGG	D08062 ;
ChEBI	CHEBI:42068 ;
ChEMBL	ChEMBL1117 ;
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 ; Key:XDXDZDZNSLXDNA-TZNDIEGXSA-N ;
	(verify)

Idarubicin (/[invalid input: 'icon']ˌaɪdəˈruːb[invalid input: 'ɨ']sɪn/) 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. ^[1]

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).

References

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