Idarubicin

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Idarubicin
Idarubicin.svg
Idarubicin ball-and-stick.png
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 YesY
ATC code L01DB06
PubChem CID 42890
DrugBank DB01177
ChemSpider 39117 YesY
UNII ZRP63D75JW YesY
KEGG D08062 YesY
ChEBI CHEBI:42068 YesY
ChEMBL CHEMBL1117 YesY
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
 YesY (what is this?)  (verify)

Idarubicin /ˌdəˈrbɨsɪn/ 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] Similar to other anthracyclines, it also induces histone eviction from chromatin.[2]

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[edit]

  1. ^ Package insert
  2. ^ Pang B, Qiao X, Janssen L, Velds A, Groothuis T, Kerkhoven R, Nieuwland M, Ovaa H, Rottenberg S, van Tellingen O, Janssen J, Huijgens P, Zwart W, Neefjes J (2013). "Drug-induced histone eviction from open chromatin contributes to the chemotherapeutic effects of doxorubicin". Nature Communications 4: 1908. doi:10.1038/ncomms2921. PMID 23715267. 

External links[edit]