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.
Legal status
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 [1]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.[2] Similar to other anthracyclines, it also induces histone eviction from chromatin.[3]

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. ^ Miller JP, Stoodley RJ (2013). "Studies directed towards anthracyclinone syntheses: The use of d-glucose as a chiral auxiliary in asymmetric Diels–Alder reactions". J. Saudi Chem. Soc. 17: 29–42. doi:10.1016/j.jscs.2011.02.019. 
  2. ^ Package insert
  3. ^ 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]