Idarubicin

Idarubicin /ˌaɪdəˈruːbɪsɪn/ or 4-demethoxydaunorubicin is an anthracycline antileukemic drug. It inserts [1] 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.[2] Similar to other anthracyclines, it also induces histone eviction from chromatin.[3]

Idarubicin
Clinical data
Other names9-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.comMonograph
MedlinePlusa691004
Pregnancy
category
  • US: D (Evidence of risk)
    ATC code
    Legal status
    Legal status
    Pharmacokinetic data
    Protein binding97%
    Elimination half-life22 hours
    Identifiers
    CAS Number
    PubChem CID
    IUPHAR/BPS
    DrugBank
    ChemSpider
    UNII
    KEGG
    ChEBI
    ChEMBL
    CompTox Dashboard (EPA)
    Chemical and physical data
    FormulaC26H27NO9
    Molar mass497.494 g/mol g·mol−1
    3D model (JSmol)
      (verify)

    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 used for treatment of acute lymphoblastic leukemia and Chronic myelogenous leukemia in blast crisis.[4]

    It is distributed under the trade names Zavedos (UK) and Idamycin (USA).

    Side effects

    Diarrhea, stomach cramps, nausea and vomiting are common among patients treated with idarubicin.[5]

    References
    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. PMC 3674280. PMID 23715267.
    4. Katzung, Bertram G., editor. (2017-11-30). Basic & clinical pharmacology. ISBN 9781259641152. OCLC 1009849139.CS1 maint: multiple names: authors list (link) CS1 maint: extra text: authors list (link)
    5. "Idarubicin Side Effects: Common, Severe, Long Term". Drugs.com. Retrieved 2019-06-21.


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