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Anthracycline antileukemic drug
Idarubicin
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
Legal status
Protein binding 97%
Elimination half-life 22 hours
(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
PubChem
CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (
EPA )
Formula C 26 H 27 N O 9
Molar mass 497.500 g·mol−1 3D model (
JSmol )
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=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
(verify)
Idarubicin 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]
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 .
[4]
It is used for treatment of
acute lymphoblastic leukemia and
chronic myelogenous leukemia in blast crisis.
[5]
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.
[6]
References
^ 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 .
^
"Idamycin Package insert" (PDF) . Pfizer . January 2006.
^ Pang B, Qiao X, Janssen L, Velds A, Groothuis T, Kerkhoven R, et al. (2013).
"Drug-induced histone eviction from open chromatin contributes to the chemotherapeutic effects of doxorubicin" . Nature Communications . 4 : 1908.
Bibcode :
2013NatCo...4.1908P .
doi :
10.1038/ncomms2921 .
PMC
3674280 .
PMID
23715267 .
^ Arwanih EY, Louisa M, Rinaldi I, Wanandi SI (December 2022).
"Resistance Mechanism of Acute Myeloid Leukemia Cells Against Daunorubicin and Cytarabine: A Literature Review" . Cureus . 14 (12): e33165.
doi :
10.7759/cureus.33165 .
PMC
9885730 .
PMID
36726936 .
^ Katzung BG (2017-11-30). Basic & clinical pharmacology . McGraw-Hill Education.
ISBN
9781259641152 .
OCLC
1009849139 .
^
"Idarubicin Side Effects: Common, Severe, Long Term" . Drugs.com . Retrieved 2019-06-21 .
External links