Misplaced Pages

Idarubicin

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Anthracycline antileukemic drug Pharmaceutical compound
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
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding97%
Elimination half-life22 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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC26H27NO9
Molar mass497.500 g·mol
3D model (JSmol)
SMILES
  • O=C2c1c(O)c5c(c(O)c1C(=O)c3ccccc23)C(O)(C(=O)C)C5O4O((O)(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 /ˌaɪdəˈruːbɪsɪn/ or 4-demethoxydaunorubicin is an anthracycline antileukemic drug. It inserts 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. Similar to other anthracyclines, it also induces histone eviction from chromatin.

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.

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.

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. "Idamycin Package insert" (PDF). Pfizer. January 2006.
  3. 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.
  4. 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.
  5. Katzung BG (2017-11-30). Basic & clinical pharmacology. McGraw-Hill Education. ISBN 9781259641152. OCLC 1009849139.
  6. "Idarubicin Side Effects: Common, Severe, Long Term". Drugs.com. Retrieved 2019-06-21.

External links

Intracellular chemotherapeutic agents / antineoplastic agents (L01)
SPs/MIs
(M phase)
Block microtubule assembly
Block microtubule disassembly
DNA replication
inhibitor
DNA precursors/
antimetabolites
(S phase)
Folic acid
Purine
Pyrimidine
Deoxyribonucleotide
Topoisomerase inhibitors
(S phase)
I
II
II+Intercalation
Crosslinking of DNA
(CCNS)
Alkylating
Platinum-based
Nonclassical
Intercalation
Photosensitizers/PDT
Other
Enzyme inhibitors
Receptor antagonists
Other/ungrouped
Stub icon

This antineoplastic or immunomodulatory drug article is a stub. You can help Misplaced Pages by expanding it.

Categories: