Chemistry:Idarubicin
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| 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 |
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| Protein binding | 97% |
| Elimination half-life | 22 hours |
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| Formula | C26H27NO9 |
| Molar mass | 497.500 g·mol−1 |
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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]
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
- ↑ "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. 2013. doi:10.1016/j.jscs.2011.02.019.
- ↑ "Idamycin Package insert". Pfizer. January 2006. http://www.pfizer.com/files/products/uspi_idamycin.pdf.
- ↑ "Drug-induced histone eviction from open chromatin contributes to the chemotherapeutic effects of doxorubicin". Nature Communications 4: 1908. 2013. doi:10.1038/ncomms2921. PMID 23715267. Bibcode: 2013NatCo...4.1908P.
- ↑ "Resistance Mechanism of Acute Myeloid Leukemia Cells Against Daunorubicin and Cytarabine: A Literature Review". Cureus 14 (12): e33165. December 2022. doi:10.7759/cureus.33165. PMID 36726936.
- ↑ Basic & clinical pharmacology. McGraw-Hill Education. 2017-11-30. ISBN 9781259641152. OCLC 1009849139.
- ↑ "Idarubicin Side Effects: Common, Severe, Long Term" (in en). https://www.drugs.com/sfx/idarubicin-side-effects.html.
External links
- Idarubicin bound to proteins in the PDB
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