Idarubicin
- L01DB06 (WHO)
- US: ℞-only
- (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
- 58957-92-9 Y
- 42890
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- 39117 Y
- ZRP63D75JW
- D08062 Y
- CHEBI:42068 Y
- ChEMBL1117 Y
- DTXSID7023142
- Interactive image
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- 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
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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
- ^ 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
- Idarubicin bound to proteins in the PDB
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(M phase)
Block microtubule assembly | |
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Block microtubule disassembly |
inhibitor
DNA precursors/ antimetabolites (S phase) |
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Topoisomerase inhibitors (S phase) |
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Crosslinking of DNA (CCNS) |
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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