Idarubicin

Idarubicin
Clinical data
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	L01DB06 (WHO) ;
Legal status
Legal status	US: ℞-only ;
Pharmacokinetic data
Protein binding	97%
Elimination half-life	22 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	58957-92-9 ;
PubChem CID	42890;
IUPHAR/BPS	7083;
DrugBank	DB01177 ;
ChemSpider	39117 ;
UNII	ZRP63D75JW;
KEGG	D08062 ;
ChEBI	CHEBI:42068 ;
ChEMBL	ChEMBL1117 ;
CompTox Dashboard (EPA)	DTXSID7023142 ;
Chemical and physical data
Formula	C26H27NO9
Molar mass	497.500 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 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 ^[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.

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

^ 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.
^ Package insert
^ 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.
^ Katzung, Bertram G., editor. (2017-11-30). Basic & clinical pharmacology. 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

[Miller-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

[Pang-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.

[5] "Idarubicin Side Effects: Common, Severe, Long Term". Drugs.com. Retrieved 2019-06-21.

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