WordNet

a complex consisting of an organic base in association with hydrogen chloride

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/09/15 17:59:53」(JST)

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Idarubicin /ˌaɪdəˈruːbɨsɪn/ 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 distributed under the trade names Zavedos (UK) and Idamycin (USA).

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. PMID 23715267.

External links

Idarubicin bound to proteins in the PDB

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UpToDate Contents

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1. アントラサイクリン系化学療法剤の心毒性 cardiotoxicity of anthracycline like chemotherapy agents
2. 若年成人における急性骨髄性白血病に対する導入療法 induction therapy for acute myeloid leukemia in younger adults
3. 成人における急性前骨髄球性白血病の初期治療 initial treatment of acute promyelocytic leukemia in adults
4. 高齢者における急性骨髄性白血病の治療 treatment of acute myeloid leukemia in older adults
5. 再発性または難治性の急性骨髄性白血病の治療 treatment of relapsed or refractory acute myeloid leukemia

English Journal

Lipiodol Trans-arterial Chemoembolization of Hepatocellular Carcinoma with Idarubicin: First Experience.

Favelier S, Boulin M, Hamza S, Cercueil JP, Cherblanc V, Lepage C, Hillon P, Chauffert B, Krausé D, Guiu B.SourceDigestive, Thoracic and Oncologic Unit, Department of Diagnostic and Interventional Radiology, University Hospital of Dijon, 14, rue Paul Gaffarel, Dijon, 21000, France.
Cardiovascular and interventional radiology.Cardiovasc Intervent Radiol.2013 Aug;36(4):1039-46. doi: 10.1007/s00270-012-0532-8. Epub 2012 Dec 8.
BACKGROUND: There is still no consensus about the best chemotherapeutic agent for transarterial chemoembolization (TACE). A recent in vitro study demonstrated that idarubicin, an anthracycline, was by far the most cytotoxic drug on human hepatocellular carcinoma (HCC) cell lines. Idarubicin is much
PMID 23224215

Idarubicin appears equivalent to dose-intense daunorubicin for remission induction in patients with acute myeloid leukemia.

Trifilio S, Zhou Z, Mehta J, Czerniak C, Pi J, Greenberg D, Koslosky M, Pantiru M, Altman J.SourceDepartment of Hematology and Oncology, Robert Lurie Cancer Center and Feinberg School of Medicine, Northwestern University, Chicago, IL, USA; Department of Pharmacy, Northwestern Memorial Hospital, Chicago, IL, USA. Electronic address: strifili@nmh.org.
Leukemia research.Leuk Res.2013 Aug;37(8):868-71. doi: 10.1016/j.leukres.2013.04.009. Epub 2013 May 31.
Daunorubicin has historically been considered the anthracycline of choice at many cancer centers for the treatment of acute myeloid leukemia (AML). Drug shortages have required the substitution of daunorubicin with idarubicin. Randomized studies have shown idarubicin (10-12mg/m(2)) to be comparable
PMID 23726414

Structure-dependent complexation of fe(3+) by anthracyclines. 2. The roles of methoxy and daunosamine functionalities.

Nawara K, Beeckman H, Krysiński P, Blanchard GJ.SourceDepartment of Chemistry, University of Warsaw , Pasteura 1, Warsaw 02-093, Poland.
The journal of physical chemistry. B.J Phys Chem B.2013 Jun 13;117(23):6868-73. doi: 10.1021/jp4023508. Epub 2013 May 31.
We have investigated the effects of the methoxy and daunosamine sugar moieties on the stability of anthracycline complexes with Fe(3+) in aqueous solution. Idarubicin and daunorubicin are structurally very similar, differing only by the presence of the methoxy substituent at the 4-position. We demon
PMID 23692121

Japanese Journal

抗がん剤漏出による皮膚傷害に対するステロイド局所注射の作用に関する基礎的研究

及川正広,武田利明,小山奈都子
岩手県立大学看護学部紀要 12, 101-105, 2010-00-00
NAID 110007652267

Related Pictures

★リンクテーブル★

リンク元	「イダルビシン」
関連記事	「hydrochloride」

「イダルビシン」

Idarubicin
Systematic (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
Clinical data
AHFS/Drugs.com	monograph
MedlinePlus	a691004
Pregnancy; category	US: D (Evidence of risk);
Legal status	US: ℞-only;
Pharmacokinetic data
Protein binding	97%
Biological half-life	22 hours
Identifiers
CAS Registry Number	58957-92-9
ATC code	L01DB06
PubChem	CID: 42890
IUPHAR/BPS	7083
DrugBank	DB01177
ChemSpider	39117
UNII	ZRP63D75JW
KEGG	D08062
ChEBI	CHEBI:42068
ChEMBL	CHEMBL1117
Synonyms	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
Chemical data
Formula	C26H27NO9
Molecular mass	497.494 g/mol
	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 ;
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