イダルビシン
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/07/19 00:47:35」(JST)
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Idarubicin
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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
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Clinical data |
AHFS/Drugs.com |
monograph |
MedlinePlus |
a691004 |
Pregnancy
category |
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Legal status |
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Pharmacokinetic data |
Protein binding |
97% |
Biological half-life |
22 hours |
Identifiers |
CAS Registry Number |
58957-92-9 Y |
ATC code |
L01DB06 |
PubChem |
CID: 42890 |
IUPHAR/BPS |
7083 |
DrugBank |
DB01177 Y |
ChemSpider |
39117 Y |
UNII |
ZRP63D75JW Y |
KEGG |
D08062 Y |
ChEBI |
CHEBI:42068 Y |
ChEMBL |
CHEMBL1117 Y |
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
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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
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InChI
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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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Key:XDXDZDZNSLXDNA-TZNDIEGXSA-N Y
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Y (what is this?) (verify) |
Idarubicin 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
UpToDate Contents
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English Journal
- Differential toxicity of anthracyclines on cultured endothelial cells.
- Kaushal V1, Kaushal GP, Mehta P.
- Endothelium : journal of endothelial cell research.Endothelium.2004 Sep-Dec;11(5-6):253-8.
- Anthracyclines are known for their endothelial toxicity. Newer derivatives may have fewer toxic effects on endothelium. The authors therefore evaluated the effects of doxorubicin, doxorubicin analogs (daunorubicin, idarubicin), and pegylated liposomal doxorubicin (doxil) in human coronary artery end
- PMID 15763945
Related Links
- Idamycin - Clinical Pharmacology Mechanism of Action Idarubicin hydrochloride is a DNA-intercalating analog of daunorubicin which has an inhibitory effect on nucleic acid synthesis and interacts with the enzyme topoisomerase II.
- Idamycin (Idarubicin) chemotherapy side effects, how it's given, how it works, precautions and self care tips for treament of leukemia and myeloid disorders ... Generic name: Idarubicin Other trade name: Idamycin PFS ® Idamycin ...
Related Pictures
★リンクテーブル★
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- 英
- idarubicin, IDR, IDAR
- 商
- イダマイシン Idamycin
- 化
- 塩酸イダルビシン idarubicin hydrochloride
- 関
- 抗悪性腫瘍薬