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I1656

Sigma-Aldrich

Idarubicin hydrochloride

solid

Synonym(s):

(7S-cis)-9-Acetyl-7-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,9,11-trihydroxy-5,12-naphthacenedione, 4-Demethoxydaunorubicin hydrochloride, DMDR, IMI-30, Idamycin

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About This Item

Empirical Formula (Hill Notation):
C26H27NO9 · HCl
CAS Number:
57852-57-0
Molecular Weight:
533.95
EC Number:
260-990-7
MDL number:
MFCD00866457
UNSPSC Code:
12352200
PubChem Substance ID:
24278488
NACRES:
NA.77

form

solid

originator

Johnson & Johnson

shipped in

wet ice

storage temp.

2-8°C

SMILES string

[H][C@@]1(C[C@@](O)(Cc2c(O)c3C(=O)c4ccccc4C(=O)c3c(O)c12)C(C)=O)O[C@H]5C[C@H](N)[C@H](O)[C@H](C)O5

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

InChI key

XDXDZDZNSLXDNA-TZNDIEGXSA-N

Gene Information

human ... TOP2A(7153)

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Application

Idarubicin is an anthracycline antibiotic that is an anti-leukemia agent with higher DNA binding capacity and greater cytotoxicity than daunorubicin.

Biochem/physiol Actions

Topoisomerase II inhibitor

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Johnson & Johnson. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H300,H351,H360

Precautionary Statements

P201 - P301 + P310 + P330

Hazard Classifications

Acute Tox. 2 Oral - Carc. 2 - Repr. 1B

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Jungwon Huh et al.
American journal of hematology, 87(10), 961-968 (2012-08-14)
Core binding factor (CBF) AML with the D816 C-KIT gene mutation demonstrate inferior treatment outcomes. However, the remaining cases without the D816 C-KIT mutation imply a requirement of more sophisticated dissection of the patients according to their prognosis. In this
Claude Gardin et al.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 31(3), 321-327 (2012-12-19)
Although standard chemotherapy remains associated with a poor outcome in older patients with acute myeloid leukemia (AML), it is unclear which patients can survive long enough to be considered as cured. This study aimed to identify factors influencing the long-term
Malgorzata Tokarska-Schlattner et al.
Molecular pharmacology, 61(3), 516-523 (2002-02-21)
Anthracyclines are among the most efficient drugs of cancer chemotherapy, but their use is limited by a significant risk of cardiotoxicity, which is still far from being understood. This study investigates whether impairment of mitochondrial creatine kinase (MtCK), a key
D Reinhardt et al.
Klinische Padiatrie, 224(6), 372-376 (2012-07-24)
The survival rate of children and adolescents suffering acute myeloid leukemia (AML) has been significantly improved within the last decades. This has been achieved by a continuously intensified therapy and progress in supportive care to prevent and treat complications. In
Monica L Guzman et al.
Proceedings of the National Academy of Sciences of the United States of America, 99(25), 16220-16225 (2002-11-27)
Acute myelogenous leukemia (AML) is typically a disease of stem progenitor cell origin. Interestingly, the leukemic stem cell (LSC) shares many characteristics with normal hematopoietic stem cells (HSCs) including the ability to self-renew and a predominantly G(0) cell-cycle status. Thus
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