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Key Documents

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:
Molecular Weight:
533.95
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Pricing and availability is not currently available.

form

solid

Quality Level

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

Signal Word

Danger

Hazard Statements

Precautionary Statements

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

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Certificates of Analysis (COA)

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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
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
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

Articles

DNA damage and repair mechanism is vital for maintaining DNA integrity. Damage to cellular DNA is involved in mutagenesis, the development of cancer among others.

Apoptosis regulation involves multiple pathways and molecules for cellular homeostasis.

Cell cycle phases (G1, S, G2, M) regulate cell growth, DNA replication, and division in proliferating cells.

Cell cycle phases (G1, S, G2, M) regulate cell growth, DNA replication, and division in proliferating cells.

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Questions

1–5 of 5 Questions  
  1. Is this soluble in DMSO, if yes then what conc.?

    1 answer
    1. This product has not been tested for solubility in DMSO. However, other sources suggest that this compound can be solubilized in DMSO at approximately 10 mg/mL. This information has not been validated.

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  2. What is the Department of Transportation shipping information for this product?

    1 answer
    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

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  3. How is idarubicin used therapeutically?

    1 answer
    1. Idarubicin is an antineoplastic drug used to treat AML (Acute Myeloid Leukemia).  In addition this compound has also been used in the treatment of breast cancer, non-Hodgkin's lymphoma, and both acute nonlymphocytic and chronic myelogenous leukemias.

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  4. What is the mode of action for idarubicin?

    1 answer
    1. Idarubicin is an intercalating analog of daunorubicin that interferes with nucleic acid synthesis.  It is an anti-tumor antibiotic used in the treatment of leukemia.

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  5. What can be used to make a solution of Idarubicin hydrochloride, Product I1656?

    1 answer
    1. We test the solubility of idarubicin hydrochloride at 20 mg/ml of methanol.  Idarubicin hydrochloride is also slightly soluble in water (10 mg/ml water with slight heat) and slightly soluble in ethanol.

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