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D1446

Sigma-Aldrich

Dexrazoxane

≥95% (HPLC)

Synonym(s):

(+)-(S)-4,4′-Propylenedi-2,6-piperazinedione, (S)-(+)-1,2-Bis(3,5-dioxopiperazin-1-yl)propane, Cardioxane, ICRF-187, NSC169780, Zinecard

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About This Item

Empirical Formula (Hill Notation):
C11H16N4O4
CAS Number:
24584-09-6
Molecular Weight:
268.27
MDL number:
MFCD00866449
UNSPSC Code:
12352200
PubChem Substance ID:
329798699
NACRES:
NA.77

Quality Level

100

Assay

≥95% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: >20 mg/mL

originator

Johnson & Johnson

storage temp.

room temp

SMILES string

C[C@@H](CN1CC(=O)NC(=O)C1)N2CC(=O)NC(=O)C2

InChI

1S/C11H16N4O4/c1-7(15-5-10(18)13-11(19)6-15)2-14-3-8(16)12-9(17)4-14/h7H,2-6H2,1H3,(H,12,16,17)(H,13,18,19)/t7-/m0/s1

InChI key

BMKDZUISNHGIBY-ZETCQYMHSA-N

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General description

Dexrazoxane is a member of bis(2,6-dioxopiperazines), that functions as a topoisomerase 2 catalytic inhibitor. Dexrazoxane is a free radical scavenger. It might protect the heart from doxorubicin-associated damage. Dexrazoxane acts as a cardiopulmonary protectant, while treating Hodgkin′s disease (HD). It functions as a chelating agent, which limits the formation of anthracycline-iron complexes. It is used to synthesize antimalarial drugs.

Application

Dexrazoxane has been used in chromatin remodelling experiments.

Biochem/physiol Actions

Dexrazoxane is a cardioprotective compound against anthracyclines. It functions by inhibiting topoisomerase II without inducing DNA strand breaks. Dexrazoxane is a + enantiomer of razoxane.

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

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Volume Transitions of Isolated Cell Nuclei Induced by Rapid Temperature Increase
Chan CJ, et al.
Biophysical Journal, 112(6), 1063-1076 (2017)
J S Whelan et al.
Annals of oncology : official journal of the European Society for Medical Oncology, 26(2), 407-414 (2014-11-26)
Four international study groups undertook a large study in resectable osteosarcoma, which included two randomised controlled trials, to determine the effect on survival of changing post-operative chemotherapy based on histological response. Patients with resectable osteosarcoma aged ≤40 years were treated
Dexrazoxane-associated risk for acute myeloid leukemia/myelodysplastic syndrome and other secondary malignancies in pediatric Hodgkin's disease
Tebbi CK, et al.
Journal of Clinical Oncology, 25(5), 493-500 (2007)
The effect of dexrazoxane on myocardial injury in doxorubicin-treated children with acute lymphoblastic leukemia
Lipshultz SE, et al.
The New England Journal of Medicine, 351(2), 145-153 (2004)
Topoisomerase IIβ-mediated DNA double-strand breaks: implications in doxorubicin cardiotoxicity and prevention by dexrazoxane
Lyu YL, et al.
Cancer Research, 67(18), 8839-8846 (2007)
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