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D1446

Sigma-Aldrich

Dexrazoxane

≥95% (HPLC)

Sinónimos:

(+)-(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

Fórmula empírica (notación de Hill):
C11H16N4O4
Número de CAS:
24584-09-6
Peso molecular:
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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
0000184144
116M4728V
084M4707V
023M4709V
100M4730

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Sigma-Aldrich

D1515

Doxorrubicina hydrochloride

Etoposide synthetic, 95.0-105.0%, powder

Sigma-Aldrich

E1383

Etoposide

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)
Plasmodium falciparum and Plasmodium yoelii: Effect of the Iron Chelation Prodrug Dexrazoxane onin VitroCultures
Loyevsky M, et al.
Experimental Parasitology, 91(2), 105-114 (1999)
Cameron K Tebbi et al.
Pediatric blood & cancer, 59(7), 1259-1265 (2012-08-23)
Hodgkin lymphoma is highly curable but associated with significant late effects. Reduction of total treatment would be anticipated to reduce late effects. This aim of this study was to demonstrate that a reduction in treatment was possible without compromising survival
Steven E Lipshultz et al.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 30(10), 1042-1049 (2012-03-01)
Doxorubicin causes cardiac injury and cardiomyopathy in children with acute lymphoblastic leukemia (ALL). Measuring biomarkers during therapy might help individualize treatment by immediately identifying cardiac injury and cardiomyopathy. Children with high-risk ALL were randomly assigned to receive doxorubicin alone (n
Martin Stěrba et al.
Antioxidants & redox signaling, 18(8), 899-929 (2012-07-17)
Anthracyclines (doxorubicin, daunorubicin, or epirubicin) rank among the most effective anticancer drugs, but their clinical usefulness is hampered by the risk of cardiotoxicity. The most feared are the chronic forms of cardiotoxicity, characterized by irreversible cardiac damage and congestive heart
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