D1446

Dexrazoxane

Name: Dexrazoxane
Brand: SIGMA

≥95% (HPLC), cardiopulmonary protectant, powder

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

UNSPSC Code:

12352200

PubChem Substance ID:

329798699

NACRES:

NA.77

MDL number:

MFCD00866449

Product Name

Dexrazoxane, ≥95% (HPLC)

SMILES string

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

InChI key

BMKDZUISNHGIBY-ZETCQYMHSA-N

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

assay

≥95% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: >20 mg/mL

originator

Johnson & Johnson

storage temp.

room temp

Quality Level

100

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Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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.

Dexrazoxane is a cardioprotective compound used to counteract the effects of anthracyclines. Dexrazoxane is believed to function as a free radical scanenger.

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.

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.

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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)

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)

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)

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)

Dexrazoxane use in pediatric patients with acute lymphoblastic or myeloid leukemia from 1999 and 2009: analysis of a national cohort of patients in the Pediatric Health Information Systems database.

Dana M Walker et al.

Pediatric blood & cancer, 60(4), 616-620 (2012-09-06)

Acute lymphoblastic (ALL) and myeloid leukemia (AML) account for approximately 26% of pediatric cancers. Anthracyclines are widely used to treat these leukemias, but dosing is limited by cardiotoxicity. Data support the efficacy of dexrazoxane as a cardioprotectant in children; however

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