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D1446

Sigma-Aldrich

Dexrazoxane

≥95% (HPLC)

Synonyme(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

Formule empirique (notation de Hill):
C11H16N4O4
Numéro CAS:
24584-09-6
Poids moléculaire :
268.27
Numéro MDL:
MFCD00866449
Code UNSPSC :
12352200
ID de substance PubChem :
329798699
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥95% (HPLC)

Forme

powder

Couleur

white to off-white

Solubilité

DMSO: >20 mg/mL

Auteur

Johnson & Johnson

Température de stockage

room temp

Chaîne SMILES 

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

Clé InChI

BMKDZUISNHGIBY-ZETCQYMHSA-N

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Description générale

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.

Actions biochimiques/physiologiques

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

Caractéristiques et avantages

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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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)
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
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
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