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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

Assay:

≥95% (HPLC)

Form:

powder

Quality level:

100

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Properties

Product Name

Dexrazoxane, ≥95% (HPLC)

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

Description

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.

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.

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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

Regulatory Information

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Articles

Discover Bioactive Small Molecules for Cell Cycle

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

Bioactive Molecules for Apoptosis

Apoptosis regulation involves multiple pathways and molecules for cellular homeostasis.

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)

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)

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)

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Global Trade Item Number

SKU	GTIN
D1446-25MG	04061833024041
D1446-5MG	04061833024058