Dexrazoxane Chemical Properties

Melting point:

194-196°C

alpha 

D +11.35° (c = 5 in DMF)

Boiling point:

531.5±50.0 °C(Predicted)

Density 

1.333±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMSO: >20mg/mL

form 

powder

pka

2.1(at 25℃)

color 

white to off-white

Merck 

14,8123

InChIKey

BMKDZUISNHGIBY-ZETCQYMHSA-N

CAS DataBase Reference

24584-09-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

UN 2811 6.1 / PGIII

WGK Germany 

3

RTECS 

TL6390000

HS Code 

2933.59.9500

Hazardous Substances Data

24584-09-6(Hazardous Substances Data)

Dexrazoxane Usage And Synthesis

Description

Dexrazoxane is the dextro-isomer of razoxane approved as a protectant against the cardiotoxicity of doxorubicin in breast cancer patients. This agent does not alter the anticancer effect of doxorubicin. Its mode of action suggests a chelation of free radicals. In mice, dexrazoxane also offers protection against cardiac side effects of epirubicin, but not mitoxantrone.

Originator

Imperial Cancer Research Fund (United Kingdom)

Uses

Dexrazoxane is a cardioprotective compound against anthracyclines. It is highly protective in reducing anthracycline-induced cardiotoxicity and extravasation injury. It functions by inhibiting topoisomerase II without inducing DNA strand breaks. Dexrazoxane is a + enantiomer of razoxane.

Uses

Dexrazoxane has been used in chromatin remodelling experiments.

Uses

Cardioprotectant.

Definition

ChEBI: (+)-dexrazoxane is a razoxane. It has a role as a chelator, an antineoplastic agent, a cardiovascular drug and an immunosuppressive agent.

brand name

Zinecard (Pharmacia & Upjohn);Cardioxane.

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.

Biological Activity

Topoisomerase II inhibitor and intracellular ion chelator. Bridges and stabilizes an interface between two ATPase promoters to inhibit topoisomerase II activity. Cardioprotective when co-administered with doxorubicin; decreases formation of reactive oxygen species (ROS) and activates the PI3K/Akt survival pathway.

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.

Clinical Use

Cardioxane? Prevention of cardiotoxicity in patients receiving doxorubicin or epirubicin for breast cancer Savene? : Treatment of extravasation caused by anthracyclines

Veterinary Drugs and Treatments

Dexrazoxane may be useful to attenuate the cardiotoxic effects of doxorubicin in patients who are showing signs of anthracycline cardiotoxicity, have cardiac disease, or are at maximum cumulative dosages of doxorubicin. It is also used to treat extravasation injuries associated with doxorubicin.
While dexrazoxane has been shown to be cardioprotective when given at dosages of 10 times the doxorubicin dose, there is evidence that it may also partially protect the cancer cells being treated.

Drug interactions

Potentially hazardous interactions with other drugs
Antiepileptics: may reduce absorption of fosphenytoin and phenytoin.
Ciclosporin: increased risk of immunosuppression with risk of lymphoproliferative disease.
Tacrolimus: increased risk of immunosuppression with risk of lymphoproliferative disease.
Vaccines: risk of generalised infections with live vaccines - avoid.

Metabolism

Dexrazoxane is hydrolysed by the enzyme dihydropyrimidine amidohydrolase in the liver and kidney to active metabolites that are capable of binding to metal ions.
It is excreted unchanged via the kidney

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