24584-09-6

Basic information

• Product Name: Dexrazoxane
• Synonyms: DEXRAZOXANE;(s)-4,4'-(1-methyl-1,2-ethanediyl)bis-2,6-piperazinedione;4’-(1-methyl-1,2-ethanediyl)bis-6-piperazinedion(+)-4;4’-propylenedi-6-piperazinedion(+)-4;adr529;cardioxane;DEXTRAZOXANE;DEXTRORAZOXANE
• CAS NO: 24584-09-6
• Molecular Formula: C₁₁H₁₆N₄O₄
• Molecular Weight: 268.27
• EINECS: 244-379-2
• Product Categories: Chelating Agent;API
• Mol File: 24584-09-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 194-196°C
• Boiling Point: 531.5 ºC at 760 mmHg
• Flash Point: 275.3 ºC
• Appearance: white to off-white/
• Density: 1.333 g/cm³
• Vapor Pressure: 2.22E-11mmHg at 25°C
• Refractive Index: 1.539
• Storage Temp.: Desiccate at RT
• Solubility: DMSO: >20mg/mL
• PKA: 2.1(at 25℃)
• Merck: 14,8123
• CAS DataBase Reference: Dexrazoxane(CAS DataBase Reference)
• NIST Chemistry Reference: Dexrazoxane(24584-09-6)
• EPA Substance Registry System: Dexrazoxane(24584-09-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• RTECS: TL6390000
• Hazardous Substances Data: 24584-09-6(Hazardous Substances Data)

Usage

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

Different sources of media describe the Uses of 24584-09-6 differently. You can refer to the following data:
1. 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.
2. Dexrazoxane has been used in chromatin remodelling experiments.

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 drugsAntiepileptics: 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

InChI:InChI=1/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

Upstream product

• 1029441-45-9 (S)-N,N,N',N'-tetrakis[(ethoxycarbonyl)methyl]-1,2-diaminopropane 
• 15250-41-6 (S)-N,N,N',N'-tetrakis[(hydroxycarbonyl)methyl]-1,2-diaminopropane 
• 21416-67-1 razoxane 
• 1029441-44-8 (S)-1,2-diaminopropane-N,N,N',N'-tetraacetic acid methyl ester 
• 4408-81-5 1,2-diaminopropane-N,N,N',N'-tetraacetic acid 

Downstream Products

• 75459-34-6 ADR-925 

Relevant articles and documents

Synthesis of chiral carbosilane dendrimers with L-cysteine and N-acetyl-L-cysteine on their surface and their application as chiral selectors for enantiomer separation by capillary electrophoresis

The synthesis of chiral carbosilane dendrimers functionalized with cysteine and N-acetylcysteine groups is presented. These dendrimers were obtained through thiol–ene addition reactions and their application as chiral selectors in capillary electrophoresis was investigated. Four drugs used as model compounds were analyzed under different experimental conditions observing that the use of a first generation dendrimer containing 4 terminal N-acetyl-L-cysteine groups enabled the enantiomeric discrimination of razoxane with a discrimination power similar to that obtained with other powerful chiral selectors such as cyclodextrins.

Dexrazoxane preparation method

The invention discloses a dexrazoxane preparation method. According to the preparation method, (S)-1,2-diaminopropane-tetraacetate and alkali metal salt thereof are used as raw materials, and ammoniumsalt is used as an ammonium source to prepare dexrazoxane. By the adoption of the preparation method, tedious technological operation is avoided, the technological operation is easier and more convenient, and therefore the preparation method is more adaptive to industrial amplifying production.

Preparation method of piperazine diketone type compound

The invention discloses a method for preparing a piperazine diketone type compound and specifically relates to a method for preparing a compound shown as a formula (I) by cyclization after substitution. The method takes (S)-1,2-diaminopropane tartrate, haloacetic acid and low-carbon alcohol as raw materials to prepare the compound shown as the formula (I). Compared with the prior art, a pluralityof disadvantages are improved and overcome by the preparation method; the preparation method has the advantages of simple steps, low cost, convenience for post-treatment, cleanness, high yield and purity, low toxicity and less pollution, and industrial production is facilitated.