Dexrazoxane

Base Information

• Chemical Name: Dexrazoxane
• CAS No.: 24584-09-6
• Molecular Formula: C11H16N4O4
• Molecular Weight: 268.272
• Hs Code.: 2933599090
• European Community (EC) Number: 635-584-1
• NSC Number: 169780
• UNII: 048L81261F
• DSSTox Substance ID: DTXSID3040647
• Nikkaji Number: J22.227E
• Wikipedia: Dexrazoxane
• Wikidata: Q524995
• NCI Thesaurus Code: C1333
• RXCUI: 42736
• Metabolomics Workbench ID: 42748
• ChEMBL ID: CHEMBL1738
• Mol file: 24584-09-6.mol

Synonyms:ADR 529;ADR-529;ADR529;Cardioxan;Cardioxane;Dexrazoxane;Dexrazoxane Hydrochloride;Hydrochloride, Dexrazoxane;ICRF 187;ICRF-187;ICRF187;NSC 169780;NSC-169780;NSC169780;Razoxane, (S)-Isomer;Razoxane, (S)-Isomer, Hydrochloride;Zinecard

Chemical Property of Dexrazoxane

Chemical Property:

• Vapor Pressure: 2.22E-11mmHg at 25°C
• Melting Point: 194-196 ºC
• Refractive Index: 1.539
• Boiling Point: 531.5 ºC at 760 mmHg
• PKA: 2.1(at 25℃)
• Flash Point: 275.3 ºC
• PSA: 98.82000
• Density: 1.333 g/cm³
• LogP: -2.17490
• Storage Temp.: Desiccate at RT
• Solubility.: DMSO: >20mg/mL
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 268.11715500
• Heavy Atom Count: 19
• Complexity: 404

Purity/Quality:

99%min ^*data from raw suppliers

Dexrazoxane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(CN1CC(=O)NC(=O)C1)N2CC(=O)NC(=O)C2
• Isomeric SMILES: C[C@@H](CN1CC(=O)NC(=O)C1)N2CC(=O)NC(=O)C2
• Recent ClinicalTrials: Risk-Based Therapy in Treating Younger Patients With Newly Diagnosed Liver Cancer
• Recent EU Clinical Trials: Efficacy of Olaratumab and Rechallenge with Doxorubicin in anthracycline pretreated, advanced soft tissue sarcoma patients.
• 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.
• 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. Dexrazoxane has been used in chromatin remodelling experiments.
• Clinical Use: Cardioxane? Prevention of cardiotoxicity in patients receiving doxorubicin or epirubicin for breast cancer Savene? : Treatment of extravasation caused by anthracyclines
• 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.

Technology Process of Dexrazoxane

There total 6 articles about Dexrazoxane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

(S)-N,N,N',N'-tetrakis[(hydroxycarbonyl)methyl]-1,2-diaminopropane (15250-41-6) → dexrazoxane (24584-09-6,24613-06-7,83713-23-9)

Guidance literature:

With ammonium formate; In water; N,N-dimethyl-formamide; at 150 ℃; for 10h; Solvent; Reagent/catalyst;

Reference yield: 85.0%

(S)-N,N,N',N'-tetrakis[(ethoxycarbonyl)methyl]-1,2-diaminopropane (1029441-45-9) → dexrazoxane (24584-09-6,24613-06-7,83713-23-9)

Guidance literature:

With sodium ethanolate; formamide; In ethyl acetate; acetone; at 20 - 70 ℃; for 3h; Solvent;

Reference yield:

(S)-1,2-diaminopropane-N,N,N',N'-tetraacetic acid methyl ester (1029441-44-8) → dexrazoxane (24584-09-6,24613-06-7,83713-23-9)

Guidance literature:

With ammonia;

upstream raw materials:

1,2-diaminopropane-N,N,N',N'-tetraacetic acid

(S)-1,2-diaminopropane-N,N,N',N'-tetraacetic acid methyl ester

razoxane

(S)-N,N,N',N'-tetrakis[(hydroxycarbonyl)methyl]-1,2-diaminopropane

Downstream raw materials:

ADR-925

Refernces

• 1、 -. "Preparation method of dexrazoxane". Paragraph 0030. . Retrieved 2021/11/14.
• 2、 -. "Dexrazoxane preparation method". Paragraph 0016; 0019; 0020; 0023. . Retrieved 2019/07/04.