Dexrazoxane
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MedKoo CAT#: 100260

CAS#: 24584-09-6

Description: Dexrazoxane is a bisdioxopiperazine with iron-chelating, chemoprotective, cardioprotective, and antineoplastic activities. After hydrolysis to an active form that is similar to ethylenediaminetetraacetic acid (EDTA), dexrazoxane chelates iron, limiting the formation of free radical-generating anthracycline-iron complexes, which may minimize anthracycline-iron complex-mediated oxidative damage to cardiac and soft tissues. This agent also inhibits the catalytic activity of topoisomerase II, which may result in tumor cell growth inhibition. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).


Price and Availability

Size
Price

100mg
USD 90
1g
USD 350
10g
USD 1650
Size
Price

250mg
USD 150
2g
USD 550
20g
USD 2350
Size
Price

500mg
USD 250
5g
USD 950
50g
Ask price

Dexazoxane, purity > 98%, is in stock. The same day shipping out after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 100260
Name: Dexrazoxane
CAS#: 24584-09-6
Chemical Formula: C11H16N4O4
Exact Mass: 268.11716
Molecular Weight: 268.27
Elemental Analysis: C, 49.25; H, 6.01; N, 20.88; O, 23.86


Synonym: ADR529; ADR-529; ADR 529; ICRF-187; ICRF187; ICRF 187; NSC169780; NSC-169780; NSC 169780; Cardioxan; Cardioxane; US brand names: Totect; Zinecard. Foreign brand names: Cardioxane Savene.

IUPAC/Chemical Name: (S)-4,4'-(propane-1,2-diyl)bis(piperazine-2,6-dione)

InChi Key: BMKDZUISNHGIBY-ZETCQYMHSA-N

InChi Code: 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

SMILES Code: C[C@H](N(C1)CC(NC1=O)=O)CN(C2)CC(NC2=O)=O


Technical Data

Appearance:
white solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Certificate of Analysis:

Safety Data Sheet (MSDS):

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

It is used to protect the heart against the cardiotoxic side effects of anthracyclines, such as doxorubicin. FDA has also approved a dexrazoxane hydrochloride drug, brand name Totect or Savene (developed by TopoTarget), for use as a treatment of extravasation resulting from IV anthracycline chemotherapy. Extravasation is an adverse event in which chemotherapies containing anthracylines leak out of the blood vessel and necrotize the surrounding tissue.
 
ZINECARD® (dexrazoxane for injection) is a sterile, pyrogen-free lyophilizate intended for intravenous administration. It is a cardioprotective agent for use in conjunction with doxorubicin. Chemically, dexrazoxane is (S)-4,4'-(1-methyl-1,2-ethanediyl)bis-2,6piperazinedione.  Dexrazoxane, a potent intracellular chelating agent is a derivative of EDTA. Dexrazoxane is a whitish crystalline powder which melts at 191° to 197°C. It is sparingly soluble in water and 0.1 N HCl, slightly soluble in ethanol and methanol and practically insoluble in nonpolar organic solvents. The pKa is 2.1. Dexrazoxane has an octanol/water partition coefficient of 0.025 and degrades rapidly above a pH of 7.0. ZINECARD is available in 250 mg and 500 mg single use only vials. Each 250 mg vial contains dexrazoxane hydrochloride equivalent to 250 mg dexrazoxane. Hydrochloric Acid, NF is added for pH adjustment. When reconstituted as directed with the 25 mL vial of 0.167 Molar (M/6) Sodium Lactate Injection, USP diluent provided, each mL contains: 10 mg dexrazoxane. The pH of the resultant solution is 3.5 to 5.5. Each 500 mg vial contains dexrazoxane hydrochloride equivalent to 500 mg dexrazoxane. Hydrochloric Acid, NF is added for pH adjustment. When reconstituted as directed with the 50 mL vial of 0.167 Molar (M/6) Sodium Lactate Injection, USP diluent provided, each mL contains: 10 mg dexrazoxane. The pH of the resultant solution is 3.5 to 5.5.
The mechanism by which ZINECARD exerts its cardioprotective activity is not fully understood. Dexrazoxane is a cyclic derivative of EDTA that readily penetrates cell membranes. Results of laboratory studies suggest that dexrazoxane is converted intracellularly to a ring-opened chelating agent that interferes with iron-mediated free radical generation thought to be responsible, in part, for anthracycline induced cardiomyopathy.
The mechanism by which ZINECARD exerts its cardioprotective activity is not fully understood. Dexrazoxane is a cyclic derivative of EDTA that readily penetrates cell membranes. Results of laboratory studies suggest that dexrazoxane is converted intracellularly to a ring-opened chelating agent that interferes with iron-mediated free radical generation thought to be responsible, in part, for anthracycline induced cardiomyopathy.


References

1: Salvatorelli E, Menna P, Minotti G. Managing anthracycline-induced cardiotoxicity: beginning with the end in mind. Future Cardiol. 2015 Jul;11(4):363-6. doi: 10.2217/FCA.15.35. Epub 2015 Aug 4. PubMed PMID: 26239550.

2: Kremer LC, van Dalen EC. Dexrazoxane in Children With Cancer: From Evidence to Practice. J Clin Oncol. 2015 Aug 20;33(24):2594-6. doi: 10.1200/JCO.2015.61.7928. Epub 2015 Jul 20. PubMed PMID: 26195707.

3: Gonzalez Y, Pokrzywinski KL, Rosen ET, Mog S, Aryal B, Chehab LM, Vijay V, Moland CL, Desai VG, Dickey JS, Rao VA. Reproductive hormone levels and differential mitochondria-related oxidative gene expression as potential mechanisms for gender differences in cardiosensitivity to Doxorubicin in tumor-bearing spontaneously hypertensive rats. Cancer Chemother Pharmacol. 2015 Sep;76(3):447-59. doi: 10.1007/s00280-015-2786-8. Epub 2015 Jun 25. PubMed PMID: 26108538.

4: Chow EJ, Asselin BL, Schwartz CL, Doody DR, Leisenring WM, Aggarwal S, Baker KS, Bhatia S, Constine LS, Freyer DR, Lipshultz SE, Armenian SH. Late Mortality After Dexrazoxane Treatment: A Report From the Children's Oncology Group. J Clin Oncol. 2015 Aug 20;33(24):2639-45. doi: 10.1200/JCO.2014.59.4473. Epub 2015 May 26. PubMed PMID: 26014292.

5: Fabbi P, Spallarossa P, Garibaldi S, Barisione C, Mura M, Altieri P, Rebesco B, Monti MG, Canepa M, Ghigliotti G, Brunelli C, Ameri P. Doxorubicin impairs the insulin-like growth factor-1 system and causes insulin-like growth factor-1 resistance in cardiomyocytes. PLoS One. 2015 May 8;10(5):e0124643. doi: 10.1371/journal.pone.0124643. eCollection 2015. PubMed PMID: 25955698; PubMed Central PMCID: PMC4425434.

6: Conway A, McCarthy AL, Lawrence P, Clark RA. The prevention, detection and management of cancer treatment-induced cardiotoxicity: a meta-review. BMC Cancer. 2015 May 7;15:366. doi: 10.1186/s12885-015-1407-6. PubMed PMID: 25948399; PubMed Central PMCID: PMC4427936.

7: Singh D, Thakur A, Tang WH. Utilizing cardiac biomarkers to detect and prevent chemotherapy-induced cardiomyopathy. Curr Heart Fail Rep. 2015 Jun;12(3):255-62. doi: 10.1007/s11897-015-0258-4. PubMed PMID: 25869733; PubMed Central PMCID: PMC4425995.

8: Maruyama K, Koshihara N. Pharmacological and clinical profile of dexrazoxane (SAVENE(®) Intravenous Infusion 500 mg), a therapeutic agent for anthracycline extravasation. Nihon Yakurigaku Zasshi. 2015;145(1):27-34. doi: 10.1254/fpj.145.27. PubMed PMID: 25743233.

9: Sun F, Qi X, Geng C, Li X. Dexrazoxane protects breast cancer patients with diabetes from chemotherapy-induced cardiotoxicity. Am J Med Sci. 2015 May;349(5):406-12. doi: 10.1097/MAJ.0000000000000432. PubMed PMID: 25723884.

10: Boulanger J, Ducharme A, Dufour A, Fortier S, Almanric K; Comité de l’évolution de la pratique des soins pharmaceutiques (CEPSP); Comité de l’évolution des pratiques en oncologie (CEPO). Management of the extravasation of anti-neoplastic agents. Support Care Cancer. 2015 May;23(5):1459-71. doi: 10.1007/s00520-015-2635-7. Epub 2015 Feb 26. Review. PubMed PMID: 25711653.