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MedKoo Cat#: 100260 | Name: Dexrazoxane
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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).

Chemical Structure

Dexrazoxane
Dexrazoxane
CAS#24584-09-6 (free base)

Theoretical Analysis

MedKoo Cat#: 100260

Name: Dexrazoxane

CAS#: 24584-09-6 (free base)

Chemical Formula: C11H16N4O4

Exact Mass: 268.1172

Molecular Weight: 268.27

Elemental Analysis: C, 49.25; H, 6.01; N, 20.88; O, 23.86

Price and Availability

Size Price Availability Quantity
50mg USD 90.00 Ready to ship
100mg USD 150.00 Ready to ship
250mg USD 300.00 Ready to ship
500mg USD 500.00 Ready to ship
1g USD 850.00 Ready to ship
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Related CAS #
24584-09-6 (free base) 1263283-43-7 (HCl) 149003-01-0 (HCl)
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
Appearance
white solid powder
Purity
>98% (or refer to the Certificate of Analysis)
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).
HS Tariff Code
2934.99.9001
More Info
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.
Biological target:
Dexrazoxane (ICRF-187) is a cardioprotective agent.
In vitro activity:
To determine whether dexrazoxane exerts cardioprotective effect through its direct action on the cardiomyocytes, dexrazoxane (200 μM) was applied to neonatal mouse ventricular myocytes before doxorubicin treatment. Then cell viability was examined with MTT assay. The outcome illustrated that treatment with dexrazoxane prior to doxorubicin exposure substantially increased the cell viability (Fig. 3G). In addition, LDH release was detected, another index of cellular damage. Doxorubicin induced a remarkable increase in LDH leakage, which was blocked by dexrazoxane treatment (Fig. 3H). DNA electrophoresis assay also proved that dexrazoxane could attenuate doxorubicin-induced cell death (Fig. 3I). Our study infers that dexrazoxane could increase cardiomyocyte viability and mitigate cardiotoxicity after doxorubicin treatment. Reference: Biochem Biophys Res Commun. 2020 Feb 26;523(1):140-146. https://linkinghub.elsevier.com/retrieve/pii/S0006-291X(19)32347-2
In vivo activity:
Dexrazoxane treatment was evaluated for 6 weeks in cav1 mice and wild-type controls. This study provides the first evidence for a reduced reactive oxygen species formation in the vessels of dexrazoxane-treated cav1 mice. This reduced oxidative stress resulted in a markedly reduced rate of apoptosis, which finally was translated into a significantly improved heart function in dexrazoxane-treated cav1 mice. These hemodynamic improvements were accompanied by significantly lowered proatrial natriuretic peptide levels. Notably, these protective properties of dexrazoxane were not evident in wild-type animals. Taken together, these novel findings indicate that dexrazoxane significantly reduces vascular reactive oxygen species formation cav1. Because this is paralleled by an improved cardiac performance in cav1 mice, these data suggest dexrazoxane as a novel therapeutic strategy in this specific cardiomyopathy. Reference: J Cardiovasc Pharmacol. 2013 Jun;61(6):545-52. https://doi.org/10.1097/FJC.0b013e31828de47c
Solvent mg/mL mM
Solubility
DMSO 54.0 201.29
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 268.27 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
1. Yu X, Ruan Y, Shen T, Qiu Q, Yan M, Sun S, Dou L, Huang X, Wang Q, Zhang X, Man Y, Tang W, Jin Z, Li J. Dexrazoxane Protects Cardiomyocyte from Doxorubicin-Induced Apoptosis by Modulating miR-17-5p. Biomed Res Int. 2020 Mar 1;2020:5107193. doi: 10.1155/2020/5107193. PMID: 32190669; PMCID: PMC7071803.
In vivo protocol:
1. Polanski AK, Ebner A, Ebner B, Hofmann A, Steinbronn N, Brandt A, Forkmann M, Tausche AK, Morawietz H, Strasser RH, Wunderlich C. Dexrazoxane prevents the development of the impaired cardiac phenotype in caveolin-1-disrupted mice. J Cardiovasc Pharmacol. 2013 Jun;61(6):545-52. doi: 10.1097/FJC.0b013e31828de47c. PMID: 23474841. 2. Yu X, Ruan Y, Shen T, Qiu Q, Yan M, Sun S, Dou L, Huang X, Wang Q, Zhang X, Man Y, Tang W, Jin Z, Li J. Dexrazoxane Protects Cardiomyocyte from Doxorubicin-Induced Apoptosis by Modulating miR-17-5p. Biomed Res Int. 2020 Mar 1;2020:5107193. doi: 10.1155/2020/5107193. PMID: 32190669; PMCID: PMC7071803.
1: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Dexrazoxane. 2020 Nov 16. PMID: 30000029. 2: de Baat EC, van Dalen EC, Mulder RL, Hudson MM, Ehrhardt MJ, Engels FK, Feijen EAM, Grotenhuis HB, Leerink JM, Kapusta L, Kaspers GJL, Merkx R, Mertens L, Skinner R, Tissing WJE, de Vathaire F, Nathan PC, Kremer LCM, Mavinkurve- Groothuis AMC, Armenian S. Primary cardioprotection with dexrazoxane in patients with childhood cancer who are expected to receive anthracyclines: recommendations from the International Late Effects of Childhood Cancer Guideline Harmonization Group. Lancet Child Adolesc Health. 2022 Dec;6(12):885-894. doi: 10.1016/S2352-4642(22)00239-5. Epub 2022 Sep 27. PMID: 36174614. 3: de Baat EC, Mulder RL, Armenian S, Feijen EA, Grotenhuis H, Hudson MM, Mavinkurve-Groothuis AM, Kremer LC, van Dalen EC. Dexrazoxane for preventing or reducing cardiotoxicity in adults and children with cancer receiving anthracyclines. Cochrane Database Syst Rev. 2022 Sep 27;9(9):CD014638. doi: 10.1002/14651858.CD014638.pub2. PMID: 36162822; PMCID: PMC9512638. 4: Chow EJ, Aggarwal S, Doody DR, Aplenc R, Armenian SH, Baker KS, Bhatia S, Blythe N, Colan SD, Constine LS, Freyer DR, Kopp LM, Laverdière C, Leisenring WM, Sasaki N, Vrooman LM, Asselin BL, Schwartz CL, Lipshultz SE. Dexrazoxane and Long-Term Heart Function in Survivors of Childhood Cancer. J Clin Oncol. 2023 Apr 20;41(12):2248-2257. doi: 10.1200/JCO.22.02423. Epub 2023 Jan 20. PMID: 36669148; PMCID: PMC10448941. 5: Eneh C, Lekkala MR. Dexrazoxane. 2023 Jul 17. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2023 Jan–. PMID: 32809394. 6: Weiss G, Loyevsky M, Gordeuk VR. Dexrazoxane (ICRF-187). Gen Pharmacol. 1999 Jan;32(1):155-8. doi: 10.1016/s0306-3623(98)00100-1. PMID: 9888268. 7: Chow EJ, Aplenc R, Vrooman LM, Doody DR, Huang YV, Aggarwal S, Armenian SH, Baker KS, Bhatia S, Constine LS, Freyer DR, Kopp LM, Leisenring WM, Asselin BL, Schwartz CL, Lipshultz SE. Late health outcomes after dexrazoxane treatment: A report from the Children's Oncology Group. Cancer. 2022 Feb 15;128(4):788-796. doi: 10.1002/cncr.33974. Epub 2021 Oct 13. PMID: 34644414; PMCID: PMC8792306. 8: Bhagat A, Kleinerman ES. Anthracycline-Induced Cardiotoxicity: Causes, Mechanisms, and Prevention. Adv Exp Med Biol. 2020;1257:181-192. doi: 10.1007/978-3-030-43032-0_15. PMID: 32483740. 9: Rahimi P, Barootkoob B, ElHashash A, Nair A. Efficacy of Dexrazoxane in Cardiac Protection in Pediatric Patients Treated With Anthracyclines. Cureus. 2023 Apr 8;15(4):e37308. doi: 10.7759/cureus.37308. PMID: 37182052; PMCID: PMC10166653. 10: Langer SW. Dexrazoxane for anthracycline extravasation. Expert Rev Anticancer Ther. 2007 Aug;7(8):1081-8. doi: 10.1586/14737140.7.8.1081. PMID: 18028016. 11: Wu V. Dexrazoxane: a cardioprotectant for pediatric cancer patients receiving anthracyclines. J Pediatr Oncol Nurs. 2015 May-Jun;32(3):178-84. doi: 10.1177/1043454214554008. Epub 2014 Nov 3. PMID: 25366577. 12: Langer SW. Dexrazoxane for the treatment of chemotherapy-related side effects. Cancer Manag Res. 2014 Sep 15;6:357-63. doi: 10.2147/CMAR.S47238. PMID: 25246808; PMCID: PMC4168851. 13: Hu H, Xie C, Weng Z, Yu P, Wang Y, Shan L. Dexrazoxane Alleviated Doxorubicin-Induced Nephropathy in Rats. Pharmacology. 2022;107(3-4):206-215. doi: 10.1159/000521220. Epub 2022 Jan 12. PMID: 35021174. 14: Goey AK, Schellens JH, Beijnen JH, Huitema AD. Dexrazoxaan bij anthracycline-geïnduceerde cardiotoxiciteit en anthracycline-extravasatie [Dexrazoxane in anthracycline induced cardiotoxicity and extravasation]. Ned Tijdschr Geneeskd. 2010;154:A1155. Dutch. PMID: 20619024. 15: Cvetković RS, Scott LJ. Dexrazoxane : a review of its use for cardioprotection during anthracycline chemotherapy. Drugs. 2005;65(7):1005-24. doi: 10.2165/00003495-200565070-00008. PMID: 15892593. 16: Hasinoff BB, Herman EH. Dexrazoxane: how it works in cardiac and tumor cells. Is it a prodrug or is it a drug? Cardiovasc Toxicol. 2007;7(2):140-4. doi: 10.1007/s12012-007-0023-3. PMID: 17652819. 17: Wiseman LR, Spencer CM. Dexrazoxane. A review of its use as a cardioprotective agent in patients receiving anthracycline-based chemotherapy. Drugs. 1998 Sep;56(3):385-403. doi: 10.2165/00003495-199856030-00009. PMID: 9777314. 18: Vidall C, Roe H, Dougherty L, Harrold K. Dexrazoxane: a management option for anthracycline extravasations. Br J Nurs. 2013 Sep 12-25;22(17):S6 -12. doi: 10.12968/bjon.2013.22.Sup17.S6. PMID: 24067273. 19: Seifert CF, Nesser ME, Thompson DF. Dexrazoxane in the prevention of doxorubicin-induced cardiotoxicity. Ann Pharmacother. 1994 Sep;28(9):1063-72. doi: 10.1177/106002809402800912. Erratum in: Ann Pharmacother 1994 Dec;28(12):1413. PMID: 7803884. 20: Jones RL. Utility of dexrazoxane for the reduction of anthracycline-induced cardiotoxicity. Expert Rev Cardiovasc Ther. 2008 Nov;6(10):1311-7. doi: 10.1586/14779072.6.10.1311. PMID: 19018683.