Dexrazoxane
Dexrazoxane
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| Systematic (IUPAC) name |
| 4-[(2S)-2-(3,5-dioxopiperazin-1-yl)propyl]piperazine-2,6-dione |
| Clinical data |
| AHFS/Drugs.com |
monograph |
| MedlinePlus |
a609010 |
| Pregnancy cat. |
? |
| Legal status |
? |
| Identifiers |
| CAS number |
24584-09-6 Y |
| ATC code |
V03AF02 |
| PubChem |
CID 71384 |
| DrugBank |
APRD00090 |
| ChemSpider |
64479 Y |
| UNII |
048L81261F Y |
| KEGG |
D03730 Y |
| ChEBI |
CHEBI:50223 Y |
| ChEMBL |
CHEMBL1738 Y |
| Chemical data |
| Formula |
C11H16N4O4 |
| Mol. mass |
268.269 g/mol |
| SMILES |
eMolecules & PubChem |
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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 Y
Key:BMKDZUISNHGIBY-ZETCQYMHSA-N Y
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N(what is this?) (verify)
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Dexrazoxane hydrochloride (Zinecard by Pfizer in USA and Canada; Cardioxane by Novartis for EU and other countries) is a cardioprotective agent.
Uses
It is used to protect the heart against the cardiotoxic side effects of anthracyclines,[1] such as doxorubicin.[2]
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.[3][4] Extravasation is an adverse event in which chemotherapies containing anthracylines leak out of the blood vessel and necrotize the surrounding tissue.
Mechanism
As a derivative of EDTA, dexrazoxane chelates iron, thus reduce the number of metal ions complexed with anthracycline and, consequently, decrease the formation of superoxide radicals.[5] It was speculated that dexrazoxane could be used for futher investigation to synthesize new antimalarial drugs.[6]
References
- ^ Lipshultz, Steven E.; Rifai, Nader; Dalton, Virginia M.; Levy, Donna E.; Silverman, Lewis B.; Lipsitz, Stuart R.; Colan, Steven D.; Asselin, Barbara L. et al. (2004). "The Effect of Dexrazoxane on Myocardial Injury in Doxorubicin-Treated Children with Acute Lymphoblastic Leukemia". New England Journal of Medicine 351 (2): 145–53. doi:10.1056/NEJMoa035153. PMID 15247354.
- ^ Bjelogrlic, Snezana K.; Radic, Jelena; Radulovic, Sinisa; Jokanovic, Milan; Jovic, Viktor (2007). "Effects of Dexrazoxane and Amifostine on Evolution of Doxorubicin Cardiomyopathy in Vivo". Experimental Biology and Medicine 232 (11): 1414–24. doi:10.3181/0705-RM-138. PMID 18040065.
- ^ Totect label on FDA's website
- ^ Kane, Robert C.; McGuinn, W. David; Dagher, Ramzi; Justice, Robert; Pazdur, Richard (2008). "Dexrazoxane (Totect™): FDA Review and Approval for the Treatment of Accidental Extravasation Following Intravenous Anthracycline Chemotherapy". The Oncologist 13 (4): 445–50. doi:10.1634/theoncologist.2007-0247. PMID 18448560.
- ^ Jones, Robin L. (2008). "Utility of dexrazoxane for the reduction of anthracycline-induced cardiotoxicity". Expert Review of Cardiovascular Therapy 6 (10): 1311–7. doi:10.1586/14779072.6.10.1311. PMID 19018683.
- ^ Loyevsky, Mark; Sacci, John B.; Boehme, Patricia; Weglicki, William; John, Christy; Gordeuk, Victor R. (1999). "Plasmodium falciparum and Plasmodium yoelii: Effect of the Iron Chelation Prodrug Dexrazoxane on in Vitro Cultures". Experimental Parasitology 91 (2): 105–14. doi:10.1006/expr.1998.4371. PMID 9990337.