Dexrazoxane

Dexrazoxane

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
InChI 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
N(what is this?)  (verify)

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

1. ^ 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. 
2. ^ 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. 
3. ^ Totect label on FDA's website
4. ^ 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. 
5. ^ 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. 
6. ^ 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. 

This pharmacology-related article is a stub. You can help Wikipedia by expanding it.v · Categories: Chelating agents Chemotherapeutic adjuvants Imides Enantiopure drugs Piperazines Lactams Pharmacology stubs Wikimedia Foundation. 2010. Игры ⚽ Поможем сделать НИР Pitchfork bifurcation Trilaminar embryo Look at other dictionaries: dexrazoxane — noun A particular cardioprotective drug, used to protect the heart against the cardiotoxic side effects of anthracyclines …   Wiktionary dexrazoxane — dex·ra·zox·ane (deks″ra zokґsān) a derivative of ethylenediaminetetraacetic acid (EDTA) used as a cardioprotectant in chemotherapy to counteract doxorubicin induced cardiomyopathy; administered intravenously …   Medical dictionary dexrazoxane — A drug used to protect the heart from the toxic effects of anthracycline drugs such as doxorubicin. It is a type of chemoprotective agent …   English dictionary of cancer terms Extravasation (intravenous) — Infobox Disease Name = PAGENAME Caption = DiseasesDB = ICD10 = ICD9 = ICDO = OMIM = MedlinePlus = eMedicineSubj = eMedicineTopic = MeshID = D005119 Extravasation is the accidental administration of intravenously (IV) infused medicinal drugs into… …   Wikipedia Chelation — Metal EDTA chelate Chelation is the formation or presence of two or more separate coordinate bonds between a polydentate (multiple bonded) ligand and a single central atom.[1] Usually these ligands are organic compounds, and are calle …   Wikipedia Chelation therapy — is the administration of chelating agents to remove heavy metals from the body. For the most common forms of heavy metal intoxication those involving lead, arsenic or mercury the standard of care in the United States dictates the use of… …   Wikipedia ATC code V03 — A section of the Anatomical Therapeutic Chemical Classification System.V VariousV03A All other therapeutic productsV03AB Antidotes:V03AB01 Ipecacuanha:V03AB02 Nalorphine:V03AB03 Edetates:V03AB04 Pralidoxime:V03AB05 Prednisolone and… …   Wikipedia Folinic acid — Systematic (IUPAC) name (2S) 2 {[4 [(2 amino 5 formyl 4 oxo 5,6,7,8 tetrahydro 1H pteridin 6 yl)methylamino] benzoyl]amino}pentanedioic acid Clinical data …   Wikipedia Mesna — This article is about the sulfonate. For the thiolate MeSNa, see Sodium methanethiolate. Mesna Systematic (IUPAC) name sodium 2 sulfanylethanesulfonate Clinical data …   Wikipedia Dimercaprol — Dimercaprol …   Wikipedia 18+ © Academic, 2000-2025 Contact us: Technical Support, Advertising Dictionaries export, created on PHP, Joomla, Drupal, WordPress, MODx. Mark and share Search through all dictionaries Translate… Search Internet Share the article and excerpts Direct link … Do a right-click on the link above and select “Copy Link”