関: dexrazoxane

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/05/15 22:41:21」(JST)

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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. It was discovered by Kurt Hellmann in 1972. Dexrazoxane is a sterile, pyrogen-free lyophilizate intended for intravenous administration. The IV administration of dexrazoxane is in acidic condition with HCl adjusting the pH.^[1]

Uses

Dexrazoxane has been used to protect the heart against the cardiotoxic side effects of chemotherapeutic drugs such as anthracyclines,^[2] such as daunorubicin or doxorubicin or other chemotherapeutic agents.^[3] However, in July 2011 the US Food and Drug Administration released a statement restricting use only in adult patients with cancer who have received > 300 mg/m2 doxorubicin (an anthracycline) or > 540 mg/m2 epirubicin (another chemotherapeutic agent) and general approval for use for cardioprotection.^[4]^[5] that showed a possibly higher rate of secondary malignancies and acute myelogenous leukemia in pediatric patients treated for different cancers with both dexrazoxane and other chemotherapeutic agents that are associated with secondary malignancies.^[6]

The United States Food and Drug Administration 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.^[7]^[8] 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 and thus reduces the number of metal ions complexed with anthracycline and, consequently, decrease the formation of superoxide radicals.^[9] The exact chelation mechanism is unknown, but it has been postulated that dexrazoxane can be converted into ring-opened form intracellularly and interfere with iron-mediated free radical generation that is in part thought to be responsible for anthryacycline induced cadiomyopathy.^[10] It was speculated that dexrazoxane could be used for further investigation to synthesize new antimalarial drugs.^[11]

References

^ http://www.rxlist.com/zinecard-drug.htm
^ 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.
^ Tebbi CK, et al. J Clin Oncol 2007; 25: 493–500
^ Salzer WL, et al. Leukemia 2010; 24: 355–70
^ "FDA Statement on Dexrazoxane".
^ 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.
^ http://labeling.pfizer.com/ShowLabeling.aspx?id=514
^ 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.

English Journal

Interface-free capillary electrophoresis-mass spectrometry system with nanospray ionization-Analysis of dexrazoxane in blood plasma.

Tycova A1, Vido M2, Kovarikova P3, Foret F4.
Journal of chromatography. A.J Chromatogr A.2016 Sep 30;1466:173-9. doi: 10.1016/j.chroma.2016.08.042. Epub 2016 Aug 23.
The newly developed interface-free capillary electrophoresis-nanospray/mass spectrometry system (CE-nESI/MS) was applied for rapid analysis of the cardioprotective drug dexrazoxane and its hydrolysed form ADR-925 in deproteinized blood plasma samples. The aim of this study was to test the simplest p
PMID 27613146

PAK1-cofilin phosphorylation mediates human lung adenocarcinoma cells migration induced by apelin-13.

Lv D1, Li L1, Lu Q1, Li Y1, Xie F1, Li H1, Cao J1, Liu M1, Wu D1, He L1, Chen L1.
Clinical and experimental pharmacology & physiology.Clin Exp Pharmacol Physiol.2016 May;43(5):569-79. doi: 10.1111/1440-1681.12563.
Adipocytokines apelin peptide, the ligand of APJ (putative receptor related to the angiotensin receptor AT1), plays key roles in the pathogenesis and deterioration of cancer. In lung cancer, apelin elevating microvessel densities has been reported. Our previous research has characterized that apelin
PMID 26918678

Impaired mitochondrial function is abrogated by dexrazoxane in doxorubicin-treated childhood acute lymphoblastic leukemia survivors.

Lipshultz SE1,2, Anderson LM3, Miller TL4, Gerschenson M3, Stevenson KE5, Neuberg DS5, Franco VI1, LiButti DE3, Silverman LB5,6,7, Vrooman LM5,6,7, Sallan SE5,6,7; Dana-Farber Cancer Institute Acute Lymphoblastic Leukemia Consortium.
Cancer.Cancer.2016 Mar 15;122(6):946-53. doi: 10.1002/cncr.29872. Epub 2016 Jan 13.
BACKGROUND: Impaired cardiac function in doxorubicin-treated childhood cancer survivors is partly mediated by the disruption of mitochondrial energy production. Doxorubicin intercalates into mitochondrial DNA (mtDNA) and disrupts genes encoding for polypeptides that make adenosine triphosphate.METHO
PMID 26762648

Japanese Journal

Porokeratosis striata lichenoides of Nekam, treated with razoxane

Br J Dermatol 109, 73, 1983
NAID 30014649888

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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
Identifiers
CAS Registry Number	24584-09-6
ATC code	V03AF02
PubChem	CID 71384
DrugBank	DB00380
ChemSpider	64479
UNII	048L81261F
KEGG	D03730
ChEBI	CHEBI:50223
ChEMBL	CHEMBL1738
Chemical data
Formula	C11H16N4O4
Molecular mass	268.269 g/mol
	SMILES O=C2NC(=O)CN(C[C@@H](N1CC(=O)NC(=O)C1)C)C2;
	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 ; Key:BMKDZUISNHGIBY-ZETCQYMHSA-N ;
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英: razoxane
関: デクスラゾキサン

[1] ttp://www.rxlist.com/zinecard-drug.htm

[pmid15247354-2] 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.

[pmid18040065-3] 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.

[4] Tebbi CK, et al. J Clin Oncol 2007; 25: 493–500

[5] Salzer WL, et al. Leukemia 2010; 24: 355–70

[6] "FDA Statement on Dexrazoxane".

[7] Totect label on FDA's website

[pmid18448560-8] 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.

[9] 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.

[10] ttp://labeling.pfizer.com/ShowLabeling.aspx?id=514

[11] 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.

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razoxane