| 词条 | Dexrazoxane |
| 释义 |
| verifiedrevid = 460780226 | IUPAC_name = 4-[(2S)-2-(3,5-Dioxopiperazin-1-yl)propyl]piperazine-2,6-dione | image = Dexrazoxane.svg | tradename = | Drugs.com = {{drugs.com|monograph|dexrazoxane-hydrochloride}} | MedlinePlus = a609010 | pregnancy_AU = | pregnancy_US = | pregnancy_category = | licence_EU = yes | legal_AU = | legal_UK = | legal_US = | legal_status = | routes_of_administration = | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | IUPHAR_ligand = 7330 | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 24584-09-6 | ATC_prefix = V03 | ATC_suffix = AF02 | ATC_supplemental = | PubChem = 71384 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB00380 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 64479 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 048L81261F | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D03730 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 50223 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 1738 | C=11 | H=16 | N=4 | O=4 | molecular_weight = 268.269 g/mol | smiles = O=C2NC(=O)CN(C[C@@H](N1CC(=O)NC(=O)C1)C)C2 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = BMKDZUISNHGIBY-ZETCQYMHSA-N }}Dexrazoxane hydrochloride (Zinecard, Cardioxane) is a cardioprotective agent. It was discovered by Kurt Hellmann in 1972. The IV administration of dexrazoxane is in acidic condition with HCl adjusting the pH.[1] UsesDexrazoxane 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 names Totect and Savene (approved in the EU) marketed by Clinigen Group, 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. MechanismAs 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 cardiomyopathy.[10] It was speculated that dexrazoxane could be used for further investigation to synthesize new antimalarial drugs.[11] References1. ^http://www.rxlist.com/zinecard-drug.htm {{Detoxifying agents for antineoplastic treatment}}{{Chelating agents}}2. ^{{cite journal |doi=10.1056/NEJMoa035153 |title=The Effect of Dexrazoxane on Myocardial Injury in Doxorubicin-Treated Children with Acute Lymphoblastic Leukemia |year=2004 |last1=Lipshultz |first1=Steven E. |last2=Rifai |first2=Nader |last3=Dalton |first3=Virginia M. |last4=Levy |first4=Donna E. |last5=Silverman |first5=Lewis B. |last6=Lipsitz |first6=Stuart R. |last7=Colan |first7=Steven D. |last8=Asselin |first8=Barbara L. |last9=Barr |first9=Ronald D. |last10=Clavell |first10=Luis A. |last11=Hurwitz |first11=Craig A. |last12=Moghrabi |first12=Albert |last13=Samson |first13=Yvan |last14=Schorin |first14=Marshall A. |last15=Gelber |first15=Richard D. |last16=Sallan |first16=Stephen E. |journal=New England Journal of Medicine |volume=351 |issue=2 |pages=145–53 |pmid=15247354|display-authors=8 }} 3. ^{{cite journal |doi=10.3181/0705-RM-138 |title=Effects of Dexrazoxane and Amifostine on Evolution of Doxorubicin Cardiomyopathy in Vivo |year=2007 |last1=Bjelogrlic |first1=Snezana K. |last2=Radic |first2=Jelena |last3=Radulovic |first3=Sinisa |last4=Jokanovic |first4=Milan |last5=Jovic |first5=Viktor |journal=Experimental Biology and Medicine |volume=232 |issue=11 |pages=1414–24 |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. ^{{cite web|url= http://www.fda.gov/Drugs/DrugSafety/ucm263729.htm|title= FDA Statement on Dexrazoxane}} 7. ^Totect label on FDA's website 8. ^{{cite journal |doi=10.1634/theoncologist.2007-0247 |title=Dexrazoxane (Totect™): FDA Review and Approval for the Treatment of Accidental Extravasation Following Intravenous Anthracycline Chemotherapy |year=2008 |last1=Kane |first1=Robert C. |last2=McGuinn |first2=W. David |last3=Dagher |first3=Ramzi |last4=Justice |first4=Robert |last5=Pazdur |first5=Richard |journal=The Oncologist |volume=13 |issue=4 |pages=445–50 |pmid=18448560}} 9. ^{{cite journal |doi=10.1586/14779072.6.10.1311 |title=Utility of dexrazoxane for the reduction of anthracycline-induced cardiotoxicity |year=2008 |last1=Jones |first1=Robin L. |journal=Expert Review of Cardiovascular Therapy |volume=6 |issue=10 |pages=1311–7 |pmid=19018683}} 10. ^http://labeling.pfizer.com/ShowLabeling.aspx?id=514 11. ^{{cite journal |doi=10.1006/expr.1998.4371 |title=Plasmodium falciparum and Plasmodium yoelii: Effect of the Iron Chelation Prodrug Dexrazoxane on in Vitro Cultures |year=1999 |last1=Loyevsky |first1=Mark |journal=Experimental Parasitology |volume=91 |issue=2 |pages=105–14 |pmid=9990337 |last2=Sacci |first2=John B. |last3=Boehme |first3=Patricia |last4=Weglicki |first4=William |last5=John |first5=Christy |last6=Gordeuk |first6=Victor R.}} 6 : Chelating agents|Chelating agents used as drugs|Chemotherapeutic adjuvants|Imides|Enantiopure drugs|Diketopiperazines |
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