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Home > Other Building Blocks > 24584-09-6
24584-09-6 | 2,6-Piperazinedione, 4,4'-[(1S)-1-methyl-1,2-ethanediyl]bis-
CAS No: 24584-09-6 Catalog No: AG002ONZ MDL No:MFCD00866449
Product Description
Catalog Number:
AG002ONZ
Chemical Name:
2,6-Piperazinedione, 4,4'-[(1S)-1-methyl-1,2-ethanediyl]bis-
CAS Number:
24584-09-6
Molecular Formula:
C11H16N4O4
Molecular Weight:
268.2691
MDL Number:
MFCD00866449
IUPAC Name:
4-[(2S)-2-(3,5-dioxopiperazin-1-yl)propyl]piperazine-2,6-dione
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
InChI Key:
BMKDZUISNHGIBY-ZETCQYMHSA-N
SMILES:
O=C1NC(=O)CN(C1)C[C@@H](N1CC(=O)NC(=O)C1)C
UNII:
048L81261F
NSC Number:
169780
Properties
Complexity:
404
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
1
Defined Bond Stereocenter Count:
0
Exact Mass:
268.117g/mol
Formal Charge:
0
Heavy Atom Count:
19
Hydrogen Bond Acceptor Count:
6
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
268.273g/mol
Monoisotopic Mass:
268.117g/mol
Rotatable Bond Count:
3
Topological Polar Surface Area:
98.8A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-1.4
Literature
| Title | Journal |
|---|---|
| Investigation of novel dexrazoxane analogue JR-311 shows significant cardioprotective effects through topoisomerase IIbeta but not its iron chelating metabolite. | Toxicology 20171201 |
| Dexrazoxane Averts Idarubicin-Evoked Genomic Damage by Regulating Gene Expression Profiling Associated With the DNA Damage-Signaling Pathway in BALB/c Mice. | Toxicological sciences : an official journal of the Society of Toxicology 20171101 |
| Early transcriptional changes in cardiac mitochondria during chronic doxorubicin exposure and mitigation by dexrazoxane in mice. | Toxicology and applied pharmacology 20160315 |
| Early and delayed cardioprotective intervention with dexrazoxane each show different potential for prevention of chronic anthracycline cardiotoxicity in rabbits. | Toxicology 20130915 |
| Response-dependent and reduced treatment in lower risk Hodgkin lymphoma in children and adolescents, results of P9426: a report from the Children's Oncology Group. | Pediatric blood & cancer 20121215 |
| Use of the cardioprotectants thymosin β4 and dexrazoxane during congenital heart surgery: proposal for a randomized, double-blind, clinical trial. | Annals of the New York Academy of Sciences 20121001 |
| BET 3: emergency management of anthracycline extravasation. | Emergency medicine journal : EMJ 20120901 |
| Protective effects of dexrazoxane against acute ischaemia/reperfusion injury of rat hearts. | Canadian journal of physiology and pharmacology 20120901 |
| Dexrazoxane for the prevention of cardiac toxicity and treatment of extravasation injury from the anthracycline antibiotics. | Current pharmaceutical biotechnology 20120801 |
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| Effects of MnDPDP and ICRF-187 on Doxorubicin-Induced Cardiotoxicity and Anticancer Activity. | Translational oncology 20120801 |
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| Changes in cardiac biomarkers during doxorubicin treatment of pediatric patients with high-risk acute lymphoblastic leukemia: associations with long-term echocardiographic outcomes. | Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20120401 |
| Dexrazoxane provided moderate protection in a catecholamine model of severe cardiotoxicity. | Canadian journal of physiology and pharmacology 20120401 |
| Dexrazoxane ameliorates doxorubicin-induced injury in mouse ovarian cells. | Biology of reproduction 20120301 |
| Clinical and genetic determinants of anthracycline-induced cardiac iron accumulation. | International journal of cardiology 20120209 |
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| Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps). | PLoS computational biology 20111201 |
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| An in vitro comparison of the effects of the iron-chelating agents, CP94 and dexrazoxane, on protoporphyrin IX accumulation for photodynamic therapy and/or fluorescence guided resection. | Photochemistry and photobiology 20110101 |
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| Amifostine and dexrazoxane enhance the rapid loss of bone mass and further deterioration of vertebrae architecture in female rats. | Calcified tissue international 20050901 |
| Molecular pharmacology of the interaction of anthracyclines with iron. | Molecular pharmacology 20050801 |
| CD95/Apo-1/Fas: independent cell death induced by doxorubicin in normal cultured cardiomyocytes. | Cancer immunology, immunotherapy : CII 20050701 |
| Monitoring cardiac function in patients receiving doxorubicin. | Seminars in nuclear medicine 20050701 |
| Dexrazoxane for the prevention of cardiomyopathy in anthracycline treated pediatric cancer patients. | Pediatric blood & cancer 20050615 |
| Metabolism of the cardioprotective drug dexrazoxane and one of its metabolites by isolated rat myocytes, hepatocytes, and blood. | Drug metabolism and disposition: the biological fate of chemicals 20050601 |
| Prediction of genotoxicity of chemical compounds by statistical learning methods. | Chemical research in toxicology 20050601 |
| Dexrazoxane protects against myelosuppression from the DNA cleavage-enhancing drugs etoposide and daunorubicin but not doxorubicin. | Clinical cancer research : an official journal of the American Association for Cancer Research 20050515 |
| Myocardial content of selected elements in experimental anthracycline-induced cardiomyopathy in rabbits. | Biometals : an international journal on the role of metal ions in biology, biochemistry, and medicine 20050401 |
| Gender-dependent reductions in vertebrae length, bone mineral density and content by doxorubicin are not reduced by dexrazoxane in young rats: effect on growth plate and intervertebral discs. | Calcified tissue international 20050301 |
| Cardioprotective interventions for cancer patients receiving anthracyclines. | The Cochrane database of systematic reviews 20050125 |
| The antitumor anthracyclines doxorubicin and daunorubicin do not inhibit cell growth through the formation of iron-mediated reactive oxygen species. | Anti-cancer drugs 20050101 |
| Anthracycline-induced cardiotoxicity in children with cancer: strategies for prevention and management. | Paediatric drugs 20050101 |
| Dexrazoxane : a review of its use for cardioprotection during anthracycline chemotherapy. | Drugs 20050101 |
| The prevention and management of cardiovascular complications of chemotherapy in patients with cancer. | American journal of cardiovascular drugs : drugs, devices, and other interventions 20050101 |
| Clinical nurse specialist and evidence-based practice: managing anthracycline extravasation. | Journal of pediatric oncology nursing : official journal of the Association of Pediatric Oncology Nurses 20050101 |
| Cost Effectiveness of Cardioprotective Strategies in Patients with Aggressive Non-Hodgkin's Lymphoma. | Clinical drug investigation 20050101 |
| Mitoxantrone treatment of multiple sclerosis: safety considerations. | Neurology 20041228 |
| The iron chelating cardioprotective prodrug dexrazoxane does not affect the cell growth inhibitory effects of bleomycin. | Journal of inorganic biochemistry 20041101 |
| Evaluating the role of dexrazoxane as a cardioprotectant in cancer patients receiving anthracyclines. | Cancer treatment reviews 20041101 |
| [Cardiac prevention: the oncologic point of view]. | Bulletin du cancer 20041101 |
| Can dexrazoxane reduce myocardial injury in anthracycline-treated children with acute lymphoblastic leukemia? | Nature clinical practice. Oncology 20041101 |
| Accelerated approval of oncology products: a decade of experience. | Journal of the National Cancer Institute 20041020 |
| Concurrent therapies that protect against doxorubicin-induced cardiomyopathy. | Clinical journal of oncology nursing 20041001 |
| Feasibility and pharmacokinetic study of infusional dexrazoxane and dose-intensive doxorubicin administered concurrently over 96 h for the treatment of advanced malignancies. | Cancer chemotherapy and pharmacology 20040901 |
| The effect of dexrazoxane on myocardial injury in doxorubicin-treated children with acute lymphoblastic leukemia. | The New England journal of medicine 20040708 |
| Rabbit model for in vivo study of anthracycline-induced heart failure and for the evaluation of protective agents. | European journal of heart failure 20040601 |
| [Dexrazoxane and cardiotoxicity in repeatedly treated patients]. | Vnitrni lekarstvi 20040601 |
| [Dexrazoxane in patients with B-lymphomas or acute leukemias in the 2nd complete remission enables further therapy with cardiotoxic anthracyclines over recommended cumulative doses]. | Vnitrni lekarstvi 20040601 |
| Dexrazoxane for anthracycline extravasation and GM-CSF for skin ulceration and wound healing. | The Lancet. Oncology 20040501 |
| Cardiotoxicity of cytotoxic drugs. | Cancer treatment reviews 20040401 |
| Synthesis and characterization of the biological activity of the cisplatin analogs, cis-PtCl(2)(dexrazoxane) and cis-PtCl(2)(levrazoxane), of the topoisomerase II inhibitors dexrazoxane (ICRF-187) and levrazoxane (ICRF-186). | Journal of inorganic biochemistry 20040401 |
| Anaphylaxis to dexrazoxane (ICRF-187) following three previous uncomplicated infusions. | Allergy 20040201 |
| The current and future role of dexrazoxane as a cardioprotectant in anthracycline treatment: expert panel review. | Journal of cancer research and clinical oncology 20040101 |
| Pharmacokinetics of etoposide in cancer patients treated with high-dose etoposide and with dexrazoxane (ICRF-187) as a rescue agent. | Cancer chemotherapy and pharmacology 20040101 |
| The cardioprotector dexrazoxane augments therapeutic efficacy of mitoxantrone in experimental autoimmune encephalomyelitis. | Clinical and experimental immunology 20040101 |
| Characterisation of cytotoxicity and DNA damage induced by the topoisomerase II-directed bisdioxopiperazine anti-cancer agent ICRF-187 (dexrazoxane) in yeast and mammalian cells. | BMC pharmacology 20040101 |
| Iron chelators in cancer chemotherapy. | Current topics in medicinal chemistry 20040101 |
| Antitumor effects of two bisdioxopiperazines against two experimental lung cancer models in vivo. | BMC pharmacology 20040101 |
| The oral iron chelator ICL670A (deferasirox) does not protect myocytes against doxorubicin. | Free radical biology & medicine 20031201 |
| Supportive care of the older cancer patient. | Critical reviews in oncology/hematology 20031015 |
| The metabolites of the cardioprotective drug dexrazoxane do not protect myocytes from doxorubicin-induced cytotoxicity. | Molecular pharmacology 20030901 |
| Protein profiling in daunorubicin-induced cardiomyopathy. | General physiology and biophysics 20030901 |
| Analysis of bisdioxopiperazine dexrazoxane binding to human DNA topoisomerase II alpha: decreased binding as a mechanism of drug resistance. | Biochemistry 20030819 |
| Dexrazoxane does not protect against doxorubicin-induced damage in young rats. | American journal of physiology. Heart and circulatory physiology 20030801 |
| Metabolism of dexrazoxane (ICRF-187) used as a rescue agent in cancer patients treated with high-dose etoposide. | Cancer chemotherapy and pharmacology 20030801 |
| High-dose epirubicin, preceded by dexrazoxane, given in combination with paclitaxel plus filgrastim provides an effective mobilizing regimen to support three courses of high-dose dense chemotherapy in patients with high-risk stage II-IIIA breast cancer. | Bone marrow transplantation 20030801 |
| Dexrazoxane in combination with anthracyclines lead to a synergistic cytotoxic response in acute myelogenous leukemia cell lines. | Leukemia research 20030701 |
| Iron chelator research: past, present, and future. | Current medicinal chemistry 20030601 |
| Cardiac toxicity of antineoplastic anthracyclines. | Current medicinal chemistry. Anti-cancer agents 20030301 |
| Effect of dexrazoxane on doxorubicin pharmacokinetics in young and old rats. | Cancer chemotherapy and pharmacology 20030201 |
| Myocardial cytoprotection by trimetazidine against anthracycline-induced cardiotoxicity in anticancer chemotherapy. | Angiology 20030101 |
| Dexrazoxane-a promising antidote in the treatment of accidental extravasation of anthracyclines. | Scandinavian journal of plastic and reconstructive surgery and hand surgery 20030101 |
| Dexrazoxane (ICRF-187) protects cardiac myocytes against doxorubicin by preventing damage to mitochondria. | Cardiovascular toxicology 20030101 |
| Protection against acute adriamycin-induced cardiotoxicity by garlic: role of endogenous antioxidants and inhibition of TNF-alpha expression. | BMC pharmacology 20030101 |
| Dihydroorotase catalyzes the ring opening of the hydrolysis intermediates of the cardioprotective drug dexrazoxane (ICRF-187). | Drug metabolism and disposition: the biological fate of chemicals 20021201 |
| The doxorubicin-cardioprotective drug dexrazoxane undergoes metabolism in the rat to its metal ion-chelating form ADR-925. | Cancer chemotherapy and pharmacology 20021201 |
| Deferiprone protects against doxorubicin-induced myocyte cytotoxicity. | Free radical biology & medicine 20020715 |
| Effect of dexrazoxane on homocysteine-induced endothelial dysfunction in normal subjects. | Arteriosclerosis, thrombosis, and vascular biology 20020701 |
| In vitro search for synergy and antagonism: evaluation of docetaxel combinations in breast cancer cell lines. | Breast cancer research and treatment 20020701 |
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| Early decline in left ventricular ejection fraction predicts doxorubicin cardiotoxicity in lymphoma patients. | British journal of cancer 20020605 |
| Dexrazoxane has no impact on sensitivity of childhood leukemic blasts to daunorubicin. | Leukemia 20020501 |
| Dexrazoxane pre-treatment protects skinned rat cardiac trabeculae against delayed doxorubicin-induced impairment of crossbridge kinetics. | British journal of pharmacology 20020401 |
| Gateways to Clinical Trials. | Methods and findings in experimental and clinical pharmacology 20020401 |
| The doxorubicin cardioprotective agent dexrazoxane (ICRF-187) induces endopolyploidy in rat neonatal myocytes through inhibition of DNA topoisomerase II. | Anti-cancer drugs 20020301 |
| Troponins in experimental studies. | Acta medica (Hradec Kralove) 20020101 |
| Dexrazoxane (ICRF-187) protects cardiac myocytes against hypoxia-reoxygenation damage. | Cardiovascular toxicology 20020101 |
| Multiple myeloma and its treatment. | Clinical journal of oncology nursing 20020101 |
| Minimising the long-term adverse effects of childhood leukaemia therapy. | Drug safety 20020101 |
| Effect of sodium 2,3-dimercaptopropane-1-sulphonate (DMPS) on chronic daunorubicin toxicity in rabbits: comparison with dexrazoxane. | Acta medica (Hradec Kralove) 20020101 |
| Recent advances in the prevention of anthracycline cardiotoxicity in childhood. | Current medicinal chemistry 20011101 |
| High-dose doxorubicin, dexrazoxane, and GM-CSF in malignant mesothelioma: a phase II study-Cancer and Leukemia Group B 9631. | Lung cancer (Amsterdam, Netherlands) 20011101 |
| Cytotoxic signalling by inhibitors of DNA topoisomerase II. | Biochemical Society transactions 20011101 |
| In vitro effects of dexrazoxane (Zinecard) and classical acute leukemia therapy: time to consider expanded clinical trials? | Leukemia 20011001 |
| In vitro prevention of the emergence of multidrug resistance in a pediatric rhabdomyosarcoma cell line. | Clinical cancer research : an official journal of the American Association for Cancer Research 20011001 |
| The use of serum levels of cardiac troponin T to compare the protective activity of dexrazoxane against doxorubicin- and mitoxantrone-induced cardiotoxicity. | Cancer chemotherapy and pharmacology 20011001 |
| The effect of the catalytic topoisomerase II inhibitor dexrazoxane (ICRF-187) on CC9C10 hybridoma viability and productivity. | Cytotechnology 20011001 |
| Anthracycline-induced cardiomyopathy. | Seminars in oncology 20010801 |
| Phase I trial of 96-hour continuous infusion of dexrazoxane in patients with advanced malignancies. | Clinical cancer research : an official journal of the American Association for Cancer Research 20010601 |
| Diminished molecular response to doxorubicin and loss of cardioprotective effect of dexrazoxane in Egr-1 deficient female mice. | Canadian journal of physiology and pharmacology 20010601 |
| Dexrazoxane significantly impairs the induction of doxorubicin resistance in the human leukaemia line, K562. | British journal of cancer 20010401 |
| The catalytic DNA topoisomerase II inhibitor dexrazoxane (ICRF-187) induces differentiation and apoptosis in human leukemia K562 cells. | Molecular pharmacology 20010301 |
| Dexrazoxane is a potent and specific inhibitor of anthracycline induced subcutaneous lesions in mice. | Annals of oncology : official journal of the European Society for Medical Oncology 20010301 |
| [Cardiotoxicity of antineoplastic anthracycline antibiotics and prevention by cardioxane (Dexrazoxane) in clinical practice]. | Voprosy onkologii 20010101 |
| Signal-averaged electrocardiography in survivors of Hodgkin's disease treated with and without dexrazoxane. | Neoplasma 20010101 |
| A new conservative approach to extravasation of anthracyclines with dimethylsulfoxide and dexrazoxane. | Acta oncologica (Stockholm, Sweden) 20010101 |
| Acute dosage with dexrazoxane, but not doxorubicin, is associated with increased rates of hepatic protein synthesis in vivo. | Toxicologic pathology 20010101 |
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