Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C11H16N4O4.ClH |
| Molecular Weight | 304.73 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CC(CN1CC(=O)NC(=O)C1)N2CC(=O)NC(=O)C2
InChI
InChIKey=BIFMNMPSIYHKDN-UHFFFAOYSA-N
InChI=1S/C11H16N4O4.ClH/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);1H
Razoxane (ICRF 159; (±)1,2-di(3,5-dioxopiperazin-1-yl) propane) belongs to the family of bis-dioxopiperazines, developed in the 1960s as derivatives of the chelating agent EDTA. It exerts antineoplastic, antiangiogenic, and antimetastatic activities. It is an inhibitor of topoisomerase II. Razoxane is a cytostatic agent, blocks the entry of cultured human lymphocytes into mitosis and arrests dividing cells in prophase and early metaphase. Razoxane is an effective drug in the systemic treatment of psoriasis.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Use of dexrazoxane as a cardioprotectant in patients receiving doxorubicin or epirubicin chemotherapy for the treatment of cancer. The Provincial Systemic Treatment Disease Site Group. | 1999 Apr |
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| Induction of apoptosis by dexrazoxane (ICRF-187) through caspases in the absence of c-jun expression and c-Jun NH2-terminal kinase 1 (JNK1) activation in VM-26-resistant CEM cells. | 1999 Oct 15 |
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| Comparison of the protective effects of amifostine and dexrazoxane against the toxicity of doxorubicin in spontaneously hypertensive rats. | 2000 |
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| Single agent epirubicin as first line chemotherapy for metastatic breast cancer patients. | 2000 Jan |
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| Prevention by dexrazoxane of down-regulation of ryanodine receptor gene expression in anthracycline cardiomyopathy in the rat. | 2000 Sep |
|
| Genotoxicity of iron chelators in L5178Y mouse lymphoma cells. | 2001 |
|
| A new conservative approach to extravasation of anthracyclines with dimethylsulfoxide and dexrazoxane. | 2001 |
|
| Dexrazoxane significantly impairs the induction of doxorubicin resistance in the human leukaemia line, K562. | 2001 Apr 6 |
|
| Role of an inverted CCAAT element in human topoisomerase IIalpha gene expression in ICRF-187-sensitive and -resistant CEM leukemic cells. | 2001 Feb |
|
| Developing drugs to decrease the toxicity of chemotherapy. | 2001 Jul 15 |
|
| Phase I trial of 96-hour continuous infusion of dexrazoxane in patients with advanced malignancies. | 2001 Jun |
|
| The catalytic DNA topoisomerase II inhibitor dexrazoxane (ICRF-187) induces differentiation and apoptosis in human leukemia K562 cells. | 2001 Mar |
|
| Effects of Doxorubicin (Adriamycin) and [(+)-1,2-bis(3,5-dioxopiperazinyl-1-yl)]propane (ICRF-187) on skeletal muscle protease activities. | 2001 Mar 15 |
|
| Acute dosage with dexrazoxane, but not doxorubicin, is associated with increased rates of hepatic protein synthesis in vivo. | 2001 Nov-Dec |
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| In vitro prevention of the emergence of multidrug resistance in a pediatric rhabdomyosarcoma cell line. | 2001 Oct |
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| In vitro effects of dexrazoxane (Zinecard) and classical acute leukemia therapy: time to consider expanded clinical trials? | 2001 Oct |
|
| High-throughput fluorescence flow-injection topoisomerase II inhibition assay. | 2001 Sep 5 |
|
| Radioprotectants: current status and new directions. | 2002 |
|
| Dexrazoxane (ICRF-187) protects cardiac myocytes against hypoxia-reoxygenation damage. | 2002 |
|
| [Echocardiographic assessment of circulation system in patients during and 3-5 years after all therapy in childhood]. | 2002 |
|
| Troponins in experimental studies. | 2002 |
|
| Dexrazoxane pre-treatment protects skinned rat cardiac trabeculae against delayed doxorubicin-induced impairment of crossbridge kinetics. | 2002 Apr |
|
| The doxorubicin-cardioprotective drug dexrazoxane undergoes metabolism in the rat to its metal ion-chelating form ADR-925. | 2002 Dec |
|
| Interference with topoisomerase IIalpha potentiates melphalan cytotoxicity. | 2002 Feb |
|
| [Monitoring cardiotoxicity of anthracyclines in children and possibilities of its prevention]. | 2002 Jul |
|
| In vitro search for synergy and antagonism: evaluation of docetaxel combinations in breast cancer cell lines. | 2002 Jul |
|
| 2002 update of recommendations for the use of chemotherapy and radiotherapy protectants: clinical practice guidelines of the American Society of Clinical Oncology. | 2002 Jun 15 |
|
| The catalytic DNA topoisomerase II inhibitor ICRF-193 and all-trans retinoic acid cooperatively induce granulocytic differentiation of acute promyelocytic leukemia cells: candidate drugs for chemo-differentiation therapy against acute promyelocytic leukemia. | 2002 Nov |
|
| Dexrazoxane (ICRF-187) protects cardiac myocytes against doxorubicin by preventing damage to mitochondria. | 2003 |
|
| Evidence from studies with intact mammalian cells that merbarone and bis(dioxopiperazine)s are topoisomerase II poisons. | 2003 Feb |
|
| Measurement of renal tumour and normal tissue perfusion using positron emission tomography in a phase II clinical trial of razoxane. | 2003 Jul 21 |
|
| "Vasocrine" formation of tumor cell-lined vascular spaces: implications for rational design of antiangiogenic therapies. | 2003 Jun 1 |
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| The G2-phase decatenation checkpoint is defective in Werner syndrome cells. | 2003 Jun 15 |
|
| The metabolites of the cardioprotective drug dexrazoxane do not protect myocytes from doxorubicin-induced cytotoxicity. | 2003 Sep |
|
| Anaphylaxis to dexrazoxane (ICRF-187) following three previous uncomplicated infusions. | 2004 Feb |
|
| The cardioprotector dexrazoxane augments therapeutic efficacy of mitoxantrone in experimental autoimmune encephalomyelitis. | 2004 Jan |
|
| Pharmacokinetics of etoposide in cancer patients treated with high-dose etoposide and with dexrazoxane (ICRF-187) as a rescue agent. | 2004 Jan |
|
| The current and future role of dexrazoxane as a cardioprotectant in anthracycline treatment: expert panel review. | 2004 Jan |
|
| The effect of dexrazoxane on myocardial injury in doxorubicin-treated children with acute lymphoblastic leukemia. | 2004 Jul 8 |
|
| Anthracycline cardiotoxicity in children. | 2004 Jul 8 |
|
| [Dexrazoxane and cardiotoxicity in repeatedly treated patients]. | 2004 Jun |
|
| Dexrazoxane for anthracycline extravasation and GM-CSF for skin ulceration and wound healing. | 2004 May |
|
| Treatment options for malignant hemangioendotheliomas of the thyroid. | 2004 Oct 1 |
|
| Doxorubicin-induced myocardial injury. | 2004 Oct 28 |
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Common Name | English | ||
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| Code System | Code | Type | Description | ||
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BR9T89F617
Created by
admin on Sat Dec 16 10:20:20 GMT 2023 , Edited by admin on Sat Dec 16 10:20:20 GMT 2023
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PRIMARY | |||
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1383294-26-5
Created by
admin on Sat Dec 16 10:20:20 GMT 2023 , Edited by admin on Sat Dec 16 10:20:20 GMT 2023
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NON-SPECIFIC STOICHIOMETRY | |||
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11652428
Created by
admin on Sat Dec 16 10:20:20 GMT 2023 , Edited by admin on Sat Dec 16 10:20:20 GMT 2023
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PRIMARY |
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
