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
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C11H16N4O4 |
| Molecular Weight | 268.2691 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
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 |
|---|---|---|
| Phase II trial of the antiangiogenic agent IM862 in metastatic renal cell carcinoma. | 2004-11-01 |
|
| Doxorubicin-induced myocardial injury. | 2004-10-28 |
|
| Treatment options for malignant hemangioendotheliomas of the thyroid. | 2004-10-01 |
|
| The antitumor triazoloacridone C-1305 is a topoisomerase II poison with unusual properties. | 2004-10 |
|
| Feasibility and pharmacokinetic study of infusional dexrazoxane and dose-intensive doxorubicin administered concurrently over 96 h for the treatment of advanced malignancies. | 2004-09 |
|
| The effect of dexrazoxane on myocardial injury in doxorubicin-treated children with acute lymphoblastic leukemia. | 2004-07-08 |
|
| Anthracycline cardiotoxicity in children. | 2004-07-08 |
|
| Cardiovascular complications of cancer therapy: diagnosis, pathogenesis, and management. | 2004-06-29 |
|
| [Prevention of anthracycline cardiotoxicity]. | 2004-06-23 |
|
| [Dexrazoxane in patients with B-lymphomas or acute leukemias in the 2nd complete remission enables further therapy with cardiotoxic anthracyclines over recommended cumulative doses]. | 2004-06 |
|
| [Dexrazoxane and cardiotoxicity in repeatedly treated patients]. | 2004-06 |
|
| Rabbit model for in vivo study of anthracycline-induced heart failure and for the evaluation of protective agents. | 2004-06 |
|
| Experimental animal model for anthracycline-induced heart failure. | 2004-06 |
|
| Enhanced processing of UVA-irradiated DNA by human topoisomerase II in living cells. | 2004-05-14 |
|
| Dexrazoxane for anthracycline extravasation and GM-CSF for skin ulceration and wound healing. | 2004-05 |
|
| 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). | 2004-04 |
|
| Cardiotoxicity of cytotoxic drugs. | 2004-04 |
|
| Anaphylaxis to dexrazoxane (ICRF-187) following three previous uncomplicated infusions. | 2004-02 |
|
| The cardioprotector dexrazoxane augments therapeutic efficacy of mitoxantrone in experimental autoimmune encephalomyelitis. | 2004-01 |
|
| Pharmacokinetics of etoposide in cancer patients treated with high-dose etoposide and with dexrazoxane (ICRF-187) as a rescue agent. | 2004-01 |
|
| The current and future role of dexrazoxane as a cardioprotectant in anthracycline treatment: expert panel review. | 2004-01 |
|
| Oxidant-induced iron signaling in Doxorubicin-mediated apoptosis. | 2004 |
|
| Dexrazoxane's protection of jejunal crypt cells in the jejunum of C3Hf/Kam mice from doxorubicin-induced toxicity. | 2003-12 |
|
| Cardiac toxicity related to cancer treatment. | 2003-11-08 |
|
| Protein profiling in daunorubicin-induced cardiomyopathy. | 2003-09 |
|
| The metabolites of the cardioprotective drug dexrazoxane do not protect myocytes from doxorubicin-induced cytotoxicity. | 2003-09 |
|
| Analysis of bisdioxopiperazine dexrazoxane binding to human DNA topoisomerase II alpha: decreased binding as a mechanism of drug resistance. | 2003-08-19 |
|
| 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. | 2003-08 |
|
| Metabolism of dexrazoxane (ICRF-187) used as a rescue agent in cancer patients treated with high-dose etoposide. | 2003-08 |
|
| Dexrazoxane does not protect against doxorubicin-induced damage in young rats. | 2003-08 |
|
| Measurement of renal tumour and normal tissue perfusion using positron emission tomography in a phase II clinical trial of razoxane. | 2003-07-21 |
|
| Surrogate markers in antiangiogenesis clinical trials. | 2003-07-07 |
|
| Dexrazoxane in combination with anthracyclines lead to a synergistic cytotoxic response in acute myelogenous leukemia cell lines. | 2003-07 |
|
| The G2-phase decatenation checkpoint is defective in Werner syndrome cells. | 2003-06-15 |
|
| "Vasocrine" formation of tumor cell-lined vascular spaces: implications for rational design of antiangiogenic therapies. | 2003-06-01 |
|
| [Chemotherapy-induced cardiac toxicity and management]. | 2003-06 |
|
| Probing the role of linker substituents in bisdioxopiperazine analogs for activity against wild-type and mutant human topoisomerase II alpha. | 2003-05 |
|
| Myocardial cytoprotection by trimetazidine against anthracycline-induced cardiotoxicity in anticancer chemotherapy. | 2003-04-08 |
|
| A small prospective study of chordomas treated with radiotherapy and razoxane. | 2003-04 |
|
| Anthracyclines induce accumulation of iron in ferritin in myocardial and neoplastic cells: inhibition of the ferritin iron mobilization pathway. | 2003-04 |
|
| Effect of dexrazoxane on doxorubicin pharmacokinetics in young and old rats. | 2003-02 |
|
| Evidence from studies with intact mammalian cells that merbarone and bis(dioxopiperazine)s are topoisomerase II poisons. | 2003-02 |
|
| Dexrazoxane (ICRF-187) protects cardiac myocytes against doxorubicin by preventing damage to mitochondria. | 2003 |
|
| Dexrazoxane-a promising antidote in the treatment of accidental extravasation of anthracyclines. | 2003 |
|
| Extravasation: a dreaded complication of chemotherapy. | 2003 |
|
| Dynamics of tumour angiogenesis: effect of razoxane-induced growth rate slowdown. | 2003 |
|
| The doxorubicin-cardioprotective drug dexrazoxane undergoes metabolism in the rat to its metal ion-chelating form ADR-925. | 2002-12 |
|
| Effect of sodium 2,3-dimercaptopropane-1-sulphonate (DMPS) on chronic daunorubicin toxicity in rabbits: comparison with dexrazoxane. | 2002 |
|
| Radioprotectants: current status and new directions. | 2002 |
|
| Pharmacokinetics of the cardioprotector ADR-529 (ICRF-187) in escalating doses combined with fixed-dose doxorubicin. | 1992-11-18 |
| Substance Class |
Chemical
Created
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admin
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Edited
Mon Mar 31 23:11:14 GMT 2025
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Mon Mar 31 23:11:14 GMT 2025
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| Record UNII |
BR9T89F617
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| Record Status |
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| Record Version |
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BR9T89F617
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1383294-26-5
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11652428
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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ENANTIOMER -> RACEMATE | |||
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PARENT -> SALT/SOLVATE |
