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 |
|---|---|---|
| Pharmacokinetics of the cardioprotector ADR-529 (ICRF-187) in escalating doses combined with fixed-dose doxorubicin. | 1992 Nov 18 |
|
| 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 |
|
| The doxorubicin-cardioprotective drug dexrazoxane undergoes metabolism in the rat to its metal ion-chelating form ADR-925. | 2002 Dec |
|
| 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 |
|
| A small prospective study of chordomas treated with radiotherapy and razoxane. | 2003 Apr |
|
| Anthracyclines induce accumulation of iron in ferritin in myocardial and neoplastic cells: inhibition of the ferritin iron mobilization pathway. | 2003 Apr |
|
| 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 Aug |
|
| Metabolism of dexrazoxane (ICRF-187) used as a rescue agent in cancer patients treated with high-dose etoposide. | 2003 Aug |
|
| Dexrazoxane does not protect against doxorubicin-induced damage in young rats. | 2003 Aug |
|
| Analysis of bisdioxopiperazine dexrazoxane binding to human DNA topoisomerase II alpha: decreased binding as a mechanism of drug resistance. | 2003 Aug 19 |
|
| Dexrazoxane's protection of jejunal crypt cells in the jejunum of C3Hf/Kam mice from doxorubicin-induced toxicity. | 2003 Dec |
|
| Effect of dexrazoxane on doxorubicin pharmacokinetics in young and old rats. | 2003 Feb |
|
| Evidence from studies with intact mammalian cells that merbarone and bis(dioxopiperazine)s are topoisomerase II poisons. | 2003 Feb |
|
| Dexrazoxane in combination with anthracyclines lead to a synergistic cytotoxic response in acute myelogenous leukemia cell lines. | 2003 Jul |
|
| Measurement of renal tumour and normal tissue perfusion using positron emission tomography in a phase II clinical trial of razoxane. | 2003 Jul 21 |
|
| Surrogate markers in antiangiogenesis clinical trials. | 2003 Jul 7 |
|
| [Chemotherapy-induced cardiac toxicity and management]. | 2003 Jun |
|
| "Vasocrine" formation of tumor cell-lined vascular spaces: implications for rational design of antiangiogenic therapies. | 2003 Jun 1 |
|
| The G2-phase decatenation checkpoint is defective in Werner syndrome cells. | 2003 Jun 15 |
|
| Myocardial cytoprotection by trimetazidine against anthracycline-induced cardiotoxicity in anticancer chemotherapy. | 2003 Mar-Apr |
|
| Probing the role of linker substituents in bisdioxopiperazine analogs for activity against wild-type and mutant human topoisomerase II alpha. | 2003 May |
|
| Protein profiling in daunorubicin-induced cardiomyopathy. | 2003 Sep |
|
| The metabolites of the cardioprotective drug dexrazoxane do not protect myocytes from doxorubicin-induced cytotoxicity. | 2003 Sep |
|
| Cardiac toxicity related to cancer treatment. | 2003 Sep-Oct |
|
| Oxidant-induced iron signaling in Doxorubicin-mediated apoptosis. | 2004 |
|
| 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 Apr |
|
| Cardiotoxicity of cytotoxic drugs. | 2004 Apr |
|
| 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 |
|
| [Prevention of anthracycline cardiotoxicity]. | 2004 Jul-Aug |
|
| [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 Jun |
|
| [Dexrazoxane and cardiotoxicity in repeatedly treated patients]. | 2004 Jun |
|
| Rabbit model for in vivo study of anthracycline-induced heart failure and for the evaluation of protective agents. | 2004 Jun |
|
| Experimental animal model for anthracycline-induced heart failure. | 2004 Jun |
|
| Cardiovascular complications of cancer therapy: diagnosis, pathogenesis, and management. | 2004 Jun 29 |
|
| Dexrazoxane for anthracycline extravasation and GM-CSF for skin ulceration and wound healing. | 2004 May |
|
| Enhanced processing of UVA-irradiated DNA by human topoisomerase II in living cells. | 2004 May 14 |
|
| Phase II trial of the antiangiogenic agent IM862 in metastatic renal cell carcinoma. | 2004 Nov 1 |
|
| The antitumor triazoloacridone C-1305 is a topoisomerase II poison with unusual properties. | 2004 Oct |
|
| Treatment options for malignant hemangioendotheliomas of the thyroid. | 2004 Oct 1 |
|
| Doxorubicin-induced myocardial injury. | 2004 Oct 28 |
|
| Feasibility and pharmacokinetic study of infusional dexrazoxane and dose-intensive doxorubicin administered concurrently over 96 h for the treatment of advanced malignancies. | 2004 Sep |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 10:20:20 GMT 2023
by
admin
on
Sat Dec 16 10:20:20 GMT 2023
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| Record UNII |
BR9T89F617
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| Record Status |
Validated (UNII)
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| Record Version |
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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
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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ENANTIOMER -> RACEMATE | |||
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PARENT -> SALT/SOLVATE |
