RAZOXANE

Details

Stereochemistry	RACEMIC
Molecular Formula	C11H16N4O4
Molecular Weight	268.2691
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(CN1CC(=O)NC(=O)C1)N2CC(=O)NC(=O)C2

InChI

InChIKey=BMKDZUISNHGIBY-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

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	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6652043 | https://www.ncbi.nlm.nih.gov/pubmed/1654204 | https://www.ncbi.nlm.nih.gov/pubmed/5442346 | https://www.cancer.gov/publications/dictionaries/cancer-drug/def/razoxane

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	15354209
Doxorubicin-induced myocardial injury.	2004-10-28	15509827
Treatment options for malignant hemangioendotheliomas of the thyroid.	2004-10-01	15380572
The antitumor triazoloacridone C-1305 is a topoisomerase II poison with unusual properties.	2004-10	15258255
Feasibility and pharmacokinetic study of infusional dexrazoxane and dose-intensive doxorubicin administered concurrently over 96 h for the treatment of advanced malignancies.	2004-09	15173955
The effect of dexrazoxane on myocardial injury in doxorubicin-treated children with acute lymphoblastic leukemia.	2004-07-08	15247354
Anthracycline cardiotoxicity in children.	2004-07-08	15247351
Cardiovascular complications of cancer therapy: diagnosis, pathogenesis, and management.	2004-06-29	15226229
[Prevention of anthracycline cardiotoxicity].	2004-06-23	15206234
[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	15346637
[Dexrazoxane and cardiotoxicity in repeatedly treated patients].	2004-06	15346632
Rabbit model for in vivo study of anthracycline-induced heart failure and for the evaluation of protective agents.	2004-06	15182761
Experimental animal model for anthracycline-induced heart failure.	2004-06	15182760
Enhanced processing of UVA-irradiated DNA by human topoisomerase II in living cells.	2004-05-14	15044480
Dexrazoxane for anthracycline extravasation and GM-CSF for skin ulceration and wound healing.	2004-05	15120669
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	15041241
Cardiotoxicity of cytotoxic drugs.	2004-04	15023436
Anaphylaxis to dexrazoxane (ICRF-187) following three previous uncomplicated infusions.	2004-02	14763950
The cardioprotector dexrazoxane augments therapeutic efficacy of mitoxantrone in experimental autoimmune encephalomyelitis.	2004-01	14678264
Pharmacokinetics of etoposide in cancer patients treated with high-dose etoposide and with dexrazoxane (ICRF-187) as a rescue agent.	2004-01	14574459
The current and future role of dexrazoxane as a cardioprotectant in anthracycline treatment: expert panel review.	2004-01	14564513
Oxidant-induced iron signaling in Doxorubicin-mediated apoptosis.	2004	15038980
Dexrazoxane's protection of jejunal crypt cells in the jejunum of C3Hf/Kam mice from doxorubicin-induced toxicity.	2003-12	12827292
Cardiac toxicity related to cancer treatment.	2003-11-08	14603553
Protein profiling in daunorubicin-induced cardiomyopathy.	2003-09	14986890
The metabolites of the cardioprotective drug dexrazoxane do not protect myocytes from doxorubicin-induced cytotoxicity.	2003-09	12920203
Analysis of bisdioxopiperazine dexrazoxane binding to human DNA topoisomerase II alpha: decreased binding as a mechanism of drug resistance.	2003-08-19	12911317
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	12858195
Metabolism of dexrazoxane (ICRF-187) used as a rescue agent in cancer patients treated with high-dose etoposide.	2003-08	12750840
Dexrazoxane does not protect against doxorubicin-induced damage in young rats.	2003-08	12714334
Measurement of renal tumour and normal tissue perfusion using positron emission tomography in a phase II clinical trial of razoxane.	2003-07-21	12865914
Surrogate markers in antiangiogenesis clinical trials.	2003-07-07	12838293
Dexrazoxane in combination with anthracyclines lead to a synergistic cytotoxic response in acute myelogenous leukemia cell lines.	2003-07	12681361
The G2-phase decatenation checkpoint is defective in Werner syndrome cells.	2003-06-15	12810661
"Vasocrine" formation of tumor cell-lined vascular spaces: implications for rational design of antiangiogenic therapies.	2003-06-01	12782586
[Chemotherapy-induced cardiac toxicity and management].	2003-06	12852345
Probing the role of linker substituents in bisdioxopiperazine analogs for activity against wild-type and mutant human topoisomerase II alpha.	2003-05	12695544
Myocardial cytoprotection by trimetazidine against anthracycline-induced cardiotoxicity in anticancer chemotherapy.	2003-04-08	12678198
A small prospective study of chordomas treated with radiotherapy and razoxane.	2003-04	12707714
Anthracyclines induce accumulation of iron in ferritin in myocardial and neoplastic cells: inhibition of the ferritin iron mobilization pathway.	2003-04	12644586
Effect of dexrazoxane on doxorubicin pharmacokinetics in young and old rats.	2003-02	12647015
Evidence from studies with intact mammalian cells that merbarone and bis(dioxopiperazine)s are topoisomerase II poisons.	2003-02	12643037
Dexrazoxane (ICRF-187) protects cardiac myocytes against doxorubicin by preventing damage to mitochondria.	2003	14501028
Dexrazoxane-a promising antidote in the treatment of accidental extravasation of anthracyclines.	2003	12841619
Extravasation: a dreaded complication of chemotherapy.	2003	12821535
Dynamics of tumour angiogenesis: effect of razoxane-induced growth rate slowdown.	2003	12705630
The doxorubicin-cardioprotective drug dexrazoxane undergoes metabolism in the rat to its metal ion-chelating form ADR-925.	2002-12	12451479
Effect of sodium 2,3-dimercaptopropane-1-sulphonate (DMPS) on chronic daunorubicin toxicity in rabbits: comparison with dexrazoxane.	2002	12515046
Radioprotectants: current status and new directions.	2002	12466639
Pharmacokinetics of the cardioprotector ADR-529 (ICRF-187) in escalating doses combined with fixed-dose doxorubicin.	1992-11-18	1433357

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:08:34 GMT 2025` Edited by `admin` on `Mon Mar 31 18:08:34 GMT 2025`
Record UNII	5AR83PR647
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

ICI 59118

Preferred Name

English

RAZOXANE

Official Name

English

ICRF-159

Code

English

RAZOXANE [MI]

Common Name

English

NSC-129943

Code

English

ICRF 159

Code

English

Razoxane [WHO-DD]

Common Name

English

(±)-4,4'-PROPYLENEDI-2,6-PIPERAZINEDIONE

Systematic Name

English

RAZOXANE [MART.]

Common Name

English

razoxane [INN]

Common Name

English

ICI-59118

Code

English

2,6-PIPERAZINEDIONE, 4,4'-(1-METHYL-1,2-ETHANEDIYL)BIS-

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C360