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

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
Pharmacokinetics of the cardioprotector ADR-529 (ICRF-187) in escalating doses combined with fixed-dose doxorubicin.	1992 Nov 18	1433357
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	10474762
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	10487526
Signal-averaged electrocardiography in survivors of Hodgkin's disease treated with and without dexrazoxane.	2001	11327539
Linker length in podophyllotoxin-acridine conjugates determines potency in vivo and in vitro as well as specificity against MDR cell lines.	2001 Dec	12375883
Developing drugs to decrease the toxicity of chemotherapy.	2001 Jul 15	11454894
Dexrazoxane is a potent and specific inhibitor of anthracycline induced subcutaneous lesions in mice.	2001 Mar	11332155
Effects of Doxorubicin (Adriamycin) and [(+)-1,2-bis(3,5-dioxopiperazinyl-1-yl)]propane (ICRF-187) on skeletal muscle protease activities.	2001 Mar 15	11243912
The use of serum levels of cardiac troponin T to compare the protective activity of dexrazoxane against doxorubicin- and mitoxantrone-induced cardiotoxicity.	2001 Oct	11710630
Radioprotectants: current status and new directions.	2002	12466639
[Echocardiographic assessment of circulation system in patients during and 3-5 years after all therapy in childhood].	2002	12182001
[Cardioxan--a drug of prevention of anthracycline-related cardiotoxicity in pediatric oncology].	2002	12101558
Dexrazoxane pre-treatment protects skinned rat cardiac trabeculae against delayed doxorubicin-induced impairment of crossbridge kinetics.	2002 Apr	11934811
Dihydroorotase catalyzes the ring opening of the hydrolysis intermediates of the cardioprotective drug dexrazoxane (ICRF-187).	2002 Dec	12433815
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	12065567
The doxorubicin cardioprotective agent dexrazoxane (ICRF-187) induces endopolyploidy in rat neonatal myocytes through inhibition of DNA topoisomerase II.	2002 Mar	11984069
Dexrazoxane has no impact on sensitivity of childhood leukemic blasts to daunorubicin.	2002 May	11986942
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	12423680
Dexrazoxane (ICRF-187) protects cardiac myocytes against doxorubicin by preventing damage to mitochondria.	2003	14501028
Dynamics of tumour angiogenesis: effect of razoxane-induced growth rate slowdown.	2003	12705630
Dexrazoxane's protection of jejunal crypt cells in the jejunum of C3Hf/Kam mice from doxorubicin-induced toxicity.	2003 Dec	12827292
Measurement of renal tumour and normal tissue perfusion using positron emission tomography in a phase II clinical trial of razoxane.	2003 Jul 21	12865914
[Chemotherapy-induced cardiac toxicity and management].	2003 Jun	12852345
"Vasocrine" formation of tumor cell-lined vascular spaces: implications for rational design of antiangiogenic therapies.	2003 Jun 1	12782586
Myocardial cytoprotection by trimetazidine against anthracycline-induced cardiotoxicity in anticancer chemotherapy.	2003 Mar-Apr	12678198
Protein profiling in daunorubicin-induced cardiomyopathy.	2003 Sep	14986890
Oxidant-induced iron signaling in Doxorubicin-mediated apoptosis.	2004	15038980
The cardioprotector dexrazoxane augments therapeutic efficacy of mitoxantrone in experimental autoimmune encephalomyelitis.	2004 Jan	14678264
Rabbit model for in vivo study of anthracycline-induced heart failure and for the evaluation of protective agents.	2004 Jun	15182761
Doxorubicin-induced myocardial injury.	2004 Oct 28	15509827

Name

Type

Language

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

ICI 59118

Code

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