Dexrazoxane hydrochloride

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C11H16N4O4.ClH
Molecular Weight	304.73
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.C[C@@H](CN1CC(=O)NC(=O)C1)N2CC(=O)NC(=O)C2

InChI

InChIKey=BIFMNMPSIYHKDN-FJXQXJEOSA-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/t7-;/m0./s1

HIDE SMILES / InChI

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	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19536310
Curator's Comment: description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020212s017lbl.pdf

Dexrazoxane is a cardioprotective drug used in patients with breast cancer to reduce cardiomyopathy associated with doxorubicin administration. Dexrazoxane is believed to act by two mechanisms: it inhibits DNA topoisomerase II and acts as a chelator for iron ions.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA topoisomerase II 66 Target ID: CHEMBL2094255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19536310	Inhibitor 8504		13.0 µM [IC50]
Iron 18 Target ID: CHEMBL2363058 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020212s017lbl.pdf	Chelating Agent 139		17.4 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Breast cancer 432 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020212s017lbl.pdf	Secondary		Approved 8583	ZINECARD Approved Use Zinecard is indicated for reducing the incidence and severity of cardiomyopathy associated with doxorubicin administration in women with metastatic breast cancer who have received a cumulative doxorubicin dose of 300 mg/m2 and who will continue to receive doxorubicin therapy to maintain tumor control. Launch Date 1995

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.5 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020212s017lbl.pdf	500 mg/m² single, intravenous dose: 500 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: DOXORUBICIN	DOXORUBICIN	DEXRAZOXANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
100% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020212s017lbl.pdf	500 mg/m² single, intravenous dose: 500 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: DOXORUBICIN	DOXORUBICIN	DEXRAZOXANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
250 mg/m2 1 times / 4 weeks multiple, intravenous MTD Dose: 250 mg/m2, 1 times / 4 weeks Route: intravenous Route: multiple Dose: 250 mg/m2, 1 times / 4 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/11410492/	unhealthy, 57 years (range: 46-76 years) Health Status: unhealthy Age Group: 57 years (range: 46-76 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/11410492/	Disc. AE: Thrombocytopenia... AEs leading to discontinuation/dose reduction: Thrombocytopenia (grade 4, 2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/11410492/
900 mg/m2 1 times / 3 weeks multiple, intravenous Highest studied dose Dose: 900 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 900 mg/m2, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/1433357/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/1433357/	DLT: Neutropenia... Dose limiting toxicities: Neutropenia (4 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/1433357/
600 mg/m2 1 times / 3 weeks multiple, intravenous RP2D Dose: 600 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 600 mg/m2, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/1433357/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/1433357/	DLT: Neutropenia... Dose limiting toxicities: Neutropenia (4 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/1433357/
500 mg/m2 1 times / day multiple, intravenous Recommended Dose: 500 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 500 mg/m2, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020212s017lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020212s017lbl.pdf	Other AEs: Alopecia, Nausea... Other AEs: Alopecia (94%) Nausea (77%) Vomiting (59%) Malaise and fatigue (61%) Anorexia (42%) Stomatitis (34%) Fever (34%) Infection (23%) Diarrhea (21%) Injection site pain (12%) Sepsis (17%) Neurotoxicity (17%) Erythema (5%) Phlebitis (6%) Esophagitis (6%) Dysphagia (8%) Hemorrhage (2%) Extravasation (1%) Urticaria (2%) Administration site recall reaction (1%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020212s017lbl.pdf
500 mg/m2 1 times / day multiple, intravenous Recommended Dose: 500 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 500 mg/m2, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020212s017lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020212s017lbl.pdf	Other AEs: Alopecia, Nausea... Other AEs: Alopecia (100%) Nausea (51%) Vomiting (42%) Malaise and fatigue (48%) Anorexia (27%) Stomatitis (26%) Fever (22%) Infection (19%) Diarrhea (14%) Injection site pain (13%) Sepsis (12%) Neurotoxicity (10%) Erythema (4%) Phlebitis (3%) Esophagitis (3%) Hemorrhage (3%) Extravasation (3%) Urticaria (2%) Administration site recall reaction (1%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020212s017lbl.pdf

AEs

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-1307	http://www.3bsc.com/index/pro_info.php?id=55023
AA Blocks	AA002OL7	https://www.aablocks.com/goods/Goods/detail?id=AA002OL7
Aaron Chemicals	AR002PCZ	http://www.aaronchem.com/24584-09-6
abcr GmbH	AB436257	http://www.abcr.com/shop/en/AB436257
Acadechem	ACDS-062689	http://www.acadechemical.com/product/137388
Achemo Scientific Limited	AC-74299	http://www.achemo.com/search/?Keyword= 24584-09-6
Achemtek	0104-020754	http://www.achemtek.com/24584-09-6
AEchem Scientific Corp., USA	AE1-014835	http://www.aechemsc.com/info_products/AE1-014835.php
AHH Chemical co.,ltd	MT-49873	http://www.ahhchemical.com/product/MT-49873.html
AK Scientific, Inc. (AKSCI)	69488	http://www.aksci.com/item_detail.php?cat=69488
AK Scientific, Inc. (AKSCI)	J90038	http://www.aksci.com/item_detail.php?cat=J90038
Alfa Chemistry	AP24584096	https://reagents.alfa-chemistry.com/product/dexrazoxane-cas-24584-09-6-8513.html
Ambinter	Amb22744843	http://www.ambinter.com/reference/22744843
Angene	AGN-PC-0O877E	http://www.angenechemical.com/productshow/AGN-PC-0O877E.html
Anward	ANW-44923	http://www.anward.com/pro_result/31374
ApexBio Technology	A1602	http://www.apexbt.com/dexrazoxane-hcl-icrf-187-adr-529.html
AstaTech, Inc.	25916	http://www.astatechinc.com/CPSResult.php?CRNO=29109
Aurora Fine Chemicals LLC	A17.905.381	http://online.aurorafinechemicals.com/info?ID=A17.905.381
Aurum Pharmatech LLC	MP-0159	http://www.Aurumpharmatech.com/Product/ProductDetails/MP_0159
AvaChem Scientific	3082B	http://www.avachem.com/productSearch.asp?3082B
Avantor Inc	TCD4227-100MG	https://us.vwr.com/store/product/16811739/dexrazoxane-98-0-by-titrimetric-analysis
BioSynth	J-015579	https://www.biosynth.com/en/products/all-products/products/J-015579.html
BioSynth	J-520219	https://www.biosynth.com/en/products/all-products/products/J-520219.html
BLD Pharm	BD123889	http://www.bldpharm.com/products/24584-09-6.html
Chem Scene	CS-2769	http://www.chemscene.com/24584-09-6.html
Chemenu	CM120112	http://www.chemenu.com/products/CM120112
ChemMol	49408757	http://www.chemmol.com/chemmol/49408757.html
Chemspace	CSSB00000054680	https://chem-space.com/CSSB00000054680
CSNpharm	CSN10785	https://www.csnpharm.com/products/dexrazoxane.html
DAOGE BIOPHARMA	DG21-14309	https://www.daogechem.com/product/24584-09-6.html
eNovation Chemicals	D672527	https://www.enovationchem.com/ProductDetails.asp?ProductID=D672527
eNovation Chemicals	D764439	https://www.enovationchem.com/ProductDetails.asp?ProductID=D764439
eNovation Chemicals	Y0980546	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y0980546
Glentham Life Sciences	GP2739	http://www.glentham.com/products/product/GP2739/
Huateng Pharma	F80010873	http://en.huatengsci.com/product/Dexrazoxane.html
iChemical	EBD45155	http://www.ichemical.com/products/24584-09-6.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN00337707	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00337707
Matrix Scientific	126235	https://www.matrixscientific.com/126235.html
MedChem Express	HY-B0581	https://www.medchemexpress.com/dexrazoxane.html
MuseChem	I002831	https://www.musechem.com/product/I002831.html
Oakwood	93447	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=78621&ExtHyperLink=1
OChem	6570	http://www.ocheminc.com/index.php?act=psearch&pid=584D096
Parchem	28706	http://www.parchem.com/chemical-supplier-distributor/Dexrazoxane-018706.aspx
Renno Tech	RP29555	http://www.rennotech.com/product_show.asp?id=35162
Sigma-Aldrich	05587_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/05587?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	D1446_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/d1446?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S047032	http://www.sinfoobiotech.com/product/1050430
Smolecule	S548609	http://www.smolecule.com/products/s548609
TCI (Tokyo Chemical Industry)	D4227	http://www.tcichemicals.com/eshop/en/us/commodity/D4227/index.html
THE BioTek	bt-288014	https://www.thebiotek.com/product/inhibitors/bt-288014
Yuhao Chemical	LT4788	http://www.chemyuhao.com/24584-09-6.html

PubMed

Title	Date	PubMed
Multicenter randomized phase III study of the cardioprotective effect of dexrazoxane (Cardioxane) in advanced/metastatic breast cancer patients treated with anthracycline-based chemotherapy.	2006-04	16423847
Matrix metalloproteinase-2 and -9 are induced differently by doxorubicin in H9c2 cells: The role of MAP kinases and NAD(P)H oxidase.	2006-02-15	16213474
Experimental study of dexrazoxane-anthracycline combinations using the model of isolated perfused rat heart.	2006-02-08	16129573
Altered responsiveness of the guinea-pig isolated ileum to smooth muscle stimulants and to electrical stimulation after in situ ischemia.	2006-02	16341232
Late anthracycline cardiotoxicity protection by dexrazoxane (ICRF-187) in pediatric patients: echocardiographic follow-up.	2006-02	16034614
Suppression of mitoxantrone cardiotoxicity in multiple sclerosis patients by dexrazoxane.	2006-01	16374818
Treatment of anthracycline extravasation in mice with dexrazoxane with or without DMSO and hydrocortisone.	2006-01	16001176
Effect of epirubicin-based chemotherapy and dexrazoxane supplementation on QT dispersion in non-Hodgkin lymphoma patients.	2005-12	16325366
Cardioprotective effect of dexrazoxane during treatment with doxorubicin: a study using low-dose dobutamine stress echocardiography.	2005-12	16035077
Long-term serial echocardiographic examination of late anthracycline cardiotoxicity and its prevention by dexrazoxane in paediatric patients.	2005-11	16044276
Phase II study of doxorubicin and bevacizumab for patients with metastatic soft-tissue sarcomas.	2005-10-01	16192597
Combining etoposide and dexrazoxane synergizes with radiotherapy and improves survival in mice with central nervous system tumors.	2005-09-15	16166453
Amifostine and dexrazoxane enhance the rapid loss of bone mass and further deterioration of vertebrae architecture in female rats.	2005-09	16151678
Metabolism of the one-ring open metabolites of the cardioprotective drug dexrazoxane to its active metal-chelating form in the rat.	2005-09	15980099
Clinical nurse specialist and evidence-based practice: managing anthracycline extravasation.	2005-08-05	16079361
Molecular pharmacology of the interaction of anthracyclines with iron.	2005-08	15883202
Monitoring cardiac function in patients receiving doxorubicin.	2005-07	16098293
CD95/Apo-1/Fas: independent cell death induced by doxorubicin in normal cultured cardiomyocytes.	2005-07	15703961
Dexrazoxane for the prevention of cardiomyopathy in anthracycline treated pediatric cancer patients.	2005-06-15	15700251
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005-06	15962942
Metabolism of the cardioprotective drug dexrazoxane and one of its metabolites by isolated rat myocytes, hepatocytes, and blood.	2005-06	15764716
Dexrazoxane protects against myelosuppression from the DNA cleavage-enhancing drugs etoposide and daunorubicin but not doxorubicin.	2005-05-15	15897593
Myocardial content of selected elements in experimental anthracycline-induced cardiomyopathy in rabbits.	2005-04	15954742
Gender-dependent reductions in vertebrae length, bone mineral density and content by doxorubicin are not reduced by dexrazoxane in young rats: effect on growth plate and intervertebral discs.	2005-03	15570399
Cardioprotective interventions for cancer patients receiving anthracyclines.	2005-01-25	15674919
The antitumor anthracyclines doxorubicin and daunorubicin do not inhibit cell growth through the formation of iron-mediated reactive oxygen species.	2005-01	15613911
The prevention and management of cardiovascular complications of chemotherapy in patients with cancer.	2005	15984906
Dexrazoxane : a review of its use for cardioprotection during anthracycline chemotherapy.	2005	15892593
Anthracycline-induced cardiotoxicity in children with cancer: strategies for prevention and management.	2005	15871628
Mitoxantrone treatment of multiple sclerosis: safety considerations.	2004-12-28	15623667
Antitumor effects of two bisdioxopiperazines against two experimental lung cancer models in vivo.	2004-12-24	15617579
Characterisation of cytotoxicity and DNA damage induced by the topoisomerase II-directed bisdioxopiperazine anti-cancer agent ICRF-187 (dexrazoxane) in yeast and mammalian cells.	2004-12-02	15575955
Can dexrazoxane reduce myocardial injury in anthracycline-treated children with acute lymphoblastic leukemia?	2004-11	16264791
[Cardiac prevention: the oncologic point of view].	2004-11	15899627
Evaluating the role of dexrazoxane as a cardioprotectant in cancer patients receiving anthracyclines.	2004-11	15531396
The iron chelating cardioprotective prodrug dexrazoxane does not affect the cell growth inhibitory effects of bleomycin.	2004-11	15522409
Accelerated approval of oncology products: a decade of experience.	2004-10-20	15494600
Concurrent therapies that protect against doxorubicin-induced cardiomyopathy.	2004-10	15515283
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
[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
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
Iron chelators in cancer chemotherapy.	2004	15579100
Protection against acute adriamycin-induced cardiotoxicity by garlic: role of endogenous antioxidants and inhibition of TNF-alpha expression.	2003-12-20	14687418
Protein profiling in daunorubicin-induced cardiomyopathy.	2003-09	14986890

Patents

Sample Use Guides

In Vivo Use Guide

The recommended dosage ratio of dexrazoxane to doxorubicin is 10:1 (e.g., 500 mg/m2 dexrazoxane to 50 mg/m2 doxorubicin). Do not administer doxorubicin before dexrazoxane.

Route of Administration: Intravenous

In Vitro Use Guide

Human osteoblasts P2 cells and Human ginigiva fibroblasts P2 cells were treated with zoledronic acid (50 umol/L) and the cytoprotectant dexrazoxane (600 umol/L). At that concentration dexrazoxane showed significant cytoprotective effect.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:14:04 GMT 2025` Edited by `admin` on `Mon Mar 31 18:14:04 GMT 2025`
Record UNII	5346058Q7S
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Dexrazoxane hydrochloride

Common Name

English

CARDIOXAN

Preferred Name

English

DEXRAZOXANE HYDROCHLORIDE [VANDF]

Common Name

English

RAZOXANE (+)-FORM HYDROCHLORIDE [MI]

Common Name

English

ZINECARD

Brand Name

English

Dexrazoxane hydrochloride [WHO-DD]

Common Name

English

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

Systematic Name

English

ICRF-187 HYDROCHLORIDE

Code

English

(+)-RAZOXANE HYDROCHLORIDE

Common Name

English

RAZOXANE HYDROCHLORIDE, (S)-

Common Name

English

TOTECT

Brand Name

English

DEXRAZOXANE HCL

Common Name

English

ADR-529 HYDROCHLORIDE

Code

English

SAVENE

Brand Name

English

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

Common Name

English

CARDIOXANE

Brand Name

English

DEXRAZOXANE HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

Classification Tree Code System Code

EMA ASSESSMENT REPORTS

SAVENE (AUTHORIZED: EXTRAVASTATION OF DIAGNOSTIC AND THERAPEUTIC MATERIALS)