ContaminantDB: Dexrazoxane

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (2)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:26:45 UTC

Update Date

2026-04-05 13:52:02 UTC

Accession Number

CHEM002184

Identification

Common Name

Dexrazoxane

Class

Small Molecule

Description

An antimitotic agent with immunosuppressive properties. Dexrazoxane, the (+)-enantiomorph of razoxane, provides cardioprotection against anthracycline toxicity. It appears to inhibit formation of a toxic iron-anthracycline complex. The Food and Drug Administration has designated dexrazoxane as an orphan drug for use in the prevention or reduction in the incidence and severity of anthracycline-induced cardiomyopathy.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Antineoplastic Agent
Cardiovascular Agent
Chelating Agent
Drug
Food Toxin
Immunosuppressive Agent
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-(S)-4,4'-Propylenedi-2,6-piperazinedione	ChEBI
(+)-1,2-Bis(3,5-dioxo-1-piperazinyl)propane	ChEBI
Dexrazoxano	ChEBI
Dexrazoxanum	ChEBI
Dextrorazoxane	ChEBI
Desrazoxane	HMDB
Icrf-187	HMDB
ADR 529	HMDB
Cardioxan	HMDB
Cardioxane	HMDB
Dexrazoxane hydrochloride	HMDB
ICRF187	HMDB
Razoxane, (S)-isomer	HMDB
Zinecard	HMDB
ADR-529	HMDB
Razoxane, (S)-isomer, hydrochloride	HMDB
Hydrochloride, dexrazoxane	HMDB
ICRF 187	HMDB
Dexrazoxane	ChEBI

Chemical Formula

C₁₁H₁₆N₄O₄

Average Molecular Mass

268.269 g/mol

Monoisotopic Mass

268.117 g/mol

CAS Registry Number

24584-09-6

IUPAC Name

4-[(2S)-2-(3,5-dioxopiperazin-1-yl)propyl]piperazine-2,6-dione

Traditional Name

dexrazoxane

SMILES

C[C@@H](CN1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1

InChI Identifier

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)/t7-/m0/s1

InChI Key

BMKDZUISNHGIBY-ZETCQYMHSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Dioxopiperazine
N-alkylpiperazine
1,4-diazinane
Piperazine
Carboxylic acid imide
Dicarboximide
Carboxylic acid imide, n-unsubstituted
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Amine
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

razoxane (CHEBI:50223 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

immunosuppressive agent

Chemical Roles

chelator

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	191-197°C
Boiling Point	Not Available
Solubility	Sparingly soluble

Predicted Properties

Property	Value	Source
Water Solubility	10.4 g/L	ALOGPS
logP	-1	ALOGPS
logP	-2.7	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	11.2	ChemAxon
pKa (Strongest Basic)	3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	98.82 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	64.25 m³·mol⁻¹	ChemAxon
Polarizability	26.12 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0m2c-4910000000-46d13032d5f2c6472d9b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0490000000-80b0b21a495d2cc911a4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1910000000-5a4bec9ae0f631c4c328	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052b-8900000000-da472776fdfa9ff649dd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0090000000-3ed9d12564a96e4f79a2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9010000000-913da0d82e09de14ca70	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-1b65fef6f408f48c6b59	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0910000000-8bbf646c07221a874c7c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0aor-3790000000-825583366aa2049c6487	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0abc-9610000000-e2da7526d67ac758a836	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0090000000-bd2978e4c0725b5d29bd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05p6-5890000000-a1cb5b2cd96d828fbdaa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9400000000-50d8c9f710f08bb20677	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

IV administration results in complete bioavailability.

Mechanism of Toxicity

The mechanism by which dexrazoxane exerts its cardioprotective activity is not fully understood. Dexrazoxane is a cyclic derivative of EDTA that readily penetrates cell membranes. Results of laboratory studies suggest that dexrazoxane (a prodrug) is converted intracellularly to a ring-opened bidentate chelating agent that chelates to free iron and interferes with iron-mediated free radical generation thought to be responsible, in part, for anthracycline-induced cardiomyopathy. It should be noted that dexrazoxane may also be protective through its inhibitory effect on topoisomerase II.

Metabolism

Dexrazoxane is hydrolysed by the enzyme dihydropyrimidine amidohydrolase in the liver and kidney to active metabolites that are capable of binding to metal ions. Route of Elimination: Urinary excretion plays an important role in the elimination of dexrazoxane. Forty-two percent of the 500 mg/m2 dose of dexrazoxane was excreted in the urine. Half Life: 2.5 hours

Toxicity Values

Intraperitoneal, mouse LD₁₀ = 500 mg/kg. Intravenous, dog LD₁₀ = 2 gm/kg.

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For reducing the incidence and severity of cardiomyopathy associated with doxorubicin administration in women with metastatic breast cancer who have received a cumulative doxorubicin hydrochloride dose of 300 mg/m^2 and would benefit from continued doxorubicin therapy. Also approved for the treatment of extravasation from intravenous anthracyclines.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Intraperitoneal, mouse LD₁₀ = 500 mg/kg. Intravenous, dog LD₁₀ = 2 gm/kg.

Treatment

There is no known antidote for dexrazoxane. Instances of suspected overdose should be managed with good supportive care until resolution of myelosuppression and related conditions is complete. Management of overdose should include treatment of infections, fluid regulation, and maintenance of nutritional requirements. (7)

Concentrations

Not Available

External Links

DrugBank ID

DB00380

HMDB ID

HMDB0014524

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID