dexrazoxane   Click here for help

GtoPdb Ligand ID: 7330

Synonyms: ADR-529 | Cardioxane® | ICRF-187 | Savene® | Zinecard®
Approved drug
dexrazoxane is an approved drug (FDA (1995), EMA (2006))
Compound class: Synthetic organic
Comment: Dexrazoxane is an EDTA derivative with iron-chelating activity.

dexrazoxane is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 8
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 105.8
Molecular weight 268.12
XLogP -1.3
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES OC1=NC(=O)CN(C1)CC(N1CC(=NC(=O)C1)O)C
Isomeric SMILES OC1=NC(=O)CN(C1)C[C@@H](N1CC(=NC(=O)C1)O)C
InChI 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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Used to reduce the incidence and severity of cardiomyopathy associated with chemotherapy with anthracycline drugs. Dexrazoxane is also used to control tissue damage caused by accidental leakage of anthracycline at iv sites.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
As dexrazoxane is a derivative of the chelating agent EDTA, its ability to reduce/prevent cardiomyopathy is believed to involve chelation of iron which leads to reduced levels of iron-mediated free radical generation. These free radicals are thought to irreversibly damage DNA which causes damage to the heart muscle.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com
European Medicines Agency (EMA)