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.
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 CDK toolkit. 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
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.

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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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1995), EMA (2006))
IUPAC Name Click here for help
6-hydroxy-4-[(2S)-2-(5-hydroxy-3-oxo-1,2,3,6-tetrahydropyrazin-1-yl)propyl]-2,3,4,5-tetrahydropyrazin-2-one
International Nonproprietary Names Click here for help
INN number INN
6544 dexrazoxane
Synonyms Click here for help
ADR-529 | Cardioxane® | ICRF-187 | Savene® | Zinecard®
Database Links Click here for help
CAS Registry No. 24584-09-6
ChEMBL Ligand CHEMBL1738
DrugBank Ligand DB00380
DrugCentral Ligand 839
GtoPdb PubChem SID 178103902
PubChem CID 71384
Search Google for chemical match using the InChIKey BMKDZUISNHGIBY-ZETCQYMHSA-N
Search Google for chemicals with the same backbone BMKDZUISNHGIBY
Search PubMed clinical trials dexrazoxane
Search PubMed titles dexrazoxane
Search PubMed titles/abstracts dexrazoxane
UniChem Compound Search for chemical match using the InChIKey BMKDZUISNHGIBY-ZETCQYMHSA-N
UniChem Connectivity Search for chemical match using the InChIKey BMKDZUISNHGIBY-ZETCQYMHSA-N
Wikipedia Dexrazoxane