imexon   Click here for help

GtoPdb Ligand ID: 8273

Synonyms: Amplimexon® (proposed trade name) | BM 06002 | BM-06002
Compound class: Synthetic organic
Comment: Imexon is a cyclizised 2-cyanoaziridine compound being investigated as an antitumour agent [4-5]. 2-cyanoaziridine compounds bind thiols such as cysteine, depleting them and allowing the accumulation of reactive oxygen species. This effect activates antioxidant gene expression, signifying induction of an oxidative stress response [1] and leads to irreversible cell damage and apoptosis.
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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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 4
Hydrogen bond donors 1
Rotatable bonds 0
Topological polar surface area 58.46
Molecular weight 111.04
XLogP -1.36
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 NC1=NC(=O)N2C1C2
Isomeric SMILES NC1=NC(=O)N2C1C2
InChI InChI=1S/C4H5N3O/c5-3-2-1-7(2)4(8)6-3/h2H,1H2,(H2,5,6,8)
InChI Key BIXBBIPTYBJTRY-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
The EMA has granted imexon orphan drug designation for the treatment of ovarian cancer. In addition to ovarian cancer the FDA has granted orphan designation for treatment of multiple myeloma, metastatic malignant melanoma and pancreatic adenocarcinoma. Several Phase 2 clinical trials have been completed. Click here to view ClinicalTrials.gov's full list of registered Phase 2 imexon trials.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Imexon acts as a pro-oxidant, inducing an oxidative stress response in tumour cells [2]. The tumour microenvironment typically has a low level of antioxidant defenses, rendering malignant cells vulnerable to pro-oxidant redox chemotherapeutics [3,6].