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
References
1. Baker AF, Landowski T, Dorr R, Tate WR, Gard JM, Tavenner BE, Dragovich T, Coon A, Powis G. (2007)
The antitumor agent imexon activates antioxidant gene expression: evidence for an oxidative stress response.
Clin Cancer Res, 13 (11): 3388-94. [PMID:17545547]
2. Dvorakova K, Payne CM, Tome ME, Briehl MM, McClure T, Dorr RT. (2000)
Induction of oxidative stress and apoptosis in myeloma cells by the aziridine-containing agent imexon.
Biochem Pharmacol, 60 (6): 749-58. [PMID:10930529]
3. Engel RH, Evens AM. (2006)
Oxidative stress and apoptosis: a new treatment paradigm in cancer.
Front Biosci, 11: 300-12. [PMID:16146732]
4. Hersh EM, Gschwind CR, Taylor CW, Dorr RT, Taetle R, Salmon SE. (1992)
Antiproliferative and antitumor activity of the 2-cyanoaziridine compound imexon on tumor cell lines and fresh tumor cells in vitro.
J Natl Cancer Inst, 84 (16): 1238-44. [PMID:1640482]
5. Remers WA, Dorr RT. (2012)
Chemistry and pharmacology of imexon and related cyanoaziridines.
Curr Med Chem, 19 (33): 5745-53. [PMID:22998528]
6. Wondrak GT. (2009)
Redox-directed cancer therapeutics: molecular mechanisms and opportunities.
Antioxid Redox Signal, 11 (12): 3013-69. [PMID:19496700]