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E7820   Click here for help

GtoPdb Ligand ID: 14234

Synonyms: E-7820
PDB Ligand
Compound class: Synthetic organic
Comment: E7820 was initially reported as an integrin α2 inhibitor [1,3-4]. It has subsequently been identified to act as a molecular glue class degrader that promotes proteasome-dependent degradation of the splicing factor RBM39 by the DCAF15 cullin RING ligase complex CRL4DCAF15 [2].
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 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 6
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 114.16
Molecular weight 336.37
XLogP 0.65
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 CC1=CC=C(C2=C1C(=CN2)C#N)NS(=O)(=O)C3=CC(=CC=C3)C#N
Isomeric SMILES CC1=C2C(=CNC2=C(C=C1)NS(=O)(=O)C3=CC=CC(=C3)C#N)C#N
InChI InChI=1S/C17H12N4O2S/c1-11-5-6-15(17-16(11)13(9-19)10-20-17)21-24(22,23)14-4-2-3-12(7-14)8-18/h2-7,10,20-21H,1H3
InChI Key LWGUASZLXHYWIV-UHFFFAOYSA-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
E7820 was progressed to clinical evaluation as an anti-tumour agent. Clinical trial NCT01133990 was terminated early as the combination of E7820 and FOLFIRI was not tolerated and no efficacy analysis was possible.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT05024994 A Study of E7820 in People With Bone Marrow (Myeloid) Cancers Phase 2 Interventional Memorial Sloan Kettering Cancer Center
NCT01347645 Irinotecan Plus E7820 Versus FOLFIRI in Second-Line Therapy in Patients With Locally Advanced or Metastatic Colon or Rectal Cancer Phase 1/Phase 2 Interventional Eisai Inc.
NCT00309179 A Phase II Study of the Safety and Efficacy of E7820 Plus Cetuximab in Colorectal Cancer, Preceded by a Run-in Study in Advanced Solid Tumors Phase 2 Interventional Eisai Inc.