ezutromid   Click here for help

GtoPdb Ligand ID: 11110

Synonyms: 5-ethylsulfonyl-NBO | SMT C1100 | SMTC 1100 | SMTC1100
Compound class: Synthetic organic
Comment: Ezutromid (SMT C1100) is a clinical stage compound that was developed for its ability to increase expression of utrophin (UTRN; P46939), as a substitute for missing the dystrophin (DMD; P11532) in Duchenne muscular dystrophy (DMD) patients [1]. It is orally active. The aryl hydrocarbon receptor (AhR) has been reported as a molecular target for ezutromid, with ezutromid behaving as an AhR antagonist [2]. Ezutromid and other AhR antagonists up-regulate utrophin, adding to the proposition that this pathway offers disease-modifying potential for DMD.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 68.55
Molecular weight 337.08
XLogP 4.3
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES CCS(=O)(=O)c1ccc2c(c1)nc(o2)c1ccc2c(c1)cccc2
Isomeric SMILES CCS(=O)(=O)c1ccc2c(c1)nc(o2)c1ccc2c(c1)cccc2
InChI InChI=1S/C19H15NO3S/c1-2-24(21,22)16-9-10-18-17(12-16)20-19(23-18)15-8-7-13-5-3-4-6-14(13)11-15/h3-12H,2H2,1H3
Selectivity at other protein targets
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Aryl hydrocarbon receptor Hs Antagonist Antagonist 7.3 pKd - 2
pKd 7.3 (Kd 5x10-8 M) [2]
Description: apparent binding affinity determined using affinity‐based protein profiling (AfBPP), in a cellular context.