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
1. Tinsley JM, Fairclough RJ, Storer R, Wilkes FJ, Potter AC, Squire SE, Powell DS, Cozzoli A, Capogrosso RF, Lambert A et al.. (2011)
Daily treatment with SMTC1100, a novel small molecule utrophin upregulator, dramatically reduces the dystrophic symptoms in the mdx mouse.
PLoS ONE, 6 (5): e19189. [PMID:21573153]
2. Wilkinson IVL, Perkins KJ, Dugdale H, Moir L, Vuorinen A, Chatzopoulou M, Squire SE, Monecke S, Lomow A, Geese M et al.. (2020)
Chemical Proteomics and Phenotypic Profiling Identifies the Aryl Hydrocarbon Receptor as a Molecular Target of the Utrophin Modulator Ezutromid.
Angew Chem Int Ed Engl, 59 (6): 2420-2428. [PMID:31755636]