compound 73 [WO2017106607A1]   Click here for help

GtoPdb Ligand ID: 11307

Synonyms: enpatoran (proposed INN)
Compound class: Synthetic organic
Comment: This chemical structure (as the IUPAC name) was obtained from the special release of proposed INNs for COVID-related therapeutics that was published by the WHO in October 2020. The INN structure was identified as being identical to compound 73 from Merck's patent WO2017106607A1 (2017) in which it is claimed as a Toll-like receptor (TLR)7 and TLR8 antagonist for the treatment of immune disorders [2]. We speculate that this is Merck's clinical lead M5049, which is expected to prevent activation of TLR7/8 which detect single-stranded RNA from viruses including SARS-CoV-2 [1]. M5049 is administered orally. At the time of generating this entry (Nov 2020) there had been no formal name>structure disclosure of M5049. We will update this record when new details are published.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 65.94
Molecular weight 320.12
XLogP 3.24
No. Lipinski's rules broken 0
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Canonical SMILES N#Cc1ccc(c2c1nccc2)N1C[C@H](N)C[C@@H](C1)C(F)(F)F
Isomeric SMILES N#Cc1ccc(c2c1nccc2)N1C[C@H](N)C[C@@H](C1)C(F)(F)F
InChI InChI=1S/C16H15F3N4/c17-16(18,19)11-6-12(21)9-23(8-11)14-4-3-10(7-20)15-13(14)2-1-5-22-15/h1-5,11-12H,6,8-9,21H2/t11-,12+/m0/s1
Selectivity at catalytic receptors
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
TLR7 Hs Antagonist Antagonist >6.0 pIC50 - 2
pIC50 >6.0 (IC50 <1x10-6 M) [2]
Description: Inhibition of activation of a TLR7/NFkB reporter in HEK293 cells (binned value).