etazolate   

GtoPdb Ligand ID: 7336

Synonyms: EHT-0202 | SQ 20009
Compound class: Synthetic organic
Comment: Has anxiolytic effects as positive allosteric modulator of the GABAA receptor at the barbiturate binding site, as an adenosine antagonist of the A1 and A2 receptor subtypes and as a phosphodiesterase inhibitor selective for the PDE4 isoform. It is currently in clinical trials for the treatment of Alzheimer's disease with a possible MMOA of upregulating alpha-secretase activity.
2D Structure
Click here for structure editor
Physico-chemical Properties
Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 81.4
Molecular weight 289.15
XLogP 3.43
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CCOC(=O)c1cnc2c(c1NN=C(C)C)cnn2CC
Isomeric SMILES CCOC(=O)c1cnc2c(c1NN=C(C)C)cnn2CC
InChI InChI=1S/C14H19N5O2/c1-5-19-13-10(8-16-19)12(18-17-9(3)4)11(7-15-13)14(20)21-6-2/h7-8H,5-6H2,1-4H3,(H,15,18)
InChI Key OPQRBXUBWHDHPQ-UHFFFAOYSA-N
Bioactivity Comments
Multiple molecular modes of action have been reported for etazolate but these are not established as polypharmacology for any individual in vivo effect. Reports suggest that one of these, selective GABAA receptor modulation, stimulates alpha-secretase and consequent sAPPalpha production in rodents [1] .
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
GABAA receptor β3 subunit Hs Allosteric modulator Binding 5.5 pIC50 - 3
pIC50 5.5 (IC50 3.5x10-6 M) [3]
Description: inhibition of [35S]TBPS binding