etazolate   Click here for help

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.
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2D Structure
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Physico-chemical Properties
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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
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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
References
1. Marcade M, Bourdin J, Loiseau N, Peillon H, Rayer A, Drouin D, Schweighoffer F, Désiré L. (2008)
Etazolate, a neuroprotective drug linking GABA(A) receptor pharmacology to amyloid precursor protein processing.
J. Neurochem., 106 (1): 392-404. [PMID:18397369]
2. Vellas B, Sol O, Snyder PJ, Ousset PJ, Haddad R, Maurin M, Lemarié JC, Désiré L, Pando MP, EHT0202/002 study group. (2011)
EHT0202 in Alzheimer's disease: a 3-month, randomized, placebo-controlled, double-blind study.
Curr Alzheimer Res, 8 (2): 203-12. [PMID:21222604]
3. Zezula J, Slany A, Sieghart W. (1996)
Interaction of allosteric ligands with GABAA receptors containing one, two, or three different subunits.
Eur. J. Pharmacol., 301 (1-3): 207-14. [PMID:8773466]