AVE1231   Click here for help

GtoPdb Ligand ID: 11206

Synonyms: A-293 | A293 | AVE-1231
Compound class: Synthetic organic
Comment: AVE1231 is a K2P3.1 (TASK-1) channel blocker [2-3]. It was originally reported as a inhibitor of hKv1.5 currents [1,4], and was being developed as an atrial-selective drug therapy by Sanofi-Aventis for the treatment of atrial fibrillation, but the programme was terminated at Phase 1.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 11
Topological polar surface area 105.77
Molecular weight 405.17
XLogP 4.37
No. Lipinski's rules broken 0
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Canonical SMILES CCCCS(=O)(=O)Nc1ccccc1C(=O)N[C@@H](c1ccc(nc1)OC)CC
Isomeric SMILES CCCCS(=O)(=O)Nc1ccccc1C(=O)N[C@@H](c1ccc(nc1)OC)CC
InChI InChI=1S/C20H27N3O4S/c1-4-6-13-28(25,26)23-18-10-8-7-9-16(18)20(24)22-17(5-2)15-11-12-19(27-3)21-14-15/h7-12,14,17,23H,4-6,13H2,1-3H3,(H,22,24)/t17-/m1/s1
1. Ehrlich JR, Ocholla H, Ziemek D, Rütten H, Hohnloser SH, Gögelein H. (2008)
Characterization of human cardiac Kv1.5 inhibition by the novel atrial-selective antiarrhythmic compound AVE1231.
J Cardiovasc Pharmacol, 51 (4): 380-7. [PMID:18427281]
2. Shvetsova AA, Gaynullina DK, Schmidt N, Bugert P, Lukoshkova EV, Tarasova OS, Schubert R. (2020)
TASK-1 channel blockade by AVE1231 increases vasocontractile responses and BP in 1- to 2-week-old but not adult rats.
Br J Pharmacol, 177 (22): 5148-5162. [PMID:32860629]
3. Wiedmann F, Kiper AK, Bedoya M, Ratte A, Rinné S, Kraft M, Waibel M, Anad P, Wenzel W, González W et al.. (2019)
Identification of the A293 (AVE1231) Binding Site in the Cardiac Two-Pore-Domain Potassium Channel TASK-1: a Common Low Affinity Antiarrhythmic Drug Binding Site.
Cell Physiol Biochem, 52 (5): 1223-1235. [PMID:31001961]
4. Wirth KJ, Brendel J, Steinmeyer K, Linz DK, Rütten H, Gögelein H. (2007)
In vitro and in vivo effects of the atrial selective antiarrhythmic compound AVE1231.
J Cardiovasc Pharmacol, 49 (4): 197-206. [PMID:17438404]