varenicline   

GtoPdb Ligand ID: 5459

Synonyms: Champix® | Chantix® | compound 9a [PMID: 16171993] | CP 526555
varenicline is an approved drug (FDA and EMA (2006))
Compound class: Synthetic organic
Comment: Marketed formulations usually contain varenicline tartrate (PubChem CID 9906942). ChEMBL represents this compound without specified stereochemistry (see link above).
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 0
Topological polar surface area 37.81
Molecular weight 211.11
XLogP 0.37
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES N1CC2CC(C1)c1c2cc2c(c1)nccn2
Isomeric SMILES N1C[C@@H]2C[C@H](C1)c1c2cc2c(c1)nccn2
InChI InChI=1S/C13H13N3/c1-2-16-13-5-11-9-3-8(6-14-7-9)10(11)4-12(13)15-1/h1-2,4-5,8-9,14H,3,6-7H2/t8-,9+
InChI Key JQSHBVHOMNKWFT-DTORHVGOSA-N
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
nicotinic acetylcholine receptor α4 subunit Hs Agonist Agonist 10.0 – 10.4 pKi - 1-2
pKi 10.4 (Ki 4x10-11 M) α4β2 [2]
Description: In vitro affinity for recombinant human α4β2 receptors in membranes from transfected CHO-K1 cells, determined by displacement of [3H]-(−)-cytisine.
pKi 10.0 (Ki 1.1x10-10 M) [1]
Description: Binding affinity to human nicotinic acetylcholine receptor α4β2 expressed in IMR32 cells using [3H]epibatidine radioligand.
nicotinic acetylcholine receptor α3 subunit Hs Agonist Agonist 7.4 pKi - 2
pKi 7.4 (Ki 3.96x10-8 M) α3β4 [2]
Ligand mentioned in the following text fields