varenicline   Click here for help

GtoPdb Ligand ID: 5459

Synonyms: Champix® | Chantix® | compound 9a [PMID: 16171993] | CP 526555
Approved drug PDB Ligand
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
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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
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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
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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