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).
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: varenicline

2D Structure
Click here for structure editor
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
References
1. Coe JW, Brooks PR, Wirtz MC, Bashore CG, Bianco KE, Vetelino MG, Arnold EP, Lebel LA, Fox CB, Tingley 3rd FD et al.. (2005)
3,5-Bicyclic aryl piperidines: a novel class of alpha4beta2 neuronal nicotinic receptor partial agonists for smoking cessation.
Bioorg. Med. Chem. Lett., 15 (22): 4889-97. [PMID:16171993]
2. Nirogi R, Mohammed AR, Shinde AK, Ravella SR, Bogaraju N, Subramanian R, Mekala VR, Palacharla RC, Muddana N, Thentu JB et al.. (2020)
Discovery and Development of 3-(6-Chloropyridine-3-yloxymethyl)-2-azabicyclo[3.1.0]hexane Hydrochloride (SUVN-911): A Novel, Potent, Selective, and Orally Active Neuronal Nicotinic Acetylcholine α4β2 Receptor Antagonist for the Treatment of Depression.
J. Med. Chem., 63 (6): 2833-2853. [PMID:32026697]