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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA and EMA (2006))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(1R,12S)-5,8,14-triazatetracyclo[10.3.1.0^{2,11}.0^{4,9}]hexadeca-2(11),3,5,7,9-pentaene
International Nonproprietary Names Click here for help
INN number INN
8366 varenicline
Synonyms Click here for help
Champix® | Chantix® | compound 9a [PMID: 16171993] | CP 526555
Database Links Click here for help
CAS Registry No. 249296-44-4
ChEBI CHEBI:84500
ChEMBL Ligand CHEMBL1396
DrugBank Ligand DB01273
DrugCentral Ligand 2808
GtoPdb PubChem SID 178102109
PubChem CID 5310966
RCSB PDB Ligand QMR
Search Google for chemical match using the InChIKey JQSHBVHOMNKWFT-DTORHVGOSA-N
Search Google for chemicals with the same backbone JQSHBVHOMNKWFT
Search PubMed clinical trials varenicline
Search PubMed titles varenicline
Search PubMed titles/abstracts varenicline
UniChem Compound Search for chemical match using the InChIKey JQSHBVHOMNKWFT-DTORHVGOSA-N
UniChem Connectivity Search for chemical match using the InChIKey JQSHBVHOMNKWFT-DTORHVGOSA-N
Wikipedia Varenicline

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Tocris
Varenicline tartrate (links to external site)
Cat. No. 3754