venlafaxine   Click here for help

GtoPdb Ligand ID: 7321

Synonyms: Effexor® | WY-45030
Approved drug
venlafaxine is an approved drug (FDA (1993))
Compound class: Synthetic organic
Comment: Venlafaxine is a selective serotonin-norepinephrine reuptake inhibitor (SNRI); a bicyclic antidepressant. Venlafaxine is a racemic mixture of R (PubChem CID 9795623) and S (PubChem CID 11846746) stereoisomers, which have assay data in PubChem but its is unclear if these apply to the experimentally separated forms. Marketed formulations may contain venlafaxine hydrochloride (PubChem CID 62923).
The major active metabolite of venlafaxine, desvenlafaxine (O-desmethylvenlafaxine) has also been developed as a drug.
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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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View more information in the IUPHAR Pharmacology Education Project: venlafaxine

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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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 2
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 32.7
Molecular weight 277.2
XLogP 2.83
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 COc1ccc(cc1)C(C1(O)CCCCC1)CN(C)C
Isomeric SMILES COc1ccc(cc1)C(C1(O)CCCCC1)CN(C)C
InChI InChI=1S/C17H27NO2/c1-18(2)13-16(17(19)11-5-4-6-12-17)14-7-9-15(20-3)10-8-14/h7-10,16,19H,4-6,11-13H2,1-3H3
InChI Key PNVNVHUZROJLTJ-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1993))
IUPAC Name Click here for help
1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexan-1-ol
International Nonproprietary Names Click here for help
INN number INN
6358 venlafaxine
Synonyms Click here for help
Effexor® | WY-45030
Database Links Click here for help
CAS Registry No. 93413-69-5
ChEMBL Ligand CHEMBL637
DrugBank Ligand DB00285
DrugCentral Ligand 2813
GtoPdb PubChem SID 178103894
PubChem CID 5656
Search Google for chemical match using the InChIKey PNVNVHUZROJLTJ-UHFFFAOYSA-N
Search Google for chemicals with the same backbone PNVNVHUZROJLTJ
Search PubMed clinical trials venlafaxine
Search PubMed titles venlafaxine
Search PubMed titles/abstracts venlafaxine
UniChem Compound Search for chemical match using the InChIKey PNVNVHUZROJLTJ-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey PNVNVHUZROJLTJ-UHFFFAOYSA-N
Wikipedia Venlafaxine