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paroxetine   Click here for help

GtoPdb Ligand ID: 4790

Synonyms: paroxetine hydrochloride (anhydrous or hemihydrate) | Paxil® | Seroxat®
Approved drug PDB Ligand
paroxetine is an approved drug (FDA (1992))
Compound class: Synthetic organic
Comment: Paroxetine is a selective serotonin-reuptake inhibitor (SSRI) antidepressant. An X-ray structure of crystals of paroxetine bound SERT, shows a single central binding site [1] (see PDB entry 5I6X)..
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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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paroxetine is commercially available from our sponsors

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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 1
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 39.72
Molecular weight 329.14
XLogP 3.32
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES Fc1ccc(cc1)C1CCNCC1COc1ccc2c(c1)OCO2
Isomeric SMILES Fc1ccc(cc1)[C@@H]1CCNC[C@H]1COc1ccc2c(c1)OCO2
InChI InChI=1S/C19H20FNO3/c20-15-3-1-13(2-4-15)17-7-8-21-10-14(17)11-22-16-5-6-18-19(9-16)24-12-23-18/h1-6,9,14,17,21H,7-8,10-12H2/t14-,17-/m0/s1
InChI Key AHOUBRCZNHFOSL-YOEHRIQHSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. US FDA (1992)
IUPAC Name Click here for help
(3S,4R)-3-[(2H-1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine
International Nonproprietary Names Click here for help
INN number INN
4327 paroxetine
Synonyms Click here for help
paroxetine hydrochloride (anhydrous or hemihydrate) | Paxil® | Seroxat®
Database Links Click here for help
CAS Registry No. 61869-08-7 (source: Scifinder)
ChEBI CHEBI:7936
ChEMBL Ligand CHEMBL490
DrugBank Ligand DB00715
DrugCentral Ligand 2068
GtoPdb PubChem SID 178101492
PubChem CID 43815
RCSB PDB Ligand 8PR
Search Google for chemical match using the InChIKey AHOUBRCZNHFOSL-YOEHRIQHSA-N
Search Google for chemicals with the same backbone AHOUBRCZNHFOSL
Search PubMed clinical trials paroxetine
Search PubMed titles paroxetine
Search PubMed titles/abstracts paroxetine
SynPHARM 13002 (in complex with SERT)
83552 (in complex with SERT)
UniChem Compound Search for chemical match using the InChIKey AHOUBRCZNHFOSL-YOEHRIQHSA-N
UniChem Connectivity Search for chemical match using the InChIKey AHOUBRCZNHFOSL-YOEHRIQHSA-N
Wikipedia Paroxetine

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Product supplier links are provided as a service to assist in identifying commercial suppliers of reagents that are mentioned on the IUPHAR/BPS Guide to PHARMACOLOGY database website, and do not imply their endorsement by NC-IUPHAR.

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MedChemExpress
Paroxetine (links to external site)
Cat. No. HY-122272