paroxetine   

GtoPdb Ligand ID: 4790

Synonyms: paroxetine hydrochloride (anhydrous or hemihydrate) | Paxil® | Seroxat®
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)..

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: paroxetine

2D Structure

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

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 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
SMILES / InChI / InChIKey

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 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
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1992))
IUPAC Name
(3S,4R)-3-[(2H-1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine
International Nonproprietary Names
INN number INN
4327 paroxetine
Synonyms
paroxetine hydrochloride (anhydrous or hemihydrate) | Paxil® | Seroxat®
Database Links
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
Search UniChem for chemical match using the InChIKey AHOUBRCZNHFOSL-YOEHRIQHSA-N
Search UniChem for chemicals with the same backbone AHOUBRCZNHFOSL
SynPHARM 13002 (in complex with SERT)
83552 (in complex with SERT)
Wikipedia Paroxetine