escitalopram   Click here for help

GtoPdb Ligand ID: 7177

Synonyms: Cipralex® | Lexapro® | LU-26-054-0
Approved drug PDB Ligand
escitalopram is an approved drug (FDA (2002))
Compound class: Synthetic organic
Comment: Escitalopram is a selective serotonin-reuptake inhibitor (SSRI) drug. It is the S-enantiomer of citalopram.
Marketed formulations may contain escitalopram oxalate (PubChem CID 146571). An X-ray structure of SERT bound by escitalopram ((S)-citalopram) reveals two binding sites for the drug: one central site, and one allosteric site [1]. When (S)-citalopram binds the allosteric site, it prevents unbinding of ligand at the central site, thereby preventing further ligand transport.
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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: escitalopram

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 3
Hydrogen bond donors 0
Rotatable bonds 5
Topological polar surface area 36.26
Molecular weight 324.16
XLogP 3.54
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 N#Cc1ccc2c(c1)COC2(CCCN(C)C)c1ccc(cc1)F
Isomeric SMILES N#Cc1ccc2c(c1)CO[C@@]2(CCCN(C)C)c1ccc(cc1)F
InChI InChI=1S/C20H21FN2O/c1-23(2)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-24-20/h4-9,12H,3,10-11,14H2,1-2H3/t20-/m0/s1
InChI Key WSEQXVZVJXJVFP-FQEVSTJZSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2002))
IUPAC Name Click here for help
(1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile
International Nonproprietary Names Click here for help
INN number INN
7953 escitalopram
Synonyms Click here for help
Cipralex® | Lexapro® | LU-26-054-0
Database Links Click here for help
CAS Registry No. 59729-33-8
ChEMBL Ligand CHEMBL1508
DrugBank Ligand DB01175
DrugCentral Ligand 1053
GtoPdb PubChem SID 178103752
PubChem CID 146570
RCSB PDB Ligand 68P
Search Google for chemical match using the InChIKey WSEQXVZVJXJVFP-FQEVSTJZSA-N
Search Google for chemicals with the same backbone WSEQXVZVJXJVFP
Search PubMed clinical trials escitalopram
Search PubMed titles escitalopram
Search PubMed titles/abstracts escitalopram
SynPHARM 79385 (in complex with SERT)
83551 (in complex with SERT)
UniChem Compound Search for chemical match using the InChIKey WSEQXVZVJXJVFP-FQEVSTJZSA-N
UniChem Connectivity Search for chemical match using the InChIKey WSEQXVZVJXJVFP-FQEVSTJZSA-N
Wikipedia escitalopram