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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2D Structure
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Physico-chemical Properties
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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
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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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2002))
IUPAC Name Click here for help
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
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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