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
No information available.
Summary of Clinical Use Click here for help
Used to improve symptoms of depression and anxiety in patients with major depressive disorder, panic disorder, generalized anxiety disorder or social phobia and reduce compulsive behaviour and obsessional thoughts in patients with obsessive compulsive disorder (OCD).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
SSRIs increase serotonin levels at post-synaptic sites by inhibiting the pre-synaptic serotonin transporter (SLC6A4) normally involved in its re-uptake. This enhances serotonergic neurotransmission with the clinical outcomes being improved mood and decreased anxiety. See the DrugBank link for further details.
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