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
SMILES / InChI / InChIKey
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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
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SynPHARM 79385 (in complex with SERT)
83551 (in complex with SERT)
Wikipedia escitalopram