Escitalopram

Escitalopram, sold under the brand names Lexapro and Cipralex, among others, is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. Escitalopram is mainly used to treat major depressive disorder and generalized anxiety disorder. It is taken by mouth, available commercially as an oxalate salt exclusively.

This article is about the left handed version of the medication. For its racemic form, see citalopram.

Escitalopram
Clinical data
Pronunciation/ˌɛsəˈtæləˌpræm/ pronunciationⓘ
Trade namesCipralex, Lexapro, others
AHFS/Drugs.comMonograph
MedlinePlusa603005
License data
Pregnancy
category
  • AU: C
Routes of
administration		By mouth
Drug classSelective serotonin reuptake inhibitor (SSRI)
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: WARNINGRx-only
  • EU: Rx-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability80%
Protein binding~56%
MetabolismLiver, specifically the enzymes CYP3A4 and CYP2C19
MetabolitesDesmethylcitalopram, didesmethylcitalopram
Elimination half-life27–32 hours
Identifiers
  • (S)-1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.244.188
Chemical and physical data
FormulaC20H21FN2O
Molar mass324.399 g·mol−1
3D model (JSmol)
SMILES
  • Fc1ccc(cc1)[C@@]3(OCc2cc(C#N)ccc23)CCCN(C)C
  • 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 Y
  • Key:WSEQXVZVJXJVFP-FQEVSTJZSA-N Y
 NY (what is this?)  (verify)

Common side effects include trouble sleeping, nausea, sexual problems, and feeling tired. More serious side effects may include suicidal thoughts in people up to the age of 24 years. It is unclear if use during pregnancy or breastfeeding is safe. Escitalopram is the (S)-enantiomer of citalopram (which exists as a racemate), hence the name es-citalopram.

Escitalopram was approved for medical use in the United States in 2002. Escitalopram is rarely replaced by twice the dose of citalopram, though escitalopram is safer and more effective. It is on the World Health Organization's List of Essential Medicines. In 2021, it was the fifteenth most commonly prescribed medication in the United States, with more than 30 million prescriptions.

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