Escitalopram

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[1]
Other names(S)-Citalopram; S-Citalopram; S-(+)-Citalopram; S(+)-Citalopram; (+)-Citalopram; LU-26054; MLD-55
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
Pharmacokinetic data
Bioavailability~80%[7][8]
Protein binding~55–56% (low)[7][8]
MetabolismLiver (CYP2C19, CYP3A4, CYP2D6)[7][8]
Metabolites• Desmethylcitalopram[7][8]
• Didesmethylcitalopram[7][8]
Elimination half-life~27–32 hours[7]
ExcretionUrine (major; 8–10% unchanged), feces (minor)[8]
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 Edit this at Wikidata
Chemical and physical data
FormulaC20H21FN2O
Molar mass324.399 g·mol−1
3D model (JSmol)
ChiralityLevorotatory enantiomer
  • 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 checkY
  • Key:WSEQXVZVJXJVFP-FQEVSTJZSA-N checkY
  (verify)

Escitalopram, sold under the brand names Lexapro and Cipralex, among others, is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class.[9] Escitalopram is mainly used to treat major depressive disorder and generalized anxiety disorder.[9] It is taken by mouth,[9] available commercially as an oxalate salt exclusively.

Common side effects include headache, nausea, sexual problems, mild sedation, and trouble sleeping.[9] More serious side effects may include suicidal thoughts in people up to the age of 24 years.[9] It is unclear if use during pregnancy or breastfeeding is safe.[10] Escitalopram is the (S)-enantiomer of citalopram (which exists as a racemate), hence the name es-citalopram.[9]

Escitalopram was approved for medical use in the United States in 2002.[9] Escitalopram is rarely replaced by twice the dose of citalopram; escitalopram is safer and more effective.[11] It is on the World Health Organization's List of Essential Medicines.[12] In 2022, it was the fifteenth most commonly prescribed medication in the United States, with more than 30 million prescriptions.[13][14] In Australia, it was one of the top 10 most prescribed medications between 2017 and 2023.[15]

  1. ^ Cite error: The named reference drugsINT was invoked but never defined (see the help page).
  2. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  3. ^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
  4. ^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 3 August 2023.
  5. ^ "Lexapro- escitalopram tablet, film coated; Lexapro- escitalopram solution". DailyMed. 17 November 2023. Retrieved 31 December 2023.
  6. ^ Human Medicines Division (September 2022). "Active substance(s): escitalopram" (PDF). List of nationally authorised medicinal products. European Medicines Agency. Archived (PDF) from the original on 6 September 2022. Retrieved 6 September 2022.
  7. ^ a b c d e f Pastoor D, Gobburu J (January 2014). "Clinical pharmacology review of escitalopram for the treatment of depression". Expert Opin Drug Metab Toxicol. 10 (1): 121–128. doi:10.1517/17425255.2014.863873. PMID 24289655.
  8. ^ a b c d e f Rao N (2007). "The clinical pharmacokinetics of escitalopram". Clin Pharmacokinet. 46 (4): 281–290. doi:10.2165/00003088-200746040-00002. PMID 17375980.
  9. ^ a b c d e f g "X". The American Society of Health-System Pharmacists. Archived from the original on 29 December 2017. Retrieved 28 December 2017.
  10. ^ "Escitalopram (Lexapro) Use During Pregnancy". Drugs.com. Archived from the original on 31 December 2017. Retrieved 31 December 2017.
  11. ^ "Protocol for switching patients from escitalopram to citalopram". NHS. 2015. Archived from the original on 10 August 2020. Retrieved 13 February 2018.
  12. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  13. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  14. ^ "Escitalopram Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
  15. ^ "Medicines in the health system". Australian Institute of Health and Welfare. 2 July 2024. Retrieved 30 September 2024.