View source for Escitalopram

{{Short description|SSRI antidepressant}}
{{Use dmy dates|date=August 2024}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Infobox drug
| Verifiedfields = verified
| Watchedfields = verified
| verifiedrevid = 443735539
| image = Escitalopram.svg
| image_class = skin-invert-image
| width = 225
| alt = 
| image2 = Escitalopram-based-on-xtal-3D-bs-17.png
| image_class2 = bg-transparent
| width2 = 
| alt2 = 
| caption = 

<!-- Clinical data -->
| pronounce = {{IPAc-en|ˌ|ɛ|s|ə|ˈ|t|æ|l|ə|ˌ|p|ɹ|æ|m|}} 
| tradename = Cipralex, Lexapro, others<ref name=drugsINT/>
| Drugs.com = {{drugs.com|monograph|escitalopram-oxalate}}
| MedlinePlus = a603005
| DailyMedID = Escitalopram
| pregnancy_AU = C
| pregnancy_AU_comment = 
| pregnancy_category = 
| routes_of_administration = [[Oral administration|By mouth]]
| class = [[Selective serotonin reuptake inhibitor]] (SSRI)
| ATC_prefix = N06
| ATC_suffix = AB10
| ATC_supplemental = 

<!-- Legal status -->
| legal_AU = S4
| legal_AU_comment = <ref>{{cite web | title=Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017 | website=Therapeutic Goods Administration (TGA) | date=21 June 2022 | url=https://www.tga.gov.au/resources/publication/publications/prescription-medicines-registration-new-generic-medicines-and-biosimilar-medicines-2017 | access-date=30 March 2024}}</ref>
| legal_BR = C1
| legal_BR_comment = <ref>{{cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=31 March 2023 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=3 August 2023 |access-date=3 August 2023 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=4 April 2023}}</ref>
| legal_CA = Rx-only
| legal_CA_comment = 
| legal_DE = <!-- Anlage I, II, III or Unscheduled-->
| legal_DE_comment = 
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment = 
| legal_UK = POM
| legal_UK_comment = 
| legal_US = Rx-only
| legal_US_comment = <ref name="Lexapro FDA label">{{cite web | title=Lexapro- escitalopram tablet, film coated; Lexapro- escitalopram solution | website=DailyMed | date=17 November 2023 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=13bb8267-1cab-43e5-acae-55a4d957630a | access-date=31 December 2023}}</ref>
| legal_EU = Rx-only
| legal_EU_comment = <ref>{{cite web |url=https://www.ema.europa.eu/documents/psusa/escitalopram-list-nationally-authorised-medicinal-products-psusa/00001265/202112_en.pdf |title=Active substance(s): escitalopram | author = Human Medicines Division | work = List of nationally authorised medicinal products | publisher = European Medicines Agency | date = September 2022 |access-date=6 September 2022 |archive-date=6 September 2022 |archive-url=https://web.archive.org/web/20220906054312/https://www.ema.europa.eu/en/documents/psusa/escitalopram-list-nationally-authorised-medicinal-products-psusa/00001265/202112_en.pdf |url-status=live }}</ref>
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV-->
| legal_UN_comment = 
| legal_status = Rx-only

<!-- Pharmacokinetic data -->
| bioavailability= ~80%<ref name="PastoorGobburu2014">{{cite journal | vauthors = Pastoor D, Gobburu J | title = Clinical pharmacology review of escitalopram for the treatment of depression | journal = Expert Opin Drug Metab Toxicol | volume = 10 | issue = 1 | pages = 121–128 | date = January 2014 | pmid = 24289655 | doi = 10.1517/17425255.2014.863873 | url = }}</ref><ref name="Rao2007">{{cite journal | vauthors = Rao N | title = The clinical pharmacokinetics of escitalopram | journal = Clin Pharmacokinet | volume = 46 | issue = 4 | pages = 281–290 | date = 2007 | pmid = 17375980 | doi = 10.2165/00003088-200746040-00002 | url = }}</ref>
| protein_bound = ~55–56% (low)<ref name="PastoorGobburu2014" /><ref name="Rao2007" />
| metabolism = [[Liver]] ([[CYP2C19]], [[CYP3A4]], [[CYP2D6]])<ref name="PastoorGobburu2014" /><ref name="Rao2007" />
| metabolites = • [[Desmethylcitalopram]]<ref name="PastoorGobburu2014" /><ref name="Rao2007" /><br />• [[Didesmethylcitalopram]]<ref name="PastoorGobburu2014" /><ref name="Rao2007" />
| onset = 
| elimination_half-life = ~27–32 hours<ref name="PastoorGobburu2014" />
| duration_of_action = 
| excretion = [[Urine]] (major; 8–10% unchanged), [[feces]] (minor)<ref name="Rao2007" />

<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 128196-01-0
| CAS_supplemental = 
| PubChem = 146570
| IUPHAR_ligand = 
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01175
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 129277
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 4O4S742ANY
| KEGG_Ref = 
| KEGG = D07913
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 36791
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1508
| NIAID_ChemDB = 
| PDB_ligand = 
| synonyms = (''S'')-Citalopram; ''S''-Citalopram; ''S''-(+)-Citalopram; ''S''(+)-Citalopram; (+)-Citalopram; LU-26054; MLD-55

<!-- Chemical and physical data -->
| IUPAC_name = (''S'')-1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile
| C=20 | H=21 | F=1 | N=2 | O=1
| chirality = [[Levorotatory]] [[enantiomer]]
| SMILES = Fc1ccc(cc1)[C@@]3(OCc2cc(C#N)ccc23)CCCN(C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WSEQXVZVJXJVFP-FQEVSTJZSA-N
}}

<!-- Definition and medical uses -->
'''Escitalopram''' ({{IPAc-en|pron|ˌ|ɛ|s|ə|ˈ|t|æ|l|ə|ˌ|p|ɹ|æ|m|}} {{Audio|escitalopram_pronunciation.ogg|}} {{respell|eh|sə|TA|lə|pram}}), sold under the brand names '''Lexapro''' and '''Cipralex''', among others, is an [[Antidepressant|antidepressant medication]] of the [[selective serotonin reuptake inhibitor]] (SSRI) class.<ref name=AHFS2017/> It is mainly used to treat [[major depressive disorder]],<ref name=AHFS2017>{{cite web|title=X|url=https://www.drugs.com/monograph/escitalopram-oxalate.html|publisher=The American Society of Health-System Pharmacists|access-date=28 December 2017|archive-date=29 December 2017|archive-url=https://web.archive.org/web/20171229232258/https://www.drugs.com/monograph/escitalopram-oxalate.html|url-status=live}}</ref> [[generalized anxiety disorder]],<ref name=AHFS2017/> [[panic disorder]], [[obsessive–compulsive disorder]] (OCD), and [[social anxiety disorder]]. Escitalopram is [[Oral administration|taken by mouth]].<ref name=AHFS2017/>  For commercial use, it is formulated as an [[oxalic acid|oxalate]] salt exclusively.

<!-- Side effects and mechanism -->
Common side effects include [[headache]], [[nausea]], [[Sexual dysfunction|sexual problems]],  mild [[Somnolence|sedation]], and [[trouble sleeping]].<ref name=AHFS2017/> More serious side effects may include [[suicidal thoughts]] in people up to the age of 24 years.<ref name=AHFS2017/> It is unclear if use during [[pregnancy]] or [[breastfeeding]] is safe.<ref>{{cite web|title=Escitalopram (Lexapro) Use During Pregnancy|url=https://www.drugs.com/pregnancy/escitalopram.html|website=Drugs.com|access-date=31 December 2017|archive-date=31 December 2017|archive-url=https://web.archive.org/web/20171231212719/https://www.drugs.com/pregnancy/escitalopram.html|url-status=live}}</ref> Escitalopram is the (''S'')-[[enantiomer]] of [[citalopram]] (which exists as a [[racemate]]), hence the name ''es-citalopram''.<ref name=AHFS2017/>

<!-- History and culture -->
Escitalopram was approved for medical use in the United States in 2002.<ref name=AHFS2017/> Escitalopram is rarely replaced by twice the dose of [[citalopram]]; escitalopram is safer and more effective.<ref name=NHS2015>{{cite web|title=Protocol for switching patients from escitalopram to citalopram|url=http://www.ipswichandeastsuffolkccg.nhs.uk/LinkClick.aspx?fileticket=6JoKJA8nPsg%3D|website=NHS|access-date=13 February 2018|date=2015|archive-date=10 August 2020|archive-url=https://web.archive.org/web/20200810021518/http://www.ipswichandeastsuffolkccg.nhs.uk/LinkClick.aspx?fileticket=6JoKJA8nPsg%3D|url-status=live}}</ref> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO23rd">{{cite book | vauthors = ((World Health Organization)) | title = The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023) | year = 2023 | hdl = 10665/371090 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2023.02 | hdl-access=free }}</ref> In 2023, it was the second most prescribed antidepressant and fourteenth most commonly prescribed medication in the United States, with more than 37{{nbsp}}million prescriptions.<ref name="Top300Drugs">{{cite web | title=Top 300 of 2023 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=12 August 2025 | archive-date=12 August 2025 | archive-url=https://web.archive.org/web/20250812130026/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Escitalopram Drug Usage Statistics, United States, 2014 - 2023 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Escitalopram | access-date = 12 August 2025 }}</ref> In Australia, it was one of the top 10 most prescribed medications between 2017 and 2023.<ref>{{cite web | title=Medicines in the health system | website=Australian Institute of Health and Welfare | date=2 July 2024 | url=https://www.aihw.gov.au/reports/medicines/medicines-in-the-health-system | access-date=30 September 2024}}</ref>

Other first-line SSRIs that have similar results include [[sertraline]], [[paroxetine]], and [[fluoxetine]], among others.

==Medical uses==
Escitalopram is approved by the US [[Food and Drug Administration]] (FDA) for the treatment of [[major depressive disorder]] in adolescents and adults, and [[generalized anxiety disorder]] (GAD) in adults, in dosage from 5 to 20 mg.<ref name=AHFS2017/><ref name="MSR" /> In European countries including the United Kingdom, it is approved for depression and [[Anxiety disorder|anxiety disorders]]; these include: generalized anxiety disorder, [[social anxiety disorder]] (SAD), [[obsessive-compulsive disorder|obsessive–compulsive disorder]] (OCD), and [[panic disorder]] with or without [[agoraphobia]]. In Australia it is approved for major depressive disorder.<ref>{{cite journal|title=Escitalopram oxalate|url=https://www.nps.org.au/australian-prescriber/articles/escitalopram-oxalate|language=en|doi=10.18773/austprescr.2003.107|volume=26|year=2003|journal=Australian Prescriber|pages=146–151|doi-access=free|access-date=15 March 2020|archive-date=10 June 2020|archive-url=https://web.archive.org/web/20200610103705/https://www.nps.org.au/australian-prescriber/articles/escitalopram-oxalate|url-status=live}}</ref><ref>{{cite news|url=https://www.reuters.com/article/lundbeck-idUSDKT00159920070112|title=Lundbeck's Cipralex gets EU ok for OCD treatment|date=12 January 2007|work=Reuters|access-date=15 March 2020|language=en|archive-date=10 June 2020|archive-url=https://web.archive.org/web/20200610102100/https://www.reuters.com/article/lundbeck-idUSDKT00159920070112|url-status=live}}</ref><ref>{{cite web|url=https://www.medicines.org.uk/emc/product/7718/smpc|title=Cipralex 10 mg film-coated tablets - Summary of Product Characteristics (SmPC) - (emc)|website=www.medicines.org.uk|access-date=15 March 2020|archive-date=10 June 2020|archive-url=https://web.archive.org/web/20200610102137/https://www.medicines.org.uk/emc/product/7718/smpc|url-status=live}}</ref>

===Depression===
Escitalopram is among the most effective and well-tolerated antidepressants for the short-term treatment of major depressive disorder in adults.<ref>{{cite journal |date=3 April 2018 |title=The most effective antidepressants for adults revealed in major review |url=https://evidence.nihr.ac.uk/alert/the-most-effective-antidepressants-for-adults-revealed-in-major-review |journal=NIHR Evidence |type=Plain English summary |publisher=National Institute for Health and Care Research |doi=10.3310/signal-00580|url-access=subscription }}</ref><ref>{{cite journal | vauthors = Cipriani A, Furukawa TA, Salanti G, Chaimani A, Atkinson LZ, Ogawa Y, Leucht S, Ruhe HG, Turner EH, Higgins JP, Egger M, Takeshima N, Hayasaka Y, Imai H, Shinohara K, Tajika A, Ioannidis JP, Geddes JR | title = Comparative efficacy and acceptability of 21 antidepressant drugs for the acute treatment of adults with major depressive disorder: a systematic review and network meta-analysis | journal = Lancet | volume = 391 | issue = 10128 | pages = 1357–1366 | date = April 2018 | pmid = 29477251 | pmc = 5889788 | doi = 10.1016/S0140-6736(17)32802-7 }}</ref> It also seems to be the safest one to give to children and adolescents.<ref>{{cite journal |date=1 September 2020 |title=Psychiatric drugs given to children and adolescents have been ranked in order of safety | journal=NIHR Evidence |type=Plain English summary |publisher=National Institute for Health and Care Research |doi=10.3310/alert_40795|s2cid=241309451 }}</ref><ref>{{cite journal | vauthors = Solmi M, Fornaro M, Ostinelli EG, Zangani C, Croatto G, Monaco F, Krinitski D, Fusar-Poli P, Correll CU | title = Safety of 80 antidepressants, antipsychotics, anti-attention-deficit/hyperactivity medications and mood stabilizers in children and adolescents with psychiatric disorders: a large scale systematic meta-review of 78 adverse effects | journal = World Psychiatry | volume = 19 | issue = 2 | pages = 214–232 | date = June 2020 | pmid = 32394557 | pmc = 7215080 | doi = 10.1002/wps.20765 }}</ref>

Controversy existed regarding the effectiveness of escitalopram compared with its predecessor, citalopram. The importance of this issue followed from the greater cost of escitalopram relative to the generic mixture of isomers of citalopram, prior to the expiration of the escitalopram patent in 2012, which led to charges of [[evergreening]]. Accordingly, this issue has been examined in at least 10 different systematic reviews and meta analyses. {{as of|2012}}, reviews had concluded (with caveats in some cases) that escitalopram is modestly superior to citalopram in efficacy and tolerability.<ref>{{cite journal | vauthors = Ramsberg J, Asseburg C, Henriksson M | title = Effectiveness and cost-effectiveness of antidepressants in primary care: a multiple treatment comparison meta-analysis and cost-effectiveness model | journal = PLOS ONE | volume = 7 | issue = 8 | article-number = e42003 | year = 2012 | pmid = 22876296 | pmc = 3410906 | doi = 10.1371/journal.pone.0042003 | doi-access = free | bibcode = 2012PLoSO...742003R }}</ref><ref>{{cite journal | vauthors = Cipriani A, Purgato M, Furukawa TA, Trespidi C, Imperadore G, Signoretti A, Churchill R, Watanabe N, Barbui C | title = Citalopram versus other anti-depressive agents for depression | journal = The Cochrane Database of Systematic Reviews | volume = 2012 | issue = 7 | article-number = CD006534 | date = July 2012 | pmid = 22786497 | pmc = 4204633 | doi = 10.1002/14651858.CD006534.pub2 }}</ref><ref name=pmid22381728>{{cite journal | vauthors = Favré P | title = [Clinical efficacy and achievement of a complete remission in depression: increasing interest in treatment with escitalopram] | language = fr | journal = L'Encéphale | volume = 38 | issue = 1 | pages = 86–96 | date = February 2012 | pmid = 22381728 | doi = 10.1016/j.encep.2011.11.003 | trans-title = Clinical efficacy and achievement of a complete remission in depression: Increasing interest in treatment with escitalopram }}</ref><ref>{{cite journal | vauthors = Sicras-Mainar A, Navarro-Artieda R, Blanca-Tamayo M, Gimeno-de la Fuente V, Salvatella-Pasant J | title = Comparison of escitalopram vs. citalopram and venlafaxine in the treatment of major depression in Spain: clinical and economic consequences | journal = Current Medical Research and Opinion | volume = 26 | issue = 12 | pages = 2757–2764 | date = December 2010 | pmid = 21034375 | doi = 10.1185/03007995.2010.529430 | s2cid = 43179425 }}</ref>

=== Anxiety disorders ===
Escitalopram appears to be effective in treating generalized anxiety disorder, with relapse on escitalopram at 20% rather than placebo at 50%, which translates to a [[number needed to treat]] of 3.33.<ref>{{cite journal | vauthors = Slee A, Nazareth I, Bondaronek P, Liu Y, Cheng Z, Freemantle N | title = Pharmacological treatments for generalised anxiety disorder: a systematic review and network meta-analysis | language = English | journal = Lancet | volume = 393 | issue = 10173 | pages = 768–777 | date = February 2019 | pmid = 30712879 | doi = 10.1016/S0140-6736(18)31793-8 | s2cid = 72332967 | url = https://discovery.ucl.ac.uk/id/eprint/10070219/ }}</ref><ref name=pmid19961809>{{cite journal | vauthors = Bech P, Lönn SL, Overø KF | title = Relapse prevention and residual symptoms: a closer analysis of placebo-controlled continuation studies with escitalopram in major depressive disorder, generalized anxiety disorder, social anxiety disorder, and obsessive-compulsive disorder | journal = The Journal of Clinical Psychiatry | volume = 71 | issue = 2 | pages = 121–129 | date = February 2010 | pmid = 19961809 | doi = 10.4088/JCP.08m04749blu }}</ref> Escitalopram appears effective in treating social anxiety disorder as well.<ref name=pmid26971233>{{cite journal | vauthors = Baldwin DS, Asakura S, Koyama T, Hayano T, Hagino A, Reines E, Larsen K | title = Efficacy of escitalopram in the treatment of social anxiety disorder: A meta-analysis versus placebo | journal = European Neuropsychopharmacology | volume = 26 | issue = 6 | pages = 1062–1069 | date = June 2016 | pmid = 26971233 | doi = 10.1016/j.euroneuro.2016.02.013 | doi-access = free }}</ref>

=== Other ===
Escitalopram may reduce premenstrual symptoms in women with [[premenstrual syndrome]] and [[premenstrual dysphoric disorder]]. It seems to be more effective when taken continuously compared to luteal phase administration.<ref name="pmid23744611">{{cite journal |vauthors=Jespersen C, Lauritsen MP, Frokjaer VG, Schroll JB |date=August 2024 |title=Selective serotonin reuptake inhibitors for premenstrual syndrome and premenstrual dysphoric disorder |journal=The Cochrane Database of Systematic Reviews |volume=2024 |issue=8 |article-number=CD001396 |doi=10.1002/14651858.CD001396.pub4 |pmc=11323276 |pmid=39140320 }}</ref> It is also occasionally prescribed [[Off-label use|off-label]] for insomnia secondary to a mental disorder, and [[vasomotor symptoms]] (hot flashes) associated with menopause.<ref name="MSR" />

==Side effects==
Escitalopram has a relatively favorable side effect profile compared to other antidepressant medications. Some of the most common side effect in order of frequency are, headache, nausea, somnolence, insomnia, dry mouth, fatigue, decreased libido, constipation, and flu-like symptoms<ref name=":2" />

Similar to other [[Selective serotonin reuptake inhibitor|SSRIs]], escitalopram has been shown to affect sexual function, causing [[delayed ejaculation]], and [[anorgasmia]].<ref name="pmid16430968">{{cite journal | vauthors = Clayton A, Keller A, McGarvey EL | title = Burden of phase-specific sexual dysfunction with SSRIs | journal = Journal of Affective Disorders | volume = 91 | issue = 1 | pages = 27–32 | date = March 2006 | pmid = 16430968 | doi = 10.1016/j.jad.2005.12.007 }}</ref><ref>{{cite web |url= https://www.allergan.com/Assets/PDF/Lexapro_pi.pdf|title=Lexapro prescribing information|access-date=23 August 2017| archive-date=15 August 2018| archive-url= https://web.archive.org/web/20180815200647/https://www.allergan.com/assets/pdf/lexapro_pi.pdf|url-status=live}}</ref>

There is also evidence that SSRIs are correlated with an increase in [[suicidal ideation]] in certain individuals. An analysis conducted by the FDA found a statistically insignificant 1.5 to 2.4-fold (depending on the statistical technique used) increase of [[suicidality]] among the adults treated with escitalopram for psychiatric indications.<ref name= FDA>{{cite web| vauthors =Levenson M, Holland C| title =Antidepressants and Suicidality in Adults: Statistical Evaluation. (Presentation at Psychopharmacologic Drugs Advisory Committee; December 13, 2006)| website =[[Food and Drug Administration]]| access-date =13 May 2007| url = https://www.fda.gov/ohrms/dockets/ac/06/slides/2006-4272s1-04-FDA.ppt| archive-date =27 September 2007| archive-url = https://web.archive.org/web/20070927214932/https://www.fda.gov/ohrms/dockets/ac/06/slides/2006-4272s1-04-FDA.ppt}}</ref><ref name =FDA2>{{cite web | url = https://www.fda.gov/ohrms/dockets/ac/06/briefing/2006-4272b1-01-FDA.pdf | title = Clinical Review: Relationship Between Antidepressant Drugs and Suicidality in Adults | access-date = 22 September 2007 | vauthors = Stone MB, Jones ML | date = 17 November 2006 | website = Overview for 13 December Meeting of Pharmacological Drugs Advisory Committee (PDAC) | publisher = FDA | pages = 11–74 | archive-date = 16 March 2007 | archive-url = https://web.archive.org/web/20070316092329/https://www.fda.gov/ohrms/dockets/ac/06/briefing/2006-4272b1-01-FDA.pdf }}</ref><ref name =FDA3>{{cite web | url = https://www.fda.gov/ohrms/dockets/ac/06/briefing/2006-4272b1-01-FDA.pdf | title = Statistical Evaluation of Suicidality in Adults Treated with Antidepressants | access-date = 22 September 2007 | vauthors = Levenson M, Holland C | date = 17 November 2006 | website = Overview for 13 December Meeting of Pharmacological Drugs Advisory Committee (PDAC) | publisher = FDA | pages = 75–140 | archive-date = 16 March 2007 | archive-url = https://web.archive.org/web/20070316092329/https://www.fda.gov/ohrms/dockets/ac/06/briefing/2006-4272b1-01-FDA.pdf }}</ref> The authors of a related study note the general problem with statistical approaches: due to the rarity of suicidal events in clinical trials, it is hard to draw firm conclusions with a sample smaller than two million patients.<ref name= "pmid17453659">{{cite journal | vauthors = Khan A, Schwartz K | title = Suicide risk and symptom reduction in patients assigned to placebo in duloxetine and escitalopram clinical trials: analysis of the FDA summary basis of approval reports | journal = Annals of Clinical Psychiatry | volume = 19 | issue = 1 | pages = 31–36 | year = 2007 | pmid = 17453659 | doi = 10.1080/10401230601163550 }}</ref>

[[Citalopram]] and escitalopram are associated with a mild dose-dependent [[QT interval]] prolongation,<ref name="pmid23360890">{{cite journal | vauthors = Castro VM, Clements CC, Murphy SN, Gainer VS, Fava M, Weilburg JB, Erb JL, Churchill SE, Kohane IS, Iosifescu DV, Smoller JW, Perlis RH | title = QT interval and antidepressant use: a cross sectional study of electronic health records | journal = BMJ | volume = 346 | pages = f288 | date = January 2013 | pmid = 23360890 | pmc = 3558546 | doi = 10.1136/bmj.f288 }}</ref> which is a measure of how rapidly the heart muscle repolarizes after each heartbeat. Prolongation of the QT interval is a risk factor for [[torsades de pointes]] (TdP), a heart rhythm disturbance that is sometimes fatal. Despite the observed change in the QT interval, the risk of TdP from escitalopram appears to be quite low, and it is similar to other antidepressants that are not known to affect the QT interval. A 2013 review<ref name="Lam-2013">{{cite journal | vauthors = Lam RW | title = Antidepressants and QTc prolongation | journal = Journal of Psychiatry & Neuroscience | volume = 38 | issue = 2 | pages = E5–E6 | date = March 2013 | pmid = 23422053 | pmc = 3581598 | doi = 10.1503/jpn.120256 | quote = "In summary, the effects of citalopram and other antidepressants in therapeutic doses on QTc are not likely to be of clinical relevance unless other known risk factors are present." }}</ref> discusses several reasons to be optimistic about the safety of escitalopram. It references a crossover study in which 113 subjects were each given four different treatments in randomized order: placebo, 10 mg/day escitalopram, 30 mg/day escitalopram, or 400 mg/day [[moxifloxacin]] (a [[Scientific_control#Positive|positive control]] known to cause QTc prolongation). At 10 mg/day, escitalopram increased the QTc interval by 4.5 milliseconds (ms). At 30 mg/day, the QTc increased by 10.7 ms.<ref name="fda-citalopram-2017">{{cite web |author1=US FDA |title=FDA Drug Safety Communication: Revised recommendations for Celexa (citalopram hydrobromide) related to a potential risk of abnormal heart rhythms with high doses |url=https://www.fda.gov/drugs/drug-safety-and-availability/fda-drug-safety-communication-revised-recommendations-celexa-citalopram-hydrobromide-related |archive-url=https://web.archive.org/web/20191213203345/https://www.fda.gov/drugs/drug-safety-and-availability/fda-drug-safety-communication-revised-recommendations-celexa-citalopram-hydrobromide-related |archive-date=13 December 2019 |publisher=US FDA |access-date=1 May 2024 |date=15 December 2017}}</ref> A QTc increase of less than 60 ms is not likely to confer significant risk.<ref name="Lam-2013" /> The 30 mg/day escitalopram dose induced significantly less QTc prolongation than a therapeutically equivalent 60 mg/day dose of [[citalopram]], which increased the QTc interval by 18.5 ms.<ref name="Lam-2013" /> <!-- Add the study "Prescribe Lexapro instead" here. -->

More data about the cardiac risk from escitalopram can be found in a large observational study from Sweden that took note of all the medications used by all the patients presenting with TdP, and found the incidence of TdP in escitalopram users to be only 0.7 cases of TdP for every 100,000 patients who took the drug (ages 18-64), and only 4.1 cases of TdP for every 100,000 elderly patients who took the drug (ages 65 and up).<ref name="sweden-2020">{{cite journal | vauthors = Danielsson B, Collin J, Nyman A, Bergendal A, Borg N, State M, Bergfeldt L, Fastbom J | title = Drug use and torsades de pointes cardiac arrhythmias in Sweden: a nationwide register-based cohort study | journal = BMJ Open | volume = 10 | issue = 3 | article-number = e034560 | date = March 2020 | pmid = 32169926 | pmc = 7069257 | doi = 10.1136/bmjopen-2019-034560 | ref = sweden-2020 }}</ref> Of the 9 antidepressants that were used by patients with TdP, escitalopram ranked 7th by TdP incidence in elderly patients (only [[venlafaxine]] and [[amitriptyline]] had less risk), and it ranked 5th of 9 by TdP incidence in patients ages 18-64. Antidepressants as a class had a relatively low risk of TdP, and most patients on an antidepressant who experienced TdP were also taking another drug that prolonged QT interval. Specifically, 80% of the escitalopram users who experienced TdP were taking at least one other drug known to cause TdP. For comparison, the most popular [[antiarrhythmic]] drug in the study was [[sotalol]] with 52,750 users, and sotalol had a TdP incidence of 81.1 cases and 41.2 cases of TdP per 100,000 users in the ≥65 and 18-64-year-old demographics, respectively.<ref name="sweden-2020" />

Drugs that prolong the QT interval, such as escitalopram, should be used with caution in those with congenital [[long QT syndrome]] or known pre-existing QT interval prolongation, or in combination with other medicines that prolong the QT interval. [[ECG]] measurements should be considered for patients with [[Cardiac Disease|cardiac disease]], and [[electrolyte disturbances]] should be corrected before starting treatment. In December 2011, the UK implemented new restrictions on the maximum daily doses at 20&nbsp;mg for adults and 10&nbsp;mg for those older than 65 years or with [[liver impairment]].<ref name=":0">{{cite web | url = http://www.mhra.gov.uk/Safetyinformation/DrugSafetyUpdate/CON137769 | title = Citalopram and escitalopram: QT interval prolongation—new maximum daily dose restrictions (including in elderly patients), contraindications, and warnings | date = December 2011 | publisher = [[Medicines and Healthcare products Regulatory Agency]] | access-date = 5 March 2013 | archive-date = 6 March 2013 | archive-url = https://web.archive.org/web/20130306065253/http://www.mhra.gov.uk/Safetyinformation/DrugSafetyUpdate/CON137769 | url-status = live }}</ref><ref name="pmid19556032">{{cite journal |vauthors=van Gorp F, Whyte IM, Isbister GK |date=September 2009 |title=Clinical and ECG effects of escitalopram overdose |journal=Annals of Emergency Medicine |volume=54 |issue=3 |pages=404–408 |doi=10.1016/j.annemergmed.2009.04.016 |pmid=19556032}}</ref> The US Food and Drug Administration and Health Canada did not similarly order restrictions on escitalopram dosage, only on its predecessor [[citalopram]].<ref>{{cite journal | vauthors = Hasnain M, Howland RH, Vieweg WV | title = Escitalopram and QTc prolongation | journal = Journal of Psychiatry & Neuroscience | volume = 38 | issue = 4 | pages = E11 | date = July 2013 | pmid = 23791140 | pmc = 3692726 | doi = 10.1503/jpn.130055 }}</ref> 

Like other SSRIs, escitalopram has also been reported to cause [[hyponatremia]] (low sodium levels), with rates ranging from 0.5 to 32%, which can often be attributed to [[Syndrome of inappropriate antidiuretic hormone secretion|SIADH]].<ref>{{cite journal | vauthors = Leth-Møller KB, Hansen AH, Torstensson M, Andersen SE, Ødum L, Gislasson G, Torp-Pedersen C, Holm EA | title = Antidepressants and the risk of hyponatremia: a Danish register-based population study | journal = BMJ Open | volume = 6 | issue = 5 | article-number = e011200 | date = May 2016 | pmid = 27194321 | pmc = 4874104 | doi = 10.1136/bmjopen-2016-011200 }}</ref> This is typically not dose-dependent and at higher risk for occurrence within the first few weeks of starting treatment.<ref>{{cite journal | vauthors = Naschitz JE | title = Escitalopram Dose-Dependent Hyponatremia | journal = Journal of Clinical Pharmacology | volume = 58 | issue = 6 | pages = 834–835 | date = June 2018 | pmid = 29878443 | doi = 10.1002/jcph.1091 }}</ref>

Like other SSRIs, escitalopram often exacerbates symptoms of [[mania]] and [[hypomania]] in individuals misdiagnosed with a depressive disorder instead of a [[bipolar disorder]], making it crucial for clinicians to rule out bipolar disorders before prescribing escitalopram.<ref name="MSR" />

===Very common effects===
Very common effects (>10% incidence) include:<ref name="MSR">{{cite web |title=Lexapro (escitalopram) dosing, indications, interactions, adverse effects, and more |url=https://reference.medscape.com/drug/lexapro-escitalopram-342961 |url-status=live |archive-url=https://web.archive.org/web/20131202233318/http://reference.medscape.com/drug/lexapro-escitalopram-342961#showall |archive-date=2 December 2013 |access-date=9 April 2025 |work=Medscape}}</ref><ref name = EMC>{{cite web| title= Cipralex 5, 10 and 20 mg film-coated tablets - Summary of Product Characteristics (SPC)|work=electronic Medicines Compendium|date=2 October 2013|access-date=27 November 2013| url=http://www.medicines.org.uk/emc/medicine/27012/SPC/Cipralex+5%2c+10+and+20+mg+film-coated+tablets/| archive-date=3 December 2013| archive-url= https://web.archive.org/web/20131203010421/http://www.medicines.org.uk/emc/medicine/27012/SPC/Cipralex+5%2c+10+and+20+mg+film-coated+tablets/| url-status=live}}</ref><ref name = TGA>{{cite web|title=Escitalopram-Lupin Tablets (LUPIN AUSTRALIA PTY. LTD)|work=TGA eBusiness Services|publisher=Lupin Australia Pty Ltd|date=21 December 2011|access-date=27 November 2013| url=https://www.ebs.tga.gov.au/ebs/picmi/picmirepository.nsf/pdf?OpenAgent&id=CP-2012-PI-01532-3|format=PDF|archive-date=29 March 2019|archive-url=https://web.archive.org/web/20190329053352/https://www.ebs.tga.gov.au/ebs/picmi/picmirepository.nsf/pdf?OpenAgent&id=CP-2012-PI-01532-3|url-status=live}}</ref><ref name="Lexapro FDA label" /><ref>{{cite journal | vauthors = Mancano MA | title = Unequal Sized Pupils Due to Escitalopram; Adverse Events to Dietary Supplements Causing Emergency Department Visits; Compulsive Masturbation Due to Pramipexole; Metformin-Induced Lactic Acidosis Masquerading As an Acute Myocardial Infarction | journal = Hospital Pharmacy | volume = 51 | issue = 5 | pages = 358–361 | date = May 2016 | pmid = 27303087 | pmc = 4896342 | doi = 10.1310/hpj5105-358 | publisher = Thomas Land Publishers, Inc. }}</ref>

* [[Headache]] (24%)
* [[Nausea]] (18%)
* [[Ejaculation disorders]] (9–14%)
* [[Somnolence]] (4–13%)
* [[Insomnia]] (7–12%)

===Common (1–10% incidence)===
Common effects (1–10% incidence) include:

{{div col|colwidth=}}
* Abnormal [[dreams]]
* [[Anisocoria]]
* [[Anorgasmia]]
* [[Anxiety]]
* [[Arthralgia]] (joint pain)
* [[Constipation]]
* [[Anorexia (symptom)|Decreased]] or [[polyphagia|increased]] [[appetite]]
* [[Diarrhea]]
* [[Mydriasis|Dilated pupils]]
* [[Dizziness]]
* [[Dry mouth]]
* [[Excessive sweating]]
* [[Fatigue]]
* [[Fever]]
* [[Impotence]] (erectile dysfunction)
* [[Libido]] changes
* [[Myalgia]] (muscular aches and pains)
* [[Paraesthesia]] (abnormal skin sensation)
* [[Psychomotor agitation|Restlessness]]
* [[Sinusitis]] (nasal congestion)
* [[Tremor]]
* [[Vomiting]]
* [[Yawn|Yawning]]
{{div col end}}

=== Psychomotor effects ===
The most common effect is fatigue or somnolence, particularly in older adults,<ref name=":1">{{cite journal | vauthors = Lenze EJ |date=20 May 2009 |title=Escitalopram Treatment of Generalized Anxiety Disorder in Older Adults—Reply |journal=JAMA |volume=301 |issue=19 |page=1987 |doi=10.1001/jama.2009.652 |issn=0098-7484}}</ref> although patients with pre-existing daytime sleepiness and fatigue may experience paradoxical improvement of these symptoms.<ref>{{cite journal | vauthors = Shen J, Hossain N, Streiner DL, Ravindran AV, Wang X, Deb P, Huang X, Sun F, Shapiro CM | title = Excessive daytime sleepiness and fatigue in depressed patients and therapeutic response of a sedating antidepressant | journal = Journal of Affective Disorders | volume = 134 | issue = 1–3 | pages = 421–426 | date = November 2011 | pmid = 21616541 | doi = 10.1016/j.jad.2011.04.047 }}</ref>

Escitalopram has not been shown to affect serial reaction time, logical reasoning, serial subtraction, multitasking, or [[Mackworth Clock]] task performance.<ref>{{cite journal | vauthors = Rosekind MR, Gregory KB, Mallis MM | title = Alertness management in aviation operations: enhancing performance and sleep | journal = Aviation, Space, and Environmental Medicine | volume = 77 | issue = 12 | pages = 1256–1265 | date = December 2006 | pmid = 17183922 | doi = 10.3357/asem.1879.2006 | doi-broken-date = 18 July 2025 }}</ref>

===Sexual dysfunction===
Some people experience persistent sexual side effects when taking SSRIs or after discontinuing them.<ref name=DSM>{{cite book|title=Diagnostic and Statistical Manual of Mental Disorders| author = American Psychiatric Association |publisher=American Psychiatric Publishing |year=2013 |isbn=978-0-89042-555-8 |edition=5th |location=Arlington, VA |pages=[https://archive.org/details/diagnosticstatis0005unse/page/449 446–449] }}</ref> Symptoms of medication-induced sexual dysfunction from antidepressants include difficulty with orgasm, erection, or ejaculation.<ref name= DSM/> Other symptoms may be genital anesthesia, [[anhedonia]], decreased libido, vaginal lubrication issues, and nipple insensitivity in women. Rates are unknown, and there is no established treatment.<ref>{{cite journal | vauthors = Bala A, Nguyen HM, Hellstrom WJ | title = Post-SSRI Sexual Dysfunction: A Literature Review | journal = Sexual Medicine Reviews | volume = 6 | issue = 1 | pages = 29–34 | date = January 2018 | pmid = 28778697 | doi = 10.1016/j.sxmr.2017.07.002 }}</ref>

===Pregnancy===
Antidepressant exposure (including escitalopram) is associated with shorter duration of pregnancy (by three days), increased risk of preterm delivery (by 55%), lower birth weight (by 75&nbsp;g), and lower [[Apgar score]]s (by <0.4 points). Antidepressant exposure is not associated with an increased risk of spontaneous abortion.<ref>{{cite journal | vauthors = Ross LE, Grigoriadis S, Mamisashvili L, Vonderporten EH, Roerecke M, Rehm J, Dennis CL, Koren G, Steiner M, Mousmanis P, Cheung A | title = Selected pregnancy and delivery outcomes after exposure to antidepressant medication: a systematic review and meta-analysis | journal = JAMA Psychiatry | volume = 70 | issue = 4 | pages = 436–443 | date = April 2013 | pmid = 23446732 | doi = 10.1001/jamapsychiatry.2013.684 | s2cid = 2065578 | doi-access = }}</ref> There is a tentative association of SSRI use during pregnancy with heart problems in the baby.<ref name=Gent2015/> The advantages of their use during pregnancy may thus not outweigh the possible negative effects on the baby.<ref name=Gent2015>{{cite journal | vauthors = Gentile S | title = Early pregnancy exposure to selective serotonin reuptake inhibitors, risks of major structural malformations, and hypothesized teratogenic mechanisms | journal = Expert Opinion on Drug Metabolism & Toxicology | volume = 11 | issue = 10 | pages = 1585–1597 | date = 1 July 2015 | pmid = 26135630 | doi = 10.1517/17425255.2015.1063614 | s2cid = 43329515 }}</ref>

===Withdrawal===
{{Main|Antidepressant discontinuation syndrome}}

Escitalopram discontinuation, particularly abruptly, may cause certain [[Drug withdrawal#Prescription medicine|withdrawal]] [[symptom]]s such as "electric shock" sensations,<ref name="pmid18480703">{{cite journal |vauthors=Prakash O, Dhar V |date=June 2008 |title=Emergence of electric shock-like sensations on escitalopram discontinuation |journal=Journal of Clinical Psychopharmacology |volume=28 |issue=3 |pages=359–360 |doi=10.1097/JCP.0b013e3181727534 |pmid=18480703}}</ref> colloquially called "brain shivers" or "[[brain zaps]]" by those affected. Frequent symptoms in one study were [[dizziness]] (44%), muscle tension (44%), [[chills]] (44%), confusion or trouble concentrating (40%), amnesia (28%), and crying (28%). Very slow tapering is recommended.<ref>{{cite journal |vauthors=Yasui-Furukori N, Hashimoto K, Tsuchimine S, Tomita T, Sugawara N, Ishioka M, Nakamura K |date=June 2016 |title=Characteristics of Escitalopram Discontinuation Syndrome: A Preliminary Study |journal=Clinical Neuropharmacology |volume=39 |issue=3 |pages=125–127 |doi=10.1097/WNF.0000000000000139 |pmid=27171568 |s2cid=45460237}}</ref> There have been spontaneous reports of discontinuation of escitalopram and other SSRIs and SNRIs, especially when abrupt, leading to dysphoric mood, [[irritability]], agitation, anxiety, headache, [[lethargy]], [[emotional lability]], [[insomnia]], and [[hypomania]]. Other symptoms such as [[Panic attack|panic attacks]], hostility, [[aggression]], [[impulsivity]], [[akathisia]] (psychomotor restlessness), [[mania]], worsening of depression, and suicidal ideation can emerge when the dose is adjusted down.<ref>{{cite web |title=Lexapro (Escitalopram Oxalate) Drug Information: Warnings and Precautions - Prescribing Information at RxList |url=http://www.rxlist.com/cgi/generic/lexapro_wcp.htm |archive-url=https://web.archive.org/web/20080616071244/http://www.rxlist.com/cgi/generic/lexapro_wcp.htm |archive-date=16 June 2008 |access-date=9 August 2015}}</ref>

==Overdose==
Excessive doses of escitalopram usually cause relatively minor untoward effects, such as agitation and [[tachycardia]]. However, [[dyskinesia]], [[hypertonia]], and [[clonus]] may occur in some cases. Severe side effects of escitalopram overdose include seizures (which may be delayed), cardiovascular toxicity including QRS/QTc prolongation which can lead to arrhythmias ([[Torsades de pointes]], ventricular fibrillation, and ventricular tachycardia), hypertension, and serotonin syndrome. Treatment of escitalopram overdoses typically involves supportive care, such as giving [[Activated charcoal (medication)|Activated charcoal]] or giving benzodiazepines for seizures.<ref name=":2">{{Cite web | publisher= Allergan |title=Lexapro prescribing guide |url=https://www.accessdata.fda.gov/drugsatfda_docs/label/2023/021323s055,021365s039lbl.pdf}}</ref> Because of the risk of arrhythmias (which may be delayed) prolonged cardiac monitoring is strongly recommended<ref name=":2" />

== Interactions ==
Escitalopram weakly inhibits [[CYP2D6]], and hence may increase plasma levels of some CYP2D6 substrates such as [[aripiprazole]], [[risperidone]], [[tramadol]], [[codeine]], etc.<ref name="PastoorGobburu2014" /> As escitalopram is only a weak inhibitor of CYP2D6, analgesia from tramadol may not be affected.<ref>{{cite journal | vauthors = Noehr-Jensen L, Zwisler ST, Larsen F, Sindrup SH, Damkier P, Brosen K | title = Escitalopram is a weak inhibitor of the CYP2D6-catalyzed O-demethylation of (+)-tramadol but does not reduce the hypoalgesic effect in experimental pain | journal = Clinical Pharmacology and Therapeutics | volume = 86 | issue = 6 | pages = 626–633 | date = December 2009 | pmid = 19710642 | doi = 10.1038/clpt.2009.154 | s2cid = 29063004 }}</ref> Escitalopram (at the maximum dose of 20{{nbsp}}mg/day) has been found to increase [[Cmax (pharmacology)|peak levels]] of the CYP2D6 substrate [[desipramine]] by 40% and total exposure by 100%.<ref name="Rao2007" /> Likewise, it has been found to increase peak levels of the CYP2D6 substrate [[metoprolol]] by 50% and overall exposure by 82%.<ref name="Rao2007" /> Escitalopram does not inhibit [[CYP3A4]], [[CYP1A2]], [[CYP2C9]], [[CYP2C19]], or [[CYP2E1]].<ref name="PastoorGobburu2014" /><ref name="Rao2007" />

Exposure to escitalopram is increased moderately, by about 50%, when it is taken with [[omeprazole]], a CYP2C19 inhibitor.<ref name="PastoorGobburu2014" /> The authors of this study suggested that this increase is unlikely to be of clinical concern.<ref name="pmid16120067">{{cite journal | vauthors = Malling D, Poulsen MN, Søgaard B | title = The effect of cimetidine or omeprazole on the pharmacokinetics of escitalopram in healthy subjects | journal = British Journal of Clinical Pharmacology | volume = 60 | issue = 3 | pages = 287–290 | date = September 2005 | pmid = 16120067 | pmc = 1884771 | doi = 10.1111/j.1365-2125.2005.02423.x }}</ref> Combination of [[citalopram]] with [[fluoxetine]] or [[fluvoxamine]] resulted in increased exposure to the escitalopram enantiomer, owing to the strong inhibition of CYP2C19 and CYP2D6 by these agents.<ref name="Rao2007" /> [[Bupropion]], a known strong CYP2D6 inhibitor, has been found to significantly increase citalopram plasma concentration and systemic exposure (peak levels increased by 30%, total exposure increased by 40%); {{as of|2018|April|lc=y}} the interaction with escitalopram had not been studied, but some monographs warned of the potential interaction.<ref name="Drugs.com-Cit-Bup-Interact">{{cite web|title=Drug interactions between bupropion and Lexapro|url=https://www.drugs.com/drug-interactions/bupropion-with-lexapro-440-0-1013-565.html?professional=1|website=Drugs.com|access-date=22 April 2018|archive-date=23 April 2018|archive-url=https://web.archive.org/web/20180423033440/https://www.drugs.com/drug-interactions/bupropion-with-lexapro-440-0-1013-565.html?professional=1|url-status=live}}</ref> Citalopram did not affect the pharmacokinetics of bupropion or its metabolites in the study.<ref name="Drugs.com-Cit-Bup-Interact" />

Escitalopram should be taken with caution when using [[Hypericum perforatum|St. John's wort]], [[ginseng]], [[Dextromethorphan|dextromethorphan (DXM)]], [[linezolid]], tramadol, and other serotonergic drugs due to the risk of [[serotonin syndrome]].<ref>{{cite book|title=2006 Lippincott's Nursing Drug Guide| vauthors = Karch A |publisher=Lippincott Williams & Wilkins|year=2006|isbn=978-1-58255-436-5|location=Philadelphia, Baltimore, New York, London, Buenos Aires, Hong Kong, Sydney, Tokyo}}</ref><ref>{{cite journal | vauthors = Boyer EW, Shannon M | title = The serotonin syndrome | journal = The New England Journal of Medicine | volume = 352 | issue = 11 | pages = 1112–1120 | date = March 2005 | pmid = 15784664 | doi = 10.1056/NEJMra041867 }}</ref> As an SSRI, escitalopram should not be given concurrently with [[Monoamine oxidase inhibitor|MAOIs]].<ref name="GG" />

Escitalopram, similarly to other SSRIs, may increase bleeding risk with [[Nonsteroidal anti-inflammatory drug|NSAIDs]] ([[ibuprofen]], [[naproxen]], [[mefenamic acid]]), [[Antiplatelet drug|antiplatelet drugs]], [[Anticoagulant|anticoagulants]], [[Omega-3 fatty acid|omega-3 fatty acids]], [[vitamin E]], and garlic [[Dietary supplement|supplements]] due to escitalopram's inhibitory effects on [[platelet aggregation]] via blocking [[Serotonin transporter|serotonin transporters]] on platelets.<ref>{{cite web |title=UpToDate |url=https://www.uptodate.com/content-not-available |access-date=10 August 2022 |website=www.uptodate.com |archive-date=9 August 2022 |archive-url=https://web.archive.org/web/20220809223839/https://www.uptodate.com/content-not-available |url-status=live }}</ref>

Escitalopram can also prolong the QT interval, and hence it is not recommended in patients who are concurrently on other medications that also can prolong the QT interval. These drugs include [[antiarrhythmics]], [[antipsychotic]]s, [[tricyclic antidepressant]]s, some [[antihistamine]]s ([[astemizole]], [[mizolastine]]), [[Macrolide antibiotic|macrolide]] and [[Quinolone antibiotic|fluoroquinolone]] [[Antibiotic|antibiotics]], some [[5-HT3 antagonist|5-HT<sub>3</sub> receptor antagonists]] (except palonosetron), and some [[antiretrovirals]] ([[ritonavir]], [[saquinavir]], [[lopinavir]]).<ref name=":0" />

==Pharmacology==

===Mechanism of action===
{| class="wikitable" style="float:right;width:200px;margin:10px;"
|+Binding profile<ref name="pmid24424469">{{cite journal | vauthors = Sanchez C, Reines EH, Montgomery SA | title = A comparative review of escitalopram, paroxetine, and sertraline: Are they all alike? | journal = International Clinical Psychopharmacology | volume = 29 | issue = 4 | pages = 185–196 | date = July 2014 | pmid = 24424469 | pmc = 4047306 | doi = 10.1097/YIC.0000000000000023 }}</ref><ref name = "HH">{{cite journal | vauthors = Chae YJ, Jeon JH, Lee HJ, Kim IB, Choi JS, Sung KW, Hahn SJ | title = Escitalopram block of hERG potassium channels | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | volume = 387 | issue = 1 | pages = 23–32 | date = January 2014 | pmid = 24045971 | doi = 10.1007/s00210-013-0911-y | s2cid = 15062534 }}</ref>
|-

! style="font-weight:bold; background-color:#c0c0c0;" | Site
! style="font-weight:bold; background-color:#c0c0c0;" | K<sub>i</sub> (nM)
|-
| [[Serotonin transporter|SERT]]
| style="text-align:right;" | 0.8–1.1
|-
| [[Norepinephrine transporter|NET]]
| style="text-align:right;" | 7,800
|-
| [[Dopamine transporter|DAT]]
| style="text-align:right;" | 27,400
|-
| [[5-HT1A receptor|5-HT<sub>1A</sub>]]
| style="text-align:right;" | >1,000
|-
| [[5-HT2A receptor|5-HT<sub>2A</sub>]]
| style="text-align:right;" | >1,000
|-
| [[5-HT2C|5-HT<sub>2C</sub>]]
| style="text-align:right;" | 2,500
|-
| [[Alpha-1 adrenergic receptor|α<sub>1</sub>]]
| style="text-align:right;" | 3,900
|-
| [[Alpha-2 adrenergic receptor|α<sub>2</sub>]]
| style="text-align:right;" | >1,000
|-
| [[Dopamine receptor D2|D<sub>2</sub>]]
| style="text-align:right;" | >1,000
|-
| [[Histamine H1 receptor|H<sub>1</sub>]]
| style="text-align:right;" | 2,000
|-
| [[Muscarinic acetylcholine receptor|mACh]]
| style="text-align:right;" | 1,240
|-
| [[hERG]]
| style="text-align:right;" | 2,600 (IC<sub>50</sub>)
|}

Escitalopram increases intrasynaptic levels of the neurotransmitter [[serotonin]] by blocking the [[reuptake]] of the neurotransmitter into the presynaptic neuron. Over time, this leads to a downregulation of pre-synaptic [[5-HT1A receptor|5-HT<sub>1A</sub> receptors]], which is associated with an improvement in passive stress tolerance, and delayed downstream increase in expression of [[brain-derived neurotrophic factor]], which may contribute to a reduction in negative affective biases.<ref>{{cite journal | vauthors = Carhart-Harris RL, Nutt DJ | title = Serotonin and brain function: a tale of two receptors | journal = Journal of Psychopharmacology | volume = 31 | issue = 9 | pages = 1091–1120 | date = September 2017 | pmid = 28858536 | pmc = 5606297 | doi = 10.1177/0269881117725915 }}</ref><ref>{{cite journal | vauthors = Harmer CJ, Duman RS, Cowen PJ | title = How do antidepressants work? New perspectives for refining future treatment approaches | language = English | journal = The Lancet. Psychiatry | volume = 4 | issue = 5 | pages = 409–418 | date = May 2017 | pmid = 28153641 | pmc = 5410405 | doi = 10.1016/S2215-0366(17)30015-9 }}</ref>

Of the SSRIs currently available, escitalopram has the highest [[Selectivity (pharmacology)|selectivity]] for the [[serotonin transporter]] (SERT) compared to the [[norepinephrine transporter]] (NET), making the side-effect profile relatively mild in comparison to less-selective SSRIs.<ref name="GG">Brunton L, Chabner B, Knollman B. Goodman and Gilman's The Pharmacological Basis of Therapeutics, Twelfth Edition. McGraw Hill Professional; 2010.</ref> In addition to its antagonist action at the [[orthosteric site]] of SERT, escitalopram also binds to an [[Allosteric serotonin reuptake inhibitor|allosteric site]] on the transporter, thereby decreasing its disassociation rate.<ref>{{cite journal | vauthors = Zhong H, Haddjeri N, Sánchez C | title = Escitalopram, an antidepressant with an allosteric effect at the serotonin transporter--a review of current understanding of its mechanism of action | journal = Psychopharmacology | volume = 219 | issue = 1 | pages = 1–13 | date = January 2012 | pmid = 21901317 | doi = 10.1007/s00213-011-2463-5 }}</ref> Escitalopram binds to this allosteric site at a greater affinity than other SSRIs.<ref>{{cite journal | vauthors = Mansari ME, Wiborg O, Mnie-Filali O, Benturquia N, Sánchez C, Haddjeri N | title = Allosteric modulation of the effect of escitalopram, paroxetine and fluoxetine: in-vitro and in-vivo studies | journal = The International Journal of Neuropsychopharmacology | volume = 10 | issue = 1 | pages = 31–40 | date = February 2007 | pmid = 16448580 | doi = 10.1017/S1461145705006462 | url = https://hal.science/hal-03893598 }}</ref> The clinical relevance of this action is unknown. 

===Pharmacokinetics===
Escitalopram is a substrate of [[P-glycoprotein]] and hence P-glycoprotein inhibitors such as [[verapamil]] and [[quinidine]] may improve its [[Blood–brain barrier| blood-brain barrier]] penetrability.<ref name = ESC/> In a preclinical study in rats combining escitalopram with a P-glycoprotein inhibitor, its antidepressant-like effects were enhanced.<ref name = ESC>{{cite journal | vauthors = O'Brien FE, O'Connor RM, Clarke G, Dinan TG, Griffin BT, Cryan JF | title = P-glycoprotein inhibition increases the brain distribution and antidepressant-like activity of escitalopram in rodents | journal = Neuropsychopharmacology | volume = 38 | issue = 11 | pages = 2209–2219 | date = October 2013 | pmid = 23670590 | pmc = 3773671 | doi = 10.1038/npp.2013.120 }}</ref>

==Chemistry==
Escitalopram is the (''S'')-[[enantiomer]] (left-handed version) of the [[racemate]] [[citalopram]], which is responsible for its name: ''es''citalopram.<ref name=AHFS2017/><ref name="Meylers 2016">{{cite book |title=Meyler's Side Effects of Drugs |date=2016 |publisher=Elsevier |page=383 |edition=6 |chapter=Citalopram and escitalopram}}</ref>

==History==
[[Image:Cipralex.jpg|thumb|right|Cipralex brand escitalopram 10 mg package and tablet sheet. It is a reference escitalopram formulation, and was produced by [[Lundbeck]].]]
Escitalopram was developed in cooperation between [[Lundbeck]] and [[Forest Laboratories]]. Its development was initiated in 1997, and the resulting new drug application was submitted to the US FDA in March 2001. The short time (3.5 years) it took to develop escitalopram can be attributed to the previous experience of Lundbeck and Forest with citalopram, which has similar pharmacology.<ref>{{cite web | title=2000 Annual Report. p 28 and 33 | url=http://www.materials.lundbeck.com/lundbeck/82/fullpdf/1.pdf | year=2000 | publisher=Lundbeck | access-date=7 April 2007 | archive-date=27 September 2007 | archive-url=https://web.archive.org/web/20070927215329/http://www.materials.lundbeck.com/lundbeck/82/fullpdf/1.pdf | url-status=live }}</ref>

==Society and culture==
===Brand names===
Escitalopram is sold under many brand names worldwide such as Cipralex, Lexapro, Lexam, Mozarin, Aciprex, Depralin, Ecytara, Elicea, Gatosil, Nexpram, Nexito, Nescital, Szetalo, Stalopam, Pramatis, Betesda, Scippa and Rexipra.<ref name=drugsINT>{{cite web | url = https://www.drugs.com/international/escitalopram.html | work = Drugs.com International | title = Escitalopram | archive-url = https://web.archive.org/web/20200619204531/https://www.drugs.com/international/escitalopram.html | archive-date=19 June 2020 | access-date = 25 April 2015 }}</ref><ref name=gdziepolek>{{cite web | url = https://www.gdziepolek.pl/produkty/50443/mozarin-tabletki-powlekane/zamienniki | work = Gdziepolek.pl | title = Mozarin, zamienniki i podobne rodukty | archive-url = https://web.archive.org/web/20201017185633/https://www.gdziepolek.pl/produkty/50443/mozarin-tabletki-powlekane/zamienniki | archive-date=17 October 2020 | access-date = 17 October 2020 | language = Polish }}</ref>

=== Legal status ===
The FDA issued the approval of escitalopram for major depression in August 2002, and for generalized anxiety disorder in December 2003. In May 2006, the FDA approved a generic version of escitalopram by [[Teva Pharmaceutical Industries|Teva]].<ref>{{cite web | vauthors = Miranda H | title = FDA OKs Generic Depression Drug – Generic Version of Lexapro Gets Green Light | url = http://www.webmd.com/content/article/122/114778.htm | website = WebMD | access-date = 10 October 2007 | archive-date = 5 January 2007 | archive-url = https://web.archive.org/web/20070105232212/http://www.webmd.com/content/article/122/114778.htm | url-status = live }}</ref> In July 2006, the [[United States District Court for the District of Delaware|U.S. District Court of Delaware]] decided in favor of Lundbeck regarding a patent infringement dispute and ruled the patent on escitalopram valid.<ref>{{cite news |vauthors=Laforte ME |title=US court upholds Lexapro patent |date=14 July 2006 |url=http://www.firstwordplus.com/Fws.do?articleid=7474B41ED0D14C20894E262219E24B62 |publisher=FirstWord |access-date=10 October 2007 |archive-date=30 October 2021 |archive-url=https://web.archive.org/web/20211030132727/http://www.firstwordplus.com/Fws.do?articleid=7474B41ED0D14C20894E262219E24B62 |url-status=live }}</ref>

In 2006, Forest Laboratories was granted an 828-day (2 years and 3 months) extension on its US patent for escitalopram.<ref>{{cite press release| title = Forest Laboratories Receives Patent Term Extension for Lexapro| publisher = PRNewswire-FirstCall| date = 2 March 2006| url = http://www.frx.com/news/PressRelease.aspx?ID=824655| access-date = 19 January 2009| archive-date = 15 April 2009| archive-url = https://web.archive.org/web/20090415161937/http://www.frx.com/news/PressRelease.aspx?ID=824655| url-status = live}}</ref> This pushed the patent expiration date from 7 December 2009, to 14 September 2011. Together with the 6-month pediatric exclusivity, the final expiration date was 14 March 2012.

===Allegations of illegal marketing===
In 2004, separate civil suits alleging illegal marketing of citalopram and escitalopram for use by children and teenagers by Forest were initiated by two whistleblowers: a physician named Joseph Piacentile and a Forest salesman named Christopher Gobble.<ref>{{cite web | vauthors = Frankel A | date = 27 February 2009 | url = http://www.law.com/jsp/article.jsp?id=1202428657301 | title = Forest Laboratories: A Tale of Two Whistleblowers | archive-url = https://web.archive.org/web/20090228182230/http://www.law.com/jsp/article.jsp?id=1202428657301 | archive-date=28 February 2009 | work = [[The American Lawyer]] }}</ref> In February 2009, the suits were joined. Eleven states and the District of Columbia filed notices of intent to intervene as plaintiffs in the action.

The suits alleged that Forest illegally engaged in off-label promotion of Lexapro for use in children; hid the results of a study showing lack of effectiveness in children; paid [[Kickback (bribery)|kickbacks]] to physicians to induce them to prescribe Lexapro to children; and conducted so-called "seeding studies" that were, in reality, marketing efforts to promote the drug's use by doctors.<ref>{{cite web | url = http://amlawdaily.typepad.com/forestfca.pdf | title = United States of America v. Forest Laboratories | archive-url = https://web.archive.org/web/20090311044425/http://amlawdaily.typepad.com/forestfca.pdf | archive-date=11 March 2009 | work = US District Court for the district of Massachusetts }}</ref><ref>{{cite web | url = https://www.nytimes.com/2009/02/26/business/26drug.html | title = Drug Maker Is Accused of Fraud | archive-url = https://web.archive.org/web/20201111221358/http://www.nytimes.com/2009/02/26/business/26drug.html | archive-date=11 November 2020 | vauthors = Meier B, Carey B | work = [[The New York Times]] | date = 25 February 2009 }}</ref> Forest denied the allegations<ref>{{cite web | url = http://www.frx.com/news/PressRelease.aspx?ID=1260234 | title = Forest Laboratories, Inc. Provides Statement in Response to Complaint Filed by U.S. Government | archive-url = https://archive.today/20130124030551/http://www.frx.com/news/PressRelease.aspx?ID=1260234 | archive-date=24 January 2013 | work = Forest press-release | date = 26 February 2009 }}</ref> but ultimately agreed to settle with the plaintiffs for over $313 million.<ref>{{cite web|url=https://www.justice.gov/opa/pr/drug-maker-forest-pleads-guilty-pay-more-313-million-resolve-criminal-charges-and-false|title=Drug Maker Forest Pleads Guilty; To Pay More Than $313 Million to Resolve Criminal Charges and False Claims Act Allegations|website=www.justice.gov|date=15 September 2010|access-date=22 November 2020|archive-date=30 November 2020|archive-url=https://web.archive.org/web/20201130151443/https://www.justice.gov/opa/pr/drug-maker-forest-pleads-guilty-pay-more-313-million-resolve-criminal-charges-and-false|url-status=live}}</ref>

== See also ==
* [[List of antidepressants]]

== References ==
{{Reflist}}

== External links ==
* {{cite web | vauthors = Harris G | title=A Peek at How Forest Laboratories Pushed Lexapro | website=[[The New York Times]] | date=1 September 2009 | url= https://www.nytimes.com/2009/09/02/business/02drug.html }}

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