Pharmaceutical compound EscitalopramClinical dataPronunciation/ˌɛsəˈtæləˌpræm/ Trade namesCipralex, Lexapro, others[1]Other names(S)-Citalopram; S-Citalopram; S-(+)-Citalopram; S(+)-Citalopram; (+)-Citalopram; LU-26054; MLD-55AHFS/Drugs.comMonographMedlinePlusa603005License data US DailyMed: Escitalopram Pregnancycategory AU: C Routes ofadministrationBy mouthDrug classSelective serotonin reuptake inhibitor (SSRI)ATC codeN06AB10 (WHO) Legal statusLegal status AU: S4 (Prescription only)[2] BR: Class C1 (Other controlled substances)[3] CA: ℞-only UK: POM (Prescription only) US: ℞-only[4] EU: Rx-only[5] In general: ℞ (Prescription only) Pharmacokinetic dataBioailability~80%[6][7]Protein binding~55–56% (low)[6][7]MetabolismLiver (CYP2C19, CYP3A4, CYP2D6)[6][7]Metabolites• Desmethylcitalopram[6][7]• Didesmethylcitalopram[6][7]Elimination half-life~27–32 hours[6]ExcretionUrine (major; 8–10% unchanged), feces (minor)[7]Identifiers IUPAC name (S)-1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile CAS Number128196-01-0 YPubChem CID146570DrugBankDB01175 YChemSpider129277 YUNII4O4S742ANYKEGGD07913ChEBICHEBI:36791 YChEMBLChEMBL1508 YCompTox Dashboard (EPA)DTXSID8048440 ECHA InfoCard100.244.188 Chemical and physical dataFormulaC20H21FN2OMolar mass324.399 g·mol−13D model (JSmol)Interactive imageChiralityLevorotatory enantiomer SMILES Fc1ccc(cc1)[C@@]3(OCc2cc(C#N)ccc23)CCCN(C)C 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 YKey:WSEQXVZVJXJVFP-FQEVSTJZSA-N Y (verify)
Escitalopram ( /ˌɛsəˈtæləˌpræm/ ⓘ eh-sə-TA-lə-pram), sold under the brand names Lexapro and Cipralex, among others, is an antidepressant medication of the selective serotonin reuptake inhibitor (SSRI) class.[8] It is mainly used to treat major depressive disorder,[8] generalized anxiety disorder,[8] panic disorder, obsessive–compulsive disorder (OCD), and social anxiety disorder. Escitalopram is taken by mouth.[8] For commercial use, it is formulated as an oxalate salt exclusively.
Common side effects include headache, nausea, sexual problems, mild sedation, and trouble sleeping.[8] More serious side effects may include suicidal thoughts in people up to the age of 24 years.[8] It is unclear if use during pregnancy or breastfeeding is safe.[9] Escitalopram is the (S)-enantiomer of citalopram (which exists as a racemate), hence the name es-citalopram.[8]
Escitalopram was approved for medical use in the United States in 2002.[8] Escitalopram is rarely replaced by twice the dose of citalopram; escitalopram is safer and more effective.[10] It is on the World Health Organization's List of Essential Medicines.[11] In 2023, it was the second most prescribed antidepressant and fourteenth most commonly prescribed medication in the United States, with more than 37 million prescriptions.[12][13] In Australia, it was one of the top 10 most prescribed medications between 2017 and 2023.[14]
Other first-line SSRIs that he similar results include sertraline, paroxetine, and fluoxetine, among others.
Medical uses[edit]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.[8][15] In European countries including the United Kingdom, it is approved for depression and anxiety disorders; these include: generalized anxiety disorder, social anxiety disorder (SAD), obsessive–compulsive disorder (OCD), and panic disorder with or without agoraphobia. In Australia it is approved for major depressive disorder.[16][17][18]
Depression[edit]Escitalopram is among the most effective and well-tolerated antidepressants for the short-term treatment of major depressive disorder in adults.[19][20] It also seems to be the safest one to give to children and adolescents.[21][22]
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[update], reviews had concluded (with ceats in some cases) that escitalopram is modestly superior to citalopram in efficacy and tolerability.[23][24][25][26]
Anxiety disorders[edit]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.[27][28] Escitalopram appears effective in treating social anxiety disorder as well.[29]
Other[edit]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.[30] It is also occasionally prescribed off-label for insomnia secondary to a mental disorder, and vasomotor symptoms (hot flashes) associated with menopause.[15]
Side effects[edit]Escitalopram has a relatively forable 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[31]
Similar to other SSRIs, escitalopram has been shown to affect sexual function, causing delayed ejaculation, and anorgasmia.[32][33]
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.[34][35][36] 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.[37]
Citalopram and escitalopram are associated with a mild dose-dependent QT interval prolongation,[38] 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[39] 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 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.[40] A QTc increase of less than 60 ms is not likely to confer significant risk.[39] 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.[39]
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).[41] 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.[41]
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, and electrolyte disturbances should be corrected before starting treatment. In December 2011, the UK implemented new restrictions on the maximum daily doses at 20 mg for adults and 10 mg for those older than 65 years or with liver impairment.[42][43] The US Food and Drug Administration and Health Canada did not similarly order restrictions on escitalopram dosage, only on its predecessor citalopram.[44]
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 SIADH.[45] This is typically not dose-dependent and at higher risk for occurrence within the first few weeks of starting treatment.[46]
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.[15]
Very common effects[edit]Very common effects (>10% incidence) include:[15][47][48][4][49]
Headache (24%) Nausea (18%) Ejaculation disorders (9–14%) Somnolence (4–13%) Insomnia (7–12%) Common (1–10% incidence)[edit]Common effects (1–10% incidence) include:
Abnormal dreams Anisocoria Anorgasmia Anxiety Arthralgia (joint pain) Constipation Decreased or increased appetite Diarrhea Dilated pupils Dizziness Dry mouth Excessive sweating Fatigue Fever Impotence (erectile dysfunction) Libido changes Myalgia (muscular aches and pains) Paraesthesia (abnormal skin sensation) Restlessness Sinusitis (nasal congestion) Tremor Vomiting Yawning Psychomotor effects[edit]The most common effect is fatigue or somnolence, particularly in older adults,[50] although patients with pre-existing daytime sleepiness and fatigue may experience paradoxical improvement of these symptoms.[51]
Escitalopram has not been shown to affect serial reaction time, logical reasoning, serial subtraction, multitasking, or Mackworth Clock task performance.[52]
Sexual dysfunction[edit]Some people experience persistent sexual side effects when taking SSRIs or after discontinuing them.[53] Symptoms of medication-induced sexual dysfunction from antidepressants include difficulty with orgasm, erection, or ejaculation.[53] 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.[54]
Pregnancy[edit]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 g), and lower Apgar scores (by 1,000 5-HT2A >1,000 5-HT2C 2,500 α1 3,900 α2 >1,000 D2 >1,000 H1 2,000 mACh 1,240 hERG 2,600 (IC50)
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 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.[69][70]
Of the SSRIs currently ailable, escitalopram has the highest 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.[65] In addition to its antagonist action at the orthosteric site of SERT, escitalopram also binds to an allosteric site on the transporter, thereby decreasing its disassociation rate.[71] Escitalopram binds to this allosteric site at a greater affinity than other SSRIs.[72] The clinical relevance of this action is unknown.
Pharmacokinetics[edit]Escitalopram is a substrate of P-glycoprotein and hence P-glycoprotein inhibitors such as verapamil and quinidine may improve its blood-brain barrier penetrability.[73] In a preclinical study in rats combining escitalopram with a P-glycoprotein inhibitor, its antidepressant-like effects were enhanced.[73]
Chemistry[edit]Escitalopram is the (S)-enantiomer (left-handed version) of the racemate citalopram, which is responsible for its name: escitalopram.[8][74]
History[edit] 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.[75]
Society and culture[edit] Brand names[edit]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.[1][76]
Legal status[edit]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.[77] In July 2006, the U.S. District Court of Delaware decided in for of Lundbeck regarding a patent infringement dispute and ruled the patent on escitalopram valid.[78]
In 2006, Forest Laboratories was granted an 828-day (2 years and 3 months) extension on its US patent for escitalopram.[79] 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[edit]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.[80] 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 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.[81][82] Forest denied the allegations[83] but ultimately agreed to settle with the plaintiffs for over $313 million.[84]
See also[edit] List of antidepressants References[edit] ^ a b "Escitalopram". Drugs.com International. Archived from the original on 19 June 2020. Retrieved 25 April 2015. ^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024. ^ 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. ^ a b "Lexapro- escitalopram tablet, film coated; Lexapro- escitalopram solution". DailyMed. 17 November 2023. Retrieved 31 December 2023. ^ 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. ^ a b c d e f g h i 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. ^ a b c d e f g h i j Rao N (2007). "The clinical pharmacokinetics of escitalopram". Clin Pharmacokinet. 46 (4): 281–290. doi:10.2165/00003088-200746040-00002. PMID 17375980. ^ a b c d e f g h i j "X". The American Society of Health-System Pharmacists. Archived from the original on 29 December 2017. Retrieved 28 December 2017. ^ "Escitalopram (Lexapro) Use During Pregnancy". Drugs.com. Archived from the original on 31 December 2017. Retrieved 31 December 2017. ^ "Protocol for switching patients from escitalopram to citalopram". NHS. 2015. Archived from the original on 10 August 2020. Retrieved 13 February 2018. ^ 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. ^ "Top 300 of 2023". ClinCalc. Archived from the original on 12 August 2025. Retrieved 12 August 2025. ^ "Escitalopram Drug Usage Statistics, United States, 2014 - 2023". ClinCalc. Retrieved 12 August 2025. ^ "Medicines in the health system". Australian Institute of Health and Welfare. 2 July 2024. Retrieved 30 September 2024. ^ a b c d "Lexapro (escitalopram) dosing, indications, interactions, adverse effects, and more". Medscape. Archived from the original on 2 December 2013. Retrieved 9 April 2025. ^ "Escitalopram oxalate". Australian Prescriber. 26: 146–151. 2003. doi:10.18773/austprescr.2003.107. Archived from the original on 10 June 2020. Retrieved 15 March 2020. ^ "Lundbeck's Cipralex gets EU ok for OCD treatment". Reuters. 12 January 2007. Archived from the original on 10 June 2020. Retrieved 15 March 2020. ^ "Cipralex 10 mg film-coated tablets - Summary of Product Characteristics (SmPC) - (emc)". www.medicines.org.uk. Archived from the original on 10 June 2020. Retrieved 15 March 2020. ^ "The most effective antidepressants for adults revealed in major review". NIHR Evidence (Plain English summary). National Institute for Health and Care Research. 3 April 2018. doi:10.3310/signal-00580. ^ Cipriani A, Furukawa TA, Salanti G, Chaimani A, Atkinson LZ, Ogawa Y, et al. (April 2018). "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". Lancet. 391 (10128): 1357–1366. doi:10.1016/S0140-6736(17)32802-7. PMC 5889788. PMID 29477251. ^ "Psychiatric drugs given to children and adolescents he been ranked in order of safety". NIHR Evidence (Plain English summary). National Institute for Health and Care Research. 1 September 2020. doi:10.3310/alert_40795. S2CID 241309451. ^ Solmi M, Fornaro M, Ostinelli EG, Zangani C, Croatto G, Monaco F, et al. (June 2020). "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". World Psychiatry. 19 (2): 214–232. doi:10.1002/wps.20765. PMC 7215080. PMID 32394557. ^ Ramsberg J, Asseburg C, Henriksson M (2012). "Effectiveness and cost-effectiveness of antidepressants in primary care: a multiple treatment comparison meta-analysis and cost-effectiveness model". PLOS ONE. 7 (8) e42003. Bibcode:2012PLoSO...742003R. doi:10.1371/journal.pone.0042003. PMC 3410906. PMID 22876296. ^ Cipriani A, Purgato M, Furukawa TA, Trespidi C, Imperadore G, Signoretti A, et al. (July 2012). "Citalopram versus other anti-depressive agents for depression". The Cochrane Database of Systematic Reviews. 2012 (7) CD006534. doi:10.1002/14651858.CD006534.pub2. PMC 4204633. PMID 22786497. ^ Fré P (February 2012). "[Clinical efficacy and achievement of a complete remission in depression: increasing interest in treatment with escitalopram]" [Clinical efficacy and achievement of a complete remission in depression: Increasing interest in treatment with escitalopram]. L'Encéphale (in French). 38 (1): 86–96. doi:10.1016/j.encep.2011.11.003. PMID 22381728. ^ Sicras-Mainar A, Narro-Artieda R, Blanca-Tamayo M, Gimeno-de la Fuente V, Salvatella-Pasant J (December 2010). "Comparison of escitalopram vs. citalopram and venlafaxine in the treatment of major depression in Spain: clinical and economic consequences". Current Medical Research and Opinion. 26 (12): 2757–2764. doi:10.1185/03007995.2010.529430. PMID 21034375. S2CID 43179425. ^ Slee A, Nazareth I, Bondaronek P, Liu Y, Cheng Z, Freemantle N (February 2019). "Pharmacological treatments for generalised anxiety disorder: a systematic review and network meta-analysis". Lancet. 393 (10173): 768–777. doi:10.1016/S0140-6736(18)31793-8. PMID 30712879. S2CID 72332967. ^ Bech P, Lönn SL, Overø KF (February 2010). "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". The Journal of Clinical Psychiatry. 71 (2): 121–129. doi:10.4088/JCP.08m04749blu. PMID 19961809. ^ Baldwin DS, Asakura S, Koyama T, Hayano T, Hagino A, Reines E, et al. (June 2016). "Efficacy of escitalopram in the treatment of social anxiety disorder: A meta-analysis versus placebo". European Neuropsychopharmacology. 26 (6): 1062–1069. doi:10.1016/j.euroneuro.2016.02.013. PMID 26971233. ^ Jespersen C, Lauritsen MP, Frokjaer VG, Schroll JB (August 2024). "Selective serotonin reuptake inhibitors for premenstrual syndrome and premenstrual dysphoric disorder". The Cochrane Database of Systematic Reviews. 2024 (8) CD001396. doi:10.1002/14651858.CD001396.pub4. PMC 11323276. PMID 39140320. ^ a b c "Lexapro prescribing guide" (PDF). Allergan. ^ Clayton A, Keller A, McGarvey EL (March 2006). "Burden of phase-specific sexual dysfunction with SSRIs". Journal of Affective Disorders. 91 (1): 27–32. doi:10.1016/j.jad.2005.12.007. PMID 16430968. ^ "Lexapro prescribing information" (PDF). Archived (PDF) from the original on 15 August 2018. Retrieved 23 August 2017. ^ Levenson M, Holland C. "Antidepressants and Suicidality in Adults: Statistical Evaluation. (Presentation at Psychopharmacologic Drugs Advisory Committee; December 13, 2006)". Food and Drug Administration. Archived from the original on 27 September 2007. Retrieved 13 May 2007. ^ Stone MB, Jones ML (17 November 2006). "Clinical Review: Relationship Between Antidepressant Drugs and Suicidality in Adults" (PDF). Overview for 13 December Meeting of Pharmacological Drugs Advisory Committee (PDAC). FDA. pp. 11–74. Archived from the original (PDF) on 16 March 2007. Retrieved 22 September 2007. ^ Levenson M, Holland C (17 November 2006). "Statistical Evaluation of Suicidality in Adults Treated with Antidepressants" (PDF). Overview for 13 December Meeting of Pharmacological Drugs Advisory Committee (PDAC). FDA. pp. 75–140. Archived from the original (PDF) on 16 March 2007. Retrieved 22 September 2007. ^ Khan A, Schwartz K (2007). "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". Annals of Clinical Psychiatry. 19 (1): 31–36. doi:10.1080/10401230601163550. PMID 17453659. ^ Castro VM, Clements CC, Murphy SN, Gainer VS, Fa M, Weilburg JB, et al. (January 2013). "QT interval and antidepressant use: a cross sectional study of electronic health records". BMJ. 346: f288. doi:10.1136/bmj.f288. PMC 3558546. PMID 23360890. ^ a b c Lam RW (March 2013). "Antidepressants and QTc prolongation". Journal of Psychiatry & Neuroscience. 38 (2): E5 – E6. doi:10.1503/jpn.120256. PMC 3581598. PMID 23422053. 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. ^ US FDA (15 December 2017). "FDA Drug Safety Communication: Revised recommendations for Celexa (citalopram hydrobromide) related to a potential risk of abnormal heart rhythms with high doses". US FDA. Archived from the original on 13 December 2019. Retrieved 1 May 2024. ^ a b Danielsson B, Collin J, Nyman A, Bergendal A, Borg N, State M, et al. (March 2020). "Drug use and torsades de pointes cardiac arrhythmias in Sweden: a nationwide register-based cohort study". BMJ Open. 10 (3) e034560. doi:10.1136/bmjopen-2019-034560. PMC 7069257. PMID 32169926. ^ a b "Citalopram and escitalopram: QT interval prolongation—new maximum daily dose restrictions (including in elderly patients), contraindications, and warnings". Medicines and Healthcare products Regulatory Agency. December 2011. Archived from the original on 6 March 2013. Retrieved 5 March 2013. ^ van Gorp F, Whyte IM, Isbister GK (September 2009). "Clinical and ECG effects of escitalopram overdose". Annals of Emergency Medicine. 54 (3): 404–408. doi:10.1016/j.annemergmed.2009.04.016. PMID 19556032. ^ Hasnain M, Howland RH, Vieweg WV (July 2013). "Escitalopram and QTc prolongation". Journal of Psychiatry & Neuroscience. 38 (4): E11. doi:10.1503/jpn.130055. PMC 3692726. PMID 23791140. ^ Leth-Møller KB, Hansen AH, Torstensson M, Andersen SE, Ødum L, Gislasson G, et al. (May 2016). "Antidepressants and the risk of hyponatremia: a Danish register-based population study". BMJ Open. 6 (5) e011200. doi:10.1136/bmjopen-2016-011200. PMC 4874104. PMID 27194321. ^ Naschitz JE (June 2018). "Escitalopram Dose-Dependent Hyponatremia". Journal of Clinical Pharmacology. 58 (6): 834–835. doi:10.1002/jcph.1091. PMID 29878443. ^ "Cipralex 5, 10 and 20 mg film-coated tablets - Summary of Product Characteristics (SPC)". electronic Medicines Compendium. 2 October 2013. Archived from the original on 3 December 2013. Retrieved 27 November 2013. ^ "Escitalopram-Lupin Tablets (LUPIN AUSTRALIA PTY. LTD)" (PDF). TGA eBusiness Services. Lupin Australia Pty Ltd. 21 December 2011. Archived from the original on 29 March 2019. Retrieved 27 November 2013. ^ Mancano MA (May 2016). "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". Hospital Pharmacy. 51 (5). Thomas Land Publishers, Inc.: 358–361. doi:10.1310/hpj5105-358. PMC 4896342. PMID 27303087. ^ Lenze EJ (20 May 2009). "Escitalopram Treatment of Generalized Anxiety Disorder in Older Adults—Reply". JAMA. 301 (19): 1987. doi:10.1001/jama.2009.652. ISSN 0098-7484. ^ Shen J, Hossain N, Streiner DL, Rindran , Wang X, Deb P, et al. (November 2011). "Excessive daytime sleepiness and fatigue in depressed patients and therapeutic response of a sedating antidepressant". Journal of Affective Disorders. 134 (1–3): 421–426. doi:10.1016/j.jad.2011.04.047. PMID 21616541. ^ Rosekind MR, Gregory KB, Mallis MM (December 2006). "Alertness management in iation operations: enhancing performance and sleep". Aviation, Space, and Environmental Medicine. 77 (12): 1256–1265. doi:10.3357/asem.1879.2006 (inactive 18 July 2025). PMID 17183922.{{cite journal}}: CS1 maint: DOI inactive as of July 2025 (link) ^ a b American Psychiatric Association (2013). Diagnostic and Statistical Manual of Mental Disorders (5th ed.). Arlington, VA: American Psychiatric Publishing. pp. 446–449. ISBN 978-0-89042-555-8. ^ Bala A, Nguyen HM, Hellstrom WJ (January 2018). "Post-SSRI Sexual Dysfunction: A Literature Review". Sexual Medicine Reviews. 6 (1): 29–34. doi:10.1016/j.sxmr.2017.07.002. PMID 28778697. ^ Ross LE, Grigoriadis S, Mamisashvili L, Vonderporten EH, Roerecke M, Rehm J, et al. (April 2013). "Selected pregnancy and delivery outcomes after exposure to antidepressant medication: a systematic review and meta-analysis". JAMA Psychiatry. 70 (4): 436–443. doi:10.1001/jamapsychiatry.2013.684. PMID 23446732. S2CID 2065578. ^ a b Gentile S (1 July 2015). "Early pregnancy exposure to selective serotonin reuptake inhibitors, risks of major structural malformations, and hypothesized teratogenic mechanisms". Expert Opinion on Drug Metabolism & Toxicology. 11 (10): 1585–1597. doi:10.1517/17425255.2015.1063614. PMID 26135630. S2CID 43329515. ^ Prakash O, Dhar V (June 2008). "Emergence of electric shock-like sensations on escitalopram discontinuation". Journal of Clinical Psychopharmacology. 28 (3): 359–360. doi:10.1097/JCP.0b013e3181727534. PMID 18480703. ^ Yasui-Furukori N, Hashimoto K, Tsuchimine S, Tomita T, Sugawara N, Ishioka M, et al. (June 2016). "Characteristics of Escitalopram Discontinuation Syndrome: A Preliminary Study". Clinical Neuropharmacology. 39 (3): 125–127. doi:10.1097/WNF.0000000000000139. PMID 27171568. S2CID 45460237. ^ "Lexapro (Escitalopram Oxalate) Drug Information: Warnings and Precautions - Prescribing Information at RxList". Archived from the original on 16 June 2008. Retrieved 9 August 2015. ^ Noehr-Jensen L, Zwisler ST, Larsen F, Sindrup SH, Damkier P, Brosen K (December 2009). "Escitalopram is a weak inhibitor of the CYP2D6-catalyzed O-demethylation of (+)-tramadol but does not reduce the hypoalgesic effect in experimental pain". Clinical Pharmacology and Therapeutics. 86 (6): 626–633. doi:10.1038/clpt.2009.154. PMID 19710642. S2CID 29063004. ^ Malling D, Poulsen MN, Søgaard B (September 2005). "The effect of cimetidine or omeprazole on the pharmacokinetics of escitalopram in healthy subjects". British Journal of Clinical Pharmacology. 60 (3): 287–290. doi:10.1111/j.1365-2125.2005.02423.x. PMC 1884771. PMID 16120067. ^ a b "Drug interactions between bupropion and Lexapro". Drugs.com. Archived from the original on 23 April 2018. Retrieved 22 April 2018. ^ Karch A (2006). 2006 Lippincott's Nursing Drug Guide. Philadelphia, Baltimore, New York, London, Buenos Aires, Hong Kong, Sydney, Tokyo: Lippincott Williams & Wilkins. ISBN 978-1-58255-436-5. ^ Boyer EW, Shannon M (March 2005). "The serotonin syndrome". The New England Journal of Medicine. 352 (11): 1112–1120. doi:10.1056/NEJMra041867. PMID 15784664. ^ a b Brunton L, Chabner B, Knollman B. Goodman and Gilman's The Pharmacological Basis of Therapeutics, Twelfth Edition. McGraw Hill Professional; 2010. ^ "UpToDate". www.uptodate.com. Archived from the original on 9 August 2022. Retrieved 10 August 2022. ^ Sanchez C, Reines EH, Montgomery SA (July 2014). "A comparative review of escitalopram, paroxetine, and sertraline: Are they all alike?". International Clinical Psychopharmacology. 29 (4): 185–196. doi:10.1097/YIC.0000000000000023. PMC 4047306. PMID 24424469. ^ Chae YJ, Jeon JH, Lee HJ, Kim IB, Choi JS, Sung KW, et al. (January 2014). "Escitalopram block of hERG potassium channels". Naunyn-Schmiedeberg's Archives of Pharmacology. 387 (1): 23–32. doi:10.1007/s00210-013-0911-y. PMID 24045971. S2CID 15062534. ^ Carhart-Harris RL, Nutt DJ (September 2017). "Serotonin and brain function: a tale of two receptors". Journal of Psychopharmacology. 31 (9): 1091–1120. doi:10.1177/0269881117725915. PMC 5606297. PMID 28858536. ^ Harmer CJ, Duman RS, Cowen PJ (May 2017). "How do antidepressants work? New perspectives for refining future treatment approaches". The Lancet. Psychiatry. 4 (5): 409–418. doi:10.1016/S2215-0366(17)30015-9. PMC 5410405. PMID 28153641. ^ Zhong H, Haddjeri N, Sánchez C (January 2012). "Escitalopram, an antidepressant with an allosteric effect at the serotonin transporter--a review of current understanding of its mechanism of action". Psychopharmacology. 219 (1): 1–13. doi:10.1007/s00213-011-2463-5. PMID 21901317. ^ Mansari ME, Wiborg O, Mnie-Filali O, Benturquia N, Sánchez C, Haddjeri N (February 2007). "Allosteric modulation of the effect of escitalopram, paroxetine and fluoxetine: in-vitro and in-vivo studies". The International Journal of Neuropsychopharmacology. 10 (1): 31–40. doi:10.1017/S1461145705006462. PMID 16448580. ^ a b O'Brien FE, O'Connor RM, Clarke G, Dinan TG, Griffin BT, Cryan JF (October 2013). "P-glycoprotein inhibition increases the brain distribution and antidepressant-like activity of escitalopram in rodents". Neuropsychopharmacology. 38 (11): 2209–2219. doi:10.1038/npp.2013.120. PMC 3773671. PMID 23670590. ^ "Citalopram and escitalopram". Meyler's Side Effects of Drugs (6 ed.). Elsevier. 2016. p. 383. ^ "2000 Annual Report. p 28 and 33" (PDF). Lundbeck. 2000. Archived (PDF) from the original on 27 September 2007. Retrieved 7 April 2007. ^ "Mozarin, zamienniki i podobne rodukty". Gdziepolek.pl (in Polish). Archived from the original on 17 October 2020. Retrieved 17 October 2020. ^ Miranda H. "FDA OKs Generic Depression Drug – Generic Version of Lexapro Gets Green Light". WebMD. Archived from the original on 5 January 2007. Retrieved 10 October 2007. ^ Laforte ME (14 July 2006). "US court upholds Lexapro patent". FirstWord. Archived from the original on 30 October 2021. Retrieved 10 October 2007. ^ "Forest Laboratories Receives Patent Term Extension for Lexapro" (Press release). PRNewswire-FirstCall. 2 March 2006. Archived from the original on 15 April 2009. Retrieved 19 January 2009. ^ Frankel A (27 February 2009). "Forest Laboratories: A Tale of Two Whistleblowers". The American Lawyer. Archived from the original on 28 February 2009. ^ "United States of America v. Forest Laboratories" (PDF). US District Court for the district of Massachusetts. Archived from the original (PDF) on 11 March 2009. ^ Meier B, Carey B (25 February 2009). "Drug Maker Is Accused of Fraud". The New York Times. Archived from the original on 11 November 2020. ^ "Forest Laboratories, Inc. Provides Statement in Response to Complaint Filed by U.S. Government". Forest press-release. 26 February 2009. Archived from the original on 24 January 2013. ^ "Drug Maker Forest Pleads Guilty; To Pay More Than $313 Million to Resolve Criminal Charges and False Claims Act Allegations". www.justice.gov. 15 September 2010. Archived from the original on 30 November 2020. Retrieved 22 November 2020. External links[edit] Harris G (1 September 2009). "A Peek at How Forest Laboratories Pushed Lexapro". The New York Times. vteAntidepressants (N06A)Specific reuptake inhibitors or receptor modulatorsSSRIsTooltip Selective serotonin reuptake inhibitors Citalopram Escitalopram Fluoxetine# Fluvoxamine Indalpine‡ Paroxetine Sertraline Zimelidine‡ SNRIsTooltip Serotonin–norepinephrine reuptake inhibitors Desvenlafaxine Duloxetine Levomilnacipran Milnacipran Tofenacin Venlafaxine NRIsTooltip Norepinephrine reuptake inhibitors Atomoxetine Reboxetine Viloxazine NDRIsTooltip Norepinephrine–dopamine reuptake inhibitors Amineptine‡ Bupropion Nomifensine‡ NaSSAsTooltip Noradrenergic and specific serotonergic antidepressants Mianserin Mirtazapine Setiptiline SARIsTooltip Serotonin antagonist and reuptake inhibitors Etoperidone Nefazodone Trazodone SMSTooltip Serotonin modulator and stimulators Vilazodone Vortioxetine Others Agomelatine Amisulpride Dextromethorphan/bupropion Esketamine Etryptamine‡ Gepirone Indeloxazine Flupentixol Ketamine§ Medifoxamine‡ Metryptamine‡ Oxaflozane‡ Pivagabine‡ Tandospirone Teniloxazine Tianeptine Tricyclic and tetracyclic antidepressantsTCAsTooltip Tricyclic antidepressants Amineptine‡ Amitriptyline# Amitriptylinoxide Amoxapine Butriptyline‡ Clomipramine# Demexiptiline‡ Desipramine Dibenzepin Dimetacrine‡ Dosulepin Doxepin Imipramine Imipraminoxide‡ Iprindole‡ Lofepramine Melitracen Metapramine‡ Nitroxazepine Nortriptyline Noxiptiline Opipramol Pipofezine Propizepine‡ Protriptyline Quinupramine‡ Tianeptine Trimipramine TeCAsTooltip Tetracyclic antidepressants Maprotiline Mianserin Mirtazapine Setiptiline Others Tiazesim Monoamine oxidase inhibitorsNon-selective Irreversible: Benmoxin‡ Iproclozide‡ Iproniazid‡ Isocarboxazid Isoniazid# Linezolid# Mebanazine‡ Nialamide‡ Octamoxin‡ Phenelzine Pheniprazine‡ Phenoxypropazine‡ Pivhydrazine‡ Safrazine‡ Tedizolid Tranylcypromine Reversible: Caroxazone‡ Mixed: Bifemelane MAOATooltip Monoamine oxidase A-selective Reversible: Eprobemide Metralindole Minaprine‡ Moclobemide Pirlindole Tetrindole Toloxatone MAOBTooltip Monoamine oxidase B-selective Irreversible: Selegiline Adjunctive therapies Atypical antipsychotics (aripiprazole, brexpiprazole, lurasidone, olanzapine, quetiapine, risperidone) Buspirone Lithium (lithium carbonate, lithium citrate) Thyroid hormones (triiodothyronine (T3), levothyroxine (T4)) Miscellaneous Ademetionine (SAMe) GABAkine neurosteroids (brexanolone, zuranolone) Hypericum perforatum (St. John's Wort) Oxitriptan (5-HTP) Rubidium chloride (RbCl) Tryptophan #WHO-EM ‡Withdrawn from market Clinical trials: †Phase III §Never to phase III vteAnxiolytics (N05B)5-HT1ARTooltip 5-HT1A receptor agonists Buspirone Gepirone Tandospirone GABAARTooltip GABAA receptor PAMsTooltip positive allosteric modulators Benzodiazepines: Adinazolam Alprazolam Bromazepam Camazepam Chlordiazepoxide Clobazam Clonazepam Clorazepate Clotiazepam Cloxazolam Diazepam# Ethyl loflazepate Etizolam Fludiazepam Halazepam Ketazolam Lorazepam# Medazepam Nordazepam Oxazepam Pinazepam Prazepam; Others: Alpidem‡ Barbiturates (e.g., phenobarbital) Carbamates (e.g., meprobamate) Carisoprodol Chlormezanone‡ Ethanol (alcohol) Etifoxine Gabapentinoids(α2δ VDCC blockers) Gabapentin Gabapentin enacarbil Phenibut Pregabalin Antidepressants SSRIsTooltip Selective serotonin reuptake inhibitors (e.g., escitalopram) SNRIsTooltip Serotonin-norepinephrine reuptake inhibitors (e.g., duloxetine) SARIsTooltip Serotonin antagonist and reuptake inhibitors (e.g., trazodone) TCAsTooltip Tricyclic antidepressants (e.g., clomipramine#) TeCAsTooltip Tetracyclic antidepressants (e.g., mirtazapine) MAOIsTooltip Monoamine oxidase inhibitors (e.g., phenelzine); Others: Agomelatine Bupropion Tianeptine Vilazodone Vortioxetine Sympatholytics(Antiadrenergics) Alpha-1 blockers (e.g., prazosin) Alpha-2 agonists (e.g., clonidine, dexmedetomidine, guanfacine) Beta blockers (e.g., propranolol, atenolol, betaxolol, nadolol, oxprenolol, pindolol) Others Benzoctamine Cycloserine Fabomotizole Hydroxyzine Lorpiprazole Mebicar Mepiprazole Nicotine (tobacco) Opipramol Oxaflozane‡ Phenaglycodol Phenibut Picamilon Selank Tiagabine Tofisopam Validolum #WHO-EM ‡Withdrawn from market Clinical trials: †Phase III §Never to phase III vteOCD pharmacotherapiesAntidepressants SSRIsTooltip Selective serotonin reuptake inhibitors (citalopram, escitalopram, fluoxetine, fluvoxamine, paroxetine, sertraline) SNRIsTooltip Serotonin-norepinephrine reuptake inhibitors (venlafaxine) TCAsTooltip Tricyclic antidepressants (clomipramine) Others Typical antipsychotics (haloperidol) Atypical antipsychotics (aripiprazole, olanzapine, quetiapine, risperidone) vteMonoamine reuptake inhibitorsDATTooltip Dopamine transporter(DRIsTooltip Dopamine reuptake inhibitors) Piperazines: DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 JJC8-088 Nefazodone Vanoxerine Piperidines: 4-Fluoropethidine Benocyclidine (BTCP) Desoxypipradrol Dexmethylphenidate Difemetorex Ethylphenidate HDMP-28 Methylphenidate Pethidine (meperidine) Phencyclidine Pipradrol Serdexmethylphenidate Tenocyclidine Pyrrolidines: Diphenylprolinol MDPV Naphyrone Prolintane Pyrovalerone Tropanes: Altropane Benzatropine (benztropine) Brasofensine CFT Cocaine Dichloropane Difluoropine Etybenzatropine (ethybenztropine) FE-β-CPPIT FP-β-CPPIT Ioflupane (123I) RTI-55 RTI-112 RTI-113 RTI-121 RTI-126 RTI-150 RTI-177 RTI-229 RTI-336 Tesofensine Troparil Tropoxane WF-11 WF-23 WF-31 WF-33 Others: Adrafinil Amifitadine Armodafinil Amfonelic acid Amineptine Ansofaxine BTQ BTS 74,398 Bupropion Chaenomeles speciosa Ciclazindol Dasotraline Desmethylsertraline Desmethylsibutramine (BTS-54354) Diclofensine Didesmethylsibutramine (BTS-54505) Dimethocaine Diphenylpyraline Dizocilpine (MK-801) DOV-102,677 DOV-216,303 Efirenz Ephenidine Esketamine EXP-561 Fencamfamin Fezolamine Fluorenol GYKI-52895 Hydroxybupropion Indatraline Ketamine Lafadofensine Lefetamine Levophacetoperane Liafensine LR-5182 Manifaxine Mazindol Medifoxamine Mesocarb Metaphit MIN-117 (WF-516) Modafinil Nefopam Nomifensine NS-2359 O-2172 Oroxylin A Perafensine Pridefine Radafaxine Rimcazole Sertraline Sibutramine Solriamfetol Tametraline Tedatioxetine Threohydrobupropion Tripelennamine Venlafaxine NETTooltip Norepinephrine transporter(NRIsTooltip Norepinephrine reuptake inhibitors) Selective norepinephrine reuptake inhibitors: Amedalin Alseroxylon Ciclazindol Daledalin Edivoxetine Esreboxetine Lortalamine Mazindol Nisoxetine Reboxetine Talopram Talsupram Tandamine Teniloxazine Viloxazine Norepinephrine–dopamine reuptake inhibitors: Amineptine Bupropion Fencamine Fencamfamin Hydroxybupropion Lefetamine Levophacetoperane LR-5182 Manifaxine Methylphenidate Nomifensine O-2172 Radafaxine Serdexmethylphenidate Solriamfetol Serotonin–norepinephrine reuptake inhibitors: Atomoxetine (tomoxetine) CP-39,332 Desvenlafaxine Duloxetine Eclanamine Levomilnacipran McN5652 Milnacipran N-Methyl-PPPA Nafenodone PPPA Tofenacin Venlafaxine Serotonin–norepinephrine–dopamine reuptake inhibitors: 3,3-Diphenylcyclobutanamine Amifitadine Ansofaxine Bicifadine Brasofensine Centanafadine Cocaine Dasotraline Desmethylsertraline Desmethylsibutramine (BTS-54354) Diclofensine Didesmethylsibutramine (BTS-54505) DOV-102677 DOV-216303 EXP-561 Fezolamine HDMP-28 HP-505 Indatraline JNJ-7925476 JZ-IV-10 Lafadofensine Liafensine Mazindol Naphyrone Nefazodone Nefopam NS-2359 Perafensine PRC200 Pridefine SEP-228431 SEP-228432 Sibutramine Tedatioxetine Tesofensine Threohydrobupropion Tropanes (e.g., cocaine) Tricyclic antidepressants: Amitriptyline Butriptyline Cianopramine Clomipramine Desipramine Dosulepin (dothiepin) Doxepin Imipramine Lofepramine Melitracen Nortriptyline Protriptyline Trimipramine Tetracyclic antidepressants: Amoxapine Maprotiline Mianserin Oxaprotiline Setiptiline Others: Antihistamines (e.g., brompheniramine, chlorphenamine, pheniramine, tripelennamine) Antipsychotics (e.g., loxapine, ziprasidone) Arylcyclohexylamines (e.g., ketamine, phencyclidine) Dopexamine Ephenidine Ginkgo biloba Indeloxazine Nefazodone Opioids (e.g., desmetramadol, methadone, pethidine (meperidine), tapentadol, tramadol, levorphanol) SERTTooltip Serotonin transporter(SRIsTooltip Serotonin reuptake inhibitors) Selective serotonin reuptake inhibitors: 6-Nitroquipazine Alaproclate Centpropazine Cericlamine Citalopram Dapoxetine Desmethylcitalopram Didesmethylcitalopram Escitalopram Femoxetine Fluoxetine Fluvoxamine Indalpine Ifoxetine Norfluoxetine Omiloxetine Panuramine Paroxetine PIM-35 Pirandamine RTI-353 Seproxetine Sertraline Zimelidine Selective serotonin reuptake inhibitors and serotonin receptor modulators: Etoperidone Litoxetine Lubazodone LY-393558 Quipazine SB-649915 TGBA01AD Trazodone Vilazodone Vortioxetine Serotonin–norepinephrine reuptake inhibitors: Atomoxetine (tomoxetine) Bicifadine CP-39332 Desvenlafaxine Duloxetine Eclanamine Levomilnacipran McN5652 Milnacipran N-Methyl-PPPA PPPA Tofenacin Venlafaxine Serotonin–norepinephrine–dopamine reuptake inhibitors: 3,3-Diphenylcyclobutanamine Amifitadine Ansofaxine Bicifadine Brasofensine Centanafadine Cocaine Dasotraline Desmethylsertraline Desmethylsibutramine (BTS-54354) Diclofensine Didesmethylsibutramine (BTS-54505) DOV-102677 DOV-216303 EXP-561 Fezolamine HDMP-28 HP-505 Indatraline JNJ-7925476 JZ-IV-10 Lafadofensine Liafensine Mazindol Naphyrone Nefazodone Nefopam NS-2359 Perafensine PRC200 Pridefine SEP-228431 SEP-228432 Sibutramine Tedatioxetine Tesofensine Threohydrobupropion Tropanes (e.g., cocaine) Tricyclic antidepressants: Amitriptyline Cianopramine Clomipramine Cyanodothiepin Desipramine Dosulepin (dothiepin) Doxepin Imipramine Lofepramine Nortriptyline Pipofezine Protriptyline Others: A-80426 Amoxapine Antihistamines (e.g., brompheniramine, chlorphenamine, dimenhydrinate, diphenhydramine, mepyramine (pyrilamine), pheniramine, tripelennamine) Antipsychotics (e.g., loxapine, ziprasidone) Arylcyclohexylamines (e.g., 3-MeO-PCP, esketamine, ketamine, methoxetamine, phencyclidine) Cyclobenzaprine Delucemine Dextromethorphan Dextrorphan Efirenz Hypidone Medifoxamine Mesembrine Mifepristone MIN-117 (WF-516) N-Me-5-HT Opioids (e.g., dextropropoxyphene, methadone, pethidine (meperidine), levorphanol, tapentadol, tramadol) Roxindole VMATsTooltip Vesicular monoamine transporters Amiodarone Amphetamines (e.g., amphetamine, methamphetamine, MDMA) APP AZIK Bietaserpine Deserpidine Deutetrabenazine Dihydrotetrabenazine Efirenz GBR-12935 GZ-793A Ibogaine Ketanserin Lobeline Methoxytetrabenazine Reserpine Rose bengal Tetrabenazine Valbenazine Vanoxerine (GBR-12909) Others Unsorted: Cendifensine DAT enhancers: Luteolin DAT modulators: Agonist-like: SoRI-9804 SoRI-20040; Antagonist-like: SoRI-20041 See also: Receptor/signaling modulators • Monoamine releasing agents • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins vteSigma receptor modulatorsσ1 Agonists: 3-PPP 4-PPBP 5-MeO-DMT Alazocine (SKF-10047) Amantadine Arketamine BD-737 BD-1052 Blarcamesine Captodiame Citalopram CGRPTooltip Calcitonin gene-related peptide Cloperastine Cocaine Cutamesine (SA-4503) Cyclazocine Dehydroepiandrosterone (DHEA) (prasterone) Dehydroepiandrosterone sulfate (DHEA-S) (prasterone sulfate) Dextrallorphan Dextromethorphan (DXM) Dextrorphan (DXO) Dimemorfan Dimethyltryptamine (DMT) Ditolylguanidine (DTG) Donepezil Eliprodil Escitalopram Fabomotizole (afobazole) Fluoxetine Fluvoxamine Ifenprodil Igmesine (JO-1784) IPAB Ketamine L-687384 MDMA (midomafetamine) Memantine Methamphetamine Methoxetamine Methylphenidate Nepinalone Neuropeptide Y Noscapine OPC-14523 Opipramol Pentazocine Pentoxyverine (carbetapentane) PRE-084 Pregnenolone Pregnenolone sulfate Pridopidine Racemethorphan (methorphan) Racemorphan (morphanol) UMB-23 UMB-82 Antagonists: 3-PPP AC-927 BD-1008 BD-1031 BD-1047 BD-1060 BD-1063 BD-1067 BMY-14802 (BMS-181100) CM-156 Dup-734 E-5842 E-52862 (S1RA) Haloperidol LR-132 LR-172 MS-377 NE-100 NPC-16377 Panamesine (EMD-57455) PD-144418 Pentazocine Progesterone Rimcazole (BW-234U) Sertraline SR-31742A Allosteric modulators: Phenytoin; Positive: Methylphenylpiracetam SOMCL-668 Unknown/unsorted: 3-Methoxydextrallorphan 3-MeO-PCP 4C-T-2 4-IBP 4-IPBS 4-MeO-PCP 5-MeO-DALT 5-MeO-DiPT Amitriptyline Azidopamil Chlorpromazine Clemastine Clomipramine Clorgiline D-Deprenyl DiPTTooltip N,N-Diisopropyltryptamine DPTTooltip N,N-Dipropyltryptamine Ibogaine Imipramine KCR-12-83.1 Nemonapride Noribogaine RHL-033 RS-67,333 RTI-55 Saffron Safinamide Selegiline Spipethiane Trifluoperazine W-18 YKP10A σ2 Agonists: 3-PPP Arketamine BD-1047 BD1063 Ditolylguanidine (DTG) DKR-1005 DKR-1051 Haloperidol Ifenprodil Ketamine MDMA (midomafetamine) Methamphetamine OPC-14523 Opipramol PB-28 Phencyclidine Siramesine (Lu 28-179) UKH-1114 Antagonists: AC-927 BD-1008 BD-1067 CM-156 LR-172 MIN-101 Panamesine (EMD-57455) SAS-0132 Zervimesine (CT-1812) Unknown/unsorted: 3-Methoxydextrallorphan 3-MeO-PCE 4-MeO-PCP 5-MeO-DALT 5-MeO-DiPT Clemastine DiPTTooltip N,N-Diisopropyltryptamine DPTTooltip N,N-Dipropyltryptamine Ibogaine Lu 29-252 Nemonapride Nepinalone Noribogaine Pentazocine RS-67,333 Safinamide TMATooltip 3,4,5-Trimethoxyamphetamine UMB-23 UMB-82 W-18 Unsorted Agonists: Berberine Ethylketazocine Fourphit Metaphit Naluzotan Tapentadol Tenocyclidine Antagonists: AHD1 AZ66 Lamotrigine Naloxone SM-21 UMB-100 UMB-101 UMB-103 UMB-116 YZ-011 YZ-069 YZ-185 Allosteric modulators: SKF-83959 Unknown/unsorted: 18-Methoxycoronaridine BMY-13980 Butaclamol Caramiphen Carvotroline Chlorphenamine (chlorpheniramine) Chlorpromazine Cinnarizine Cinuperone Clocapramine Dezocine EMD-59983 Hypericin (St. John's wort) Fluphenazine Gevotroline (WY-47384) Mepyramine (pyrilamine) Molindone Perphenazine Pimozide Proadifen Promethazine Propranolol Quinidine Remoxipride SL 82.0715 SR-31747A Tiospirone (BMY-13859) Venlafaxine See also: Receptor/signaling modulators Portal: Medicine