{"ATC Code":"N06AB10","Abbreviation":[],"Adverse Effects":"Although escitalopram and SSRIs have a lower toxicity profile than older antidepressants, they have still been associated with significant adverse effects. The most frequently reported adverse effects include insomnia, sexual dysfunction (particularly reduced libido, anorgasmia, and male ejaculatory delay), nausea, increased sweating, fatigue, and somnolence. QT prolongation and serotonin syndrome are rare but potentially severe adverse effects associated with escitalopram.","Aliases":["Citalopram","S(+)-Citalopram","S-(+)-Citalopram","Esertia","Seroplex","Cipralex","Esitol","escitalopramum","(1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile","5-Isobenzofurancarbonitrile, 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-, (1S)-","1-(3-(Dimethylamino)propyl)-1-(p-fluorophenyl)-5-phthalancarbonitrile","LU-26-054","5-Isobenzofurancarbonitrile, 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydro-, (1S)-","(1S)-1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile","RefChem:5803","N06AB10","(s)-1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile","(1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-isobenzofuran-5-carbonitrile","68P","PS28 - Escitalopram","Spectrum_001401","Tocris-1427","Spectrum2_000551","Spectrum3_001062","Spectrum4_001212"],"Biological Half-Life":"The elimination half-life of escitalopram is 27-32 hours, though this is increased by approximately 50% in the elderly and doubled in patients with reduced hepatic function. The elimination half-life of escitalopram's primary metabolite, S-desmethylcitalopram, is approximately 54 hours at steady state.","CAS":"128196-01-0","ChEBI":"CHEBI:36791","ChEMBL":"CHEMBL1508","ChemicalClasses":["alkylbenzene"],"Chirality":"absolute","Drug Classes":"Breast Feeding; Lactation; Milk, Human; Antidepressive Agents; Serotonin Uptake Inhibitors; Antidepressive Agents, Second-Generation","Drug Indication":"Escitalopram is indicated for the acute and maintenance treatment of major depressive disorder (MDD) in adults and pediatric patients 12 years old and older and for the acute treatment of generalized anxiety disorder (GAD) in adults and pediatric patients 7 years old and older. It is additionally indicated for symptomatic relief of obsessive-compulsive disorder (OCD) in Canada.","Drug Warnings":"/BOXED WARNING/ WARNING: Antidepressants increased the risk compared to placebo of suicidal thinking and behavior (suicidality) in children, adolescents, and young adults in short-term studies of major depressive disorder (MDD) and other psychiatric disorders. Anyone considering the use of Lexapro or any other antidepressant in a child, adolescent, or young adult must balance this risk with the clinical need. Short-term studies did not show an increase in the risk of suicidality with antidepressants compared to placebo in adults beyond age 24; there was a reduction in risk with antidepressants compared to placebo in adults aged 65 and older. Depression and certain other psychiatric disorders are themselves associated with increases in the risk of suicide. Patients of all ages who are started on antidepressant therapy should be monitored appropriately and observed closely for clinical worsening, suicidality, or unusual changes in behavior. Families and caregivers should be advised of the need for close observation and communication with the prescriber. Lexapro is not approved for use in pediatric patients less than 12 years of age.","Esters":[],"European Community (EC) Number":"812-870-6","FDA Pharmacological Classification":"4O4S742ANY","Formating":[],"HMDB ID":"HMDB0005028","HeavyAtomCount":24,"Human Drugs":"Antidepressants -\u003e Selective serotonin reuptake inhibitors (SSRI)","IUPACName":"(1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-2-benzofuran-5-carbonitrile","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","InChIKey":"WSEQXVZVJXJVFP-FQEVSTJZSA-N","Interactions":"Although the antidepressant and anxiolytic effects of selective serotonin reuptake inhibitors and serotonin-noradrenaline reuptake inhibitors are well-documented, less is known about their cognitive effects. Escitalopram, a selective serotonin reuptake inhibitor, and atomoxetine, a selective noradrenaline reuptake inhibitor, were used to evaluate the interaction between noradrenergic and serotonergic neurotransmission in the modulation of contextual fear conditioning in rats. Contextual fear-conditioning test was used to investigate the acute effects of escitalopram, alone or in combination with atomoxetine, in different stages of learning and memory in rats. Furthermore, microdialysis in freely moving animals was used to investigate the effect of escitalopram on serotonin, dopamine, and noradrenaline levels in the rat hippocampus.  Escitalopram significantly increased conditioned responses when applied before the acquisition, but decreased responses, when applied before the recall test. When administered during memory consolidation, escitalopram dose-dependently enhanced conditioned responding. These effects were blocked by atomoxetine. Escitalopram (at a dose that affects memory consolidation) increased hippocampal serotonin levels fourfold without changing dopamine or noradrenaline. Atomoxetine, at dose levels that blocked the effects of escitalopram on contextual fear conditioning, increased the extracellular levels of noradrenaline eightfold but did not change dopamine or serotonin. A combined treatment of escitalopram and atomoxetine caused a significant attenuation of escitalopram-induced increase in serotonin levels, while noradrenaline levels were not affected. These findings indicate that escitalopram affects fear memory in rats, likely modulated by increases in serotonin levels in the brain. This effect is impaired by atomoxetine, probably due to a noradrenaline-mediated decrease in serotonin levels. Further studies are warranted to study the effects of potential differences among antidepressant therapies on long-term cognitive outcomes.","MeSH Pharmacological Classification":"Compounds that specifically inhibit the reuptake of serotonin in the brain.","Melting Point":"147-152C","MolecularFormula":"C\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e21\u003c/sub\u003eFN\u003csub\u003e2\u003c/sub\u003eO","MolecularWeight":"324.4 g/mol","Opticalactivity":"( + )","Pharmacodynamics":"Escitalopram belongs to a class of medications called selective serotonin re-uptake inhibitors (SSRIs). These agents cause an increase in serotonin levels in neuronal synapses by preventing the re-uptake of serotonin (5-HT) into the presynaptic terminals of serotonergic neurons. As compared to other SSRIs, it appears to have a relatively quick onset of effect due to its potency.  SSRIs as a class have been associated with abnormal bleeding, particularly in patients receiving concomitant therapy with other medications affecting hemostasis, and with the development of serotonin syndrome. Use escitalopram with caution in patients with a higher-than-baseline risk of bleeding and in patients receiving concomitant therapy with other serotonergic drugs. Escitalopram may also cause a discontinuation syndrome with abrupt removal of the drug, and should be slowly tapered if discontinuation of therapy is warranted.","Physical Description":"Solid","PubChemId":146570,"Record Description":["LiverTox|CNS|Antidepressant|SSRI"],"RefCount":3,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Escitalopram","Name":"Escitalopram","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q423757","Name":"Escitalopram","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/drugs/DB01175","Name":"Escitalopram","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/146570","Name":"Escitalopram","Sub":false}]},{"Name":"ChEMBL","Urls":[{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1508","Name":"Escitalopram","Sub":false}]},{"Name":"ChEBI","Urls":[{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:36791","Name":"Escitalopram","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=128196-01-0","Name":"Escitalopram","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0005028","Name":"Escitalopram","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/D07913","Name":"Escitalopram","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/4O4S742ANY","Name":"Escitalopram","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID8048440","Name":"Escitalopram","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 146570, Escitalopram. Accessed September 1, 2025. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/146570\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/146570\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Escitalopram. UNII: 4O4S742ANY. Global Substance Registration System. Accessed September 1, 2025. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/4O4S742ANY\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/4O4S742ANY\u003c/a\u003e"],"SMILES":"CN(C)CCC[C@@]1(C2=C(CO1)C=C(C=C2)C#N)C3=CC=C(C=C3)F","SaltData":[{"AcidCount":1,"Amine":"Escitalopram","AmineCount":1,"Formula":"C(=O)(C(=O)O)O","Name":"oxalate","Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 169.18 106.711\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#ff0d0d\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".7\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h170v107H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"M106.223 1.043 96.177 6.84M89.87 6.839 79.826 1.038M93.023 12.51l-.002 11.39M93.021 23.9l-13.2 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class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Title":"Escitalopram oxalate","UNII":"5U85DBW7LO"},{"AcidCount":1,"Amine":"Escitalopram","AmineCount":1,"Formula":"Br","Name":"hydrobromide","Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 131.584 106.711\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#3050f8\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".7\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h132v107H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"M106.223 1.043 96.177 6.84M89.87 6.839 79.826 1.038M93.023 12.51l-.002 11.39M93.021 23.9l-13.2 7.618M79.821 31.518l-.002 15.24\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"M66.619 54.026v.7M68.505 52.688v1.2M70.391 51.349l-.001 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class=\"hi\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"m56.773 40.836-5.752.602M62.033 44.069l2.293 5.153\" class=\"hi\"/\u003e\u003cpath stroke=\"#90e050\" d=\"m100.279 100.688-3.384-4.659\" class=\"hi\"/\u003e\u003c/g\u003e\u003cg class=\"mol\"\u003e\u003cg fill=\"#a62929\" stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M125.906 50.906q.917 0 1.387.274.47.268.47.94 0 .435-.244.721-.238.285-.69.363v.036q.309.047.559.178t.393.375q.149.238.149.619 0 .667-.458 1.03-.459.363-1.245.363h-1.72v-4.899zm.119 2.089q.631 0 .863-.202.238-.202.238-.601 0-.405-.285-.578-.286-.178-.911-.178h-.81v1.559zm-.905.512v1.774h.988q.655 0 .905-.25.256-.256.256-.666 0-.381-.268-.619-.262-.239-.94-.239zm5.476-1.446q.101 0 .22.012.125.006.208.029l-.071.554q-.089-.018-.196-.03-.108-.017-.203-.017-.28 0-.53.154-.244.155-.393.435-.148.274-.148.649v1.958h-.602v-3.673h.494l.066.667h.03q.178-.298.458-.518t.667-.22M123.945 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Gastric evacuation by lavage and use of activated charcoal should be considered. Careful observation and cardiac and vital sign monitoring are recommended, along with general symptomatic and supportive care. Due to the large volume of distribution of escitalopram, forced diuresis, dialysis, hemoperfusion, and exchange transfusion are unlikely to be of benefit. There are no specific antidotes for Escitalopram. (L1712)","UNII":"4O4S742ANY","Wikidata":"Q423757","Wikipedia":"Escitalopram","XLogP":3.2}