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			{{Short description|SSRI antidepressant}}
	{{drugbox | verifiedrevid = 418043619
			{{About|the ] form of the drug|its (''S'')-]|Escitalopram}}
	| drug_name = Citalopram
			{{Use dmy dates|date=September 2024}}
	| IUPAC_name = (''RS'')-1--1-<br/>(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile
			{{cs1 config|name-list-style=vanc|display-authors=6}}
	| image = Citalopram structure.svg
			{{Drugbox
	| imagename = 1 : 1 mixture (racemate)
			| Watchedfields = changed
	| width = 200px
			| verifiedrevid = 443526669
	| CASNo_Ref = {{cascite|correct|CAS}}
			| image = Citalopram racemic.svg
			| image_class = skin-invert-image
			| width = 190
			| caption = (''R'')-(−)-citalopram (top),<br />(''S'')-(+)-citalopram (bottom)
			| chirality = ]
			<!--Clinical data-->| pronounce = {{IPAc-en|s|aɪ|ˈ|t|æ|l|ə|ˌ|p|r|æ|m|,_|s|ɪ|-}};{{refn|{{MerriamWebsterDictionary|Citalopram}}}}
			| tradename = Celexa, Cipramil, others<ref name="Citalopram International" />
			| Drugs.com = {{drugs.com|monograph|citalopram-hydrobromide}}
			| MedlinePlus = a699001
			| DailyMedID = Citalopram
			| pregnancy_AU = C
			| pregnancy_AU_comment = <ref name="Drugs.com pregnancy" />
			| dependency_liability = Low
			| addiction_liability = Low
			| routes_of_administration = ], ]<ref name=intravenous>{{cite journal | vauthors = Kasper S, Müller-Spahn F | title = Intravenous antidepressant treatment: focus on citalopram | journal = European Archives of Psychiatry and Clinical Neuroscience | volume = 252 | issue = 3 | pages = 105–109 | date = June 2002 | pmid = 12192466 | doi = 10.1007/s00406-002-0363-8 | s2cid = 24991131 }}</ref><ref name=ivocd/><ref name=citalopramvsclomipramine/>
			| class = ] (SSRI)<ref name=AHFS2018/>
			| ATC_prefix = N06
			| ATC_suffix = AB04
			| ATC_supplemental =
			| legal_AU = S4
			| 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=16 August 2023 |publisher=] |language=pt-BR |publication-date=4 April 2023}}</ref>
			| legal_CA = Rx-only
			| legal_UK = POM
			| legal_US = Rx-only
			| legal_US_comment = <ref name="Celexa FDA label" />
			<!--Pharmacokinetic data-->| bioavailability = 80% <br/>peak at 4 hours<ref name=AHFS2018/>
			| protein_bound = <80%<ref name="Celexa FDA label">{{cite web | title=Celexa- citalopram tablet, film coated | website=DailyMed | date=15 August 2019 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=4259d9b1-de34-43a4-85a8-41dd214e9177 | access-date=28 October 2020}}</ref>
			| metabolism = ] (] and ])
			| metabolites = ] (DCT) and ] (DDCT)
			| elimination_half-life = 35 hours
			| excretion = Mostly as unmetabolized citalopram, partly DCT, and traces of DDCT in urine
			<!-- Identifiers -->| index2_label = as salt
			| receptors = <!-- Not needed as its not endogenous substance -->
			| CAS_number_Ref = {{cascite|correct|??}}
			| CAS_number = 59729-33-8
			| PubChem = 2771
			| IUPHAR_ligand = 7547
			| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
			| DrugBank = DB00215
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| ChemSpiderID = 2669
	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = 0DHU5B8D6V		| UNII = 0DHU5B8D6V
			| KEGG_Ref = {{keggcite|correct|kegg}}
	| InChI = 1/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
			| KEGG = D07704
	| smiles = Fc1ccc(cc1)C3(OCc2cc(C#N)ccc23)CCCN(C)C
			| KEGG2_Ref = {{keggcite|correct|kegg}}
	| InChIKey = WSEQXVZVJXJVFP-UHFFFAOYAV
			| KEGG2 = D00822
			| ChEBI_Ref = {{ebicite|correct|EBI}}
			| ChEBI = 3723
	| ChEMBL_Ref = {{ebicite|correct|EBI}}		| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 549		| ChEMBL = 549
			<!--Chemical data-->| IUPAC_name = (''RS'')-1--1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile
			| C = 20
			| H = 21
			| F = 1
			| N = 2
			| O = 1
			| SMILES = Fc1ccc(cc1)C3(OCc2cc(C#N)ccc23)CCCN(C)C
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| 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		| 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
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = WSEQXVZVJXJVFP-UHFFFAOYSA-N		| StdInChIKey = WSEQXVZVJXJVFP-UHFFFAOYSA-N
	| CAS_number = 59729-33-8
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 2669
	| ATC_prefix = N06
	| ATC_suffix = AB04
	| ATC_supplemental = N06AB10
	| ChEBI = 3723
	| PubChem = 2771
	| DrugBank = DB00215
	| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = D07704
	| C=20 | H=21 | F=1 | N=2 | O=1
	| molecular_weight = 324.392 g/mol
	| bioavailability = 80% <br/>peak at 4 hours<ref>http://www.psychiatrictimes.com/medications/citalopram-hydrobromide-tablet</ref>
	| protein_bound =
	| metabolism = ] (] & ])
	| elimination_half-life = 35 hours
	| excretion = Mostly as unmetabolized citalopram, partly DCT and traces of DDCT in urine
	| pregnancy_US = C
	| legal_status = Rx-only
	| routes_of_administration = Oral
	}}		}}
			<!-- Definition and medical uses -->
	'''Citalopram''' ({{IPAc-en|icon|s|aɪ|ˈ|t|æ|l|ɵ|p|r|æ|m}};<ref>{{cite news | first= | last= | coauthors= | title=citalopram | date= | publisher= | url =http://medical.merriam-webster.com/medical/citalopram | work =Merriam-Webster, Incorporated | pages = | accessdate = 2008-10-13 | language = }}</ref>
			'''Citalopram''', sold under the brand name '''Celexa''' among others, is an ] of the ] (SSRI) class.<ref name=AHFS2018/><ref name="Celexa FDA label" /> It is used to treat ], ], ], and ].<ref name=AHFS2018>{{cite web |title=Citalopram Hydrobromide Monograph for Professionals |url=https://www.drugs.com/monograph/citalopram-hydrobromide.html |website=Drugs.com |publisher=AHFS |access-date=23 December 2018 }}</ref> The antidepressant effects may take one to four weeks to occur.<ref name=AHFS2018/> It is typically taken ] (swallowed by mouth).<ref name=AHFS2018/><ref name="Celexa FDA label" /> In some ] countries, it is sometimes given ] (injected into a vein) to initiate treatment, before switching to the oral route of administration for continuation of treatment.<ref name=intravenous/> It has also been used intravenously in other parts of the world in some other circumstances.<ref name=ivocd/><ref name=citalopramvsclomipramine>{{cite journal |vauthors=Altamura AC, Dell'Osso B, Buoli M, Zanoni S, Mundo E |date=August 2008 |title=Intravenous augmentative citalopram versus clomipramine in partial/nonresponder depressed patients: a short-term, low dose, randomized, placebo-controlled study |url=https://pubmed.ncbi.nlm.nih.gov/18626267/ |journal=J Clin Psychopharmacol |volume=28 |issue=4 |pages=406–410 |doi=10.1097/JCP.0b013e31817d5931 |pmid=18626267 |s2cid=25013120 |access-date=12 August 2023}}</ref>
	trade names: '''Celexa''', '''Cipramil''') is an ] ] of the ] (SSRI) class. It has U.S. ] (FDA) approval to treat ], and is prescribed ] for a number of anxiety conditions.
			<!-- Side effects and mechanism -->
			Common side effects include nausea, trouble sleeping, sexual problems, shakiness, feeling tired, and sweating.<ref name=AHFS2018/> Serious side effects include an increased risk of ] in those under the age of 25, ], ], and ].<ref name=AHFS2018/> It should not be used in persons who take or have recently taken an ].<ref name=AHFS2018/> There are concerns that use during ] may harm the fetus.<ref name="Drugs.com pregnancy">{{cite web |title=Citalopram (Celexa) Use During Pregnancy |url=https://www.drugs.com/pregnancy/citalopram.html |website=Drugs.com |access-date=23 December 2018 }}</ref>
			<!-- History and culture -->
			Citalopram was approved for medical use in the United States in 1998.<ref name=AHFS2018/> It is on the ].<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> It is available as a ].<ref name=BNF76>{{cite book|title=British national formulary: BNF 76|date=2018|publisher=Pharmaceutical Press|isbn=9780857113382|page=361|edition=76}}</ref> In 2022, it was the 40th most commonly prescribed medication in the United States, with more than 15{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2022 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=30 August 2024 | archive-date=30 August 2024 | archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Citalopram Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Citalopram | access-date = 30 August 2024 }}</ref>
	==Medical uses==		==Medical uses==
	]		] (size 19.05&nbsp;mm/0.75 in)]]
	Citalopram is approved to treat the symptoms of ].<ref name="rxlist.com">Cerner Multum Inc. Rxlist.com. 2009. http://www.rxlist.com/celexa-drug.htm</ref>
	===Off-label===		===Depression===
			In the United States, citalopram is approved to treat ].<ref>{{cite book | vauthors = Sharbaf Shoar N, Fariba KA, Padhy RK | chapter = Citalopram|date=2020| chapter-url=http://www.ncbi.nlm.nih.gov/books/NBK482222/| title = StatPearls|place=Treasure Island (FL)|publisher=StatPearls Publishing|pmid=29489221|access-date=23 October 2020 }}</ref> Citalopram appears to have comparable efficacy and superior tolerability relative to other antidepressants.<ref name=":0">{{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><ref>{{cite journal | vauthors = Khoo AL, Zhou HJ, Teng M, Lin L, Zhao YJ, Soh LB, Mok YM, Lim BP, Gwee KP | title = Network Meta-Analysis and Cost-Effectiveness Analysis of New Generation Antidepressants | journal = CNS Drugs | volume = 29 | issue = 8 | pages = 695–712 | date = August 2015 | pmid = 26293743 | doi = 10.1007/s40263-015-0267-6 | s2cid = 207486435 }}</ref> In the ] ranking of ten ]s for efficacy and cost-effectiveness, citalopram is fifth in effectiveness (after ], ], ], and ]) and fourth in cost-effectiveness.<ref>See p410 of {{cite web|title=National Clinical Practice Guideline 90. Depression: The treatment and management of depression in adults, updated edition (2010).|url=https://www.nice.org.uk/guidance/cg90/evidence/full-guidance-243833293|url-status=dead|archive-url=https://web.archive.org/web/20171215084607/https://www.nice.org.uk/guidance/cg90/evidence/full-guidance-243833293|archive-date=15 December 2017|access-date=27 November 2016|publisher=National Institute for Health and Clinical Excellence (UK)}}</ref>
	Citalopram is frequently used off-label to treat ], ], ], ] and ].<ref>Poore, Jerod. Celexa. Crazy Meds. 2010. http://crazymeds.us/celexa.html</ref>
			Evidence for the effectiveness of citalopram for treating depression in children is uncertain.<ref>{{cite journal | vauthors = Cohen D | title = Should the use of selective serotonin reuptake inhibitors in child and adolescent depression be banned? | journal = Psychotherapy and Psychosomatics | volume = 76 | issue = 1 | pages = 5–14 | date = 2007 | pmid = 17170559 | doi = 10.1159/000096360 | s2cid = 1112192 }}</ref><ref>{{cite journal | vauthors = Carandang C, Jabbal R, Macbride A, Elbe D | title = A review of escitalopram and citalopram in child and adolescent depression | journal = Journal of the Canadian Academy of Child and Adolescent Psychiatry | volume = 20 | issue = 4 | pages = 315–324 | date = November 2011 | pmid = 22114615 | pmc = 3222577 }}</ref>
	Citalopram has been found to greatly reduce the symptoms of ]<ref name="pmid1424428">{{cite journal |author=Sindrup SH, Bjerre U, Dejgaard A, Brøsen K, Aaes-Jørgensen T, Gram LF |title=The selective serotonin reuptake inhibitor citalopram relieves the symptoms of diabetic neuropathy |journal=Clin. Pharmacol. Ther. |volume=52 |issue=5 |pages=547–52 |year=1992 |pmid=1424428 |doi=10.1038/clpt.1992.183}}</ref> and ].<ref name="pmid12494286">{{cite journal |author=Atmaca M, Kuloglu M, Tezcan E, Semercioz A |title=The efficacy of citalopram in the treatment of premature ejaculation (prem-e): a placebo-controlled study |journal=Int. J. Impot. Res. |volume=14 |issue=6 |pages=502–5 |year=2002 |pmid=12494286 |doi=10.1038/sj.ijir.3900918}}</ref> There is also evidence that citalopram may be effective in the treatment of ].<ref name="pmid8104273">{{cite journal |author=Andersen G, Vestergaard K, Riis JO |title=Citalopram for post-stroke pathological crying |journal=Lancet |volume=342 |issue=8875 |pages=837–9 |year=1993 |pmid=8104273|doi=10.1016/0140-6736(93)92696-Q}}</ref>
			=== Panic disorder ===
	While on its own citalopram is less effective than ] in the prevention of migraines, in refractory cases combination therapy may be more effective.<ref name="pmid15539864">{{cite journal |author=Rampello L, Alvano A, Chiechio S, ''et al.'' |title=Evaluation of the prophylactic efficacy of amitriptyline and citalopram, alone or in combination, in patients with comorbidity of depression, migraine, and tension-type headache |journal=Neuropsychobiology |volume=50 |issue=4 |pages=322–8 |year=2004 |pmid=15539864 |doi=10.1159/000080960}}</ref>
			Citalopram is licensed in the UK<ref>{{cite web|title=Citalopram 20mg Tablets - Summary of Product Characteristics (SmPC) - (emc)|url=https://www.medicines.org.uk/emc/product/5160/smpc|access-date=15 January 2023|website=www.medicines.org.uk}}</ref> and other European countries<ref>Urząd Rejestracji Produktów Leczniczych, Wyrobów Medycznych i Produktów Biobójczych (Office for Registration of Medicinal Products, Medical Devices and Biocides) {{cite web |url=http://www.urpl.gov.pl/system/drugs/dcp/charakterystyka/2012-07-02_2012-04-20-spc-citalopramvb-pl.pdf |title=Charakterystyka Produktu Leczniczego | trans-title = Characteristic Product Leczniczego | language = Polish | work = The Office for Registration of Medicinal Products, Medical Devices and Biocidal Products|access-date=24 September 2013 |url-status=dead |archive-url= https://web.archive.org/web/20131105190501/http://www.urpl.gov.pl/system/drugs/dcp/charakterystyka/2012-07-02_2012-04-20-spc-citalopramvb-pl.pdf |archive-date=5 November 2013 }}</ref> for ], with or without ].
			=== Other ===
	Citalopram and other ] can be used to treat ].<ref>Stahl, S. Stahl's Essential Psychopharmacology: The Prescriber's Guide. Cambridge University Press: New York, NY. 2009. pp. 87.</ref>
			Citalopram may be used off-label to treat ], and ],<ref>{{cite journal | vauthors = Hellerstein DJ, Batchelder S, Miozzo R, Kreditor D, Hyler S, Gangure D, Clark J | title = Citalopram in the treatment of dysthymic disorder | journal = International Clinical Psychopharmacology | volume = 19 | issue = 3 | pages = 143–148 | date = May 2004 | pmid = 15107656 | doi = 10.1097/00004850-200405000-00004 | s2cid = 24416470 }}</ref> ], ], and ].<ref>{{cite journal | vauthors = Pittenger C, Bloch MH | title = Pharmacological treatment of obsessive-compulsive disorder | journal = The Psychiatric Clinics of North America | volume = 37 | issue = 3 | pages = 375–391 | date = September 2014 | pmid = 25150568 | pmc = 4143776 | doi = 10.1016/j.psc.2014.05.006 }}</ref>
			It appears to be as effective as fluvoxamine and paroxetine in obsessive–compulsive disorder.<ref>{{cite journal | vauthors = Stein DJ, Montgomery SA, Kasper S, Tanghoj P | title = Predictors of response to pharmacotherapy with citalopram in obsessive-compulsive disorder | journal = International Clinical Psychopharmacology | volume = 16 | issue = 6 | pages = 357–361 | date = November 2001 | pmid = 11712625 | doi = 10.1097/00004850-200111000-00007 | s2cid = 38416051 }}</ref> Some data suggest the effectiveness of intravenous infusion of citalopram in resistant OCD.<ref name=ivocd>{{cite journal | vauthors = Pallanti S, Quercioli L, Koran LM | title = Citalopram intravenous infusion in resistant obsessive-compulsive disorder: an open trial | journal = The Journal of Clinical Psychiatry | volume = 63 | issue = 9 | pages = 796–801 | date = September 2002 | pmid = 12363120 | doi = 10.4088/JCP.v63n0908 }}</ref> Citalopram is well tolerated and as effective as ] in social anxiety disorder.<ref>{{cite journal | vauthors = Atmaca M, Kuloglu M, Tezcan E, Unal A | title = Efficacy of citalopram and moclobemide in patients with social phobia: some preliminary findings | journal = Human Psychopharmacology | volume = 17 | issue = 8 | pages = 401–405 | date = December 2002 | pmid = 12457375 | doi = 10.1002/hup.436 | s2cid = 34395742 }}</ref> There are studies suggesting that citalopram can be useful in reducing aggressive and impulsive behavior.<ref>{{cite journal | vauthors = Armenteros JL, Lewis JE | title = Citalopram treatment for impulsive aggression in children and adolescents: an open pilot study | journal = Journal of the American Academy of Child and Adolescent Psychiatry | volume = 41 | issue = 5 | pages = 522–529 | date = May 2002 | pmid = 12014784 | doi = 10.1097/00004583-200205000-00009 }}</ref><ref>{{cite journal | vauthors = Reist C, Nakamura K, Sagart E, Sokolski KN, Fujimoto KA | title = Impulsive aggressive behavior: open-label treatment with citalopram | journal = The Journal of Clinical Psychiatry | volume = 64 | issue = 1 | pages = 81–85 | date = January 2003 | pmid = 12590628 | doi = 10.4088/jcp.v64n0115 }}</ref> It appears to be superior to placebo for behavioural disturbances associated with dementia.<ref>{{cite journal | vauthors = Pollock BG, Mulsant BH, Rosen J, Sweet RA, Mazumdar S, Bharucha A, Marin R, Jacob NJ, Huber KA, Kastango KB, Chew ML | title = Comparison of citalopram, perphenazine, and placebo for the acute treatment of psychosis and behavioral disturbances in hospitalized, demented patients | journal = The American Journal of Psychiatry | volume = 159 | issue = 3 | pages = 460–465 | date = March 2002 | pmid = 11870012 | doi = 10.1176/appi.ajp.159.3.460 }}</ref> It has also been used successfully for hypersexuality in early Alzheimer's disease.<ref>{{cite journal | vauthors = Tosto G, Talarico G, Lenzi GL, Bruno G | title = Effect of citalopram in treating hypersexuality in an Alzheimer's disease case | journal = Neurological Sciences | volume = 29 | issue = 4 | pages = 269–270 | date = September 2008 | pmid = 18810603 | doi = 10.1007/s10072-008-0979-1 | hdl = 11573/22581 | s2cid = 11432563 }}</ref>
	A 2009 multisite randomized controlled study found no benefit and some adverse effects in autistic children from citalopram, raising doubts whether SSRIs are effective for treating repetitive behavior in children with autism.<ref>{{cite journal |author= King BH, Hollander E, Sikich L ''et al.'' |title= Lack of efficacy of citalopram in children with autism spectrum disorders and high levels of repetitive behavior: citalopram ineffective in children with autism |journal= Arch Gen Psychiatry |volume=66 |issue=6 |pages=583–90 |year=2009 |pmid=19487623 |doi=10.1001/archgenpsychiatry.2009.30 |laysummary=http://www.latimes.com/news/science/la-sci-autism-drugs2-2009jun02,0,6717060.story |laydate=2009-06-02 |laysource= Los Angeles Times}}</ref>
			A meta-analysis, including studies with fluoxetine, paroxetine, sertraline, escitalopram, and citalopram versus placebo, showed SSRIs to be effective in reducing symptoms of premenstrual syndrome, whether taken continuously or just in the luteal phase.<ref>{{cite journal | vauthors = Marjoribanks J, Brown J, O'Brien PM, Wyatt K | title = Selective serotonin reuptake inhibitors for premenstrual syndrome | journal = The Cochrane Database of Systematic Reviews | issue = 6 | pages = CD001396 | date = June 2013 | volume = 2013 | pmid = 23744611 | pmc = 7073417 | doi = 10.1002/14651858.CD001396.pub3 }}</ref>{{Update inline|reason=Updated version https://www.ncbi.nlm.nih.gov/pubmed/39140320|date = October 2024}} For alcoholism, citalopram has produced a modest reduction ] intake and increase in drink-free days in studies of alcoholics, possibly by decreasing desire or reducing the reward.<ref>{{cite journal | vauthors = Tiihonen J, Ryynänen OP, Kauhanen J, Hakola HP, Salaspuro M | title = Citalopram in the treatment of alcoholism: a double-blind placebo-controlled study | journal = Pharmacopsychiatry | volume = 29 | issue = 1 | pages = 27–29 | date = January 1996 | pmid = 8852531 | doi = 10.1055/s-2007-979538 | s2cid = 260242756 }}</ref>
	Some research suggests that citalopram interacts with cannabinoid protein-couplings in the rat brain,
	and this is put forward as a potential cause of some of the drug's antidepressant effect.<ref>Effects of chronic treatment with citalopram on cannabinoid and opioid receptor-mediated G-protein coupling in discrete rat brain regions. Shirley A. Hesketh, Adrian K. Brennan, David S. Jessop and David P. Finn. Springer Berlin / Heidelberg. Volume 198, Number 1 / May, 2008. ISSN: 0033-3158 (Print) 1432-2072 (Online) http://www.springerlink.com/content/2127100x043n3674/</ref>
			While on its own citalopram is less effective than ] in the ], in ] cases, combination therapy may be more effective.<ref name="pmid15539864">{{cite journal | vauthors = Rampello L, Alvano A, Chiechio S, Malaguarnera M, Raffaele R, Vecchio I, Nicoletti F | title = Evaluation of the prophylactic efficacy of amitriptyline and citalopram, alone or in combination, in patients with comorbidity of depression, migraine, and tension-type headache | journal = Neuropsychobiology | volume = 50 | issue = 4 | pages = 322–328 | year = 2004 | pmid = 15539864 | doi = 10.1159/000080960 | s2cid = 46362166 }}</ref>
	===Administration===
	Citalopram is typically taken in one dose, either in the morning or evening. Citalopram can be taken with or without food. The absorption of citalopram does not increase when taken with food,<ref>http://www.drugs.com/celexa.html</ref> but can help prevent against nausea. Nausea is often caused when the ] actively absorbs free serotonin, as this receptor is present within the digestive tract.<ref>Rang, H. P. (2003). Pharmacology. Edinburgh: Churchill Livingstone. p. 187. ISBN 0-443-07145-4</ref> The ] stimulate vomiting. This side effect, if present, should subside as the body adjusts to the medication.
			Citalopram and other SSRIs can be used to treat ].<ref name="Stahl_2011">{{cite book | vauthors = Stahl SM | title = The Prescriber's Guide (Stahl's Essential Psychopharmacology) | publisher = Cambridge University Press | location = Cambridge, UK | year = 2011 | isbn = 978-0-521-17364-3 }}</ref>{{rp|107}}
	Citalopram is considered safe and well-tolerated in the ] range. Distinct from some other agents in its class, citalopram exhibits linear ] and minimal ] potential, making it a better choice for the elderly or ] patients.<ref name="pmid11206593">{{cite journal |author=Keller MB |title=Citalopram therapy for depression: a review of 10 years of European experience and data from U.S. clinical trials |journal=The Journal of clinical psychiatry |volume=61 |issue=12 |pages=896–908 |year=2000 |pmid=11206593 |doi= 10.4088/JCP.v61n1202|url=http://www.biopsychiatry.com/citalopram.html}}</ref>
			A 2009 multisite randomized controlled study found no benefit and some adverse effects in autistic children from citalopram, raising doubts about whether SSRIs are effective for treating repetitive behavior in children with autism.<ref name="pmid19487623">{{cite journal | vauthors = King BH, Hollander E, Sikich L, McCracken JT, Scahill L, Bregman JD, Donnelly CL, Anagnostou E, Dukes K, Sullivan L, Hirtz D, Wagner A, Ritz L | title = Lack of efficacy of citalopram in children with autism spectrum disorders and high levels of repetitive behavior: citalopram ineffective in children with autism | journal = Archives of General Psychiatry | volume = 66 | issue = 6 | pages = 583–590 | date = June 2009 | pmid = 19487623 | pmc = 4112556 | doi = 10.1001/archgenpsychiatry.2009.30 }}
	==Adverse effects==
			*{{lay source |template = cite news|vauthors = Kaplan K|url = http://www.latimes.com/news/science/la-sci-autism-drugs2-2009jun02,0,6717060.story|title = Study finds antidepressant doesn't help autistic children |date= 2 June 2009 |website = Los Angeles Times }}</ref>
	] is often a side effect with ]. Specifically, common side effects include difficulty becoming aroused, lack of interest in sex, and ] (trouble achieving orgasm). Genital anesthesia,<ref>{{cite journal |author=Bolton JM, Sareen J, Reiss JP |title=Genital anaesthesia persisting six years after sertraline discontinuation |journal=J Sex Marital Ther |volume=32 |issue=4 |pages=327–30 |year=2006 |pmid=16709553 |doi=10.1080/00926230600666410 |url=http://www.informaworld.com/openurl?genre=article&doi=10.1080/00926230600666410&magic=pubmed |unused_data=1B69BA326FFE69C3F0A8F227DF8201D0}}</ref> loss of or decreased response to sexual stimuli, and ejaculatory ] are also possible. Although usually reversible, these sexual side effects can last for months or years after the drug has been completely withdrawn.<ref>{{cite journal |author=Csoka AB, Bahrick AS, Mehtonen O-P |title=Persistent Sexual Dysfunction after Discontinuation of Selective Serotonin Reuptake Inhibitors (SSRIs) |journal=J Sex Med. |volume=5 |issue= 1|pages=227–33 |year=2008 |doi= 10.1111/j.1743-6109.2007.00630.x|url=http://www.blackwell-synergy.com/doi/abs/10.1111/j.1743-6109.2007.00630.x |pmid=18173768}}</ref> This is known as ].
			Some research suggests citalopram interacts with cannabinoid protein-couplings in the rat brain, and this is put forward as a potential cause of some of the drug's antidepressant effects.<ref name="pmid18084745">{{cite journal | vauthors = Hesketh SA, Brennan AK, Jessop DS, Finn DP | title = Effects of chronic treatment with citalopram on cannabinoid and opioid receptor-mediated G-protein coupling in discrete rat brain regions | journal = Psychopharmacology | volume = 198 | issue = 1 | pages = 29–36 | date = May 2008 | pmid = 18084745 | doi = 10.1007/s00213-007-1033-3 | s2cid = 23357324 }}</ref>
	Citalopram theoretically causes side effects by increasing the concentration of ] in other parts of the body (e.g., the intestines). Other side effects, such as increased apathy and emotional flattening, may be caused by the decrease in ] release that is associated with increased serotonin. Citalopram is also a mild ], which may be responsible for some of its sedating properties.<ref>Stahl, S. Stahl's Essential Psychopharmacology: The Prescriber's Guide. Cambridge University Press: New York, NY. 2009. pp. 84.</ref>
			== Administration ==
	Common side effects of citalopram include ], ], ], weight changes, frequent urination, decreased sex drive, ], ],<ref>Cerner Multum Inc. Drugs.com. 2009. http://www.drugs.com/celexa.html</ref> increased ], ], ], excessive yawning, and ]. Less common side effects include ], ], ], ] changes, dilated pupils, ], ]s, ], and ]. Rare side effects include ], ], and severe ].<ref name="rxlist.com"/> If sedation occurs, the dose may be taken at bedtime rather than in the morning.
			Citalopram is typically taken in one dose, either in the morning or evening. It can be taken with or without food. Its absorption does not increase when taken with food,<ref name="Citalopram_PI_Sheet">{{cite web | url = http://www.frx.com/pi/celexa_pi.pdf | title = Celexa (citalopram hydrobromide) Tablets/Oral Solution | work = Prescribing Information | publisher = Forest Laboratories, Inc. }}</ref><ref name="Celexa FDA label" /> but doing so can help prevent nausea. Nausea is often caused when the ] actively absorb free serotonin, as this receptor is present within the digestive tract.<ref name="isbn0-443-07145-4">{{cite book | vauthors = Rang HP | title = Pharmacology | publisher = Churchill Livingstone | location = Edinburgh | year = 2003 | isbn = 978-0-443-07145-4 | page = 187 }}</ref>
			==Adverse effects==
	Males who take the drug and are unable to achieve orgasm should consult their health care practitioner. Alternative medications are available such as ]. This does not affect the ability to achieve orgasm.
			Citalopram theoretically causes side effects by increasing the concentration of ] in other parts of the body (e.g., the intestines). Other side effects, such as increased apathy and emotional flattening, may be caused by the decrease in ] release associated with increased serotonin. Citalopram is also a mild ], which may be responsible for some of its sedating properties.<ref name="Stahl_2011"/>{{rp|104}}
			Other common side effects of citalopram include ], ], ], weight changes (usually weight gain), increase in appetite, vivid dreaming, frequent urination, dry mouth,<ref name="Citalopram_PI_Sheet"/> increased ], ], ], excessive yawning, severe tinnitus, and ]. Less common side effects include ], ], ], ] changes, dilated pupils, ], ]s, ], hyperactivity and ]. Rare side effects include ], ], severe ] and ].<ref name="Citalopram_PI_Sheet"/> If sedation occurs, the dose may be taken at bedtime rather than in the morning. Some data suggest citalopram may cause nightmares.<ref>{{cite journal | vauthors = Arora G, Sandhu G, Fleser C | title = Citalopram and nightmares | journal = The Journal of Neuropsychiatry and Clinical Neurosciences | volume = 24 | issue = 2 | pages = E43 | date =Spring 2012 | pmid = 22772700 | doi = 10.1176/appi.neuropsych.11040096 }}</ref> Citalopram is associated with a higher risk of arrhythmia than other ].<ref>{{cite journal | vauthors = Qirjazi E, McArthur E, Nash DM, Dixon SN, Weir MA, Vasudev A, Jandoc R, Gula LJ, Oliver MJ, Wald R, Garg AX | title = Risk of Ventricular Arrhythmia with Citalopram and Escitalopram: A Population-Based Study | journal = PLOS ONE | volume = 11 | issue = 8 | pages = e0160768 | date = 11 August 2016 | pmid = 27513855 | pmc = 4981428 | doi = 10.1371/journal.pone.0160768 | doi-access = free | bibcode = 2016PLoSO..1160768Q }}</ref><ref>{{cite journal | vauthors = Girardin FR, Gex-Fabry M, Berney P, Shah D, Gaspoz JM, Dayer P | title = Drug-induced long QT in adult psychiatric inpatients: the 5-year cross-sectional ECG Screening Outcome in Psychiatry study | journal = The American Journal of Psychiatry | volume = 170 | issue = 12 | pages = 1468–1476 | date = December 2013 | pmid = 24306340 | doi = 10.1176/appi.ajp.2013.12060860 }}</ref>
	Citalopram and other ] can induce a ], especially in those with undiagnosed ].<ref name="Stahl, S. Stahl's Essential Psychopharmacology 2009. pp. 85">Stahl, S. Stahl's Essential Psychopharmacology: The Prescriber's Guide. Cambridge University Press: New York, NY. 2009. pp. 85.</ref>
			Citalopram and other SSRIs can induce a ], especially in those with undiagnosed ].<ref name="Stahl_2011"/>{{rp|105}}
	Citalopram should not be taken with ], ] or ] as the resulting drug interaction could lead to ].<ref>{{cite book | title = 2006 Lippincott's Nursing Drug Guide |last = Karch |first = Amy |year = 2006 |publisher = Lippincott Williams & Wilkins |location = Philadelphia, Baltimore, New York, London, Buenos Aires, Hong Kong, Sydney, Tokyo |isbn= 1-58255-436-6 }}</ref> With St John's wort, this may be caused by compounds in the plant extract reducing the efficacy of the ] ] enzymes that process citalopram.<ref>http://www.medsafe.govt.nz/Profs/PUarticles/sjw.htm accessed Feb 27 2009</ref> It has also been suggested that such compounds, including ], ] and ], could have SSRI-mimetic effects on the nervous system, although this is still subject to debate.<ref>http://www.umm.edu/altmed/articles/st-johns-000276.htm accessed Feb 27 2009</ref> One study found that ] extracts had similar effects in treating moderate depression as citalopram, with fewer side effects.<ref>{{cite journal|title=Comparative Efficacy and Safety of a Once-Daily Dosage of Hypericum Extract STW3-VI and Citalopram in Patients with Moderate Depression: A Double-Blind, Randomised, Multicentre, Placebo-Controlled Study |year=2006|journal=Pharmacopsychiatry|volume=39|pages=66–75|doi=10.1055/s-2006-931544|url=http://www.thieme-connect.com/ejournals/abstract/pharmaco/doi/10.1055/s-2006-931544|accessdate=Feb 27 2009|author=M. Gastpar, et al.|pmid=16555167|issue=2}}</ref> Tryptophan and 5-HTP are precursors to serotonin and can cause a rise in serotonin. When taken with an SSRI, such as citalopram, this can lead to levels of serotonin that can be lethal.
			According to an article published in 2020, one of the other rare side effects of Citalopram could be triggering ]; which does not resolve after the discontinuation of the medicine.<ref>Eren, O.E., Schöberl, F., Schankin, C.J. et al. Visual snow syndrome after start of citalopram—novel insights into underlying pathophysiology. Eur J Clin Pharmacol 77, 271–272 (2021). https://doi.org/10.1007/s00228-020-02996-9</ref>
			=== Sexual dysfunction ===
	Citalopram is ] in individuals taking ], due to potential for ].
			] is often a side effect of SSRIs.<ref name=":1">{{cite web |date=15 February 2022 |title=Side effects of citalopram |url=https://www.nhs.uk/medicines/citalopram/side-effects-of-citalopram/ |access-date=19 December 2022 |website=nhs.uk |language=en}}</ref> 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=9780890425558 |edition=5th |location=Arlington, VA |pages= }}</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, ], 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>
			=== Abnormal heart rhythm ===
	], including citalopram, can increase the risk of bleeding, especially when coupled with ], ], ], or other ].<ref>Citalopram PI Sheet. 2009. http://www.frx.com/pi/Citalopram_pi.pdf</ref>
			In August 2011, the FDA announced, "Citalopram causes dose-dependent ]. Citalopram should no longer be prescribed at doses greater than 40 mg per day".<ref name="FDA Drug Safety Communication Celexa">{{cite web |date=24 August 2011 |title=Abnormal heart rhythms associated with high doses of Celexa (citalopram hydrobromide) |url=https://www.fda.gov/drugs/drug-safety-and-availability/fda-drug-safety-communication-abnormal-heart-rhythms-associated-high-doses-celexa-citalopram |work=Safety Communication |publisher=U.S. ] (FDA) }}</ref> A further clarification, issued in March 2012, restricted the maximum dose to 20&nbsp;mg for subgroups of patients, including those older than 60 years and those taking an inhibitor of cytochrome P450 2C19.7.<ref>{{cite web | title=Revised recommendations for Celexa | website=U.S. ] (FDA) | date=28 March 2012 | url=https://www.fda.gov/drugs/drug-safety-and-availability/fda-drug-safety-communication-revised-recommendations-celexa-citalopram-hydrobromide-related | access-date=28 October 2020}}</ref>
			=== Endocrine effects ===
	When taken with ], the clearance of citalopram may be reduced, leading to higher blood levels of citalopram. ] inhibits the CYP450 2C19 enzyme, one of the two primary enzymes responsible for the metabolism of citalopram. Dosage adjustments may be needed due to this effect. {{citation needed|date=November 2010}}
			As with other SSRIs, citalopram can cause an increase in serum ] level.<ref>{{cite journal | vauthors = Trenque T, Herlem E, Auriche P, Dramé M | title = Serotonin reuptake inhibitors and hyperprolactinaemia: a case/non-case study in the French pharmacovigilance database | journal = Drug Safety | volume = 34 | issue = 12 | pages = 1161–1166 | date = December 2011 | pmid = 22077504 | doi = 10.2165/11595660-000000000-00000 | s2cid = 25532853 }}</ref>
			Citalopram has no significant effect on insulin sensitivity in women of reproductive age<ref>{{cite journal | vauthors = Kauffman RP, Castracane VD, White DL, Baldock SD, Owens R | title = Impact of the selective serotonin reuptake inhibitor citalopram on insulin sensitivity, leptin and basal cortisol secretion in depressed and non-depressed euglycemic women of reproductive age | journal = Gynecological Endocrinology | volume = 21 | issue = 3 | pages = 129–137 | date = September 2005 | pmid = 16335904 | doi = 10.1080/09513590500216800 | s2cid = 11286706 }}</ref> and no changes in glycaemic control were seen in another trial.<ref name="pmid1424428">{{cite journal | vauthors = Sindrup SH, Bjerre U, Dejgaard A, Brøsen K, Aaes-Jørgensen T, Gram LF | title = The selective serotonin reuptake inhibitor citalopram relieves the symptoms of diabetic neuropathy | journal = Clinical Pharmacology and Therapeutics | volume = 52 | issue = 5 | pages = 547–552 | date = November 1992 | pmid = 1424428 | doi = 10.1038/clpt.1992.183 | s2cid = 6730763 }}</ref>
			=== Exposure in pregnancy ===
	] has been reported when treatment is stopped. Tapering off citalopram therapy, as opposed to abrupt discontinuation, is recommended in order to diminish the occurrence and severity of discontinuation symptoms. Some doctors may choose to switch a patient to Prozac (Fluoxetine) when discontinuing Citalopram as Prozac has a much longer half-life (i.e. stays in the body longer compared to Citalopram).{{Citation needed|date=October 2010}} This may avoid many of the severe withdrawal symptoms associated with Citalopram discontinuation. This can be done either by administering a single 20&nbsp;mg dose of Prozac or by beginning on a low dosage of Prozac and slowly tapering down. Either of these prescriptions may be written in liquid form to allow a very slow and gradual tapering down in dosage. Alternatively, a patient wishing to stop taking Citalopram may visit a compounding pharmacy where his or her prescription may be re-arranged into progressively smaller dosages.
			Antidepressant exposure (including citalopram) during pregnancy is associated with shorter duration of ] (by three days), increased risk of preterm delivery (by 55%), lower birth weight (by 75&nbsp;g), and lower ]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 | doi-access = free }}</ref> It is uncertain whether there is an increased prevalence of septal heart defects among children whose mothers were prescribed an SSRI in early pregnancy.<ref>{{cite journal | vauthors = Pedersen LH, Henriksen TB, Vestergaard M, Olsen J, Bech BH | title = Selective serotonin reuptake inhibitors in pregnancy and congenital malformations: population based cohort study | journal = BMJ | volume = 339 | issue = sep23 1 | pages = b3569 | date = September 2009 | pmid = 19776103 | pmc = 2749925 | doi = 10.1136/bmj.b3569 }}</ref><ref>{{cite journal | vauthors = Huybrechts KF, Palmsten K, Avorn J, Cohen LS, Holmes LB, Franklin JM, Mogun H, Levin R, Kowal M, Setoguchi S, Hernández-Díaz S | title = Antidepressant use in pregnancy and the risk of cardiac defects | journal = The New England Journal of Medicine | volume = 370 | issue = 25 | pages = 2397–2407 | date = June 2014 | pmid = 24941178 | pmc = 4062924 | doi = 10.1056/NEJMoa1312828 }}</ref>
			=== Overdose ===
			Overdosage may result in vomiting, sedation, disturbances in heart rhythm, dizziness, sweating, nausea, tremors, and rarely amnesia, confusion, coma, or convulsions.<ref name="Stahl_2011" />{{rp|105}} Overdose deaths have occurred, sometimes involving other drugs, but also with citalopram as the sole agent. Citalopram and N-desmethylcitalopram may be quantified in blood or plasma to confirm a diagnosis of poisoning in hospitalized patients or to assist in a medicolegal death investigation. Blood or plasma citalopram concentrations are usually in a range of 50-400 μg/L in persons receiving the drug therapeutically, 1000–3000 μg/L in patients who survive acute overdosage, and 3–30&nbsp;mg/L in those who do not survive.<ref name="FDA Drug Safety Communication Celexa" /><ref name="pmid9140316">{{cite journal |vauthors=Personne M, Sjöberg G, Persson H |year=1997 |title=Citalopram overdose--review of cases treated in Swedish hospitals |journal=Journal of Toxicology. Clinical Toxicology |volume=35 |issue=3 |pages=237–240 |doi=10.3109/15563659709001206 |pmid=9140316}}</ref><ref name="pmid16304470">{{cite journal |vauthors=Luchini D, Morabito G, Centini F |date=December 2005 |title=Case report of a fatal intoxication by citalopram |journal=The American Journal of Forensic Medicine and Pathology |volume=26 |issue=4 |pages=352–354 |doi=10.1097/01.paf.0000188276.33030.dd |pmid=16304470 |s2cid=44840526}}</ref> It is the most dangerous of SSRIs in overdose.<ref name="Maudsley">{{cite book |title=The Maudsley Prescribing Guidelines in Psychiatry (Taylor, The Maudsley Prescribing Guidelines) |vauthors=Taylor D, Paton C, Kapur S |publisher=Wiley-Blackwell |year=2012 |isbn=9780470979693 |location=Hoboken, NJ, USA |page=588}}</ref>
	===Suicidality===		===Suicidality===
	In the United States, citalopram, like other antidepressants, carries a ] stating that it may increase suicidal thinking and behavior in those under age 24.<ref>Citalopraim PI Sheet. 2009. http://www.frx.com/pi/Citalopram_pi.pdf</ref>		In the United States, citalopram carries a ] stating it may increase suicidal thinking and behavior in those under age 24.<ref name="Citalopram_PI_Sheet" />
			=== Discontinuation syndrome ===
	===Overdosage===
			] has been reported when treatment is stopped. It includes sensory, and gastrointestinal symptoms, dizziness, lethargy, and sleep disturbances, as well as psychological symptoms such as anxiety/agitation, irritability, and poor concentration.<ref>{{cite journal |vauthors=Warner CH, Bobo W, Warner C, Reid S, Rachal J |date=August 2006 |title=Antidepressant discontinuation syndrome |journal=American Family Physician |volume=74 |issue=3 |pages=449–456 |pmid=16913164}}</ref> Electric shock-like sensations are typical for SSRI discontinuation.<ref>{{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> Withdrawal symptoms can occur when this medicine is suddenly stopped, such as ], sleeping problems (difficulty sleeping and intense dreams), feeling dizzy, agitated or anxious, nausea, vomiting, tremors, confusion, sweating, headache, diarrhea, palpitations, changes in emotions, irritability, and eye or eyesight problems. Treatment with citalopram should be reduced gradually when treatment is finished.<ref>{{cite web |date=13 October 2022 |title=Citalopram withdrawal: What to expect |url=https://www.medicalnewstoday.com/articles/citalopram-withdrawal |access-date=19 December 2022 |website=www.medicalnewstoday.com |language=en}}</ref>
	Overdosage may result in vomiting, sedation, disturbances in heart rhythm, dizziness, sweating, nausea, tremor, and rarely amnesia, confusion, coma, or convulsions.<ref name="Stahl, S. Stahl's Essential Psychopharmacology 2009. pp. 85"/> A number of overdose deaths have occurred, sometimes involving other drugs but also with citalopram as the sole agent. Citalopram and N-desmethylcitalopram may be quantitated in blood or plasma to confirm a diagnosis of poisoning in hospitalized patients or to assist in a medicolegal death investigation. Blood or plasma citalopram concentrations are usually in a range of 50-400 μg/L in persons receiving the drug therapeutically, 1000-3000 μg/L in patients who survive acute overdosage and 3–30&nbsp;mg/L in those who do not survive.<ref>Personne M, Sjöberg G, Persson H. Citalopram overdose--review of cases treated in Swedish hospitals. J. Tox. Clin. Tox. 35: 237-240, 1997.</ref><ref>Luchini D, Morabito G, Centini F. Case report of a fatal intoxication by citalopram. Am. J. For. Med. Pathol. 26: 352-354, 2005.</ref><ref>R. Baselt, ''Disposition of Toxic Drugs and Chemicals in Man'', 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 319-322.</ref>
	==Stereochemistry==		== Interactions ==
	Citalopram has one ], to which a ]] and an ''N,N''-dimethyl-3-aminopropyl group bind. Due to this ], the molecule exists in (two) ]ic forms (mirror images). They are termed ''S''-(+)-citalopram and ''R''-(–)-citalopram.
			=== Serotonin syndrome ===
	<table border=0 cellspacing=0 cellpadding=2 align=center>
			Citalopram should not be taken with ], ] or ] as the resulting drug interaction could lead to ].<ref name="isbn1-58255-436-6">{{cite book | vauthors = Karch AM | title = Lippincott's Nursing Drug Guide | publisher = Lippincott Williams & Wilkins | location = Hagerstwon, MD | year = 2006 | isbn = 978-1-58255-436-5 }}</ref> With St John's wort, this may be caused by compounds in the plant extract reducing the efficacy of the ] ] enzymes that process citalopram.<ref name="urlInteractions with St Johns wort preparations">{{cite web | url = http://www.medsafe.govt.nz/Profs/PUarticles/sjw.htm | title = Interactions with St John's wort preparations | work = Prescriber Update Articles | publisher = New Zealand Medicines and Medical Devices Safety Authority | year = 2000 }}</ref> Tryptophan and 5-HTP are precursors to serotonin.<ref>{{cite web|url=https://www.oxfordvitality.co.uk/history-5-htp-serotonin-tryptophan|title=The History of Tryptophan, Serotonin and 5-HTP|website=www.oxfordvitality.co.uk|date=21 November 2016 |language=en|access-date=22 July 2018}}</ref> When taken with an SSRI, such as citalopram, this can lead to levels of serotonin that can be lethal. This may also be the case when SSRIs are taken with SRAs (]) such as in the case of ]. It is possible that SSRIs could reduce the effects associated with an SRA since SSRIs stop the reuptake of Serotonin by blocking ]. This would allow less serotonin in and out of the transporters, thus decreasing the likelihood of ] effects. However, these concerns are still disputed as the exact pharmacodynamic effects of citalopram and MDMA have yet to be fully identified.{{citation needed|date=September 2015}} Citalopram is ] in individuals taking ], owing to a potential for ].
	<tr>
	<td align="center">]</td>
	<td align="center">]</td>
	</tr>
	<tr>
	<td align="center">]</td>
	<td align="center">]</td>
	</tr>
	<tr>
	<td align="center">'''(''S'')-(+)-citalopram'''</td>
	<td align="center">'''(''R'')-(–)-citalopram'''</td>
	</tr>
	</table>
			=== Other interactions ===
	Citalopram is sold as a ] mixture, consisting of 50% (''R'')-(−)-citalopram and 50% (''S'')-(+)-citalopram. Only the (''S'')-(+) enantiomer has the desired antidepressant effect. ] now markets the (''S'')-(+) enantiomer, the generic name of which is ]. Whereas citalopram is supplied as the ], escitalopram is sold as the ] salt (hydrooxalate).<ref name=Celexa.com></ref> In both cases, the ] forms of the amine make these otherwise ] compounds water-soluble.
			SSRIs, including citalopram, can increase the risk of bleeding, especially when coupled with ], ], ], or other ].<ref name="Citalopram_PI_Sheet" /> Taking citalopram with ] may cause higher blood levels of citalopram. This is a potentially dangerous interaction, so dosage adjustments may be needed or alternatives may be prescribed.<ref>{{cite web|title=Drug interactions between Celexa and omeprazole|url=https://www.drugs.com/drug-interactions/celexa-with-omeprazole-679-335-1750-0.html|publisher=Drugs.com|access-date=28 January 2014}}</ref><ref>{{cite web|title=citalopram (Rx) - Celexa|url=http://reference.medscape.com/drug/celexa-citalopram-342958|publisher=Medscape|access-date=28 January 2014}}</ref><ref name="Celexa FDA label" />
			== Pharmacokinetics ==
	==Metabolites==
			Citalopram is considered safe and well tolerated in the ] range. Distinct from some other agents in its class, it exhibits linear ] and minimal ] potential, making it a better choice for the elderly or ] patients.<ref name="pmid11206593">{{cite journal |vauthors=Keller MB |date=December 2000 |title=Citalopram therapy for depression: a review of 10 years of European experience and data from U.S. clinical trials |journal=The Journal of Clinical Psychiatry |volume=61 |issue=12 |pages=896–908 |doi=10.4088/JCP.v61n1202 |pmid=11206593}}</ref>
			== Stereochemistry ==
	Citalopram ]s ] and ] are significantly less active, and their contribution to the overall action of citalopram is negligible.
			Citalopram has one ], to which a ] ] and an ''N, N''-dimethyl-3-aminopropyl group bind. As a result of this ], the molecule exists in (two) ]ic forms (mirror images). They are termed ''S''-(+)-citalopram and ''R''-(–)-citalopram.
			{| style="margin:auto"
			|-
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			| align="center" | '''(''S'')-(+)-citalopram'''
			| align="center" | '''(''R'')-(–)-citalopram'''
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			Citalopram is sold as a ] mixture, consisting of 50% (''R'')-(−)-citalopram and 50% (''S'')-(+)-citalopram. Only the (''S'')-(+) enantiomer has the desired antidepressant effect.<ref name="pmid15107657">{{cite journal | vauthors = Lepola U, Wade A, Andersen HF | title = Do equivalent doses of escitalopram and citalopram have similar efficacy? A pooled analysis of two positive placebo-controlled studies in major depressive disorder | journal = International Clinical Psychopharmacology | volume = 19 | issue = 3 | pages = 149–155 | date = May 2004 | pmid = 15107657 | doi = 10.1097/00004850-200405000-00005 | s2cid = 36768144 }}</ref> ] now markets the (''S'')-(+) enantiomer, the generic name of which is ]. Whereas citalopram is supplied as the ], escitalopram is sold as the ] salt (hydrooxalate).<ref name="Citalopram_PI_Sheet"/> In both cases, the ] forms of the amine make these otherwise ] compounds water-soluble.
			==Metabolism==
			Citalopram is metabolized in the liver mostly by ], but also by ] and ]. Metabolites desmethylcitalopram and didesmethylcitalopram are significantly less energetic and their contribution to the overall action of citalopram is negligible. The half-life of citalopram is about 35 hours. Approximately 80% is cleared by the liver and 20% by the kidneys.<ref name="DrugBank">{{cite web|title=Citalopram|url=https://www.drugbank.ca/drugs/DB00215|website=DrugBank|access-date=12 February 2017|date=17 August 2016}}</ref> The elimination process is slower in the elderly and in patients with liver or ]. With once-daily dosing, steady plasma concentrations are achieved in about a week. Potent inhibitors of CYP2C19 and 3A4 might decrease citalopram clearance.<ref name="Celexa FDA label" />
			Tobacco smoke exposure was found to inhibit the biotransformation of citalopram in animals, suggesting that the elimination rate of citalopram is decreased after tobacco smoke exposure. After intragastric administration, the half-life of the ] mixture of citalopram was increased by about 287%.<ref>{{cite journal | vauthors = Majcherczyk J, Kulza M, Senczuk-Przybylowska M, Florek E, Jawien W, Piekoszewski W | title = Influence of tobacco smoke on the pharmacokinetics of citalopram and its enantiomers | journal = Journal of Physiology and Pharmacology | volume = 63 | issue = 1 | pages = 95–100 | date = February 2012 | pmid = 22460466 }}</ref>
			]
			{| class="wikitable" style="float:right;width:200px;margin:10px"
			|+Binding profile<ref>{{cite journal | vauthors = Owens JM, Knight DL, Nemeroff CB | title = | journal = L'Encéphale | volume = 28 | issue = 4 | pages = 350–355 | date = Jul–Aug 2002 | pmid = 12232544 }}</ref>
			|-
			! Receptor !! K<sub>i</sub> (nM)
			|-
			| ] || 1.6
			|-
			| ] || 6190
			|-
			| ] || 617
			|-
			| ] ||
			1211
			|-
			| ] || 1430
			|-
			| ] || 283
			|}
	==History==		==History==
			Citalopram was first synthesized in 1972 by chemist Klaus Bøgesø<ref>{{cite book | vauthors = Bøgesø KP, Sánchez C | chapter = The discovery of citalopram and its refinement to escitalopram. | title = Analogue-Based Drug Discovery | volume = III | date = December 2012 | pages = 269–94 | chapter-url= https://www.researchgate.net/publication/256067218 |access-date=23 October 2020 | doi = 10.1002/9783527651085.ch11 | isbn = 978-3-527-65108-5 | publisher = Wiley-VCH Verlag GmbH & Co. KGaA | location = Weinheim, Germany | veditors = Fischer J, Ganellin CR, Rotella DP }}</ref> and his research group at the pharmaceutical company ] and was first marketed in 1989 in Denmark. It was first marketed in the US in 1998.<ref>{{cite journal | vauthors = Rawe B, May P | journal = Molecule of the Month | date = November 2009 | url = http://www.chm.bris.ac.uk/motm/citalopram/citalopramh.htm | title = Citalopram: A new treatment for depression| access-date = 16 February 2015 | doi = 10.6084/m9.figshare.5255050 | publisher = University of Bristol }}</ref> The original ] expired in 2003, allowing other companies to legally produce and market ] versions.
	Citalopram was originally created in 1989<ref name="pmid15765832">{{cite journal |author=Dorell K, Cohen MA, Huprikar SS, Gorman JM, Jones M |title=Citalopram-induced diplopia |journal=Psychosomatics |volume=46 |issue=1 |pages=91–3 |year=2005 |pmid=15765832|doi= 10.1176/appi.psy.46.1.91}}</ref> by the pharmaceutical company ]. The ] expired in 2003, allowing other companies to legally produce ] versions. Lundbeck has recently released an updated formulation called ],{{Citation needed|date=May 2010}} which is the ''S''-] of the ] citalopram (see ]), and acquired a new patent for it. In the United States, Forest Labs manufactures and markets the drug.
	==Brand names==		==Society and culture==
			===Brand names===
	Citalopram is sold under the brand-names '''Celexa''' (U.S. and Canada, ]), '''Citalopram''' (USA, United Kingdom, Denmark), '''Citta''' (Brazil), '''Cipramil''' (Australia, Brazil, Finland, Germany, Netherlands, Ireland, Israel, Norway, Sweden, United Kingdom, New Zealand, South Africa), '''Elopram''' (Italy)<ref>http://www.drugs.com/international/elopram.html</ref> '''Citol''', '''Vodelax''' (Turkey), '''Citrol''', '''Seropram''', '''Talam''' (Europe and Australia), '''Citabax''', '''Citaxin''' (Poland), '''Citalec''' (Slovakia, Czech Republic), '''Recital''' (Israel, Thrima Inc. for Unipharm Ltd.), '''Zetalo''' (India), '''Celapram''', '''Ciazil''' (Australia, New Zealand), '''Zentius''', '''Cimal''' (South America, by Roemmers and Recalcine), '''Ciprapine''' (Ireland), '''Cilift''' (South Africa), '''Citox''' (Mexico), '''Temperax''' (Chile, Peru, Argentina), '''Talohexal''' (Australia), '''Citopam''' (Australia), '''Akarin''' (Denmark, Nycomed), '''Cipram''' (Turkey, Denmark, H. Lundbeck A/S), '''Dalsan''' (Eastern Europe), '''Pramcit''' (Pakistan), and '''Celius''' (Greece), '''Humorup''' (Argentina), '''Oropram''' (Iceland, Actavis), '''Zylotex''' (Portugal).
			Citalopram is sold under these brand names:
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			* Akarin (Denmark, Nycomed)
			* C Pram S (India)
			* Celapram (Australia,<ref name="url_Citalopram_PBS">{{cite web | url = http://www.pbs.gov.au/medicine/item/8220p-8702b-8703c | title = Pharmaceutical Benefits Scheme (PBS) - Citalopram | publisher = Australian Government | work = Australian Government Department of Health }}</ref> New Zealand),
			* Celexa (U.S. and Canada, ])
			* Celica (Australia)<ref name="url_Citalopram_PBS" />
			* Ciazil (Australia,<ref name="url_Citalopram_PBS" /> New Zealand)
			* Cilate (South Africa)
			* Cilift (South Africa)
			* Cimal (South America, by Roemmers and Recalcine)
			* Cipralex (Europe, South Africa)
			* Cipram (Denmark, Turkey, H. Lundbeck A/S)
			* Cipramil (Australia,<ref name="url_Citalopram_PBS" /> Brazil, Belgium, Chile, Finland, Germany, Netherlands, Iceland, Ireland, Israel, New Zealand, Norway, Russia, South Africa, Sweden, United Kingdom)
			* Cipraned, Cinapen (Greece)
			* Ciprapine (Ireland)
			* Ciprotan (Ireland)
			* Citabax, Citaxin (Poland)
			* Cital (Poland)
			* Citalec (Czech Republic, Slovakia)
			* Citalex (Iran, Serbia)
			* Citalo (Australia,<ref name="url_Citalopram_PBS" /> Egypt, Pakistan)
			* Citalopram (Canada, Denmark, Finland, Germany, Ireland, The Netherlands, New Zealand, Spain, Sweden, Switzerland, United Kingdom, U.S.)
			* Citol (Russia, Turkey)
			<!-- Citopam (Australia), NOT PBS <ref name="url_Citalopram_PBS" /> remove these if no-one objects -->
			* Citox (Mexico)
			* Citrol (Europe and Australia)<ref name="url_Citalopram_PBS" />
			* Citta (Brazil)
			* Dalsan (Eastern Europe)
			* Denyl (Brazil)
			* Depram (Egypt)<ref>{{Cite web |title=Depram {{!}} Apex |url=https://apexpharmaeg.com/product/depram/ |access-date=2024-12-23 |language=en-US}}</ref><ref>{{Cite web |title=Depram: all you need to know about it |url=https://www.tebdaily.com/%d8%af%d9%8a%d8%a8%d8%b1%d8%a7%d9%85-%d9%83%d9%84-%d9%85%d8%a7-%d8%aa%d8%b1%d9%8a%d8%af-%d9%85%d8%b9%d8%b1%d9%81%d8%aa%d9%87-%d8%b9%d9%86%d9%87/ |website=Teb Daily}}</ref>
			* Elopram (Italy)
			* Estar (Pakistan)
			* Humorup (Argentina)
			* Humorap (Peru, Bolivia)
			* Lopraxer (Greece)<ref>{{cite web|url=https://www.drugs.com/international/lopraxer.html|title=Lopraxer|publisher=Drugs.com}}</ref>
			* Oropram (Iceland, Actavis),
			* Opra (Russia)
			* Pram (Russia)
			* Pramcit (Pakistan)
			* Procimax (Brazil)
			* Recital (Israel, Thrima Inc. for Unipharm Ltd.)
			* Sepram (Finland)
			* Seropram (various European countries, including the Czech Republic)
			* Szetalo (India)
			* Talam (Europe and Australia)<ref name="url_Citalopram_PBS" />
			<!-- Talohexal (Australia), Note Not on PBS so unlikely to be sold<ref name="url_Citalopram_PBS" /> -->
			* Temperax (Argentina, Chile, Peru)
			* Vodelax (Turkey)
			* Zentius (South America, by Roemmers and Recalcine)
			* Zetalo (India)
			* Cipratal (Kuwait, GCC)
			* Zylotex (Portugal)<ref name="Citalopram International">{{cite web | url = https://www.drugs.com/international/citalopram.html | title = Citalopram | work = International | publisher = Drugs.com }}</ref>
			{{div col end}}
	==References==
	{{Reflist|2}}
			===European Commission fine===
	==External links==
	*
			On 19 June 2013, the ] imposed a fine of €93.8&nbsp;million on the Danish pharmaceutical company ], plus a total of €52.2&nbsp;million on several generic pharmaceutical-producing companies. This was in response to Lundbeck entering an agreement with the companies to delay their sales of generic citalopram after Lundbeck's ] on the drug had expired, thus reducing competition in breach of European ].<ref>{{cite press release |title=Antitrust: Commission fines Lundbeck and other pharma companies for delaying market entry of generic medicines |date=19 June 2013 |publisher=European Union |place=Brussels |url=http://europa.eu/rapid/press-release_IP-13-563_en.htm |access-date=20 June 2013}}</ref>
	* Cipramil Patient Information Leaflet
	*
			== Other uses ==
			Citalopram is also a ].<ref name="Ribeiro-Geary-2010">{{cite journal | vauthors = Ribeiro P, Geary TG | title=Neuronal signaling in schistosomes: current status and prospects for postgenomics | journal=] | publisher=] | volume=88 | issue=1 | year=2010 | issn=0008-4301 | doi=10.1139/z09-126 | pages=1–22}}</ref> ] have high mortality when treated with citalopram.<ref name="Ribeiro-Geary-2010" />
			== See also ==
			* ]
			== References ==
			{{Reflist}}
	{{Antidepressants}}		{{Antidepressants}}
	{{Anxiolytics}}		{{Anxiolytics}}
			{{OCD pharmacotherapies}}
	{{Serotonergics}}
			{{Monoamine reuptake inhibitors}}
			{{Sigma receptor modulators}}
			{{Portal bar | Medicine}}
			{{Authority control}}
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