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| {{drugbox |
| | #REDIRECT [[Citalopram]] |
| | IUPAC_name = 1-(3-dimethylaminopropyl)-1-(4-fluorophenyl)-<br/>1,3-dihydroisobenzofuran-5-carbonitrile
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| | image = Citalopram structure.svg
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| | CAS_number = 59729-33-8
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| | ATC_prefix = N06
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| | ATC_suffix = AB04
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| | ATC_supplemental = N06AB10
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| | PubChem = 2771
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| | DrugBank = APRD00147
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| | C=20 | H=21 | F=1 | N=2 | O=1
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| | molecular_weight = 324.392 g/mol
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| | bioavailability = 80%
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| | protein_bound =
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| | metabolism = [[hepatic]] ([[CYP3A4]] & [[CYP2C19]])
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| | elimination_half-life = 35 hours
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| | excretion = Mostly as unmetabolized Citalopram, partly DCT and traces of DDCT in urine
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| | =
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| | legal_status = Rx-only
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| | routes_of_administration = Oral
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| }}
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| {{SI}}
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| '''Citalopram''' is an [[antidepressant]] [[Medication|drug]] used to treat [[Clinical depression|depression]] associated with [[mood disorder]]s. It is also used on occasion in the treatment of [[body dysmorphic disorder]] and [[anxiety]].
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| Citalopram belongs to a class of drugs known as [[selective serotonin reuptake inhibitor]]s (SSRIs). It is sold under the brand-names '''Celexa'''™ (U.S., Forest Laboratories, Inc.), '''Cipramil'''™ , '''Citrol'''™, '''Seropram'''™ (Europe and Australia), '''Recital'''™ (Israel, Thrima Inc. for Unipharm Ltd.), '''Zetalo''' (India), '''Celepram'''™, '''Ciazil'''™ (Australia), '''Zentius'''™ (South America, Roemmers) and '''Cipram'''™ (Denmark, H. Lundbeck A/S).
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| ==History==
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| Citalopram was originally created in 1989<ref>{{cite journal | author=Karin Dorell, M.D., Mary Ann Cohen, M.D., Shirish S. Huprikar, M.D., Jack M. Gorman, M.D., and Makeda Jones, M.D. | title=Citalopram-Induced Diplopia | journal=Psychosomatics | volume=46 | issue=1 | year=2005 | pages=91-93 }}</ref> by the pharmaceutical company Lundbeck. The [[patent]] expired in 2003, allowing other companies legally to produce [[generic drug|generic]] versions.
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| Lundbeck has recently released an updated formulation called [[escitalopram]] (also known as '''Cipralex'''™ or '''Lexapro'''™), which is the ''S''-[[enantiomer]] of the [[racemic]] citalopram (see [[Citalopram#Stereochemistry|below]]), and acquired a new patent for it. In the United States, Forest Laboratories licenses the rights for both Celexa and Lexapro from Lundbeck, which is based in Denmark.
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| ==Indications==
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| ===Approved===
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| Citalopram is primarily used to treat the symptoms of [[Clinical depression|depression]] but can also be prescribed for [[Social anxiety|social anxiety disorder]], [[panic disorder]] or [[obsessive-compulsive disorder]]. Also prescribed in [[Huntington's disease]] and [[premenstrual dysphoric disorder]].
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| ===Unapproved/Off-label/Investigational===
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| Citalopram has been found to significantly reduce the symptoms of [[diabetic neuropathy]]<ref>{{cite journal | author=Sindrup SH, Bjerre U, Dejgaard A, Brosen K, Aaes-Jorgensen T, Gram LF. | title=The selective serotonin reuptake inhibitor citalopram relieves the symptoms of diabetic neuropathy. | journal=Clinical Pharmacology & Therapeutics | volume=52 | issue=5 | year=1992 | pages=547-552| id=PMID 1424428 }}</ref> and [[premature ejaculation]].<ref>{{cite journal | author=Atmaca M, Kuloglu M, Tezcan E, Semercioz A. | title=The efficacy of citalopram in the treatment of premature ejaculation: a placebo-controlled study. | journal=International Journal of Impotence Research | volume=14 | issue=6 | year=2002 | pages=502-505| id=PMID 12494286 }}</ref> There is also evidence that citalopram may be effective in the treatment of [[post-stroke pathological crying]].<ref>{{cite journal | author=Andersen G., Vestergaard K., Riis JO.
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| | title=Citalopram for post-stroke pathological crying.
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| | journal=Lancet(British edition) | volume=342 | issue=8875 | year=1993 | pages=837-839| id=PMID 8104273 }}</ref>
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| ==Dosage==
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| Initially, 10 or 20mg once daily, in the morning or evening, with or without food. If response is inadequate, consider an increase to 40 mg/day in 20 mg increments at intervals of no less than 1 week. Some elderly patients may respond to 10 mg/day. Titrate to a maximum of 40 mg/day if needed and tolerated. Hepatic impairment: 30 mg/day (maximum dosage). If Celexa therapy is to be discontinued, taper the dose over 1-2 weeks.
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| Citalopram is formulated in 10, 20 and 40mg tablets.
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| ==Side effects and drug interactions==
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| Citalopram is generally considered safe and well-tolerated in the [[medication|therapeutic]] dose range of 20 to 60 mg/day. A doctor must always monitor a patient taking an [[SSRI]] like citalopram. Distinct from some other agents in its class, Citalopram exhibits linear [[pharmacokinetics]] and minimal [[drug interaction]] potential, making it a better choice for the elderly or [[Comorbidity|comorbid]] patients.<ref name=http://www.biopsychiatry.com/citalopram.html>[http://www.biopsychiatry.com/citalopram.html http://www.biopsychiatry.com/citalopram.html]</ref>
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| Citalopram can have a number of adverse effects. In clinical trials, over 10% of patients reported one or more of the following side effects: [[fatigue (medical)|fatigue]], [[Somnolence|drowsiness]], [[Xerostomia|dry mouth]], increased [[sweating]] ([[hyperhidrosis]]), [[Tremor|trembling]], [[headache]], [[dizziness]], [[Sleep disorder|sleep disturbances]], [[insomnia]], [[cardiac arrythmia]], [[blood pressure]] changes, [[nausea]]/[[vomiting]], [[diarrhea]], heightened [[anorgasmia]] in females, [[Erectile dysfunction|impotence]] and [[ejaculation|ejaculatory]] problems in males. In rare cases (around over 1% of cases), some [[Allergy|allergic reactions]], [[Seizure|convulsions]], [[Mood swing|mood changes]], [[anxiety]] and [[Mental confusion|confusion]] have been reported. Also sedation may be present during treatment of citalopram. If this occurs it is advisable to take the dose at bedtime instead of in the morning.
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| Another uncommon side effect is [[bruxism]] (teeth grinding).<ref>{{cite web|url=http://www.mayoclinic.com/health/bruxism/DS00337/DSECTION=3|title=Bruxism/Teeth grinding|publisher=[[Mayo Clinic]]|accessdate=2007-07-25|date=2007-05-18}}</ref> When patients stop using Citalopram they may experience a feeling similar to electricity or minor shocks in their upper body and in their hands. This is caused by the chemical changes occurring in the brain and they pass with time. Occasionally, [[panic attack]]s, thoughts of [[suicide]] or [[self-harm]] may occur or increase in the first few weeks, before the antidepressant effect starts.<ref name=http://www.mentalhealth.com/drug/p30-c04.html#Head_5>{{cite web|url=http://www.mentalhealth.com/drug/p30-c04.html#Head_5|title=Citalopram Hydrobromide Brand name: Celexa Drug monograph; Contraindications|year=1999|month=August|notes=information from a Canadian monograph|publisher=Internet Mental Health|accessdate=2007-07-25}}</ref>
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| Citalopram and other SSRIs have been shown to cause sexual side effects in some patients, both males and females.<ref>Clayton A, Keller A, McGarvey EL. ''Burden of phase-specific sexual dysfunction with SSRIs.'' J Affect Disord 2006;91:27-32. PMID 16430968.</ref> Although usually reversible, these sexual side effects can sometimes last for months, years or possibly indefinitely even after the drug has been completely withdrawn. This disorder is known as [[Post SSRI Sexual Dysfunction]].
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| Citalopram is [[Contraindication|contraindicated]] in individuals taking [[Monoamine oxidase inhibitor|MAOIs]]. It is considered relatively safe in overdose, although fatal cases of dosages 840 mg to 1960 mg have been reported.<ref name="mentalhealth">{{cite web|url=http://www.mentalhealth.com/drug/p30-c04.html#Head_12|title=Citalopram Hydrobromide Brand name: Celexa Drug monograph; Symptoms and Treatment of Overdosage|year=1999|month=August|notes=information from a Canadian monograph|publisher=Internet Mental Health|accessdate=2007-07-25}}]</ref>
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| [[SSRI discontinuation syndrome|Discontinuation or withdrawal syndrome]] has been reported with commencing of treatment. Tapering of
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| Citalopram therapy, as opposed to abrupt discontinuation, is recommended in order to diminish the occurrence of discontinuation symptoms.
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| ==Stereochemistry==
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| Citalopram has a [[stereocenter]], to which a [[Fluorocarbon|4-fluoro]][[phenyl group]] and an ''N,N''-dimethyl-3-aminopropyl group bind. Due to this [[Chirality (chemistry)|chirality]] the molecule exists in (two) [[enantiomer]]ic forms (mirror images). They are termed ''S''-(+)-citalopram and ''R''-(−)-citalopram.
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| <table border=0 cellspacing=0 cellpadding=2 align=center>
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| <tr>
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| <td align="center">[[Image:S-(+)-citalopram-3D-sticks.png|200px|''S''-(+)-citalopram]]</td>
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| <td align="center">[[Image:R-(−)-citalopram-3D-sticks.png|200px|''R''-(−)-citalopram]]</td>
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| </tr>
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| <tr>
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| <td align="center">[[Image:S-(+)-citalopram.png|200px|''S''-(+)-citalopram]]</td>
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| <td align="center">[[Image:R-(-)-citalopram.png|200px|''R''-(−)-citalopram]]</td>
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| </tr>
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| <tr>
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| <td align="center">'''''S''-(+)-citalopram'''</td>
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| <td align="center">'''''R''-(−)-citalopram'''</td>
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| </tr>
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| </table>
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| Citalopram is sold as a [[racemic]] mixture, consisting of 50% ''R''-(−)-citalopram and 50% ''S''-(+)-citalopram. Only the ''S''-(+) enantiomer has the desired antidepressant effect. [[Lundbeck]] now markets the ''S''-(+) enantiomer, the generic name of which is [[escitalopram]]. Whereas citalopram is supplied as the [[Hydrobromic acid|hydrobromide]], escitalopram is sold as the [[oxalate]] salt (hydrooxalate).<ref name=Celexa.com>[http://www.celexa.com/ Celexa.com]</ref> In both cases, the [[salt (chemistry)|salt]] forms of the amine makes these otherwise [[lipophilic]] compounds water-soluble.
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| ==References==
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| <div class="references-small">
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| <references/>
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| </div>
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| ==External links==
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| Pharmacological information and treatment study information:
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| * [http://www.biopsychiatry.com/citalopram.html biopsychiatry.com]
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| * [http://www.fda.gov/cder/drug/infosheets/patient/citalopramPT.htm FDA patient fact sheet on Citalopram hydrobromide]
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| Lunbeck's official websites for citalopram under the trade name Cipramil:
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| * [http://www.cipramil.com Cipramil.com]
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| Forest's official websites for citalopram under the trade name Celexa:
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| * [http://www.celexa.com/Celexa/default.aspx Celexa.com]
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| * [http://www.frx.com/products/celexa.aspx Celexa product page on Forest Laboratories web site]
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| * [http://emc.medicines.org.uk/emc/assets/c/html/displaydoc.asp?documentid=1070 Cipramil Patient Information Leaflet] Cipramil Patient Information Leaflet
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| {{Antidepressants}}
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| <!--Other langugaes-->
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| <!--Categories-->
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| [[Category:Selective serotonin reuptake inhibitors|Citalopram]]
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| [[ru:Циталопрам]]
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