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Citalopram (brand names: Celexa, Cipramil and others) is an antidepressant drug of the selective serotonin reuptake inhibitor (SSRI) class. It has U.S. Food and Drug Administration approval to treat major depression, and is prescribed off-label for other conditions. In Australia, the UK, Germany, Portugal, Poland, and most European countries, it is licensed for depressive episodes and panic disorder with or without agoraphobia. In Spain and Denmark it is also used for obsessive–compulsive disorder.
1 Medical uses
1.1 Depression
1.2 Panic disorder
1.3 Off-label
1.4 Administration
2 Adverse effects
2.1 Post-SSRI sexual dysfunction
2.2 Abnormal heart rhythm
2.3 Endocrine effects
2.4 Exposure in pregnancy
2.5 Interactions
2.6 Overdosage
2.7 Suicidality
3 Stereochemistry
4 Metabolism
5 Pharmacology
6 History
7 Brand names
8 European Commission fine
9 See also
10 References
11 External links
Medical uses
Citalopram HBr tablets in 20-mg (coral, marked 508) and 40-mg (white, marked 509), and a United States one-cent coin (size 19.05 mm/0.75 in)
In the National Institute for Health and Clinical Excellence ranking of 10 antidepressants for efficacy and cost-effectiveness
Evidence for effectiveness of citalopram for treating depression in children is uncertain.
Panic disorder
Citalopram is licensed in the UK and other European countries
Citalopram is frequently used off-label to treat anxiety, panic disorder, dysthymia,
It has been shown to be effective in 85% of patients with generalized anxiety disorder, including some who had failed with other SSRIs.
Citalopram is well tolerated and as effective as moclobemide in social anxiety disorder.
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.
Citalopram has produced a modest reduction in alcoholic drink intake and increase in drink-free days in studies of alcoholics, possibly by decreasing desire or reducing the reward.
Citalopram has been found to reduce the symptoms of diabetic neuropathy.
While on its own citalopram is less effective than amitriptyline in the prevention of migraines, in refractory cases, combination therapy may be more effective.
Citalopram and other SSRIs can be used to treat hot flashes. : 107
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.
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 effect.
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, The 5HT3 receptors stimulate vomiting. This side effect, if present, should subside as the body adjusts to the medication.
Citalopram is considered safe and well tolerated in the therapeutic dose range. Distinct from some other agents in its class, it exhibits linear pharmacokinetics and minimal drug interaction potential, making it a better choice for the elderly or comorbid patients.
Adverse effects
Sexual dysfunction is often a side effect with SSRIs. Specifically, common side effects include difficulty becoming aroused, lack of interest in sex, and anorgasmia (trouble achieving orgasm). One study showed, however, when remission of major depressive disorder is achieved, quality of life and sexual satisfaction is reported to be higher in spite of sexual side effects.
Citalopram theoretically causes side effects by increasing the concentration of serotonin 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 dopamine release associated with increased serotonin. Citalopram is also a mild antihistamine, which may be responsible for some of its sedating properties. : 104
Common side effects of citalopram include drowsiness, insomnia, nausea, weight changes (usually weight gain), increase in appetite, vivid dreaming, frequent urination, decreased sex drive, anorgasmia, dry mouth,
Withdrawal symptoms can occur when this medicine is suddenly stopped, such as paraesthesiae, 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.
Citalopram and other SSRIs can induce a mixed state, especially in those with undiagnosed bipolar disorder. : 105
Post-SSRI sexual dysfunction
Some people experience persistent sexual side effects after they stop taking SSRIs.
Abnormal heart rhythm
In August 2011, the FDA announced, “Citalopram causes dose-dependent QT interval prolongation. Citalopram should no longer be prescribed at doses greater than 40 mg per day”.
Endocrine effects
As with other SSRIs, citalopram can cause an increase in serum prolactin level.
Citalopram has no significant effect on insulin sensitivity in women of reproductive age
Exposure in pregnancy
Antidepressant exposure (including citalopram) during pregnancy is associated with shorter duration of gestation (by three days), increased risk of preterm delivery (by 55%), lower birth weight (by 75 g), and lower Apgar scores (by <0.4 points). Antidepressant exposure is not associated with an increased risk of spontaneous abortion. Interactions Citalopram should not be taken with St John's wort, tryptophan or 5-HTP as the resulting drug interaction could lead to serotonin syndrome. Tryptophan and 5-HTP are precursors to serotonin. SSRIs, including citalopram, can increase the risk of bleeding, especially when coupled with aspirin, NSAIDs, warfarin, or other anticoagulants. Citalopram is contraindicated in individuals taking MAOIs, owing to a potential for serotonin syndrome. Taking citalopram with omeprazole may cause higher blood levels of citalopram. This is a potentially dangerous interaction, so dosage adjustments may be needed or alternatives may be prescribed. SSRI discontinuation syndrome has been reported when treatment is stopped. It includes sensory, gastrointestinal symptoms, dizziness, lethargy, and sleep disturbances, as well as psychological symptoms such as anxiety/agitation, irritability, and poor concentration. Tapering off citalopram therapy, as opposed to abrupt discontinuation, is recommended in order to diminish the occurrence and severity of discontinuation symptoms. Some doctors choose to switch a patient to Prozac (fluoxetine) when discontinuing citalopram as fluoxetine has a much longer half-life (i.e. stays in the body longer compared to citalopram). This may avoid many of the severe withdrawal symptoms associated with citalopram discontinuation. This can be done either by administering a single 20 mg dose of fluoxetine or by beginning on a low dosage of fluoxetine 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. Overdosage Overdosage may result in vomiting, sedation, disturbances in heart rhythm, dizziness, sweating, nausea, tremor, and rarely amnesia, confusion, coma, or convulsions. Suicidality In the United States, citalopram carries a boxed warning stating it may increase suicidal thinking and behavior in those under age 24. Stereochemistry Citalopram has one stereocenter, to which a 4-fluoro phenyl group and an N, N -dimethyl-3-aminopropyl group bind. As a result of this chirality, the molecule exists in (two) enantiomeric forms (mirror images). They are termed S -(+)-citalopram and R -(–)-citalopram. ( S )-(+)-citalopram ( R )-(–)-citalopram 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. In both cases, the salt forms of the amine make these otherwise lipophilic compounds water-soluble. Metabolism Citalopram is metabolized in the liver mostly by CYP2C19, but also by CYP3A4 and CYP2D6. 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. 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 racemic mixture of citalopram was increased by about 287%. Metabolism of citalopram in humans. Pharmacology This section needs expansion. You can help by adding to it. (April 2016) Binding profile Receptor K i (nM) SERT 1.6 NET 6190 5-HT 2C 617 α 1 1211 M 1 1430 H 1 283 History Citalopram was first synthesized in 1972 by chemist Klaus Bøgesø and his research group at the pharmaceutical company Lundbeck and was first marketed in 1989 in Denmark. It was first marketed in the US in 1998. The patent expired in 2003, allowing other companies to legally produce generic versions. Lundbeck has released escitalopram and acquired a new patent for it. In the United States, Forest Labs manufactures and markets the drug. Brand names Citalopram is sold under these brand-names: Akarin (Denmark, Nycomed) C Pram S (India) Celapram (Australia, New Zealand), Celexa (U.S. and Canada, Forest Laboratories, Inc. ) Celica (Australia) Ciazil (Australia, New Zealand) Cilate (South Africa) Cilift (South Africa) Cimal (South America, by Roemmers and Recalcine) Cipralex (South Africa) Cipram (Turkey, Denmark, H. Lundbeck A/S) Cipramil (Australia, Brazil, Belgium, Finland, Germany, Netherlands, Iceland, Ireland, Israel, Norway, Sweden, United Kingdom, New Zealand, South Africa, Russia) Cipraned, Cinapen (Greece) Ciprapine (Ireland) Ciprotan (Ireland) Citabax, Citaxin (Poland) Citalec (Slovakia, Czech Republic) Citalex (Iran, Serbia) Citalo (Australia, Egypt, Pakistan) Citalopram (USA, United Kingdom, New Zealand, Denmark, Finland, Germany, Spain, Sweden, Switzerland, Canada) Citol (Russia) Citox (Mexico) Citrol (Europe and Australia) Citta (Brazil) Dalsan (Eastern Europe) Denyl (Brazil) Elopram (Italy) Estar (Pakistan) Humorup (Argentina) Humorap (Peru, Bolivia) 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 Czech Republic) Szetalo (India) Talam (Europe and Australia) Temperax (Chile, Peru, Argentina) Vodelax (Turkey) Zentius (South America, by Roemmers and Recalcine) Zetalo (India) Zylotex (Portugal) European Commission fine On 19 June 2013, the European Commission imposed a fine of €93.8 million on the Danish pharmaceutical company Lundbeck, plus a total of €52.2 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 patent on the drug had expired, thus reducing competition in breach of European antitrust law. See also Mepyramine Pheniramine Escitalopram

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