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Citalopram

From Wikipedia, the free encyclopedia
This article is about theracemicform of the drug. For its (S)-enantiomer,seeEscitalopram.

Citalopram
(R)-(−)-citalopram (top),
(S)-(+)-citalopram (bottom)
Clinical data
Pronunciation/saɪˈtæləˌpræm,sɪ-/;[1]
Trade namesCelexa, Cipramil, others[2]
AHFS/DrugsMonograph
MedlinePlusa699001
License data
Pregnancy
category
Routes of
administration		oral,intravenous[4][5][6]
Drug classSelective serotonin reuptake inhibitor(SSRI)[7]
ATC code
Legal status
Legal status
Pharmacokineticdata
Bioavailability80%
peak at 4 hours[7]
Protein binding<80%[10]
MetabolismLiver(CYP3A4andCYP2C19)
MetabolitesDesmethylcitalopram(DCT) anddidesmethylcitalopram(DDCT)
Eliminationhalf-life35 hours
ExcretionMostly as unmetabolized citalopram, partly DCT and traces of DDCT in urine
Identifiers
  • (RS)-1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.056.247Edit this at Wikidata
Chemical and physical data
FormulaC20H21FN2O
Molar mass324.399g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • Fc1ccc(cc1)C3(OCc2cc(C#N)ccc23)CCCN(C)C
  • 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,3,10-11,14H2,1-2H3checkY
  • Key:WSEQXVZVJXJVFP-UHFFFAOYSA-NcheckY
(verify)

Citalopram,sold under the brand nameCelexaamong others, is anantidepressantof theselective serotonin reuptake inhibitor(SSRI) class.[7][10]It is used to treatmajor depressive disorder,obsessive compulsive disorder,panic disorder,andsocial phobia.[7]The antidepressant effects may take one to four weeks to occur.[7]It is typically takenorally(swallowed by mouth).[7][10]In someEuropeancountries, it is sometimes givenintravenously(injected into a vein) to initiate treatment, before switching to the oral route of administration for continuation of treatment.[4]It has also been used intravenously in other parts of the world in some other circumstances.[5][6]

Common side effects include nausea, trouble sleeping, sexual problems, shakiness, feeling tired, and sweating.[7]Serious side effects include an increased risk ofsuicidein those under the age of 25,serotonin syndrome,glaucoma,andQT prolongation.[7]It should not be used in persons who take or have recently taken anMAO inhibitor.[7]There are concerns that use duringpregnancymay harm the fetus.[3]

Citalopram was approved for medical use in the United States in 1998.[7]It is on theWorld Health Organization's List of Essential Medicines.[11]It is available as ageneric medication.[12]In 2021, it was the 31st most commonly prescribed medication in the United States, with more than 18million prescriptions.[13][14]

Medical uses[edit]

Citalopram HBr tablets in 20-mg (coral, marked 508) and 40-mg (white, marked 509), and aUnited States one-cent coin(size 19.05 mm/0.75 in)

Depression[edit]

In the United States, citalopram is approved to treatmajor depressive disorder.[15]Citalopram appears to have comparable efficacy and superior tolerability relative to other antidepressants.[16][17]In theNational Institute for Health and Clinical Excellenceranking of tenantidepressantsfor efficacy and cost-effectiveness, citalopram is fifth in effectiveness (aftermirtazapine,escitalopram,venlafaxine,andsertraline) and fourth in cost-effectiveness.[18]

Evidence for effectiveness of citalopram for treating depression in children is uncertain.[19][20]

Panic disorder[edit]

Citalopram is licensed in the UK[21]and other European countries[22]forpanic disorder,with or withoutagoraphobia.

Other[edit]

Citalopram may be used off-label to treatanxiety,anddysthymia,[23]premenstrual dysphoric disorder,body dysmorphic disorder,andobsessive–compulsive disorder.[24]

It appears to be as effective as fluvoxamine and paroxetine in obsessive–compulsive disorder.[25]Some data suggest the effectiveness of intravenous infusion of citalopram in resistant OCD.[5]Citalopram is well tolerated and as effective asmoclobemidein social anxiety disorder.[26]There are studies suggesting that citalopram can be useful in reducing aggressive and impulsive behavior.[27][28]It appears to be superior to placebo for behavioural disturbances associated with dementia.[29]It has also been used successfully for hypersexuality in early Alzheimer's disease.[30]

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.[31]For alcoholism, citalopram has produced a modest reductionalcoholintake and increase in drink-free days in studies of alcoholics, possibly by decreasing desire or reducing the reward.[32]

While on its own citalopram is less effective thanamitriptylinein theprevention of migraines,inrefractorycases, combination therapy may be more effective.[33]

Citalopram and other SSRIs can be used to treathot flashes.[34]: 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.[35]

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.[36]

Administration[edit]

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,[37][10]but doing so can help prevent nausea. Nausea is often caused when the5-HT3receptorsactively absorb free serotonin, as this receptor is present within the digestive tract.[38]

Adverse effects[edit]

Citalopram theoretically causes side effects by increasing the concentration ofserotoninin 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 indopaminerelease associated with increased serotonin. Citalopram is also a mildantihistamine,which may be responsible for some of its sedating properties.[34]: 104 

Other common side effects of citalopram includedrowsiness,insomnia,nausea,weight changes (usually weight gain), increase in appetite, vivid dreaming, frequent urination, dry mouth,[37]increasedsweating,trembling,diarrhea,excessive yawning, severe tinnitus, andfatigue.Less common side effects includebruxism,vomiting,cardiac arrhythmia,blood pressurechanges, dilated pupils,anxiety,mood swings,headache,hyperactivity anddizziness.Rare side effects includeconvulsions,hallucinations,severeallergic reactionsandphotosensitivity.[37]If sedation occurs, the dose may be taken at bedtime rather than in the morning. Some data suggests citalopram may cause nightmares.[39]Citalopram is associated with a higher risk of arrhythmia than otherSSRIs.[40][41]

Citalopram and other SSRIs can induce amixed state,especially in those with undiagnosedbipolar disorder.[34]: 105  According to an article published in 2020, one of the other rare side effects of Citalopram could be triggeringvisual snow syndrome;which does not resolve after the discontinuation of the medicine.[42]

Sexual dysfunction[edit]

Sexual dysfunctionis often a side effect with SSRIs.[43]Some people experience persistent sexual side effects when taking SSRIs or after discontinuing them.[44]Symptoms of medication-induced sexual dysfunction from antidepressants include difficulty with orgasm, erection, or ejaculation.[44]Other symptoms may be genital anesthesia,anhedonia,decreased libido, vaginal lubrication issues, and nipple insensitivity in women. Rates are unknown, and there is no established treatment.[45]

Abnormal heart rhythm[edit]

In August 2011, the FDA announced, "Citalopram causes dose-dependentQT interval prolongation.Citalopram should no longer be prescribed at doses greater than 40 mg per day ".[46]A further clarification, issued in March 2012, restricted the maximum dose to 20 mg for subgroups of patients, including those older than 60 years and those taking an inhibitor of cytochrome P450 2C19.7.[47]

Endocrine effects[edit]

As with other SSRIs, citalopram can cause an increase in serumprolactinlevel.[48] Citalopram has no significant effect on insulin sensitivity in women of reproductive age[49]and no changes in glycaemic control were seen in another trial.[50]

Exposure in pregnancy[edit]

Antidepressant exposure (including citalopram) during pregnancy is associated with shorter duration ofgestation(by three days), increased risk of preterm delivery (by 55%), lower birth weight (by 75 g), and lowerApgar scores(by <0.4 points). Antidepressant exposure is not associated with an increased risk of spontaneous abortion.[51]It is uncertain whether there is an increased prevalence of septal heart defects among children whose mothers were prescribed an SSRI in early pregnancy.[52][53]

Overdose[edit]

Overdosage may result in vomiting, sedation, disturbances in heart rhythm, dizziness, sweating, nausea, tremor, and rarely amnesia, confusion, coma, or convulsions.[34]: 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 mg/L in those who do not survive.[46][54][55]It is the most dangerous of SSRIs in overdose.[56]

Suicidality[edit]

In the United States, citalopram carries aboxed warningstating it may increase suicidal thinking and behavior in those under age 24.[37]

Discontinuation Syndrome[edit]

SSRI discontinuation syndromehas 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.[57]Electric shock-like sensations are typical for SSRI discontinuation.[58]Withdrawal symptoms can occur when this medicine is suddenly stopped, such asparaesthesiae,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.[59]

Interactions[edit]

Serotonin Syndrome[edit]

Citalopram should not be taken withSt John's wort,tryptophanor5-HTPas the resulting drug interaction could lead toserotonin syndrome.[60]With St John's wort, this may be caused by compounds in the plant extract reducing the efficacy of thehepaticcytochrome P450enzymes that process citalopram.[61]Tryptophan and 5-HTP are precursors to serotonin.[62]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 (serotonin releasing agents) such as in the case ofMDMA.It is possible that SSRIs could reduce the effects associated due to an SRA, since SSRIs stop the reuptake of Serotonin by blockingSERT.This would allow less serotonin in and out of the transporters, thus decreasing the likelihood ofneurotoxiceffects. However, these concerns are still disputed as the exact pharmacodynamic effects of citalopram and MDMA have yet to be fully identified.[citation needed]Citalopram iscontraindicatedin individuals takingMAOIs,owing to a potential forserotonin syndrome.

Other interactions[edit]

SSRIs, including citalopram, can increase the risk of bleeding, especially when coupled withaspirin,NSAIDs,warfarin,or otheranticoagulants.[37]Taking citalopram withomeprazolemay cause higher blood levels of citalopram. This is a potentially dangerous interaction, so dosage adjustments may be needed or alternatives may be prescribed.[63][64][10]

Pharmacokinetics[edit]

Citalopram is considered safe and well tolerated in thetherapeutic doserange. Distinct from some other agents in its class, it exhibits linearpharmacokineticsand minimaldrug interactionpotential, making it a better choice for the elderly orcomorbidpatients.[65]

Stereochemistry[edit]

Citalopram has onestereocenter,to which a4-fluorophenyl groupand anN, N-dimethyl-3-aminopropyl group bind. As a result of thischirality,the molecule exists in (two)enantiomericforms (mirror images). They are termedS-(+)-citalopram andR-(–)-citalopram.

(S)-(+)-citalopram (R)-(–)-citalopram

Citalopram is sold as aracemicmixture, consisting of 50% (R)-(−)-citalopram and 50% (S)-(+)-citalopram. Only the (S)-(+) enantiomer has the desired antidepressant effect.[66]Lundbecknow markets the (S)-(+) enantiomer, the generic name of which isescitalopram.Whereas citalopram is supplied as thehydrobromide,escitalopram is sold as theoxalatesalt (hydrooxalate).[37]In both cases, thesaltforms of the amine make these otherwiselipophiliccompounds water-soluble.

Metabolism[edit]

Citalopram is metabolized in the liver mostly byCYP2C19,but also byCYP3A4andCYP2D6.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.[67]The elimination process is slower in the elderly and in patients with liver orkidney failure.With once-daily dosing, steady plasma concentrations are achieved in about a week. Potent inhibitors of CYP2C19 and 3A4 might decrease citalopram clearance.[10] 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 theracemicmixture of citalopram was increased by about 287%.[68]

Metabolism of citalopram in humans.[69][70][71]
Binding profile[72]
Receptor Ki(nM)
SERT 1.6
NET 6190
5-HT2C 617
α1

1211

M1 1430
H1 283

History[edit]

Citalopram was first synthesized in 1972 by chemist Klaus Bøgesø[73]and his research group at the pharmaceutical companyLundbeckand was first marketed in 1989 in Denmark. It was first marketed in the US in 1998.[74]The originalpatentexpired in 2003, allowing other companies to legally produce and marketgenericversions.

Society and culture[edit]

Brand names[edit]

Citalopram is sold under these brand names:

  • Akarin (Denmark, Nycomed)
  • C Pram S (India)
  • Celapram (Australia,[75]New Zealand),
  • Celexa (U.S. and Canada,Forest Laboratories, Inc.)
  • Celica (Australia)[75]
  • Ciazil (Australia,[75]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,[75]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,[75]Egypt, Pakistan)
  • Citalopram (Canada, Denmark, Finland, Germany, Ireland, New Zealand, Spain, Sweden, Switzerland, United Kingdom, U.S.)
  • Citol (Russia, Turkey)
  • Citox (Mexico)
  • Citrol (Europe and Australia)[75]
  • Citta (Brazil)
  • Dalsan (Eastern Europe)
  • Denyl (Brazil)
  • Elopram (Italy)
  • Estar (Pakistan)
  • Humorup (Argentina)
  • Humorap (Peru, Bolivia)
  • Lopraxer (Greece)[76]
  • 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)[75]
  • Temperax (Argentina, Chile, Peru)
  • Vodelax (Turkey)
  • Zentius (South America, by Roemmers and Recalcine)
  • Zetalo (India)
  • Cipratal (Kuwait, GCC)
  • Zylotex (Portugal)[2]

European Commission fine[edit]

On 19 June 2013, theEuropean Commissionimposed a fine of €93.8 million on the Danish pharmaceutical companyLundbeck,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'spatenton the drug had expired, thus reducing competition in breach of Europeanantitrust law.[77]

Other uses[edit]

Citalopram is also aparasiticide.[78]Schistosomulahave high mortality when treated with citalopram.[78]

See also[edit]

References[edit]

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