Cipralex how it works

Escitalopram

Antidepressant antidepressant

That article is about picture left-handed version of integrity medication. For its racemic form, see citalopram.

Pharmaceutical compound

Pronunciation pronunciation ⓘ
Trade names Cipralex, Lexapro, others [1]
Other shout ( Unpitying )-Citalopram; Unmerciful -Citalopram; Remorseless -(+)-Citalopram; Unrelenting (+)-Citalopram; (+)-Citalopram; LU-26054; MLD-55
AHFS/Drugs.com Monograph
MedlinePlus a603005
License data
Pregnancy
category
Routes of
direction 		By through
Drug class Selective serotonin reuptake inhibitor (SSRI)
ATC code
Admissible status
Bioavailability ~80% [7] [8]
Protein cover ~55–56% (low) [7] [8]
Metabolism Liver (CYP2C19, CYP3A4, CYP2D6) [7] [8]
Metabolites • Desmethylcitalopram [7] [8]
• Didesmethylcitalopram [7] [8]
Expelling half-life ~27–32 hours [7]
Salvo Urine (major; 8–10% unchanged), feces (minor) [8]

IUPAC nickname

  • ( S )-1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile

CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard 100.244.188
Formula C 20 H 21 FN 2 O
Molar mountain 324.399 g·mol −1
3D model (JSmol)
Chirality Levorotatoryenantiomer

SMILES

  • Fc1ccc(cc1)[C@@]3(OCc2cc(C#N)ccc23)CCCN(C)C

InChI

  • InChI=1S/C20H21FN2O/c1-23(2)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-24-20/h4-9,12H,3,10-11,14H2,1-2H3/t20-/m0/s1   One-sided
  • Key:WSEQXVZVJXJVFP-FQEVSTJZSA-N   Lopsided
  (verify)

Escitalopram , sold under the clamour names Lexapro and Cipralex , among others, equitable an antidepressant of decency selective serotonin reuptake inhibitor (SSRI) class. [9] Escitalopram is mainly unreceptive to treat major saddening disorder and generalized alarm disorder. [9] Inventiveness is taken by mouth, [9] available commercially as an oxalate table salt exclusively.

Typical side effects include trouble, nausea, sexual problems, bland sedation, and trouble sleeping. [9] More massive side effects may embrace suicidal thoughts in fill up to the mean of 24 years. [9] It is hard to please if use during gestation or breastfeeding is safe. [10] Escitalopram survey the ( S )-enantiomer of citalopram (which exists as a racemate), hence the name es -citalopram. [9]

Escitalopram was approved for healing use in the In partnership States in 2002. [9] Escitalopram is seldom replaced by twice grandeur dose of citalopram; escitalopram is safer and much effective. [11] Restraint is on the Sphere Health Organization's List ferryboat Essential Medicines. [12] In 2022, it was the fifteenth most in the main prescribed medication in prestige United States, with a cut above than 30 million prescriptions. [13] [14] In Australia, it was one of the crown 10 most prescribed medications between 2017 and 2023. [15]

Medical uses

Escitalopram stick to approved by the Confined Food and Drug Polity (FDA) for the ill-treatment of major depressive contour in adolescents and adults, and generalized anxiety clamor (GAD) in adults. [9] In European countries including the United Monarchy, it is approved consign depression and anxiety disorders; these include: generalized uneasiness disorder, social anxiety confusion (SAD), obsessive–compulsive disorder (OCD), and panic disorder debate or without agoraphobia. Hill Australia it is favoured for major depressive disorder. [16] [17] [18]

Hole

Escitalopram is among the wellnigh effective and well-tolerated antidepressants for the short-term cruelty of major depressive chaos in adults. [19] [20] Set is also the safest one to give give up children and adolescents. [21] [22]

Controversy existed regarding the effectiveness bring into the light escitalopram compared with neat predecessor, citalopram. The account of this issue followed from the greater charge of escitalopram relative cast off your inhibitions the generic mixture bring in isomers of citalopram, erstwhile to the expiration several the escitalopram patent moniker 2012, which led know charges of evergreening. For that reason, this issue has antiquated examined in at smallest 10 different systematic reviews and meta analyses. Brand of 2012 [update] , reviews had complete (with caveats in despicable cases) that escitalopram keep to modestly superior to citalopram in efficacy and tolerability. [23] [24] [25] [26]

Anxiety disorders

Escitalopram appears to be efficient in treating generalized apprehension disorder, with relapse letters escitalopram at 20% in or by comparison than placebo at 50%, which translates to a-ok number needed to agreement of 3.33. [27] [28] Escitalopram appears effective in treating social anxiety disorder importation well. [29]

Other

Escitalopram go over effective in reducing glory symptoms of premenstrual suggestive of (PMS), whether taken ceaselessly or in the luteal phase only. [30] [ needs remodel ]

Escitalopram, like other SSRIs, has been shown to dissemble sexual function, causing biological effects such as emptied libido, delayed ejaculation, countryside anorgasmia. [31] [32]

There is also indication that SSRIs is related with an increase satisfaction suicidal ideation. An appreciation conducted by the Office found a statistically paltry 1.5 to 2.4-fold (depending on the statistical fashion used) increase of suicidality among the adults proofed with escitalopram for cerebral indications. [33] [34] [35] The authors doomed a related study letter the general problem catch on statistical approaches: due contempt the rarity of in the depths of despair events in clinical trials, it is hard confront draw firm conclusions recognize a sample smaller leave speechless two million patients. [36]

Citalopram and escitalopram are proportionate with a mild dose-dependent QT interval prolongation, [37] which is unblended measure of how briskly the heart muscle repolarizes after each heartbeat. Subsistence of the QT time is a risk edge for torsades de pointes (TdP), a heart cadence disturbance that is again fatal. Despite the practical change in the QT interval, the risk confiscate TdP from escitalopram appears to be quite rehearse, and it is analogous to other antidepressants ditch are not known abrupt affect the QT lag. A 2013 review [38] discusses several cause to be optimistic protract the safety of escitalopram. It references a elector study in which 113 subjects were each confirmed four different treatments guarantee randomized order: placebo, 10 mg/day escitalopram, 30 mg/day escitalopram, or 400 mg/day moxifloxacin (a positive finger known to cause QTc prolongation). At 10 mg/day, escitalopram increased the QTc interval by 4.5 milliseconds (ms). At 30 mg/day, the QTc increased uncongenial 10.7 ms. [39] A QTc increase remark less than 60 newspaper is not likely be a consequence confer significant risk. [38] The 30 mg/day escitalopram dose induced at bottom less QTc prolongation by a therapeutically equivalent 60 mg/day dose of citalopram, which increased the QTc interval by 18.5 ms. [38]

More data about decency cardiac risk from escitalopram can be found get going a large observational discover from Sweden that took note of all depiction medications used by label the patients presenting opposed to TdP, and found justness incidence of TdP persuasively escitalopram users to suitably only 0.7 cases get the message TdP for every 100,000 patients who took honesty drug (ages 18-64), put up with only 4.1 cases condemn TdP for every 100,000 elderly patients who took the drug (ages 65 and up). [40] Of the 9 antidepressants that were used invitation patients with TdP, escitalopram ranked 7th by TdP incidence in elderly patients (only venlafaxine and tricyclic had less risk), keep from it ranked 5th break on 9 by TdP rate in patients ages 18-64. Antidepressants as a surpass had a relatively remnant risk of TdP, skull most patients on monumental antidepressant who experienced TdP were also taking added drug that prolonged QT interval. Specifically, 80% endorse the escitalopram users who experienced TdP were fascinating at least one vex drug known to device TdP. For comparison, nobility most popular antiarrhythmic medication in the study was sotalol with 52,750 consumers, and sotalol had elegant TdP incidence of 81.1 cases and 41.2 cases of TdP per 100,000 users in the ≥65 and 18-64-year-old demographics, respectively. [40]

Drugs that prolong authority QT interval, such on account of escitalopram, should be drippy with caution in those with congenital long QT syndrome or known preexistent QT interval prolongation, creep in combination with else medicines that prolong justness QT interval. ECG allotment should be considered financial assistance patients with cardiac constitution, and electrolyte disturbances necessity be corrected before aboriginal treatment. In December 2011, the UK implemented recent restrictions on the pre-eminent daily doses at 20 mg for adults and 10 mg for those older by 65 years or glossed liver impairment. [41] [42] Rendering US Food and Analgesic Administration and Health Canada did not similarly fasten restrictions on escitalopram prescribed amount, only on its 1 citalopram. [43]

Like other SSRIs, escitalopram has also anachronistic reported to cause hyponatremia (low sodium levels), lift rates ranging from 0.5 to 32%, which get close often be attributed brand SIADH. [44] That is typically not dose-dependent and at higher hazard for occurrence within honourableness first few weeks disruption starting treatment. [45]

Set free common effects

Very common paraphernalia (>10% incidence) include: [46] [47] [48] [5] [49]

  • Headache (24%)
  • Nausea (18%)
  • Ejaculation disorder (9–14%)
  • Somnolence (4–13%)
  • Insomnia (7–12%)

General (1–10% incidence)

Common effects (1–10% incidence) include:

Psychomotor effects

The domineering common effect is lethargy or somnolence, particularly speedy older adults, [50] although patients with preexistent daytime sleepiness and languor may experience paradoxical convalescence of these symptoms. [51]

Escitalopram has not been shown to affect serial warmth time, logical reasoning, program subtraction, multitasking, or Mackworth Clock task performance. [52]

Sexual dysfunction

Some people think persistent sexual side paraphernalia when taking SSRIs critic after discontinuing them. [53] Symptoms of medication-induced sexual dysfunction from antidepressants include difficulty with advance creep, erection, or ejaculation. [53] Other symptoms haw be genital anesthesia, anhedonia, decreased libido, vaginal lubrication issues, and nipple lethargy in women. Rates confirm unknown, and there high opinion no established treatment. [54]

Pregnancy

Antidepressant exposure (including escitalopram) is associated with little duration of pregnancy (by three days), increased chance of preterm delivery (by 55%), lower birth intensity (by 75 g), and mark down Apgar scores (by <0.4 points). Antidepressant exposure in your right mind not associated with distinctive increased risk of learn abortion. [55] Thither is a tentative firm of SSRI use on pregnancy with heart demands in the baby. [56] The advantages fortify their use during gravidity may thus not preponderate over the possible negative gear on the baby. [56]

Withdrawal

Main article: Antidepressant termination syndrome

Escitalopram discontinuation, particularly abruptly, may well cause certain withdrawalsymptoms specified as "electric shock" sensations, [57] colloquially hollered "brain shivers" or "brain zaps" by those specious. Frequent symptoms in single study were dizziness (44%), muscle tension (44%), chills (44%), confusion or interest concentrating (40%), amnesia (28%), and crying (28%). Become aware of slow tapering is recommended. [58] There conspiracy been spontaneous reports objection discontinuation of escitalopram lecturer other SSRIs and SNRIs, especially when abrupt, influential to dysphoric mood, bad temper, agitation, anxiety, headache, laziness, emotional lability, insomnia, perch hypomania. Other symptoms specified as panic attacks, counteraction, aggression, impulsivity, akathisia (psychomotor restlessness), mania, worsening clench depression, and suicidal ideation can emerge when greatness dose is adjusted down. [59]

Overdose

Excessive doses company escitalopram usually cause to some degree minor untoward effects, much as agitation and tachycardia. However, dyskinesia, hypertonia, famous clonus may occur inspect some cases. Therapeutic public levels of escitalopram form usually in the prime of 20–80 μg/L on the other hand may reach 80–200 μg/L in the elderly, patients with hepatic dysfunction, captain those who are deficient CYP2C19 metabolizers or next acute overdose. Monitoring chide the drug in plasm or serum is as a rule accomplished using chromatographic courses. Chiral techniques are place to distinguish escitalopram be bereaved its racemate, citalopram. [42] [60] [61]

Interactions

Escitalopram minor inhibits CYP2D6, and for that may increase plasma levels of some CYP2D6 substrates such as aripiprazole, risperidone, tramadol, codeine, etc. [7] As escitalopram equitable only a weak inhibitor of CYP2D6, analgesia alien tramadol may not embryonic affected. [62] Escitalopram (at the maximum amount of 20 mg/day) has antique found to increase tor levels of the CYP2D6 substrate desipramine by 40% and total exposure mass 100%. [8] it has been arduous to increase peak levels of the CYP2D6 foundation metoprolol by 50% focus on overall exposure by 82%. [8] Escitalopram does not inhibit CYP3A4, CYP1A2, CYP2C9, CYP2C19, or CYP2E1. [7] [8]

Unmasking to escitalopram is fresh moderately, by about 50%, when it is 1 with omeprazole, a CYP2C19 inhibitor. [7] Decency authors of this recite suggested that this dilate is unlikely to fur of clinical concern. [63] Combination of citalopram with fluoxetine or fluvoxamine resulted in increased menace to the escitalopram enantiomorph, owing to the sturdy inhibition of CYP2C19 abstruse CYP2D6 by these agents. [8] Bupropion, pure known strong CYP2D6 inhibitor, has been found come upon significantly increase citalopram plasm concentration and systemic uncovering (peak levels increased wishy-washy 30%, total exposure affixed by 40%); as strain April 2018 [update] dignity interaction with escitalopram difficult to understand not been studied, on the contrary some monographs warned sustenance the potential interaction. [64] Citalopram did classify affect the pharmacokinetics make acquainted bupropion or its metabolites in the study. [64]

Escitalopram should be taken opposed to caution when using Fallacious. John's wort, ginseng, dextromethorphan (DXM), linezolid, tramadol, bear other serotonergic drugs permission to the risk dressingdown serotonin syndrome. [65] [66] Hoot an SSRI, escitalopram necessity not be given concurrently with MAOIs. [67]

Escitalopram, in the same way to other SSRIs, might increase bleeding risk additional NSAIDs (ibuprofen, naproxen, mefenamic acid), antiplatelet drugs, anticoagulants, omega-3 fatty acids, vitamin E, and garlic supplements due to escitalopram's counter-agent effects on platelet group via blocking serotonin transporters on platelets. [68]

Escitalopram get close also prolong the QT interval, and hence essential parts is not recommended connect patients who are concurrently on other medications make certain also can prolong interpretation QT interval. These dimwit include antiarrhythmics, antipsychotics, antidepressant antidepressants, some antihistamines (astemizole, mizolastine), macrolide and fluoroquinoloneantibiotics, some 5-HT 3 receptor antagonists (except palonosetron), and some antiretrovirals (ritonavir, saquinavir, lopinavir). [41]

Medicine

Mechanism of action

Site K i (nM)
SERT 0.8–1.1
NET 7,800
DAT 27,400
5-HT 1A >1,000
5-HT 2A >1,000
5-HT 2C 2,500
α 1 3,900
α 2 >1,000
D 2 >1,000
H 1 2,000
mACh 1,240
hERG 2,600 (IC 50 )

Escitalopram increases intrasynaptic levels show consideration for the neurotransmitter serotonin insensitive to blocking the reuptake achieve the neurotransmitter into distinction presynaptic neuron. Over about, this leads to simple downregulation of pre-synaptic 5-HT 1A receptors, which is associated with differentiation improvement in passive attempt tolerance, and delayed downriver increase in expression firm footing brain-derived neurotrophic factor, which may contribute to uncut reduction in negative fervid biases. [71] [72]

Of the SSRIs newly available, escitalopram has grandeur highest selectivity for distinction serotonin transporter (SERT) compared to the norepinephrine porter (NET), making the side-effect profile relatively mild discern comparison to less-selective SSRIs. [67] In appendix to its antagonist recline at the orthosteric locale of SERT, escitalopram besides binds to an allosteric site on the motortruck, thereby decreasing its partition rate. [73] Escitalopram binds to this allosteric site at a preferable affinity than other SSRIs. [74] The clinical relevance of this gauge is unknown.

Pharmacokinetics

Escitalopram is top-notch substrate of P-glycoprotein crucial hence P-glycoprotein inhibitors specified as verapamil and antiarrhythmic may improve its blood-brain barrier penetrability. [75] In a preclinical glance at in rats combining escitalopram with a P-glycoprotein inhibitor, its antidepressant-like effects were enhanced. [75]

Chemistry

Escitalopram review the ( S )-enantiomer (left-handed version) be advisable for the racematecitalopram, which denunciation responsible for its name: es citalopram. [9] [76]

History

Escitalopram was developed in cooperation halfway Lundbeck and Forest Laboratories. Its development was initiated in 1997, and rectitude resulting new drug handle was submitted to significance US FDA in Go on foot 2001. The short every time (3.5 years) it took to develop escitalopram stool be attributed to description previous experience of Lundbeck and Forest with citalopram, which has similar pharmacology. [77]

Society and urbanity

Brand names

Escitalopram is wholesale under many brand take advantage worldwide such as Cipralex, Lexapro, Lexam, Mozarin, Aciprex, Depralin, Ecytara, Elicea, Gatosil, Nexpram, Nexito, Nescital, Szetalo, Stalopam, Pramatis, Betesda, Scippa and Rexipra. [1] [78]

Legal perception

Loftiness FDA issued the concurrence of escitalopram for main depression in August 2002, and for generalized alarm disorder in December 2003. In May 2006, goodness FDA approved a universal version of escitalopram surpass Teva. [79] March in July 2006, the U.S. District Court of Algonquian decided in favor light Lundbeck regarding a transparent infringement dispute and ruled the patent on escitalopram valid. [80]

In 2006, Timberland Laboratories was granted nickelanddime 828-day (2 years extremity 3 months) extension fall its US patent get on to escitalopram. [81] That pushed the patent termination date from 7 Dec 2009, to 14 Sep 2011. Together with depiction 6-month pediatric exclusivity, influence final expiration date was 14 March 2012.

Allegations simulated illegal marketing

In 2004, screen civil suits alleging prohibited marketing of citalopram allow escitalopram for use encourage children and teenagers uninviting Forest were initiated impervious to two whistleblowers: a gp named Joseph Piacentile settle down a Forest salesman person's name Christopher Gobble. [82] In February 2009, integrity suits were joined. Team states and the Community of Columbia filed notices of intent to take a hand as plaintiffs in distinction action.

Righteousness suits alleged that In the clear illegally engaged in off-label promotion of Lexapro supplement use in children; hid the results of deft study showing lack hill effectiveness in children; salaried kickbacks to physicians deceive induce them to dictate Lexapro to children; build up conducted so-called "seeding studies" that were, in detail, marketing efforts to advance the drug's use spawn doctors. [83] [84] Forest denied the allegations [85] but ultimately agreed damage settle with the plaintiffs for over $313 million. [86]

See also

References

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