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Escitalopram

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Escitalopram chemical structure
Escitalopram

S-(+)-1-[3-(dimethylamino)propyl]-
1-(p-fluorophenyl)-
5-phthalancarbonitrileoxalate
IUPAC name
CAS number
128196-01-0
ATC code

N06AB10

PubChem
146570
DrugBank
APRD00683
Chemical formula {{{chemical_formula}}}
Molecular weight 324.392 g/mol
(414.40 as oxalate)
Bioavailability 80%
Metabolism Liver, specifically the enzymes CYP3A4 and CYP2C19
Elimination half-life 27-32 hours
Excretion
Pregnancy category C
Legal status Rx-only
Routes of administration Oral
Lexapro pills

Lexapro pills

Escitalopram (Cipralex) is a medication developed by the Danish pharmaceutical company Lundbeck, that acts as a selective serotonin reuptake inhibitor (SSRI). It is approved for the treatment of major depressive disorder, generalized anxiety disorder, social anxiety disorder, panic disorder and obsessive compulsive disorder. In the United States the drug is marketed under the name Lexapro by Forest Laboratories. Elsewhere escitalopram is marketed under various brand names such as Cipralex, Lexapro, Sipralexa and Seroplex by Lundbeck. [1]

Escitalopram is the eutomer (i.e., the enantiomer of a chiral compound that is more effective for a particular action) of the racemic drug citalopram. Specifically, it consists of the S-enantiomer. Escitalopram has the highest affinity to the human serotonin transporter SERT and different from other SSRI binds to both, the primary and the allosteric binding site of the SERT.[2]. The allosteric binding has a self-potentiating effect of the binding to the primary binding site, leading to a more effecte serotonin-reuptake inhibition. However the increased activity has been argued by some experts to be statistically and clinically insignificant.


HistoryEdit

Escitalopram oxalate is derived from the drug citalopram which is a mixture of two mirror-image isomers, only one of which (S-citalopram) is thought to be responsible for the antidepressive effect of the medication, while the other (R-citalopram) has been shown to counteract the antidepressive effect. Lundbeck has split the isomers apart, taken the active isomer and has licensed it as the new drug Escitalopram. Escitalopram is the pure S-enantiomer (left-handed isomer) of the racemic bicyclic phthalane derivative citalopram, and is the most selective SSRI[3].

Escitalopram was released two years before the patent for citalopram was due to expire. The expiration of a patent means other companies can legally produce cheaper generic versions. On May 23, 2006, the FDA approved a generic version of escitalopram by Teva[2]. However, on July 14th, 2006 the the US District Court of Delaware decided in favour of Lundbeck regarding a patent infringement dispute and ruled the patent on escitalopram valid.[3]

Critics have argued that escitalopram, and the subsequent marketing campaign to persuade mental health professionals to prescribe it, is a ploy to promote sales of a virtually identical but considerably more expensive drug. However preclinical as well as various clinical studies have shown differentiated effects of citalopram and escitalopram as well as a clinical superiority compared to a variety of other SSRI, such as paroxetine and sertraline, as well as with newer serotonin-norepinephrine reuptake inhibitors such as venlafaxine and duloxetine. [How to reference and link to summary or text]

DosingEdit

The recommended dosage of Lexapro is 10-20 mg a day. Exceptions include the elderly, who should only take up to 10 mg a day, and pregnant women in their third trimester should not use Lexapro at all.[4] As both Generalized Anxiety Disorder (GAD) and Depression are both considered chronic conditions, treatment is recommended for several months. However, the efficacy of Lexapro over long periods of time has not been studied, therefore consistent reevaluation of the treatment is recommended for longer periods of treatment.[4]

Side effectsEdit

Main article: Selective serotonin reuptake inhibitor

The side effect profile of escitalopram is close to that of other SSRI with nausea, somnolence and gastronintestinal side effects, leading. SSRIs have been shown to cause sexual side effects in most patients, both males and females[5]. Although usually reversible, these sexual side effects can sometimes last after discontinuation. This disorder is known as Post SSRI Sexual Dysfunction. It may also cause weight gain in certain people. It may cause dizziness after exercise in children.

Cipralex

Cipralex brand escitalopram package and pill sheet

Discontinuation symptomsEdit

Main article: SSRI discontinuation syndrome

Discontinuation from antidepressants, especially abruptly, has been known to cause certain withdrawal symptoms. One possible discontinuation symptom from Escitalopram is a type of spontaneous nerve pulse known as paresthesia or "electric shock sensations", described by some patients as a feeling of small electric shocks, which may be accompanied by dizziness. These pulses may be short in duration, only milliseconds long, may affect any region of the body, and recur up to several times a minute, throughout all waking hours. They can be increased by physical activity, but are not solely linked to muscular activity. Other discontinuation symptoms include extreme sensitivity to loud sounds and bright lights, chills, hot flushes, cold sweats, reddening of the face, abdominal pain, weight gain and extreme mental fatigue. Also possible is severe irritability and sadness/depression like symptoms.[6]

FootnotesEdit

  1. http://www.lundbeck.com/products/our_products/cipralex/default.asp
  2. C. Sanchez (2006). The pharmacology of citalopram enantiomers: the antagonism by R-citalopram on the effect of S-citalopram.. Basic Clin Pharmacol Toxicol 99: 91-5.
  3. M. J. Owens and J. F. Rosenbaum (April 2002). Escitalopram: a second-generation SSRI. CNS Spectr. 7 (4 supplement 1).
  4. 4.0 4.1 Forest Laboratories, [1]
  5. A. Clayton, A. Keller and E.L. McGarvey (2006). Burden of phase-specific sexual dysfunction with SSRIs.. J Affect Disord 91: 27-32.
  6. Lexapro -- Warnings. RxList. URL accessed on 2006-10-22.

External links Edit



Antidepressants (ATC N06A) edit
Monoamine oxidase inhibitors (MAOI) Harmaline, Iproclozide, Iproniazid, Isocarboxazid, Nialamide, Phenelzine, Selegiline, Toloxatone, Tranylcypromine
Reversible inhibitor of monoamine oxidase A (RIMA) Brofaromine, Moclobemide
Dopamine reuptake inhibitor (DARI) Amineptine, Phenmetrazine, Vanoxerine, Modafinil
Norepinephrine-dopamine reuptake inhibitors Bupropion
Norepinephrine reuptake inhibitor (NRI) or (NARI) Atomoxetine, Maprotiline, Reboxetine, Viloxazine
Serotonin-norepinephrine reuptake inhibitor (SNRI) Duloxetine, Milnacipran, Venlafaxine
Selective serotonin reuptake inhibitor (SSRI) Alaproclate, Etoperidone, Citalopram, Escitalopram, Fluoxetine, Fluvoxamine, Paroxetine, Sertraline, Zimelidine
Selective serotonin reuptake enhancer (SSRE) Tianeptine
Tricyclic antidepressants (TCA) Amitriptyline, Amoxapine, Butriptyline, Clomipramine, Desipramine, Dibenzepin, Dothiepin, Doxepin, Imipramine, Iprindole, Lofepramine, Melitracen, Nortriptyline, Opipramol, Protriptyline, Trimipramine
Tetracyclic antidepressants Maprotiline, Mianserin, Nefazodone, Trazodone
Noradrenergic and specific serotonergic antidepressant (NaSSA) Mirtazapine
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