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Escitalopram

Clinical data
Pregnancy category	C
Routes of administration	Oral
ATC code	N06AB10 (WHO)
Legal status
Legal status	US: WARNING In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	80%
Protein binding	~56%
Metabolism	Liver, specifically the enzymes CYP3A4 and CYP2C19
Elimination half-life	27-32 hours
Identifiers
IUPAC name S-(+)-1-- 1-(p-fluorophenyl)- 5-phthalancarbonitrileoxalate
CAS Number	128196-01-0
PubChem CID	146570
DrugBank	APRD00683
CompTox Dashboard (EPA)	DTXSID8048440
ECHA InfoCard	100.244.188
Chemical and physical data
Formula	C20H21FN2O
Molar mass	324.392 g/mol (414.40 as oxalate) g·mol

Escitalopram (Cipralex®) is a medication developed by the Danish pharmaceutical company Lundbeck, that acts as a selective serotonin reuptake inhibitor (SSRI). It is typically used as an antidepressant to treat depression associated with mood disorders, although it also may be used in the treatment of body dysmorphic disorder and anxiety, including OCD. In the United States, the drug is marketed under the name Lexapro® by Forest Laboratories, Inc.

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.

History

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.

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, however on July 14th, 2006 the the US District Court of Delaware has decided in favour of Lundbeck regarding a patent infringement dispute and ruled the patent of escitalopram as being valid.

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 and clinical data have shown differentiated effects of citalopram and escitalopram. In particular escitalopram has shown to be more effective in depressive patients and particularly shows higher efficacy vs. citalopram and other SSRI in severely depressed patients.

Dosing

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. 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.

Side effects

Citalopram and other SSRIs have been shown to cause sexual side effects in some patients, both males and females. Although usually reversible, these sexual side effects can sometimes last for months. This disorder is known as Post SSRI Sexual Dysfunction. Also may cause weight gain in certain people.

Discontinuation symptoms

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.

One study, using a specific assessment scale, such as DESS, suggests that in the case of escitalopram the incidence rate of discontinuation symptoms are mild and comparable to that of placebo, citing it as "very well tolerated".

Footnotes

1. "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
2. ^ Forest Laboratories,
3. Clayton A, Keller A, McGarvey EL. Burden of phase-specific sexual dysfunction with SSRIs. J Affect Disord 2006;91:27-32. PMID 16430968.
4. "Lexapro -- Warnings". RxList. 12/08/2004. Retrieved 2006-10-22. {{cite web}}: Check date values in: |date= (help)
5. Wade A, Michael Lemming O, Bang Hedegaard K (2002). "Escitalopram 10 mg/day is effective and well tolerated in a placebo-controlled study in depression in primary care". Int Clin Psychopharmacol. 17 (3): 95–102. PMID 11981349.{{cite journal}}: CS1 maint: multiple names: authors list (link)

External links

• Lexapro (Forest Laboratories) Official Lexapro Homepage
• Cipralex (Lundbeck) Official Cipralex Homepage
• Pharmacological information Lexapro
• Lexapro Feedback Depression Blog

Template:ChemicalSources

• Articles lacking sources from July 2006
• Selective serotonin reuptake inhibitors