Escitalopram

Structural formula
General
Non-proprietary name	Escitalopram
other names	( S ) -1- (3-Dimethylaminopropyl) -1- (4-fluorophenyl) -1,3-dihydro-2-benzofuran-5-carbonitrile ( IUPAC ) (-) - 1- (3-Dimethylaminopropyl) -1- (4-fluorophenyl) -1,3-dihydro-2-benzofuran-5-carbonitrile Escitalopramum ( Latin )
Molecular formula	C 20 H 21 FN 2 O
External identifiers / databases
CAS number 128196-01-0 219861-08-2 (oxalate 1: 1) 481047-50-1 ( hydrobromide ) EC number 812-870-6 ECHA InfoCard 100.244.188 PubChem 146570 ChemSpider 129277 DrugBank DB01175 Wikidata Q423757
Drug information
ATC code	N06 AB10
Drug class	antidepressant
Mechanism of action	Selective Serotonin Reuptake Inhibitor (SSRI)
properties
Molar mass	324.39 g · mol -1
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS hazard labeling no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Escitalopram ( trade name Cipralex, various generics ) is a drug from the group of selective serotonin reuptake inhibitors (SSRI). It is used in the treatment of depression , panic disorder , social phobias , generalized anxiety disorder, and obsessive-compulsive disorder .

Chemically, it is the pharmacologically active enantiomer ( eutomer ) of the drug citalopram .

Mechanism of action and effectiveness

Escitalopram works in the same way as racemic citalopram and other SSRIs by selectively inhibiting the reuptake of serotonin from the synaptic cleft . This increases the concentration of the messenger substance serotonin in the synaptic cleft. It is believed that this causes a higher concentration of serotonin in the central nervous system. Serotonin acts there as a messenger substance in processes that affect the psyche and can improve mood and psychological driving force.

A meta-analysis from 2009 showed a very minor, but statistically significant, efficacy advantage of escitalopram over other SSRIs and SNRIs with a minimally lower incidence of side effects. The advantages, especially the cost-benefit ratio compared to generics of established drugs of the same class of active ingredients, have been questioned in several publications. In particular, an active benefit or a reduction in undesirable effects compared to citalopram could not be proven. In the meantime, inexpensive generics from various manufacturers are also available.

unwanted effects

One of the most common adverse effects is nausea, which affects more than 10% of patients. 1 to 10% of patients also experience diarrhea and vomiting, insomnia, sleepiness or dizziness, increased sweating, decreased appetite, tiredness or fever. Often libido - or orgasm - ejaculation - or erectile dysfunction and weight gain. Many of these side effects occur more frequently in the first or second week of treatment and decrease in intensity and frequency with continued treatment. Some of the side effects may persist for a significant amount of time after you stop taking the drug.

A high fever, excitement, confusion, tremors and brief, jerky jerks of individual muscles can be signs of the rare so-called serotonin syndrome .

Escitalopram leads to a dose-dependent prolongation of the QT interval in the ECG . In addition, isolated ventricular arrhythmias , including torsade de pointes tachycardia, have been observed post-marketing . As with citalopram, the contraindications , dosage information and the warnings and precautions for the use of escitalopram were updated accordingly in December 2012.

Pharmacokinetics

Absorption from the gastrointestinal tract after oral ingestion is almost complete and independent of food intake. The apparent volume of distribution is approximately 12-26 ml / kg. The plasma protein binding of escitalopram and its major metabolites is less than 80%.

Escitalopram is converted in the liver to demethylated and didemethylated metabolites, which, like escitalopram, are pharmacologically active. The biotransformation to the demethylated metabolites takes place mainly via the cytochrome P450 -2C19 isoenzyme. Both escitalopram and its metabolites are partly excreted as glucuronides . The elimination half-life is about 30 hours after multiple dosing; the main metabolites have a significantly longer plasma half-life than the parent compound.

The elimination takes place of escitalopram both the liver (by biotransformation) and by the kidney. Most of the dose is excreted in the urine as metabolites.

Interactions with other drugs

Serious side effects in the form of a serotonin syndrome can occur in combination with non-selective irreversible monoamine oxidase inhibitors ( MAOIs ), with reversible selective MAO-A inhibitors and the non-selective reversible MAO-inhibitor and oxazolidinone antibiotic linezolid , which is why these combinations are contraindicated . Special precautionary measures require the combination with selegiline (MAO-B-inhibitor), serotonergic drugs and drugs that lower the threshold for seizures, also with lithium , tryptophan , St. John's wort and oral anticoagulants .

A switch between escitalopram and MAO inhibitors may only be made under careful medical supervision and days without therapy must be switched on.

When switching from moclobemide to escitalopram, wait at least one day between the last dose of moclobemide and the first dose of escitalopram. When switching from escitalopram to moclobemide, an escitalopram-free interval of 7 days must be waited for.

Administration form

Escitalopram is effective orally , there are tablets (5 mg / 10 mg / 15 mg / 20 mg) and drops for oral use.

Use during pregnancy and breastfeeding

→ Main article: SSRI and pregnancy

Escitalopram should only be used in pregnant women if absolutely necessary and only after carefully weighing the benefits and risks. Sudden discontinuation during pregnancy should be avoided.

It can be assumed that escitalopram will pass into breast milk. Therefore, breastfeeding should not be performed during treatment.

Withdrawal syndrome

→ Main article: SSRI withdrawal syndrome

After prolonged use of SSRIs, discontinuation of therapy may occur in some patients with sudden withdrawal symptoms. These can be dizziness, headache, nausea, paresthesia , tremor , anxiety, palpitation , increased sweating, nervousness and sleep disorders. For this reason, the treatment is usually not ended abruptly, but gradually .

Fixed price regulation

With the expiry of patent protection, escitalopram has been classified in a fixed price group with citalopram since 2014 . This was preceded by a legal dispute between the pharmaceutical company Lundbeck , which sells the original preparation, and the Federal Joint Committee (G-BA), whose early fixing of a fixed amount was overridden six months later by the Berlin-Brandenburg Regional Social Court by means of an injunction .

Trade names

Cipralex, Seroplex (F), Lexapro (USA), Escitalex (D)

Web links

Commons : Escitalopram  - collection of images, videos and audio files

• rating

Individual evidence

1. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
2. ↑ Kennedy SH, Andersen HF, Thase ME: Escitalopram in the treatment of major depressive disorder: a meta-analysis , Curr Med Res Opin. 2009 Jan; 25 (1): 161-75, PMID 19210149 .
3. ↑ Frank König: Interactions and mechanisms of action of selected psychotropic drugs . Georg Thieme Verlag, 2003, ISBN 3-13-105452-2 , p. 161 ( limited preview in Google Book search).
4. ↑ Escitalopram: pharma-kritik Volume 25, Number 3 .
5. ↑ Citalopram versus escitalopram. PHARMAINFORMATION, Volume 23 / No. 1; Innsbruck, February 2008 .
6. ↑ arznei-telegram: The 2nd attempt: Escitalopram (Cipralex)
7. ↑ Rote-Hand-Brief on dose-dependent QT interval extension (PDF; 141 kB) retrieved from the website of the Drugs Commission of the German Medical Association (AkdÄ)
8. ↑ Rote-Hand-Brief on Citalopram from October 31, 2011 Drug Safety Mail of the AkdÄ from October 31, 2011.
9. ↑ ^{a b c} Technical information for escitalopram Lundbeck 10 mg / 20 mg film-coated tablets, information as of March 2014
10. ↑ German specialized information: Cipralex; Status: 11/2007.
11. ^ Specialist information of the Swiss Medicines Compendium: Cipralex®; Information as of April 2007.
12. ↑ Fixed amount for escitalopram tipped ( memento from January 20, 2012 in the Internet Archive ), Ärztezeitung from December 13, 2011.

This article is about a health issue. It is not used for self-diagnosis and does not replace a diagnosis by a doctor. Please note the information on health issues !