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Encyclopedia > Escitalopram
Escitalopram
Systematic (IUPAC) name
S-(+)-1-[3-(dimethylamino)propyl]-
1-(p-fluorophenyl)-
5-phthalancarbonitrileoxalate
Identifiers
CAS number 128196-01-0
ATC code N06AB10
PubChem 146570
DrugBank APRD00683
Chemical data
Formula C20H21FN2O 
Mol. mass 324.392 g/mol
(414.40 as oxalate)
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability 80%
Protein binding ~56%
Metabolism Liver, specifically the enzymes CYP3A4 and CYP2C19
Half life 27–32 hours
Excretion  ?
Therapeutic considerations
Pregnancy cat.

C Image File history File links This is a lossless scalable vector image. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System containing Psychoanaleptics. ... PubChem is a database of chemical molecules. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... A chemical formula is an easy way of expressing information about the atoms that constitute a particular chemical compound. ... For other uses, see Carbon (disambiguation). ... This article is about the chemistry of hydrogen. ... Distinguished from fluorene and fluorone. ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... This article is about the chemical element and its most stable form, or dioxygen. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... A drugs efficacy may be affected by the degree to which it binds to the proteins within blood plasma. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... Cytochrome P450 3A4 (abbreviated CYP3A4) (EC 1. ... Cytochrome P450 2C19 (abbreviated CYP2C19), a member of the cytochrome P450 mixed-function oxidase system, is involved in the metabolism of xenobiotics in the body. ... The biological half-life of a substance is the time required for half of that substance to be removed from an organism by either a physical or a chemical process. ... The kidneys are important excretory organs in vertebrates. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ...

Legal status

Prescription only The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ...

Routes Oral

Escitalopram (trade names Lexapro, Cipralex) is the pure (S) enantiomer of citalopram and is a selective serotonin reuptake inhibitor (SSRI). Escitalopram is used in the treatment of depression and anxiety. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body. ... In chemistry, enantiomers (from the Greek ἐνάντιος, opposite, and μέρος, part or portion) are stereoisomers that are nonsuperimposable complete mirror images of each other, much as ones left and right hands are the same but opposite. ... Citalopram is an antidepressant drug used to treat depression associated with mood disorders. ... SSRI redirects here; for other uses, see SSRI (disambiguation). ... It is common to feel sad, discouraged , or down once in a while, and anyone in this state might say they are suffering from depression. ... Anxiety is a physiological state characterized by cognitive, somatic, emotional, and behavioral components[1]. These components combine to create the feelings that we typically recognize as anger and known as fear, apprehension, or worry. ...

Contents

History

Escitalopram was developed in a close cooperation between Lundbeck and Forest Laboratories. Its development was initiated in the summer of 1997, and the resulting new drug application was submitted to the FDA in March 2001. The short time (3.5 years) it took to develop escitalopram can be attributed to the previous extensive experience of Lundbeck and Forest with citalopram, which has similar pharmacology.[1] FDA issued the approval of escitalopram for major depression in August 2002 and for generalized anxiety disorder in December 2003. Escitalopram can be considered an example of "lifecycle management"[2] - the strategy pharmaceutical companies use in order to extend the lifetime of a drug, in this case of the citalopram franchise. Escitalopram is an enantiomer of citalopram, used for the same indication, and for that reason it required less investment and less time to develop. Two years after escitalopram's launch, when the patent on citalopram expired, the escitalopram sales successfully made up for the loss. On May 23, 2006, the FDA approved a generic version of escitalopram by Teva.[3] However, on July 14 of that year, the U.S. District Court of Delaware decided in favor of Lundbeck regarding the patent infringement dispute and ruled the patent on escitalopram valid.[4] The United States Food and Drug Administration is the government agency responsible for regulating food, dietary supplements, drugs, cosmetics, medical devices, biologics and blood products in the United States. ... Citalopram is an antidepressant drug used to treat depression associated with mood disorders. ... In chemistry, enantiomers (from the Greek ἐνάντιος, opposite, and μέρος, part or portion) are stereoisomers that are nonsuperimposable complete mirror images of each other, much as ones left and right hands are the same but opposite. ... Citalopram is an antidepressant drug used to treat depression associated with mood disorders. ... is the 143rd day of the year (144th in leap years) in the Gregorian calendar. ... Year 2006 (MMVI) was a common year starting on Sunday of the Gregorian calendar. ... is the 195th day of the year (196th in leap years) in the Gregorian calendar. ... The United States District Court for the District of Delaware is the Federal district court having jurisdiction over the entire state of Delaware. ...


Despite the drug's similarity, preclinical as well as various clinical studies (including double-blinded studies) have shown differentiated effects of citalopram and escitalopram,[5] as well as a clinical superiority compared with a variety of other SSRIs, such as paroxetine,[6] especially in severely depressed patients, and sertraline. Compared with newer serotonin-norepinephrine reuptake inhibitors such as venlafaxine[7] and duloxetine[8] escitalopram was shown to be at least as effective. For the communication paradox, see double bind. ... Paroxetine (Paxil, Seroxat, Pexeva) is a selective serotonin reuptake inhibitor (SSRI) antidepressant. ... Zoloft bottles, with blue and green tablets Sertraline hydrochloride (also sold under brand names Zoloft, Lustral, Apo-Sertral, Asentra, Gladem, Serlift, Stimuloton, Xydep, Serlain, Concorz) is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. ... Serotonin Norepinephrine Serotonin-norepinephrine reuptake inhibitors (SNRIs) are a class of antidepressant used in the treatment of clinical depression and other affective disorders. ... Venlafaxine (Effexor, Efexor) is an antidepressant of the serotonin-norepinephrine reuptake inhibitor (SNRI) class first introduced by Wyeth in 1993. ... Duloxetine (brand names Cymbalta, Yentreve, and in parts of Europe, Xeristar or Ariclaim) is a drug which primarily targets major depressive disorder (MDD), generalized anxiety disorder (GAD), pain related to diabetic peripheral neuropathy and in some countries stress urinary incontinence (SUI). ...


Pharmacology

Escitalopram (Lexapro by Forest Laboratories in the United States and elsewhere by Lundbeck as Cipralex, Sipralexa and Seroplex)[9] is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. It is approved for the treatment of major depressive disorder and generalized anxiety disorder; other indications include social anxiety disorder, panic disorder and obsessive-compulsive disorder. Escitalopram is the S-stereoisomer (enantiomer) of the earlier Lundbeck drug citalopram (Celexa), hence the name escitalopram. Escitalopram is noted for its high selectivity of serotonin reuptake inhibition and, as a result has fewer side effects not related to its serotonergic activity.[10] Escitalopram acts by increasing intrasynaptic levels of the neurotransmitter serotonin by blocking the reuptake of the neurotransmitter into the neuron. Of the SSRIs currently on the market escitalopram has the highest affinity for the human serotonin transporter (SERT). Another enantiomer of citalopram (R-citalopram) counteracts to a certain degree the serotonin-enhancing action of escitalopram. As a result, escitalopram is a more potent antidepressant than citalopram, which is a mixture of escitalopram and R-citalopram. In order to explain this phenomenon, researchers from Lundbeck proposed that escitalopram enhances its own binding via an additional interaction with another allosteric site on the transporter.[11] Further research by the same group showed that R-citalopram also enhances binding of escitalopram,[12] and therefore the allosteric interaction cannot explain the observed counteracting effect. However, in the most recent paper the same authors again reversed their findings and reported that R-citalopram decreases binding of escitalopram to the transporter.[13] Although allosteric binding of escitalopram to the serotonin transporter is of unquestionable research interest, its clinical relevance is unclear since the binding of escitalopram to the allosteric site is at least 1000 times weaker than to the primary binding site. Forest Laboratories is a pharmaceutical company based in New York, New York, USA. It should not be confused with the Forest Products Laboratory [1] [2]. External links Forest Laboratories Category: ... H. Lundbeck A/S (also known as Lundbeck) is a Danish international pharmaceutical company engaged in the research and development, production, marketing and sale of drugs for the treatment of psychiatric and neurological disorders. ... Prozac, a selective serotonin reuptake inhibitor (SSRI) Serotonin-norepinephrine reuptake inhibitor, Venlafaxine An antidepressant is a psychiatric medication or other substance (nutrient or herb) used for alleviating depression or dysthymia (milder depression). ... SSRI redirects here; for other uses, see SSRI (disambiguation). ... It is common to feel sad, discouraged , or down once in a while, and anyone in this state might say they are suffering from depression. ... Generalized anxiety disorder (GAD) is an anxiety disorder that is characterized by excessive, uncontrollable and often irrational worry about everyday things, which is disproportionate to the actual source of worry. ... Social anxiety, sometimes known as social phobia or social anxiety disorder (SAD), is a common form of anxiety disorder that causes sufferers to experience intense anxiety in some or all of the social interactions and public events of everyday life. ... Panic Disorder is a psychiatric condition characterized by recurring panic attacks in combination with significant behavioral change or at least a month of ongoing worry about the implications or concern about having other attacks. ... In chemistry, enantiomers (from the Greek ἐνάντιος, opposite, and μέρος, part or portion) are stereoisomers that are nonsuperimposable complete mirror images of each other, much as ones left and right hands are the same but opposite. ... Citalopram is an antidepressant drug used to treat depression associated with mood disorders. ... Serotonergic means related to, capable of producing, altering, or releasing serotonin, a neurotransmitter, and can refer to the following classes of chemicals: Selective serotonin reuptake inhibitor - A common class of serotonergic antidepressants Noradrenergic and specific serotonergic antidepressant - Another class of serotonergic antidepressants serotonergic psychedelics - The serotonergic hallucinogenic drugs This is... For the professional wrestling stable, see Ravens Nest#Serotonin. ... The serotonin transporter is a monoamine transporter protein. ... In biochemistry, an enzyme or other protein is allosteric if its activity or efficiency changes in response to the binding of an effector molecule at a so-called allosteric site. ...


In vitro studies using human liver microsomes indicated that CYP3A4 and CYP2C19 are the primary isozymes involved in the N-demethylation of escitalopram. Cytochrome P450 3A4 (abbreviated CYP3A4) (EC 1. ... Cytochrome P450 2C19 (abbreviated CYP2C19), a member of the cytochrome P450 mixed-function oxidase system, is involved in the metabolism of xenobiotics in the body. ...


Side effects and drug interactions

Lexapro tablets
Lexapro tablets
Cipralex brand escitalopram package and tablet sheet
Cipralex brand escitalopram package and tablet sheet

The side effect profile of escitalopram is close to that of other SSRIs, with nausea, somnolence, and gastrointestinal side effects reported as relatively common. Escitalopram, like other SSRIs[14], has been shown to cause sexual side effects in many patients. Escitalopram is not associated with significant weight gain. For example, 0.6 kg mean weight change after 6 months of treatment with escitalopram for depression was insignificant and similar to that with placebo (0.2 kg).[15] 1.4-1.8 kg mean weight gain was reported in 8-month trials of escitalopram for depression,[16] and generalized anxiety disorder.[17] A 52-week trial of escitalopram for the long-term treatment of depression in elderly also found insignificant 0.6 kg mean weight gain.[18] Escitalopram may help reduce weight in those treated for binge eating associated obesity.[19] It may also cause dizziness after exercise in children.[citation needed] Image File history File linksMetadata Size of this preview: 800 × 600 pixelsFull resolution (2592 × 1944 pixel, file size: 512 KB, MIME type: image/jpeg) File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Image File history File linksMetadata Size of this preview: 800 × 600 pixelsFull resolution (2592 × 1944 pixel, file size: 512 KB, MIME type: image/jpeg) File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Image File history File links Download high-resolution version (1024x768, 195 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Escitalopram ... Image File history File links Download high-resolution version (1024x768, 195 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Escitalopram ... SSRI redirects here; for other uses, see SSRI (disambiguation). ... An adverse drug reaction (abbreviated ADR) or adverse drug event (abbreviated ADE) is an expression that describes the unwanted, negative consequences associated with the use of given medications. ... SSRI is an acronym that stands for several things: It is a class of antidepressants called selective serotonin reuptake inhibitor SSRI also is used as the stock symbol for Silver Standard Resources Inc. ... Somnolence (or drowsiness) is a state of near-sleep, a strong desire for sleep, or sleeping for unusually long periods. ... Human sexuality is the expression of sexual feelings. ... Generalized anxiety disorder (GAD) is an anxiety disorder that is characterized by excessive, uncontrollable and often irrational worry about everyday things, which is disproportionate to the actual source of worry. ... Binge eating is a pattern of disordered eating which consists of episodes of uncontrollable overeating. ...


A meta-analysis of clinical trials database conducted by the escitalopram manufacturer Lundbeck found no indication that escitalopram would provoke suicidal behaviour compared with placebo in patients with major depressive disorder and anxiety disorders, on the contrary, suicidal thoughts in the escitalopram group were significantly decreased.[20] An analysis conducted by the FDA found a statistically insignificant 1.5 to 2.4-fold, depending on the statistical technique used, increase of suicidality among the adults treated with escitalopram for psychiatric indications.[21][22][23] Similarly, the UK MHRA data indicate an 80% increase of suicide-related events, not reaching statistical significance, in the escitalopram vs placebo patients.[24] The authors of a related study note the general problem with statistical approaches—due to the rarity of suicidal events in clinical trials, it is hard to draw firm conclusions with a sample smaller than two million patients.[25] A single case report described a patient developing suicidal ideation after beginning treatment with escitalopram, and suicidal ideation disappearing after stopping the treatment.[26] For other uses, see Placebo (disambiguation). ... It is common to feel sad, discouraged , or down once in a while, and anyone in this state might say they are suffering from depression. ... Anxiety disorder is a blanket term covering several different forms of abnormal, pathological anxiety, fears, phobias. ... MHRA is an initialism that can stand for: Medicines and Healthcare products Regulatory Agency Modern Humanities Research Association This is a disambiguation page — a navigational aid which lists other pages that might otherwise share the same title. ... In medicine, a case report is a detailed report of the diagnosis, treatment, and follow-up of an individual patient. ... Suicidal ideation is common medical term for the mere thoughts about and of plans of committing suicide, not the actual following through or act itself. ...


Escitalopram should be taken with caution when using St John's wort.[27] Binomial name Hypericum perforatum L. St Johns wort (IPA pronunciation: , rhyming with hurt, or ) used alone refers to the species Hypericum perforatum, also known as Klamath weed or Goat weed, but, with qualifiers, is used to refer to any species of the genus Hypericum. ...


Discontinuation symptoms

Lexapro discontinuation, particularly abruptly, may cause certain withdrawal symptoms such as paresthesia (for example, electric shock sensations also known as "brain shivers" or "brain zaps"), dizziness and irritability.[28] SSRI discontinuation syndrome, also known as SSRI withdrawal syndrome or SSRI cessation syndrome, is a condition that can occur during or following the interruption, lowering of dose or discontinuation of regular SSRI or SNRI antidepressant drug usage. ... Withdrawal, also known as withdrawal syndrome, refers to the characteristic signs and symptoms that appear when a drug that causes physical dependence is regularly used for a long time and then suddenly discontinued or decreased in dosage. ... A symptom is a manifestation of a disease, indicating the nature of the disease, which is noticed by the patient. ... Paresthesia or paraesthesia (in British English) is a sensation of tingling, pricking, or numbness of a persons skin with no apparent long-term physical effect, more generally known as the feeling of pins and needles or of a limb being asleep (but not directly related to the phenomenon of... Brain zaps, (proposed name: myalotinasis from Greek for brain + jolt) also known as the electric brain thing, brain shivers, brain shocks, battery head, blips, or brain spasms, are a fairly common and notorious withdrawal symptom experienced during discontinuation (or reduction of dose) of SSRI and SNRI antidepressant drugs. ... Brain zaps, (proposed name: myalotinasis from Greek for brain + jolt) also known as the electric brain thing, brain shivers, brain shocks, battery head, blips, or brain spasms, are a fairly common and notorious withdrawal symptom experienced during discontinuation (or reduction of dose) of SSRI and SNRI antidepressant drugs. ... Many different terms are often used to describe what is collectively known as dizziness. ... Irritability is an excessive response to stimuli. ...


Footnotes

  1. ^ 2000 Annual Report. p 28 and 33 (PDF). Lundbeck (2000). Retrieved on 2007-04-07.
  2. ^ New drugs from old. Presented at the Medical Journal Club, Morriston Hospital by Scott Pegler, Pharmacist at the National Health Service (UK) on November 20, 2006 (PPT). Retrieved on 2007-04-07.
  3. ^ Miranda Hitti. "FDA OKs Generic Depression Drug -- Generic Version of Lexapro Gets Green Light", WebMD. Retrieved on 2007-10-10. 
  4. ^ Marie-Eve Laforte. "US court upholds Lexapro patent", FirstWord, July 14, 2006. Retrieved on 2007-10-10. 
  5. ^ Moore N, Verdoux H, Fantino B (2005). "Prospective, multicentre, randomized, double-blind study of the efficacy of escitalopram versus citalopram in outpatient treatment of major depressive disorder". International Clinical Psychopharmacology 20 (3): 131–137. doi:10.1097/00004850-200505000-00002. PMID 15812262. 
  6. ^ Boulenger JP, Huusom AK, Florea I, Baekdal T, Sarchiapone M (2006). "A comparative study of the efficacy of long-term treatment with escitalopram and paroxetine in severely depressed patients". Current Medical Research and Opinion 22 (7): 1331–41. doi:10.1185/030079906X115513. PMID 16834832. 
  7. ^ Bielski RJ, Ventura D, Chang CC (2004). "A double-blind comparison of escitalopram and venlafaxine extended release in the treatment of major depressive disorder". The Journal of Clinical Psychiatry 65 (9): 1190–1196. PMID 15367045. 
  8. ^ Nierenberg AA, Greist JH, Mallinckrodt CH, et al (2007). "Duloxetine versus escitalopram and placebo in the treatment of patients with major depressive disorder: onset of antidepressant action, a non-inferiority study". Current Medical Research and Opinion 23 (2): 401–416. doi:10.1185/030079906X167453. PMID 17288694. 
  9. ^ Cipralex. Lundbeck. Retrieved on 2008-01-03.
  10. ^ Burke WJ, Kratochvil CJ (2002). "Stereoisomers in Psychiatry: The Case of Escitalopram" (PDF). Prim Care Companion J Clin Psychiatry 4 (1): 20–24. PMID 15014731. 
  11. ^ For the overview of supporting data, see Sánchez C, Bøgesø KP, Ebert B, Reines EH, Braestrup C (2004). "Escitalopram versus citalopram: the surprising role of the R-enantiomer". Psychopharmacology (Berl.) 174 (2): 163–76. doi:10.1007/s00213-004-1865-z. PMID 15160261. 
  12. ^ Chen F, Larsen MB, Sánchez C, Wiborg O (2005). "The S-enantiomer of R,S-citalopram, increases inhibitor binding to the human serotonin transporter by an allosteric mechanism. Comparison with other serotonin transporter inhibitors". European Neuropsychopharmacology 15 (2): 193–198. doi:10.1016/j.euroneuro.2004.08.008. PMID 15695064. 
  13. ^ Mansari ME, Wiborg O, Mnie-Filali O, Benturquia N, Sánchez C, Haddjeri N (2007). "Allosteric modulation of the effect of escitalopram, paroxetine and fluoxetine: in-vitro and in-vivo studies". The International Journal of Neuropsychopharmacology 10 (1): 31–40. doi:10.1017/S1461145705006462. PMID 16448580. 
  14. ^ Clayton A, Keller A, McGarvey EL (2006). "Burden of phase-specific sexual dysfunction with SSRIs". Journal of Affective Disorders 91 (1): 27–32. doi:10.1016/j.jad.2005.12.007. PMID 16430968. 
  15. ^ Baldwin DS, Reines EH, Guiton C, Weiller E (2007). "Escitalopram therapy for major depression and anxiety disorders". Ann Pharmacother 41 (10): 1583–92. doi:10.1345/aph.1K089. PMID 17848424. 
  16. ^ Pigott TA, Prakash A, Arnold LM, Aaronson ST, Mallinckrodt CH, Wohlreich MM (2007). "Duloxetine versus escitalopram and placebo: an 8-month, double-blind trial in patients with major depressive disorder". Curr Med Res Opin: 1303. doi:10.1185/030079907X188107. PMID 17559729. 
  17. ^ Davidson JR, Bose A, Wang Q (2005). "Safety and efficacy of escitalopram in the long-term treatment of generalized anxiety disorder". J Clin Psychiatry 66 (11): 1441–6. PMID 16420082. 
  18. ^ Kasper S, Lemming OM, de Swart H (2006). "Escitalopram in the long-term treatment of major depressive disorder in elderly patients". Neuropsychobiology 54 (3): 152–9. doi:10.1159/000098650. PMID 17230032. 
  19. ^ Guerdjikova, Anna I.; Susan L. McElroy, Renu Kotwal, Jeffrey A. Welge, Erik Nelson, Katie Lake, David D' Alessio, Paul E. Keck Jr, James I. Hudson (2008). "High-dose escitalopram in the treatment of binge-eating disorder with obesity: a placebo-controlled monotherapy trial". Human Psychopharmacology: Clinical and Experimental 23 (1): 1–11. doi:10.1002/hup.899. PMID 18058852. 
  20. ^ Pedersen AG (2005). "Escitalopram and suicidality in adult depression and anxiety". International Clinical Psychopharmacology 20 (3): 139–143. doi:10.1097/00004850-200505000-00003. PMID 15812263. 
  21. ^ Levenson M, Holland C. Antidepressants and Suicidality in Adults: Statistical Evaluation. (Presentation at Psychopharmacologic Drugs Advisory Committee; December 13, 2006). Retrieved on 2007-05-13.
  22. ^ Stone MB, Jones ML (November 17, 2006). CLINICAL REVIEW: RELATIONSHIP BETWEEN ANTIDEPRESSANT DRUGS AND SUICIDALITY IN ADULTS (PDF). Overview for December 13 Meeting of Psychopharmacologic Drugs Advisory Committee (PDAC) 11-74. FDA. Retrieved on 2007-09-22.
  23. ^ Levenson M, Holland C (November 17, 2006). Statistical Evaluation of Suicidality in Adults Treated with Antidepressants (PDF). Overview for December 13 Meeting of Psychopharmacologic Drugs Advisory Committee (PDAC) 75-140. FDA. Retrieved on 2007-09-22.
  24. ^ Gunnell D, Saperia J, Ashby D (2005). "Selective serotonin reuptake inhibitors (SSRIs) and suicide in adults: meta-analysis of drug company data from placebo controlled, randomised controlled trials submitted to the MHRA's safety review". BMJ 330 (7488): 385. doi:10.1136/bmj.330.7488.385. PMID 15718537. Retrieved on 2007-09-25. 
  25. ^ Khan A, Schwartz K (2007). "Suicide risk and symptom reduction in patients assigned to placebo in duloxetine and escitalopram clinical trials: analysis of the FDA summary basis of approval reports". Ann Clin Psychiatry 19 (1): 31–6. doi:10.1080/10401230601163550. PMID 17453659. 
  26. ^ Budur, Kumar; Jeffrey Hutzler (June 2004). "Severe suicidal ideation with escitalopram (Lexapro): a case report". Primary Care Psychiatry 9 (2): 67–68. doi:10.1185/135525704125004222. 
  27. ^ Karch, Amy (2006). 2006 Lippincott's Nursing Drug Guide. Philadephia, Baltimore, New York, London, Buenos Aires, Hong Kong, Sydney, Tokyo: Lippincott Williams & Wilkins. ISBN 1-58255-436-6. 
  28. ^ Lexapro -- Warnings. RxList (12/08/2004). Retrieved on 2006-10-22.

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A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... 2008 (MMVIII) is the current year, a leap year that started on Tuesday of the Common Era (or Anno Domini), in accordance with the Gregorian calendar. ... is the 3rd day of the year in the Gregorian calendar. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... Year 2007 (MMVII) was a common year starting on Monday of the Gregorian calendar in the 21st century. ... is the 133rd day of the year (134th in leap years) in the Gregorian calendar. ... Year 2007 (MMVII) was a common year starting on Monday of the Gregorian calendar in the 21st century. ... is the 265th day of the year (266th in leap years) in the Gregorian calendar. ... Year 2007 (MMVII) was a common year starting on Monday of the Gregorian calendar in the 21st century. ... is the 265th day of the year (266th in leap years) in the Gregorian calendar. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... Year 2007 (MMVII) was a common year starting on Monday of the Gregorian calendar in the 21st century. ... is the 268th day of the year (269th in leap years) in the Gregorian calendar. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... Year 2006 (MMVI) was a common year starting on Sunday of the Gregorian calendar. ... is the 295th day of the year (296th in leap years) in the Gregorian calendar. ...

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In pharmacology, a psychoanaleptic is a medication which produces an arousing effect upon the patient. ... Prozac, a selective serotonin reuptake inhibitor (SSRI) Serotonin-norepinephrine reuptake inhibitor, Venlafaxine An antidepressant is a psychiatric medication or other substance (nutrient or herb) used for alleviating depression or dysthymia (milder depression). ... A section of the Anatomical Therapeutic Chemical Classification System containing Psychoanaleptics. ... MAOI redirects here. ... Iproclozide is a monoamine oxidase inhibitor antidepressant. ... Iproniazid is a monamine oxidase inhibitor (MAOI) that was developed as the first anti-depressant (Also first psychiatric drug). ... Isocarboxazid is a nonselective hydrazine-derived monoamine oxidase inhibitor used in treatment resistant depression. ... Nialamide (Espril®, Niamid®, Niaquitil®, Nuredal®, Nyazin®, and Psicodisten®) was one of the first MAOI (monoamine oxidase inhibitor) antidepressants. ... Pargyline is a monoamine oxidase B (MAO-B) inhibitor indicated for the treatment of moderate to severe hypertension. ... Phenelzine (brand name Nardil) is an antidepressant drug that belongs to the monoamine oxidase inhibitor (MAOI) class of drugs. ... Rasagiline (trade name Azilect®) is a irreversible inhibitor of monoamine oxidase used as a monotherapy in early Parkinsons disease or as an adjunct therapy in more advanced cases. ... Selegiline (l-deprenyl, Eldepryl® or Anipryl® [veterinary]) is a drug used for the treatment of early-stage Parkinsons disease and senile dementia. ... Toloxatone is a monoamine oxidase inhibitor antidepressant. ... Tranylcypromine (sold under the brand name Parnate®) is a monoamine oxidase inhibitor (MAOI) used as an antidepressant drug. ... These drugs, a subset of monoamine oxidase inhibitors (MAOIs), inhibit only isoenzyme A and are reversible. ... Brofarmine is a psychiatric drug primarily used to treat depression and anxiety. ... β-Carboline (9H-pyrid-[3,4-b]-indole) is an organic amine that is the prototype of a class of compounds known as β-Carbolines. ... Harmala, also known at various times as Telepathine and Banisterine, is a blanket term for a group of naturally occurring beta-carbolines including harmine, harmaline, and others. ... Moclobemide (sold as Aurorix®, Manerix®) is a psychiatric drug primarily used to treat depression and social anxiety. ... A neurotransmitter uptake inhibitor is a drug which inhibits the reuptake of the neurotransmitter, thus extending the duration of its effect. ... A serotonin uptake inhibitor is a drug which acts as a neurotransmitter uptake inhibitor on serotonin receptors. ... SSRI redirects here; for other uses, see SSRI (disambiguation). ... Alaproclate is an antidepressant that increases serotonin levels by inhibiting the uptake of 5-HT. Today, its primarily used to stagment the cravings for cocaine. ... Citalopram is an antidepressant drug used to treat depression associated with mood disorders. ... Dapoxetine is the International Nonproprietary Name of a drug currently being considered for approval by the FDA for the treatment of premature ejaculation in men, which would make it the first drug approved for such treatment. ... Prozac redirects here. ... Fluvoxamine (brand name as Luvox®, Faverin®, Fevarin® and Dumyrox®) is an antidepressant which functions pharmacologically as a selective serotonin reuptake inhibitor. ... Paroxetine (Paxil, Seroxat, Pexeva) is a selective serotonin reuptake inhibitor (SSRI) antidepressant. ... Zoloft bottles, with blue and green tablets Sertraline hydrochloride (also sold under brand names Zoloft, Lustral, Apo-Sertral, Asentra, Gladem, Serlift, Stimuloton, Xydep, Serlain, Concorz) is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. ... // General Remars and History Zimelidine is a pyridylallylamine and has a structure different from other antidepressants. ... Chemical structure of the tricyclic antidepressant amitriptyline. ... There are also several chemically unrelated tetracyclic antibiotics based on Tetracycline. ... Clomipramine (brand-name Anafranil®) is a tricyclic antidepressant. ... Nefazodone hydrochloride (trade name Serzone) is an antidepressant drug marketed by Bristol-Myers Squibb. ... Trazodone (trade names Desyrel, Molipaxin, Trittico, Thombran, Trialodine) is a psychoactive compound with sedative, anxiolytic, and antidepressant properties. ... Norepinephrine reuptake inhibitors (NRIs) are compounds that increase amounts of the neurotransmitter norepinephrine in the brain by inhibiting its reuptake at synapses. ... A adrenergic uptake inhibitor is a drug which blocks the reuptake of adrenergic neurotransmitters. ... Atomoxetine is the first non-stimulant drug approved for the treatment of attention-deficit hyperactivity disorder (ADHD). ... To meet Wikipedias quality standards, this article may require cleanup. ... Reboxetine is an antidepressant drug used in the treatment of clinical depression, panic disorder and ADD/ADHD. Its mesilate ( methanesulfonate) salt is sold under tradenames including Edronax®, Norebox®, Prolift®, Solvex® or Vestra®. Reboxetine has two chiral centers, but it only exists as two enantiomers, (R,R)-(-)- and (S,S)-(+)-reboxetine. ... Viloxazine is a bicyclic antidepressants[2] that inhibits the reuptake of serotonin, and to a lesser extent, dopamine and norepinephrine. ... Chemical structure of the tricyclic antidepressant amitriptyline. ... There are also several chemically unrelated tetracyclic antibiotics based on Tetracycline. ... Amitriptyline (or Amitryptyline) hydrochloride (sold as Elavil, Tryptanol, Endep, Elatrol, Tryptizol, Trepiline, Laroxyl) is a tricyclic antidepressant drug. ... Amoxapine (Asendin®; Asendis®; Defanyl®; Demolox®; Moxadil®) is a tricyclic antidepressant of the dibenzoxazepine class. ... Butriptyline (Dl-10,11-Dihydro-N,N,beta-trimethyl-5H-dibenzo[a,d]cycloheptene-5-propylamine) is a tricyclic antidepressant with sedative properties and uses similar to that of amitriptyline. ... Desipramine is a tricyclic antidepressant (TCA) that inhibits the reuptake of norepinephrine. ... Lofepramine (trademarked Gamanil) is a tricyclic antidepressant prescribed primarily for sleeping and eating disorders. ... Dibenzepin (Noveril®) is a muscarinic antagonist. ... Dosulepin hydrochloride (sometimes known outside the USA as dothiepin hydrochloride) is an antidepressant of the tricyclic family. ... Doxepin is a tricyclic antidepressant, known under many brand-names such as Aponal®, the original preparation by Boehringer-Ingelheim, now part of the Roche group; Adapine®, Sinquan® and Sinequan® (Pfizer Inc. ... Imipramine (sold as Antideprin, Deprenil, Deprimin, Deprinol, Depsonil, Dynaprin, Eupramin, Imipramil, Irmin, Janimine, Melipramin, Surplix, Tofranil) is an antidepressant medication, a tricyclic antidepressant of the dibenzazepine group. ... Iprindole (C19H28N2), a 5-HT2 antagonist, is a tricyclic antidepressant that can be fatal when combined with MDMA. Categories: | ... Melitracen (or melitracene) is a tricyclic antidepressant. ... -1... Protriptyline (Vivactil®) is a tricyclic antidepressant indicated for depression and ADHD. Categories: | ... Trimipramine is an tricyclic antidepressant with sedative and anxiolytic properties. ... To meet Wikipedias quality standards, this article may require cleanup. ... Dopamine Dopamine Reuptake Inhibitors (DARI), Dopamine Uptake Inhibitors, Dopamine Transporter Inhibitors are compounds that inhibit the reuptake of extracellular dopamine back into the presynaptic cell by blocking the cell membrane-spanning dopamine transporter. ... Phenmetrazine is an amphetamine-like drug. ... Vanoxerine, also known as GBR-12909, is a piperazine derivative which is a potent and selective dopamine reuptake inhibitor. ... Chemical structure of the tricyclic antidepressant amitriptyline. ... Amineptine is an atypical tricyclic antidepressant that selectively inhibits the reuptake of dopamine and to a lesser extent norepinephrine, thus exerting a powerful and fast-acting antidepressant effect. ... Serotonin Norepinephrine Serotonin-norepinephrine reuptake inhibitors (SNRIs) are a class of antidepressant used in the treatment of clinical depression and other affective disorders. ... Desvenlafaxine succinate, marketed under the name Pristiq, is an antidepressant of the serotonin-norepinephrine reuptake inhibitor class from Wyeth. ... Duloxetine (brand names Cymbalta, Yentreve, and in parts of Europe, Xeristar or Ariclaim) is a drug which primarily targets major depressive disorder (MDD), generalized anxiety disorder (GAD), pain related to diabetic peripheral neuropathy and in some countries stress urinary incontinence (SUI). ... Milnacipran is an antidepressant of the serotonin-norepinephrine reuptake inhibitor class. ... Nefazodone hydrochloride (trade name Serzone) is an antidepressant drug marketed by Bristol-Myers Squibb. ... Venlafaxine (Effexor, Efexor) is an antidepressant of the serotonin-norepinephrine reuptake inhibitor (SNRI) class first introduced by Wyeth in 1993. ... A Norepinephrine-dop