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EscitalopramWikipedia

Escitalopram
FromWikipedia,thefreeencyclopedia

Escitalopram,alsoknownbythebrandnamesLexaproandCipralexamongothers,isanantidepressantofthe
selectiveserotoninreuptakeinhibitor(SSRI)class.ItisapprovedbytheU.S.FoodandDrugAdministration
(FDA)forthetreatmentofadultsandchildrenover12yearsofagewithmajordepressivedisorder(MDD)or
generalizedanxietydisorder(GAD).Escitalopramisthe(S)stereoisomer(Leftenantiomer)oftheearlier
Lundbeckdrugcitalopram,hencethenameescitalopram.Whetherescitalopramexhibitssuperiortherapeutic
propertiestocitalopramormerelyrepresentsanexampleof"evergreening"iscontroversial.[2]

Escitalopram

Theutilityofantidepressantdrugsinthetreatmentofmildtomoderatedepressionisitselfcontroversial.In
thosewithveryseveredepressionthereisalargebenefit.[3]

Contents
1 Medicaluses
1.1 Depression
1.2 Anxietydisorder
1.3 Other
2 Adverseeffects
2.1 Discontinuationsymptoms
2.2 Pregnancy
2.3 Overdose
3 Pharmacology
3.1 Mechanismofaction
3.2 Interactions
4 History
5 Societyandculture
5.1 Allegationsofillegalmarketing
5.2 Brandnames
6 References
7 Citedtexts
8 Furtherreading
9 Externallinks
https://en.wikipedia.org/wiki/Escitalopram

Clinicaldata
Pronunciation
Tradenames

pronunciation
Cipralex,Lexaproandmany
others[1]

AHFS/Drugs.com Monograph(https://www.drugs.
com/monograph/escitalopramox
alate.html)
MedlinePlus

a603005(http://www.nlm.nih.go
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Medicaluses
EscitalopramhasFDAapprovalforthetreatmentofmajordepressivedisorderinadolescentsandadults,and
generalizedanxietydisorderinadults.[4]InEuropeancountriesandAustralia,itisapprovedfordepression
(MDD)andcertainanxietydisorders:generalanxietydisorder(GAD),socialanxietydisorder(SAD),obsessive
compulsivedisorder(OCD),andpanicdisorderwithorwithoutagoraphobia.

v/medlineplus/druginfo/meds/a6
03005.html)
Licensedata

USFDA:Lexapro(http://

www.accessdata.fda.gov/s
cripts/cder/drugsatfda/ind
ex.cfm?fuseaction=Searc
h.SearchAction&SearchT
erm=Lexapro&SearchTy
pe=BasicSearch)

Depression
Escitalopramwasapprovedbyregulatoryauthoritiesforthetreatmentofmajordepressivedisorderonthebasis
offourplacebocontrolled,doubleblindtrials,threeofwhichdemonstratedastatisticalsuperiorityover
placebo.[5]Nonetheless,considerablecontroversyexistsregardingthesuperiorityofescitalopramtoits
predecessorcitalopram.Theimportanceofthisissuefollowsfromthegreatercostofescitalopramrelativetothe
genericmixtureofisomerscitaloprampriortotheexpirationoftheescitaloprampatentin2012,whichledto
chargesofevergreening.Accordingly,thisissuehasbeenexaminedinatleast10differentsystematicreviews
andmetaanalyses.Themostrecentofthesehaveconcluded(withcaveatsinsomecases)thatescitalopramis
modestlysuperiortocitalopraminefficacyand/ortolerability.[6][7][8][9]
Incontrasttothesefindings,a2011reviewconcludedthatallsecondgenerationantidepressantsareequally
effective,[10]andtreatmentguidelinesissuedbytheNationalInstituteofHealthandClinicalExcellenceandby
theAmericanPsychiatricAssociationgenerallyreflectthisviewpoint.[11][12]

Pregnancy
category

AU:C
US:C(Risknotruledout)

Routesof
administration

Oral

ATCcode

N06AB10(WHO(http://www.w
hocc.no/atc_ddd_index/?code=N
06AB10))
Legalstatus

Legalstatus

AU:S4(Prescription

only)
CA :only

Anxietydisorder

UK:POM(Prescription

TheremaybeasignificantimprovementinGADsymptomsasearlyasthefirstweekandthemajorityof
patientsrespondbyweekeightwithasignificantimprovementinfunctioning.[13]Italsoseemseffectiveinthe
longterm,withrelapseonescitalopram(20%)lessthanplacebo(50%).[14]

(Prescriptiononly)

only)
US:only
Pharmacokineticdata
Bioavailability

80%

Proteinbinding

~56%

Other

Metabolism

Liver,specificallytheenzymes
CYP3A4andCYP2C19

EscitalopramaswellasotherSSRIsareeffectiveinreducingthesymptomsofpremenstrualsyndrome,whether
takeninthelutealphaseonlyorcontinuously.[16]Thereisnogooddataavailableforescitalopramforseasonal
affectivedisorderasof2011.[17]SSRIsdonotappeartobeusefulforpreventingtensionheadachesor

Biologicalhalf
life

2732hours

Escitalopramandcitalopramappearequallyeffectiveinpanicdisorder.[15]

https://en.wikipedia.org/wiki/Escitalopram

Identifiers
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migraines.[18][19]

IUPACname

CASNumber

Adverseeffects

128196010(http://www.comm
onchemistry.org/ChemicalDetail.
aspx?ref=128196010)

Escitalopram,likeotherSSRIs,hasbeenshowntoaffectsexualfunctionscausingsideeffectssuchasdecreased
libido,delayedejaculation,genitalanesthesia,[20]andanorgasmia.[21][22]
AnanalysisconductedbytheFDAfoundastatisticallyinsignificant1.5to2.4fold(dependingonthestatistical
techniqueused)increaseofsuicidalityamongtheadultstreatedwithescitalopramforpsychiatric
indications.[23][24][25]Similarly,theUKMHRAdataindicatean80%increaseofsuiciderelatedevents,not
reachingstatisticalsignificance,intheescitalopramvs.placebopatients.[26]Theauthorsofarelatedstudynote
thegeneralproblemwithstatisticalapproaches:duetotherarityofsuicidaleventsinclinicaltrials,itishardto
drawfirmconclusionswithasamplesmallerthantwomillionpatients.[27]
Escitalopramisnotassociatedwithsignificantweightgain.Forexample,0.6kgmeanweightchangeafter6
monthsoftreatmentwithescitalopramfordepressionwasinsignificantandsimilartothatwithplacebo
(0.2kg).[28]1.41.8kgmeanweightgainwasreportedin8monthtrialsofescitalopramfordepression,[29]and
generalizedanxietydisorder.[30]A52weektrialofescitalopramforthelongtermtreatmentofdepressionin
elderlyalsofoundinsignificant0.6kgmeanweightgain.[31]Escitaloprammayhelpreduceweightinthose
treatedforbingeeatingassociatedobesity.[32]
CitalopramandescitalopramareassociatedwithdosedependentQTintervalprolongation[33]andshouldnotbe
usedinthosewithcongenitallongQTsyndromeorknownpreexistingQTintervalprolongation,orin
combinationwithothermedicinesthatprolongtheQTinterval.ECGmeasurementsshouldbeconsideredfor
patientswithcardiacdisease,andelectrolytedisturbancesshouldbecorrectedbeforestartingtreatment.In
December2011,theUKimplementednewrestrictionsonthemaximumdailydoses:
forcitalopram,40mgforadults20mgforpatientsolderthan65yearsand20mgforthosewithhepatic
impairment.
forescitalopram,10mgforpatientsolderthan65yearsotherdosesremainunchanged.[34][35]
EscitalopramshouldbetakenwithcautionwhenusingSaintJohn'swort.[36]Exposuretoescitalopramis
increasedmoderately,byabout50%,whenitistakenwithomeprazole.Theauthorsofthisstudysuggestedthat
thisincreaseisunlikelytobeofclinicalconcern.[37]Cautionshouldbeusedwhentakingcoughmedicine
https://en.wikipedia.org/wiki/Escitalopram

PubChem(CID) 146570(https://pubchem.ncbi.nl
m.nih.gov/summary/summary.cg
i?cid=146570)
DrugBank

DB01175(http://www.drugbank.
ca/drugs/DB01175)

ChemSpider

129277(http://www.chemspider.
com/ChemicalStructure.129277.
html)

UNII

4O4S742ANY(http://fdasis.nlm.
nih.gov/srs/srsdirect.jsp?regno=4
O4S742ANY)

ChEBI

CHEBI:36791(https://www.ebi.
ac.uk/chebi/searchId.do?chebiId
=CHEBI:36791)

ChEMBL

CHEMBL1508(https://www.eb
i.ac.uk/chembldb/index.php/com
pound/inspect/CHEMBL1508)
Chemicalandphysicaldata

Formula

C20H21FN2O

Molarmass

324.392g/mol
(414.43asoxalate)

3Dmodel(Jmol) Interactiveimage(http://chemap
ps.stolaf.edu/jmol/jmol.php?mod
el=Fc1ccc%28cc1%29%5BC%4
0%40%5D3%28OCc2cc%28C%

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containingdextromethorphan(DXM)asserotoninsyndrome,liverdamage,andothernegativesideeffectshave
beenreported.

Discontinuationsymptoms
Escitalopramdiscontinuation,particularlyabruptly,maycausecertainwithdrawalsymptomssuchas"electric
shock"sensations[38](alsoknownas"brainshivers"or"brainzaps"),dizziness,acutedepressionsand
irritability,aswellasheightenedsensesofakathisia.[39]

23N%29ccc23%29CCCN%28
C%29C)
SMILES
InChI

(whatisthis?)(verify)

Pregnancy
ThereisatentativeassociationofSSRIuseduringpregnancywithheartproblemsinthebaby.[40]Theiruseduringpregnancyshouldthusbebalancedagainstthat
ofdepression.[40]

Overdose
Excessivedosesofescitalopramusuallycauserelativelyminoruntowardeffectssuchasagitationandtachycardia.However,dyskinesia,hypertonia,andclonus
mayoccurinsomecases.Plasmaescitalopramconcentrationsareusuallyinarangeof2080g/Lintherapeuticsituationsandmayreach80200g/Linthe
elderly,patientswithhepaticdysfunction,thosewhoarepoorCYP2C19metabolizersorfollowingacuteoverdose.Monitoringofthedruginplasmaorserumis
generallyaccomplishedusingchromatographicmethods.Chiraltechniquesareavailabletodistinguishescitalopramfromitsracemate,citalopram.[41][42][43]
EscitalopramseemstobelessdangerousthancitalopraminoverdoseandcomparabletootherSSRIs.[44]

Pharmacology
Mechanismofaction
Escitalopramincreasesintrasynapticlevelsoftheneurotransmitterserotoninbyblockingthereuptakeoftheneurotransmitterintothepresynapticneuron.Ofthe
SSRIscurrentlyonthemarket,escitalopramhasthehighestselectivityfortheserotonintransporter(SERT)comparedtothenorepinephrinetransporter(NET),
makingthesideeffectprofilerelativelymildincomparisontolessselectiveSSRIs.[46]Theoppositeenantiomer,(R)citalopram,counteractstoacertaindegree
theserotoninenhancingactionofescitalopram.Asaresult,escitalopramhasbeenclaimedtobeamorepotentantidepressantthantheracemicmixture,
citalopram,ofthetwoenantiomers.Inordertoexplainthisphenomenon,researchersfromLundbeckproposedthatescitalopramenhancesitsownbindingviaan
additionalinteractionwithanotherallostericsiteonthetransporter.[47]Furtherresearchbythesamegroupshowedthat(R)citalopramalsoenhancesbindingof
escitalopram,[48]andthereforetheallostericinteractioncannotexplaintheobservedcounteractingeffect.Inthemostrecentpaper,however,thesameauthorsagain
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reversedtheirfindingsandreportedthat(R)citalopramdecreasesbindingofescitalopramtothetransporter.[49]Although
allostericbindingofescitalopramtotheserotonintransporterisofunquestionableresearchinterest,itsclinicalrelevanceis
unclearsincethebindingofescitalopramtotheallostericsiteisatleast1000timesweakerthantotheprimarybindingsite.
EscitalopramisasubstrateofPglycoproteinandhencePglycoproteininhibitorssuchasverapamilandquinidinemayimprove
itsbloodbrainpenetrability.[50]InapreclinicalstudyinratscombiningescitalopramwithaPglycoproteininhibitorenhanced
itsantidepressantlikeeffects.[50]

Interactions

Bindingprofile[45]
Ki(nM)
Receptor
SERT

2.5

NET

6,514

5HT2C

2,531

3,870

M1

1,242

H1
Escitalopram,similarlytootherSSRIs(withtheexceptionoffluvoxamine),inhibitsCYP2D6andhencemayincreaseplasma
1,973
levelsofanumberofCYP2D6substratessuchasaripiprazole,risperidone,tramadol,codeine,etc.Asmuchoftheeffectof
codeineisattributabletoitsconversion(10%)tomorphineitseffectivenesswillbereducedbythisinhibition,notenhanced.[51]Asescitalopramisonlyaweak
inhibitorofCYP2D6,analgesiafromtramadolmaynotbeaffected.[52]EscitalopramcanalsoprolongtheQTintervalandhenceitisnotrecommendedinpatients
thatareconcurrentlyonothermedicationsthathavetheabilitytoprolongtheQTinterval.BeingaSSRI,escitalopramshouldnotbegivenconcurrentlywith
MAOIsorotherserotonergicmedications.[46]

History
EscitalopramwasdevelopedinclosecooperationbetweenLundbeckandForestLaboratories.Itsdevelopmentwasinitiated
inthesummerof1997,andtheresultingnewdrugapplicationwassubmittedtotheU.S.FDAinMarch2001.Theshort
time(3.5years)ittooktodevelopescitalopramcanbeattributedtothepreviousextensiveexperienceofLundbeckand
Forestwithcitalopram,whichhassimilarpharmacology.[53]TheFDAissuedtheapprovalofescitalopramformajor
depressioninAugust2002andforgeneralizedanxietydisorderinDecember2003.OnMay23,2006,theFDAapproveda
genericversionofescitaloprambyTeva.[54]OnJuly14ofthatyear,however,theU.S.DistrictCourtofDelawaredecided
infavorofLundbeckregardingthepatentinfringementdisputeandruledthepatentonescitalopramvalid.[55]
In2006ForestLaboratorieswasgrantedan828day(2yearsand3months)extensiononitsUSpatentforescitalopram.[56]
ThispushedthepatentexpirationdatefromDecember7,2009toSeptember14,2011.Togetherwiththe6monthpediatric
exclusivity,thefinalexpirationdatewasMarch14,2012.

Cipralexbrandescitalopram10mg
packageandtabletsheet

Societyandculture
Allegationsofillegalmarketing
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In2004,twoseparatecivilsuitsallegingillegalmarketingofcitalopramandescitalopramforusebychildrenandteenagersbyForestwereinitiatedbytwo
whistleblowers,onebyapracticingphysiciannamedJosephPiacentile,andtheotherbyaForestsalesmannamedChristopherGobble.[57]InFebruary2009,these
twosuitsreceivedsupportfromtheUSAttorneyforMassachusettsandwerecombinedintoone.ElevenstatesandtheDistrictofColumbiahavealsofilednotices
ofintentiontointerveneasplaintiffsintheaction.ThesuitsallegethatForestillegallyengagedinofflabelpromotingofLexaproforuseinchildren,thatthe
companyhidtheresultsofastudyshowinglackofeffectivenessinchildren,andthatthecompanypaidkickbackstodoctorstoinducethemtoprescribeLexapro
tochildren.Itwasalsoallegedthatthecompanyconductedsocalled"seedingstudies"thatwere,inreality,marketingeffortstopromotethedrug'suseby
doctors.[58][59]Forestrespondedtotheseallegationsthatit"iscommittedtoadheringtothehighestethicalandlegalstandards,andofflabelpromotionand
improperpaymentstomedicalprovidershaveconsistentlybeenagainstForestpolicy."[60]In2010ForestPharmaceuticalsInc.,agreedtopaymorethan$313
milliontosettlethechargesoverLexaproandtwootherdrugs,LevothroidandCelexa.[61]

Brandnames
EscitalopramissoldundermanybrandnamesworldwidesuchasCipralex.[1]

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EscitalopramWikipedia

61."USDepartmentofJusticePressrelease.September15,2010"(http://www.justic
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Citedtexts
RoyalPharmaceuticalSocietyofGreatBritain(September2009).BritishNationalFormulary(BNF58).UK:BMJGroupandRPSPublishing.ISBN9780
853697787.

Furtherreading
"ADrugMakersPlaybookRevealsaMarketingStrategy"(http://www.nytimes.com/2009/09/02/business/02drug.html)articleinTheNewYorkTimesby
GardinerHarris,September1,2009

Externallinks
U.S.NationalLibraryofMedicine:DrugInformationPortalEscitalopram(http://druginfo.nlm.nih.gov/drugportal/dpdirect.jsp?name=Escitalopram)
Lexapro(ForestLaboratories)(http://www.lexapro.com/)OfficialLexaprohomepage
Cipralex(Lundbeck)(http://www.cipralex.com/)OfficialCipralexhomepage
Pharmacologicalinformation(http://www.rxlist.com/cgi/generic/lexapro.htm)Lexapro
CiplaMedpro(http://www.cipla.co.za/)OfficialCiplaMedprohomepage
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