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Escitalopram

drug
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Also known as CipralexEsertiaEsitolESCITALOPRAM OXALATESEROPLEXS-(+)-CITALOPRAM(S)-CITALOPRAM(S)-(+)-CITALOPRAMSID11110983SID11114081SID124879737SID50100207S-CitalopramCitalopram

Summary

Escitalopram (CHEMBL1508) is an approved small-molecule antidepressant (ATC N06AB10) targeting SLC6A4; indicated across 31 conditions including major depressive disorder and depressive disorder.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: N06AB10
  • Targets: 1 (SLC6A4)
  • Indications: 31 conditions
  • Clinical trials: 491
  • Chemistry: 324.4 Da · C20H21FN2O

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL1508
NameEscitalopram
TypeSmall molecule
Max phase4
FDA approvedyes
PubChem CID146570
ChEBICHEBI:36791
ATCN06AB10
Molecular formulaC20H21FN2O
Molecular weight324.4
InChIKeyWSEQXVZVJXJVFP-FQEVSTJZSA-N

SMILES: CN(C)CCC[C@@]1(C2=C(CO1)C=C(C=C2)C#N)C3=CC=C(C=C3)F

IUPAC name: (1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-2-benzofuran-5-carbonitrile

ChEBI definition: A 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile that has S-configuration at the chiral centre. It is the active enantiomer of citalopram.

Pharmacological roles (ChEBI): antidepressant, EC 3.4.21.26 (prolyl oligopeptidase) inhibitor.

Also known as: Cipralex, Escitalopram, Esertia, Esitol, ESCITALOPRAM OXALATE, ESCITALOPRAM, ESITOL, ESERTIA, CIPRALEX, SEROPLEX, S-(+)-CITALOPRAM, (S)-CITALOPRAM

Parent form; salt/anhydrous children: CHEMBL1200322

Patent coverage: 5,696 distinct patent families (20,444 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 20,392 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
SLC6A4SERTInhibition8.680.7%P31645

Broader ChEMBL bioactivity targets: 19 (assay-derived). Sample: 5-hydroxytryptamine receptor 2B, Sodium-dependent noradrenaline transporter, 5-hydroxytryptamine receptor 2C, Sodium-dependent serotonin transporter, Alpha-1A adrenergic receptor, Histamine H1 receptor, Mu-type opioid receptor, D(3) dopamine receptor, Voltage-gated inwardly rectifying potassium channel KCNH2, Muscarinic acetylcholine receptor M1.

Bioactivity

ChEMBL activities: 35 potent at pChembl ≥ 5 of 42 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
P316529.05Ki0.89nMCHEMBL_ACT_3404778
HTR69Ki1nMCHEMBL_ACT_26025255
SLC6A49Ki1nMCHEMBL_ACT_3007629
SLC6A49Ki1nMCHEMBL_ACT_3279634
SLC6A48.75Ki1.77nMCHEMBL_ACT_18774541
SLC6A48.68IC502.1nMCHEMBL_ACT_17998834
SLC6A48.66Ki2.2nMCHEMBL_ACT_15627807
SLC6A48.59Kd2.6nMCHEMBL_ACT_14737775
SLC6A48.15AC507.1nMCHEMBL_ACT_25149830
SLC6A48.13Ki7.4nMCHEMBL_ACT_14737753
SLC6A48IC5010nMCHEMBL_ACT_17998807
HTR67.26IC5055nMCHEMBL_ACT_26025307
CYP3A46Potency1000nMCHEMBL_ACT_4957285
CYP3A46Potency1000nMCHEMBL_ACT_5026642
CYP3A46AC501000nMCHEMBL_ACT_6036429
NFKB15.95Potency1122nMCHEMBL_ACT_3671953
NFKB15.95Potency1122nMCHEMBL_ACT_4585235
KCNH25.8AC501600nMCHEMBL_ACT_25117083
HRH15.57AC502700nMCHEMBL_ACT_25211986
CYP2C195.5Potency3162nMCHEMBL_ACT_4020198
CYP2C95.5Potency3162nMCHEMBL_ACT_5057319
CYP2C95.5AC503162nMCHEMBL_ACT_6001705
CYP2C195.5AC503162nMCHEMBL_ACT_6044220
OPRM15.38AC504200nMCHEMBL_ACT_25146635
SLC6A45.34IC504600nMCHEMBL_ACT_13852391
HRH15.34AC504600nMCHEMBL_ACT_25116905
SLC6A45.29EC505100nMCHEMBL_ACT_17998883
SLC6A45.24EC505800nMCHEMBL_ACT_17998867
ADRA1A5.24AC505800nMCHEMBL_ACT_25217709
ALOX155.2Potency6310nMCHEMBL_ACT_4468528

Target pathways

Aggregated over 1 target gene(s): SLC6A4.

Top Reactome pathways

5 total, by targets touching each:

PathwayTargetsGenes
Neurotransmitter clearance1SLC6A4
Transmission across Chemical Synapses1SLC6A4
Neuronal System1SLC6A4
Serotonin clearance from the synaptic cleft1SLC6A4
SLC-mediated transport of neurotransmitters1SLC6A4

Dominant GO biological processes

GO termTargets
response to hypoxia1
neurotransmitter transport1
amino acid transport1
response to nutrient1
memory1
circadian rhythm1
response to xenobiotic stimulus1
response to toxic substance1
positive regulation of gene expression1
positive regulation of serotonin secretion1
obsolete monoamine transport1
negative regulation of cerebellar granule cell precursor proliferation1
negative regulation of synaptic transmission, dopaminergic1
response to estradiol1
sodium ion transmembrane transport1

Indications & clinical

Indications

31 indications (3 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
major depressive disorder4MONDO:0002009MONDO:0002009
depressive disorder4MONDO:0002050MONDO:0002050
obsessive-compulsive disorder3MONDO:0008114EFO:0004242
anxiety3MONDO:0011918EFO:0005230
carcinoma3MONDO:0004993EFO:0000313
dementia3MONDO:0001627HP:0000726
pulmonary hypertension3MONDO:0005149MONDO:0005149
bipolar disorder3MONDO:0004985EFO:0009963
generalized anxiety disorder3MONDO:0001942EFO:1001892
rheumatoid arthritis3MONDO:0008383EFO:0000685
neoplasm3MONDO:0005070MONDO:0004992
burning mouth syndrome3MONDO:0006687EFO:1000850
cocaine dependence2MONDO:0005186EFO:0002610
post-traumatic stress disorder2MONDO:0005146EFO:0001358
chronic kidney disease2MONDO:0005300EFO:0003884
stroke disorder2MONDO:0005098EFO:0000712
drug dependence2MONDO:0005303EFO:0003890
panic disorder2MONDO:0005383EFO:0004262
phobic disorder2MONDO:0003699EFO:1001908
social phobia2MONDO:0001247EFO:1001917
borderline personality disorder2MONDO:0001156HP:0012076
fibromyalgia2MONDO:0005546EFO:0005687
aphasia2MONDO:0000598HP:0002381
hepatitis C virus infection1MONDO:0005231EFO:0003047
Alzheimer disease1MONDO:0004975MONDO:0004975
premature ejaculation0MONDO:0001780EFO:0803321

5 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 491.

Phase distribution

PhaseTrials
PHASE4176
Not specified120
PHASE369
PHASE251
PHASE140
PHASE2/PHASE319
PHASE1/PHASE28
EARLY_PHASE18

Top trials by phase / activity

NCTPhaseStatusTitle
NCT04245436PHASE4RECRUITINGAcute and Long-Term Antidepressant Treatment Success in Adolescents With Anxiety (AtLAS-A)
NCT04245748PHASE4RECRUITINGDetermining Optimal Treatment Sequences in Anxious Depression (DOTS-AD)
NCT04336228PHASE4ACTIVE_NOT_RECRUITINGThe Role of Serotonin in Compulsive Behavior in Humans: Underlying Brain Mechanisms
NCT04623099PHASE4RECRUITINGPharmacogenetically-guided Escitalopram Treatment for Pediatric Anxiety: Aiming to Improve Safety and Efficacy (PrEcISE)
NCT05004987PHASE4RECRUITINGAβ Dynamics in LLMD
NCT05017311PHASE4RECRUITINGOptimized Predictive Treatment In Medications for Unipolar Major Depression (OPTIMUM-D)
NCT05737511PHASE4NOT_YET_RECRUITINGEfficacy of Hydroxyzine for Patients With Panic Disorder
NCT06675851PHASE4RECRUITINGReward-specific Changes of the Chemical Messenger Dopamine in the Brain of Healthy and Depressed People
NCT07478796PHASE4RECRUITINGTDM-Guided Treatment With SSRIs in Hospitalized Adults and Children
NCT00021528PHASE4COMPLETEDSequenced Treatment Alternatives to Relieve Depression (STAR*D)
NCT00047671PHASE4COMPLETEDEthnic Variations in Antidepressant Response
NCT00073697PHASE4COMPLETEDTreatment of Depression in Adults
NCT00105586PHASE4COMPLETEDDrug Therapy for Generalized Anxiety Disorder Among the Elderly
NCT00115011PHASE4COMPLETEDEscitalopram for the Treatment of Self-Injurious Skin Picking
NCT00116532PHASE4COMPLETEDEscitalopram for the Treatment of Obsessive Compulsive Disorder (OCD)
NCT00130455PHASE4TERMINATEDTreatment of Depression in the Elderly
NCT00140257PHASE4UNKNOWNDECARD: Study of Escitalopram in the Prevention of Depression in Patients With Acute Coronary Syndrome
NCT00162916PHASE4UNKNOWNAntidepressant Maintenance in Traumatic Brain Injury
NCT00162968PHASE4COMPLETEDEscitalopram as a Treatment for Pain in Polyneuropathy
NCT00166114PHASE4COMPLETEDDepression, Epinephrine, and Platelet Function
NCT00177216PHASE4COMPLETEDCharacteristics of Sleep Patterns in Young Adults With and Without Insomnia
NCT00177294PHASE4COMPLETEDAugmenting Antidepressant Treatment With Interpersonal Psychotherapy for Treating Late-life Depression
NCT00177671PHASE4COMPLETEDAntidepressant Medication Plus Donepezil for Treating Late-life Depression
NCT00183677PHASE4COMPLETEDBrain Energy Metabolism in Individuals With Major Depressive Disorder Receiving Escitalopram
NCT00209170PHASE4COMPLETEDDepression-Diabetes Mechanisms: Urban African Americans
NCT00209807PHASE4UNKNOWNEffect of Escitalopram vs. Reboxetine on Gastro-intestinal Sensitivity of Patients With Major Depressive Disorder
NCT00219349PHASE4COMPLETEDCognitive-Behavioral Therapy and Escitalopram for Generalized Anxiety Disorder(GAD)
NCT00221494PHASE4WITHDRAWNCan Additional Drug Therapy Accelerate Response Time to Antidepressants
NCT00222820PHASE4COMPLETEDDepression: The Search for Treatment-Relevant Phenotypes-Pilot Study
NCT00227292PHASE4WITHDRAWNCipralex in Treatment of Depressive Symptoms and Chronic Back Pain
NCT00229333PHASE4UNKNOWNStudy of Escitalopram Versus Placebo in the Treatment of Depressive Syndrome in Alzheimer’s Disease, Vascular Dementia, and Mixed Vascular and Alzheimer’s Dementia
NCT00231335PHASE4COMPLETEDEfficacy and Safety Study of Escitalopram Augmentation in Treatment Resistant Schizophrenia
NCT00234312PHASE4COMPLETEDMedications for the Treatment of Dysthymic Disorder and Double Depression
NCT00243477PHASE4COMPLETEDMOTIV Study- Effect of Antidepressive Treatment by Escitalopram in Patients Undergoing Coronary Artery Bypass Grafting
NCT00254007PHASE4COMPLETEDDepression and Traumatic Brain Injury
NCT00254020PHASE4COMPLETEDThe Role of Cytokine-Serotonin Interactions in Post-Stroke Depression
NCT00260624PHASE4COMPLETEDEscitalopram Treatment of Patients With Agitated Dementia
NCT00296712PHASE4COMPLETEDAre Two Antidepressants a Good Initial Treatment for Depression?
NCT00296777PHASE4COMPLETEDTreatment of Depression Following Multiple Brain Tests
NCT00352885PHASE4COMPLETEDEffectiveness of Escitalopram in Preventing or Reducing Depressive Symptoms in People Receiving Interleukin-2 Treatment

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

PharmGKB dosing guidelines (5) — CPIC / DPWG genotype-guided dosing for this drug (drug × pharmacogene):

GuidelineSourceGene(s)DosingRecommendation
Annotation of DPWG Guideline for escitalopram and CYP2C19DPWGCYP2C19yesyes
Annotation of CPIC Guideline for citalopram, escitalopram and CYP2C19CPICCYP2C19yesyes
Annotation of DPWG Guideline for citalopram, escitalopram and CYP2D6DPWGCYP2D6
Annotation of CPIC Guideline for citalopram, escitalopram and HTR2ACPICHTR2A
Annotation of CPIC Guideline for citalopram, desvenlafaxine, duloxetinCPICSLC6A4

PharmGKB also curates 27 clinical and 206 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

440 molecules share ≥1 primary target. Top 60 by shared-target count:

MoleculeSourceStatusShared targets
CRIZOTINIBChEMBL + PubChemPhase 4 (approved)SLC6A4
GENTIAN VIOLETChEMBL + PubChemPhase 4 (approved)SLC6A4
OLODATEROLChEMBL + PubChemPhase 4 (approved)SLC6A4
TADALAFILChEMBL + PubChemPhase 4 (approved)SLC6A4
TAFENOQUINEChEMBL + PubChemPhase 4 (approved)SLC6A4
UMECLIDINIUMChEMBL + PubChemPhase 4 (approved)SLC6A4
ACETOPHENAZINEChEMBLPhase 4 (approved)SLC6A4
ACRIVASTINEChEMBLPhase 4 (approved)SLC6A4
ALECTINIBChEMBLPhase 4 (approved)SLC6A4
ALLOPURINOLChEMBLPhase 4 (approved)SLC6A4
AMBENONIUMChEMBLPhase 4 (approved)SLC6A4
AMIODARONEChEMBLPhase 4 (approved)SLC6A4
AMITRIPTYLINEChEMBLPhase 4 (approved)SLC6A4
AMOXAPINEChEMBLPhase 4 (approved)SLC6A4
AMPHOTERICIN BChEMBLPhase 4 (approved)SLC6A4
APOMORPHINEChEMBLPhase 4 (approved)SLC6A4
ARFORMOTEROLChEMBLPhase 4 (approved)SLC6A4
ARIPIPRAZOLEChEMBLPhase 4 (approved)SLC6A4
ASENAPINEChEMBLPhase 4 (approved)SLC6A4
ASTEMIZOLEChEMBLPhase 4 (approved)SLC6A4
ATOMOXETINEChEMBLPhase 4 (approved)SLC6A4
ATRACURIUMChEMBLPhase 4 (approved)SLC6A4
AZATHIOPRINEChEMBLPhase 4 (approved)SLC6A4
AZELASTINEChEMBLPhase 4 (approved)SLC6A4
BALSALAZIDEChEMBLPhase 4 (approved)SLC6A4
BAZEDOXIFENEChEMBLPhase 4 (approved)SLC6A4
BENFLUOREXChEMBLPhase 4 (approved)SLC6A4
BENZPHETAMINEChEMBLPhase 4 (approved)SLC6A4
BENZTROPINEChEMBLPhase 4 (approved)SLC6A4
BENZYDAMINEChEMBLPhase 4 (approved)SLC6A4
BEPRIDILChEMBLPhase 4 (approved)SLC6A4
BOSUTINIBChEMBLPhase 4 (approved)SLC6A4
BREXPIPRAZOLEChEMBLPhase 4 (approved)SLC6A4
BROMHEXINEChEMBLPhase 4 (approved)SLC6A4
BROMODIPHENHYDRAMINEChEMBLPhase 4 (approved)SLC6A4
BROMPERIDOLChEMBLPhase 4 (approved)SLC6A4
BROMPHENIRAMINEChEMBLPhase 4 (approved)SLC6A4
BUPROPIONChEMBLPhase 4 (approved)SLC6A4
BUTENAFINEChEMBLPhase 4 (approved)SLC6A4
CABERGOLINEChEMBLPhase 4 (approved)SLC6A4
CALCIPOTRIENEChEMBLPhase 4 (approved)SLC6A4
CALCITRIOLChEMBLPhase 4 (approved)SLC6A4
CANAGLIFLOZINChEMBLPhase 4 (approved)SLC6A4
CARBINOXAMINEChEMBLPhase 4 (approved)SLC6A4
CARIPRAZINEChEMBLPhase 4 (approved)SLC6A4
CARVEDILOLChEMBLPhase 4 (approved)SLC6A4
CEFONICIDChEMBLPhase 4 (approved)SLC6A4
CELECOXIBChEMBLPhase 4 (approved)SLC6A4
CETIRIZINEChEMBLPhase 4 (approved)SLC6A4
CHLORHEXIDINEChEMBLPhase 4 (approved)SLC6A4
CHLORPHENIRAMINEChEMBLPhase 4 (approved)SLC6A4
CHLORPHENTERMINEChEMBLPhase 4 (approved)SLC6A4
CHLORPROMAZINEChEMBLPhase 4 (approved)SLC6A4
CHLORPROTHIXENEChEMBLPhase 4 (approved)SLC6A4
CINACALCETChEMBLPhase 4 (approved)SLC6A4
CINNARIZINEChEMBLPhase 4 (approved)SLC6A4
CISAPRIDEChEMBLPhase 4 (approved)SLC6A4
CITALOPRAMChEMBLPhase 4 (approved)SLC6A4
CLEMASTINEChEMBLPhase 4 (approved)SLC6A4
CLIDINIUMChEMBLPhase 4 (approved)SLC6A4

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot