Identification

Name
Escitalopram
Accession Number
DB01175
Description

Escitalopram is a selective serotonin re-uptake inhibitor (SSRI) and the S-enantiomer of racemic citalopram.11 It is used to restore serotonergic function in the treatment of depression and anxiety.18,19,20 Escitalopram is approximately 150 times more potent than citalopram’s R-enantiomer and is responsible for the vast majority of citalopram’s clinical activity, with some evidence suggesting that the R-enantiomer of racemic citalopram actively dampens the activity of escitalopram rather than existing simply as an inactive enantiomer.6,14 Amongst SSRIs, escitalopram exerts the highest degree of selectivity for the serotonin transporter (SERT) relative to other off-targets which may explain its lower rates of adverse effects as compared to other agents in this class.13 Escitalopram also differentiates itself from other SSRIs via allosteric action on its target - this may be the mechanism responsible for its observed superior efficacy and faster onset compared to other SSRIs.16,13,15

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 324.3919
Monoisotopic: 324.163791509
Chemical Formula
C20H21FN2O
Synonyms
  • (+)-Citalopram
  • (S)-Citalopram
  • Escitalopram
  • Escitalopramum
  • S-(+)-Citalopram
  • S(+)-Citalopram

Pharmacology

Indication

Escitalopram is indicated for both acute and maintenance treatment of major depressive disorder (MDD) and for the acute treatment of generalized anxiety disorder (GAD).18 It is additionally indicated for symptomatic relief of obsessive-compulsive disorder (OCD) in Canada.19

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

Escitalopram belongs to a class of medications called selective serotonin re-uptake inhibitors (SSRIs). These agents cause an increase in serotonin levels in neuronal synapses by preventing the re-uptake of serotonin (5-HT) into the presynaptic terminals of serotonergic neurons.11,6,18,19 As compared to other SSRIs, it appears to have a relatively quick onset of effect due to its potency.14,15

SSRIs as a class have been associated with abnormal bleeding, particularly in patients receiving concomitant therapy with other medications affecting hemostasis, and with the development of serotonin syndrome. Use escitalopram with caution in patients with a higher-than-baseline risk of bleeding and in patients receiving concomitant therapy with other serotonergic drugs. Escitalopram may also cause a discontinuation syndrome with abrupt removal of the drug, and should be slowly tapered if discontinuation of therapy is warranted.18,19,20

Mechanism of action

Escitalopram, like other selective serotonin re-uptake inhibitors, enhances serotonergic activity by binding to the orthosteric (i.e. primary) binding site on the serotonin transporter (SERT), the same site to which endogenous 5-HT binds, and thus prevents the re-uptake of serotonin into the presynaptic neuron.11,6,13 Escitalopram, along with paroxetine, is also considered an allosteric serotonin re-uptake inhibitor - it binds to a secondary allosteric site on the SERT molecule to more strongly inhibit 5-HT re-uptake. Its combination of orthosteric and allosteric activity on SERT allows for greater extracellular 5-HT levels, a faster onset of action, and greater efficacy as compared to other SSRIs. 16,13 The sustained elevation of synaptic 5-HT eventually causes desensitization of 5-HT1A auto-receptors, which normally shut down endogenous 5-HT release in the presence of excess 5-HT - this desensitization may be necessary for the full clinical effect of SSRIs and may be responsible for their typically prolonged onset of action.17,13

Escitalopram has shown little-to-no binding affinity at a number of other receptors, such as histamine and muscarinic receptors, and minor activity at these off-targets may explain some of its adverse effects.18,19,20,13

TargetActionsOrganism
ASodium-dependent serotonin transporter
inhibitor
Humans
UMuscarinic acetylcholine receptor M1
inhibitor
Humans
UHistamine H1 receptor
inhibitor
Humans
U5-hydroxytryptamine receptor 1A
inhibitor
Humans
U5-hydroxytryptamine receptor 2A
inhibitor
Humans
UAlpha-1 adrenergic receptors
inhibitor
Humans
U5-hydroxytryptamine receptor 2C
inhibitor
Humans
UAlpha-2 adrenergic receptors
inhibitor
Humans
UDopamine D2 receptor
inhibitor
Humans
USodium-dependent noradrenaline transporter
inhibitor
Humans
NSodium-dependent dopamine transporter
inhibitor
Humans
Absorption

Absorption of escitalopram following oral administration is expected to be almost complete, with an estimated absolute bioavailability of approximately 80%. Tmax occurs after about 4-5 hours.18,19,20 Cmax and AUC appear to follow dose proportionality - at steady state, patients receiving 10mg of escitalopram daily had a Cmax of 21 ng/mL and a 24h AUC of approximately 360 ng*h/mL, while patients receiving 30mg daily had a roughly 3-fold increase in both Cmax and 24h AUC, comparatively.6

Volume of distribution

Escitalopram appears to distribute extensively into tissues, with an apparent volume of distribution of approximately 12-26 L/kg.18,19,20

Protein binding

Escitalopram exhibits relatively low protein binding at approximately 55-56%.18,19,20,6

Metabolism

The metabolism of escitalopram is mainly hepatic, mediated primarily by CYP2C19 and CYP3A4 and, to a lesser extent, CYP2D6. Oxidative N-demethylation by the CYP enzyme system results in S-desmethylcitalopram (S-DCT) and S-didesmethylcitalopram (S-DDCT) - these metabolites do not contribute to the pharmacologic activity of escitalopram, and exist in the plasma in small quantities relative to the parent compound (28-31% and <5%, respectively).18,19,20

There is also some evidence that escitalopram is metabolized to a propionic acid metabolite by monoamine oxidase A and B in the brain, and that these enzymes constitute the major route of escitalopram metabolism in the brain.6

Hover over products below to view reaction partners

Route of elimination

After oral administration of escitalopram, approximately 8% of the total dose is eliminated in the urine as unchanged escitalopram and 10% is eliminated in the urine as S-desmethylcitalopram.18,19,20 The apparent hepatic clearance of escitalopram amounts to approximately 90% of the total dose.19

Half-life

The elimination half-life of escitalopram is 27-32 hours, though this is increased by approximately 50% in the elderly and doubled in patients with reduced hepatic function.11,18,19,20 The elimination half-life of escitalopram's primary metabolite, S-desmethylcitalopram, is approximately 54 hours at steady state.6

Clearance

The oral plasma clearance of escitalopram is 600 mL/min, of which approximately 7% is due to renal clearance.18,19,20

Adverse Effects
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Toxicity

Symptoms of overdose may include CNS effects (dizziness, convulsions, coma, somnolence), gastrointestinal distress (nausea, vomiting), and/or cardiac abnormalities (hypotension, tachycardia, ECG changes).18,19,20 There is no specific antidote for escitalopram overdose. Management of overdose should focus on monitoring for cardiac abnormalities and changes to vital signs as well as treatment with supportive measures as indicated. As escitalopram is highly distributed into tissue following oral administration, forced diuresis, dialysis, and other methods of extracting drug from plasma are unlikely to be beneficial.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Escitalopram Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Sodium-dependent serotonin transporter---(A;A)A alleleADR Directly StudiedThe presence of this polymorphism in SLC6A4 may potentially be associated with increased risk of adverse events from escitalopram.Details
Cytochrome P450 2C19CYP2C19*2Not Available681G>AEffect Directly StudiedThe presence of this polymorphism in CYP2C19 is associated with poor metabolism of escitalopram.Details
Cytochrome P450 2C19CYP2C19*3Not Available636G>AEffect Directly StudiedThe presence of this polymorphism in CYP2C19 is associated with reduced or poor metabolism of escitalopram.Details
Cytochrome P450 2C19CYP2C19*2ANot Available681G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*2BNot Available681G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*4Not Available1A>GEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*5Not Available1297C>TEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*6Not Available395G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*7Not Available19294T>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*22Not Available557G>C / 991A>GEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*24Not Available99C>T / 991A>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*35Not Available12662A>GEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbaloparatideThe therapeutic efficacy of Abaloparatide can be decreased when used in combination with Escitalopram.
AbametapirThe serum concentration of Escitalopram can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Escitalopram can be increased when combined with Abatacept.
AbciximabThe risk or severity of bleeding can be increased when Escitalopram is combined with Abciximab.
AbirateroneThe metabolism of Escitalopram can be decreased when combined with Abiraterone.
AcarboseThe risk or severity of hypoglycemia can be increased when Acarbose is combined with Escitalopram.
AcebutololThe serum concentration of Escitalopram can be increased when it is combined with Acebutolol.
AceclofenacThe risk or severity of gastrointestinal bleeding can be increased when Escitalopram is combined with Aceclofenac.
AcemetacinThe risk or severity of gastrointestinal bleeding can be increased when Escitalopram is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding can be increased when Escitalopram is combined with Acenocoumarol.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

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  • Evidence Level
    Evidence Level

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  • Action
    Action

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Food Interactions
  • Take with or without food. The absorption is unaffected by food.

Products

Product Ingredients
IngredientUNIICASInChI Key
Escitalopram oxalate5U85DBW7LO219861-08-2KTGRHKOEFSJQNS-BDQAORGHSA-N
Product Images
International/Other Brands
Cipralex / Esertia
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Act EscitalopramTabletOralTEVA Canada Limited2014-09-102018-06-12Canada flag
Act EscitalopramTabletOralTEVA Canada LimitedNot applicableNot applicableCanada flag
Act EscitalopramTabletOralTEVA Canada Limited2014-09-102018-06-12Canada flag
Act Escitalopram ODTTablet, orally disintegratingOralTEVA Canada Limited2016-08-17Not applicableCanada flag
Act Escitalopram ODTTablet, orally disintegratingOralTEVA Canada Limited2016-08-17Not applicableCanada flag
Cipralex -10mgTabletOralLundbeck Inc.2005-02-14Not applicableCanada flag
Cipralex -15mgTabletOralLundbeck Inc.Not applicableNot applicableCanada flag
Cipralex -20mgTabletOralLundbeck Inc.2005-02-14Not applicableCanada flag
Cipralex -5mgTabletOralLundbeck Inc.Not applicableNot applicableCanada flag
Cipralex MeltzTablet, orally disintegratingOralLundbeck Inc.2012-10-042018-06-15Canada flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ach-escitalopramTabletOralAccord Healthcare Inc2016-06-10Not applicableCanada flag
Ach-escitalopramTabletOralAccord Healthcare Inc2016-06-10Not applicableCanada flag
Ag-escitalopramTabletOralAngita Pharma Inc.Not applicableNot applicableCanada flag
Ag-escitalopramTabletOralAngita Pharma Inc.2018-09-06Not applicableCanada flag
Ag-escitalopramTabletOralAngita Pharma Inc.2018-09-06Not applicableCanada flag
Ag-escitalopramTabletOralAngita Pharma Inc.Not applicableNot applicableCanada flag
Apo-escitalopramTabletOralApotex Corporation2014-09-10Not applicableCanada flag
Apo-escitalopramTabletOralApotex Corporation2014-09-10Not applicableCanada flag
Auro-escitalopramTabletOralAuro Pharma IncNot applicableNot applicableCanada flag
Auro-escitalopramTabletOralAuro Pharma Inc2014-09-10Not applicableCanada flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
PramLyteEscitalopram oxalate (10 mg/1) + 1,2-docosahexanoyl-sn-glycero-3-phosphoserine calcium (6.4 mg/1) + 1,2-icosapentoyl-sn-glycero-3-phosphoserine calcium (800 ug/1) + Citric acid monohydrate (1.83 mg/1) + Cobamamide (50 ug/1) + Cocarboxylase (25 ug/1) + Ferrous cysteine glycinate (13.6 mg/1) + Flavin adenine dinucleotide (25 ug/1) + Folic acid (1 mg/1) + Glycine betaine (500 ug/1) + Leucovorin (2.5 mg/1) + Levomefolate magnesium (7 mg/1) + Magnesium ascorbate (24 mg/1) + NADH (25 ug/1) + Phosphatidyl serine (12 mg/1) + Pyridoxal phosphate (25 ug/1) + Sodium citrate (3.67 mg/1) + Zinc ascorbate (1 mg/1)KitOralAllegis Pharmaceuticals, LLC2015-09-112016-01-04US flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
PramLyteEscitalopram oxalate (10 mg/1) + Cholecalciferol (1000 [iU]/1) + Levomefolate magnesium (800 ug/1) + Mecobalamin (1000 ug/1) + Pyridoxal phosphate (5 mg/1)KitOralAllegis Pharmaceuticals, LLC2015-10-122017-09-09US flag

Categories

ATC Codes
N06AB10 — Escitalopram
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylbutylamines. These are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylbutylamines
Direct Parent
Phenylbutylamines
Alternative Parents
Isocoumarans / Fluorobenzenes / Aralkylamines / Aryl fluorides / Trialkylamines / Oxacyclic compounds / Nitriles / Dialkyl ethers / Organopnictogen compounds / Organofluorides
show 1 more
Substituents
Amine / Aralkylamine / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Carbonitrile / Dialkyl ether / Ether / Fluorobenzene / Halobenzene
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile (CHEBI:36791)

Chemical Identifiers

UNII
4O4S742ANY
CAS number
128196-01-0
InChI Key
WSEQXVZVJXJVFP-FQEVSTJZSA-N
InChI
InChI=1S/C20H21FN2O/c1-23(2)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-24-20/h4-9,12H,3,10-11,14H2,1-2H3/t20-/m0/s1
IUPAC Name
(1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile
SMILES
CN(C)CCC[[email protected]]1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1

References

Synthesis Reference

Robert Dancer, "Escitalopram hydrobromide and a method for the preparation thereof." U.S. Patent US20040167209, issued August 26, 2004.

US20040167209
General References
  1. Moore N, Verdoux H, Fantino B: Prospective, multicentre, randomized, double-blind study of the efficacy of escitalopram versus citalopram in outpatient treatment of major depressive disorder. Int Clin Psychopharmacol. 2005 May;20(3):131-7. [PubMed:15812262]
  2. Boulenger JP, Huusom AK, Florea I, Baekdal T, Sarchiapone M: A comparative study of the efficacy of long-term treatment with escitalopram and paroxetine in severely depressed patients. Curr Med Res Opin. 2006 Jul;22(7):1331-41. [PubMed:16834832]
  3. Bielski RJ, Ventura D, Chang CC: A double-blind comparison of escitalopram and venlafaxine extended release in the treatment of major depressive disorder. J Clin Psychiatry. 2004 Sep;65(9):1190-6. [PubMed:15367045]
  4. Nierenberg AA, Greist JH, Mallinckrodt CH, Prakash A, Sambunaris A, Tollefson GD, Wohlreich MM: Duloxetine versus escitalopram and placebo in the treatment of patients with major depressive disorder: onset of antidepressant action, a non-inferiority study. Curr Med Res Opin. 2007 Feb;23(2):401-16. [PubMed:17288694]
  5. Chen F, Larsen MB, Sanchez C, Wiborg O: 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. Eur Neuropsychopharmacol. 2005 Mar;15(2):193-8. [PubMed:15695064]
  6. Rao N: The clinical pharmacokinetics of escitalopram. Clin Pharmacokinet. 2007;46(4):281-90. doi: 10.2165/00003088-200746040-00002. [PubMed:17375980]
  7. von Moltke LL, Greenblatt DJ, Giancarlo GM, Granda BW, Harmatz JS, Shader RI: Escitalopram (S-citalopram) and its metabolites in vitro: cytochromes mediating biotransformation, inhibitory effects, and comparison to R-citalopram. Drug Metab Dispos. 2001 Aug;29(8):1102-9. [PubMed:11454728]
  8. Rudberg I, Reubsaet JL, Hermann M, Refsum H, Molden E: Identification of a novel CYP2C19-mediated metabolic pathway of S-citalopram in vitro. Drug Metab Dispos. 2009 Dec;37(12):2340-8. doi: 10.1124/dmd.109.029355. Epub 2009 Sep 22. [PubMed:19773541]
  9. Nikisch G, Eap CB, Baumann P: Citalopram enantiomers in plasma and cerebrospinal fluid of ABCB1 genotyped depressive patients and clinical response: a pilot study. Pharmacol Res. 2008 Nov-Dec;58(5-6):344-7. doi: 10.1016/j.phrs.2008.09.010. Epub 2008 Sep 30. [PubMed:18940259]
  10. Fisar Z: Drugs related to monoamine oxidase activity. Prog Neuropsychopharmacol Biol Psychiatry. 2016 Aug 1;69:112-24. doi: 10.1016/j.pnpbp.2016.02.012. Epub 2016 Mar 2. [PubMed:26944656]
  11. Pastoor D, Gobburu J: Clinical pharmacology review of escitalopram for the treatment of depression. Expert Opin Drug Metab Toxicol. 2014 Jan;10(1):121-8. doi: 10.1517/17425255.2014.863873. Epub 2013 Nov 30. [PubMed:24289655]
  12. Bartlett D: Drug-Induced Serotonin Syndrome. Crit Care Nurse. 2017 Feb;37(1):49-54. doi: 10.4037/ccn2017169. [PubMed:28148614]
  13. Sanchez C, Reines EH, Montgomery SA: A comparative review of escitalopram, paroxetine, and sertraline: Are they all alike? Int Clin Psychopharmacol. 2014 Jul;29(4):185-96. doi: 10.1097/YIC.0000000000000023. [PubMed:24424469]
  14. Sanchez C: The pharmacology of citalopram enantiomers: the antagonism by R-citalopram on the effect of S-citalopram. Basic Clin Pharmacol Toxicol. 2006 Aug;99(2):91-5. doi: 10.1111/j.1742-7843.2006.pto_295.x. [PubMed:16918708]
  15. Kasper S, Spadone C, Verpillat P, Angst J: Onset of action of escitalopram compared with other antidepressants: results of a pooled analysis. Int Clin Psychopharmacol. 2006 Mar;21(2):105-10. [PubMed:16421462]
  16. Zhong H, Haddjeri N, Sanchez C: Escitalopram, an antidepressant with an allosteric effect at the serotonin transporter--a review of current understanding of its mechanism of action. Psychopharmacology (Berl). 2012 Jan;219(1):1-13. doi: 10.1007/s00213-011-2463-5. Epub 2011 Sep 8. [PubMed:21901317]
  17. Gray NA, Milak MS, DeLorenzo C, Ogden RT, Huang YY, Mann JJ, Parsey RV: Antidepressant treatment reduces serotonin-1A autoreceptor binding in major depressive disorder. Biol Psychiatry. 2013 Jul 1;74(1):26-31. doi: 10.1016/j.biopsych.2012.11.012. Epub 2013 Jan 29. [PubMed:23374637]
  18. FDA Approved Drug Products: Lexapro (escitalopram) for oral use [Link]
  19. DPD Approved Drugs: Escitalopram [Link]
  20. Medsafe NZ: Escitalopram [Link]
  21. CaymenChem: Escitalopram MSDS [Link]
Human Metabolome Database
HMDB0005028
PubChem Compound
146570
PubChem Substance
46507040
ChemSpider
129277
BindingDB
50302225
RxNav
321988
ChEBI
36791
ChEMBL
CHEMBL1508
ZINC
ZINC000003800706
Therapeutic Targets Database
DAP000741
PharmGKB
PA10074
PDBe Ligand
68P
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Escitalopram
AHFS Codes
  • 28:16.04.20 — Selective-serotonin Reuptake Inhibitors
PDB Entries
5i71 / 5i73 / 5i75

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingBasic ScienceMajor Depressive Disorder (MDD)1
4Active Not RecruitingDiagnosticAsthma / Major Depressive Disorder (MDD)1
4Active Not RecruitingTreatmentDepression1
4Active Not RecruitingTreatmentDepressive Disorder, NOS / Dysthymic Disorder / Major Depressive Disorder (MDD)1
4Active Not RecruitingTreatmentMajor Depressive Disorder (MDD)1
4CompletedNot AvailableDysphoria1
4CompletedNot AvailableSchizophrenia1
4CompletedBasic ScienceDepression3
4CompletedBasic ScienceFear Conditioning1
4CompletedBasic ScienceMajor Depressive Disorder (MDD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • AQ Pharmaceuticals Inc.
  • A-S Medication Solutions LLC
  • Atlantic Biologicals Corporation
  • Bryant Ranch Prepack
  • Cardinal Health
  • Direct Pharmaceuticals Inc.
  • Diversified Healthcare Services Inc.
  • Forest Laboratories Inc.
  • Forest Pharmaceuticals
  • Heartland Repack Services LLC
  • Innoviant Pharmacy Inc.
  • Lake Erie Medical and Surgical Supply
  • Lundbeck Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Physicians Total Care Inc.
  • Prepak Systems Inc.
  • Rebel Distributors Corp.
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Southwood Pharmaceuticals
  • Stat Rx Usa
  • Vangard Labs Inc.
Dosage Forms
FormRouteStrength
Tablet, film coated10 mg
Tablet, film coated15 mg
Tablet, film coated20 mg
Tablet, film coated5 mg
Tablet, coatedOral10 mg
Solution / dropsOral10 MG/ML
Tablet, coated10 MG
Tablet, film coatedOral
TabletOral
Tablet, film coatedOral10 MG
Tablet10 mg
Tablet, film coatedOral20 MG
Solution / drops; suspension / dropsOral20 MG/ML
Tablet, orally disintegratingOral10 MG
Tablet, orally disintegratingOral20 MG
Tablet, film coatedOral15 MG
Tablet, film coatedOral5 MG
TabletOral15 mg
TabletOral20 mg
TabletOral5 mg
Tablet, film coatedOral20 mg/1
TabletOral10 mg
Tablet, coatedOral20 mg
Tablet, orally disintegratingOral15 MG
Tablet, orally disintegratingOral5 MG
Tablet, orally disintegratingOral
SolutionOral10 mg/10mL
SolutionOral5 mg/5mL
Tablet, film coatedOral10 mg/21
Tablet, film coatedOral20 mg/21
Tablet, coatedOral15 MG
Tablet, coatedOral5 MG
Tablet, orally disintegrating10 MG
Tablet, orally disintegrating15 MG
Tablet, orally disintegrating20 MG
Tablet, orally disintegrating5 MG
Tablet, delayed releaseOral12.774 mg
Solution / dropsOral20 MG/ML
Tablet, effervescent10 mg
Tablet, effervescent15 mg
Tablet, effervescent20 mg
Tablet20 mg
Tablet, coated20 MG
Solution / dropsOral20 mg/1mL
TabletOral10 mg/1
TabletOral20 mg/1
TabletOral5 mg/1
Tablet, film coatedOral10 mg/1
Tablet, film coatedOral5 mg/1
Tablet
Solution / dropsOral20 MG
KitOral
Prices
Unit descriptionCostUnit
Lexapro 20 mg tablet3.71USD tablet
Lexapro 10 mg tablet3.55USD tablet
Lexapro 5 mg tablet3.4USD tablet
Lexapro 5 mg/5ml Solution0.72USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
USRE34712No1994-08-302011-09-14US flag
CA2373757No2010-01-052020-07-07Canada flag
CA1339452No1997-09-092014-09-09Canada flag
US7420069Yes2008-09-022023-02-12US flag
US6916941Yes2005-07-122023-02-12US flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)147-152CDPD Label
water solubilitySparingly solubleFDA Label, DPD Label
logP1.34DPD Label
pKa9.5DPD Label
Predicted Properties
PropertyValueSource
Water Solubility0.00588 mg/mLALOGPS
logP3.58ALOGPS
logP3.76ChemAxon
logS-4.7ALOGPS
pKa (Strongest Basic)9.78ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area36.26 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity94.02 m3·mol-1ChemAxon
Polarizability35.3 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9966
Blood Brain Barrier+0.9729
Caco-2 permeable+0.6099
P-glycoprotein substrateSubstrate0.7597
P-glycoprotein inhibitor INon-inhibitor0.6361
P-glycoprotein inhibitor IIInhibitor0.9789
Renal organic cation transporterInhibitor0.6993
CYP450 2C9 substrateNon-substrate0.8401
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateSubstrate0.7407
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorInhibitor0.8949
CYP450 2D6 inhibitorNon-inhibitor0.5054
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5223
Ames testNon AMES toxic0.7602
CarcinogenicityNon-carcinogens0.7452
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.9054 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7735
hERG inhibition (predictor II)Inhibitor0.8994
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004i-1497000000-a840cd3176ff240d74f6

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serotonin:sodium symporter activity
Specific Function
Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into t...
Gene Name
SLC6A4
Uniprot ID
P31645
Uniprot Name
Sodium-dependent serotonin transporter
Molecular Weight
70324.165 Da
References
  1. Owens MJ, Knight DL, Nemeroff CB: Second-generation SSRIs: human monoamine transporter binding profile of escitalopram and R-fluoxetine. Biol Psychiatry. 2001 Sep 1;50(5):345-50. [PubMed:11543737]
  2. Burke WJ: Escitalopram. Expert Opin Investig Drugs. 2002 Oct;11(10):1477-86. [PubMed:12387707]
  3. Waugh J, Goa KL: Escitalopram : a review of its use in the management of major depressive and anxiety disorders. CNS Drugs. 2003;17(5):343-62. [PubMed:12665392]
  4. Sanchez C, Bergqvist PB, Brennum LT, Gupta S, Hogg S, Larsen A, Wiborg O: Escitalopram, the S-(+)-enantiomer of citalopram, is a selective serotonin reuptake inhibitor with potent effects in animal models predictive of antidepressant and anxiolytic activities. Psychopharmacology (Berl). 2003 Jun;167(4):353-62. Epub 2003 Apr 26. [PubMed:12719960]
  5. Bareggi SR, Mundo E, Dell'Osso B, Altamura AC: The use of escitalopram beyond major depression: pharmacological aspects, efficacy and tolerability in anxiety disorders. Expert Opin Drug Metab Toxicol. 2007 Oct;3(5):741-53. [PubMed:17916059]
  6. Fabre V, Hamon M: [Mechanisms of action of antidepressants: new data from Escitalopram]. Encephale. 2003 May-Jun;29(3 Pt 1):259-65. [PubMed:12876551]
  7. Zhong H, Hansen KB, Boyle NJ, Han K, Muske G, Huang X, Egebjerg J, Sanchez C: An allosteric binding site at the human serotonin transporter mediates the inhibition of escitalopram by R-citalopram: kinetic binding studies with the ALI/VFL-SI/TT mutant. Neurosci Lett. 2009 Oct 25;462(3):207-12. doi: 10.1016/j.neulet.2009.07.030. Epub 2009 Jul 16. [PubMed:19616061]
  8. Sanchez C, Reines EH, Montgomery SA: A comparative review of escitalopram, paroxetine, and sertraline: Are they all alike? Int Clin Psychopharmacol. 2014 Jul;29(4):185-96. doi: 10.1097/YIC.0000000000000023. [PubMed:24424469]
  9. FDA Approved Drug Products: Lexapro (escitalopram) for oral use [Link]
  10. DPD Approved Drugs: Escitalopram [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM1
Uniprot ID
P11229
Uniprot Name
Muscarinic acetylcholine receptor M1
Molecular Weight
51420.375 Da
References
  1. Sanchez C, Reines EH, Montgomery SA: A comparative review of escitalopram, paroxetine, and sertraline: Are they all alike? Int Clin Psychopharmacol. 2014 Jul;29(4):185-96. doi: 10.1097/YIC.0000000000000023. [PubMed:24424469]
  2. FDA Approved Drug Products: Lexapro (escitalopram) for oral use [Link]
  3. DPD Approved Drugs: Escitalopram [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Histamine receptor activity
Specific Function
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
Gene Name
HRH1
Uniprot ID
P35367
Uniprot Name
Histamine H1 receptor
Molecular Weight
55783.61 Da
References
  1. Sanchez C, Reines EH, Montgomery SA: A comparative review of escitalopram, paroxetine, and sertraline: Are they all alike? Int Clin Psychopharmacol. 2014 Jul;29(4):185-96. doi: 10.1097/YIC.0000000000000023. [PubMed:24424469]
  2. FDA Approved Drug Products: Lexapro (escitalopram) for oral use [Link]
  3. DPD Approved Drugs: Escitalopram [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...
Gene Name
HTR1A
Uniprot ID
P08908
Uniprot Name
5-hydroxytryptamine receptor 1A
Molecular Weight
46106.335 Da
References
  1. Sanchez C, Reines EH, Montgomery SA: A comparative review of escitalopram, paroxetine, and sertraline: Are they all alike? Int Clin Psychopharmacol. 2014 Jul;29(4):185-96. doi: 10.1097/YIC.0000000000000023. [PubMed:24424469]
  2. FDA Approved Drug Products: Lexapro (escitalopram) for oral use [Link]
  3. DPD Approved Drugs: Escitalopram [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Virus receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...
Gene Name
HTR2A
Uniprot ID
P28223
Uniprot Name
5-hydroxytryptamine receptor 2A
Molecular Weight
52602.58 Da
References
  1. Sanchez C, Reines EH, Montgomery SA: A comparative review of escitalopram, paroxetine, and sertraline: Are they all alike? Int Clin Psychopharmacol. 2014 Jul;29(4):185-96. doi: 10.1097/YIC.0000000000000023. [PubMed:24424469]
  2. FDA Approved Drug Products: Lexapro (escitalopram) for oral use [Link]
  3. DPD Approved Drugs: Escitalopram [Link]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...

Components:
References
  1. Sanchez C, Reines EH, Montgomery SA: A comparative review of escitalopram, paroxetine, and sertraline: Are they all alike? Int Clin Psychopharmacol. 2014 Jul;29(4):185-96. doi: 10.1097/YIC.0000000000000023. [PubMed:24424469]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-...
Gene Name
HTR2C
Uniprot ID
P28335
Uniprot Name
5-hydroxytryptamine receptor 2C
Molecular Weight
51820.705 Da
References
  1. Sanchez C, Reines EH, Montgomery SA: A comparative review of escitalopram, paroxetine, and sertraline: Are they all alike? Int Clin Psychopharmacol. 2014 Jul;29(4):185-96. doi: 10.1097/YIC.0000000000000023. [PubMed:24424469]
  2. FDA Approved Drug Products: Lexapro (escitalopram) for oral use [Link]
  3. DPD Approved Drugs: Escitalopram [Link]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Thioesterase binding
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...

Components:
References
  1. Sanchez C, Reines EH, Montgomery SA: A comparative review of escitalopram, paroxetine, and sertraline: Are they all alike? Int Clin Psychopharmacol. 2014 Jul;29(4):185-96. doi: 10.1097/YIC.0000000000000023. [PubMed:24424469]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Potassium channel regulator activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name
DRD2
Uniprot ID
P14416
Uniprot Name
D(2) dopamine receptor
Molecular Weight
50618.91 Da
References
  1. Sanchez C, Reines EH, Montgomery SA: A comparative review of escitalopram, paroxetine, and sertraline: Are they all alike? Int Clin Psychopharmacol. 2014 Jul;29(4):185-96. doi: 10.1097/YIC.0000000000000023. [PubMed:24424469]
  2. FDA Approved Drug Products: Lexapro (escitalopram) for oral use [Link]
  3. DPD Approved Drugs: Escitalopram [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Norepinephrine:sodium symporter activity
Specific Function
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A2
Uniprot ID
P23975
Uniprot Name
Sodium-dependent noradrenaline transporter
Molecular Weight
69331.42 Da
References
  1. Sanchez C, Reines EH, Montgomery SA: A comparative review of escitalopram, paroxetine, and sertraline: Are they all alike? Int Clin Psychopharmacol. 2014 Jul;29(4):185-96. doi: 10.1097/YIC.0000000000000023. [PubMed:24424469]
  2. FDA Approved Drug Products: Lexapro (escitalopram) for oral use [Link]
  3. DPD Approved Drugs: Escitalopram [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Monoamine transmembrane transporter activity
Specific Function
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A3
Uniprot ID
Q01959
Uniprot Name
Sodium-dependent dopamine transporter
Molecular Weight
68494.255 Da
References
  1. Sanchez C, Reines EH, Montgomery SA: A comparative review of escitalopram, paroxetine, and sertraline: Are they all alike? Int Clin Psychopharmacol. 2014 Jul;29(4):185-96. doi: 10.1097/YIC.0000000000000023. [PubMed:24424469]
  2. FDA Approved Drug Products: Lexapro (escitalopram) for oral use [Link]
  3. DPD Approved Drugs: Escitalopram [Link]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Sangkuhl K, Klein TE, Altman RB: PharmGKB summary: citalopram pharmacokinetics pathway. Pharmacogenet Genomics. 2011 Nov;21(11):769-72. doi: 10.1097/FPC.0b013e328346063f. [PubMed:21546862]
  2. Rao N: The clinical pharmacokinetics of escitalopram. Clin Pharmacokinet. 2007;46(4):281-90. doi: 10.2165/00003088-200746040-00002. [PubMed:17375980]
  3. Flockhart Table of Drug Interactions [Link]
  4. FDA Approved Drug Products: Lexapro (escitalopram) for oral use [Link]
  5. DPD Approved Drugs: Escitalopram [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Baumann P: Pharmacokinetic-pharmacodynamic relationship of the selective serotonin reuptake inhibitors. Clin Pharmacokinet. 1996 Dec;31(6):444-69. [PubMed:8968657]
  2. Han KM, Chang HS, Choi IK, Ham BJ, Lee MS: CYP2D6 P34S Polymorphism and Outcomes of Escitalopram Treatment in Koreans with Major Depression. Psychiatry Investig. 2013 Sep;10(3):286-93. doi: 10.4306/pi.2013.10.3.286. Epub 2013 Sep 16. [PubMed:24302953]
  3. Noehr-Jensen L, Zwisler ST, Larsen F, Sindrup SH, Damkier P, Brosen K: Escitalopram is a weak inhibitor of the CYP2D6-catalyzed O-demethylation of (+)-tramadol but does not reduce the hypoalgesic effect in experimental pain. Clin Pharmacol Ther. 2009 Dec;86(6):626-33. doi: 10.1038/clpt.2009.154. Epub 2009 Aug 26. [PubMed:19710642]
  4. Rao N: The clinical pharmacokinetics of escitalopram. Clin Pharmacokinet. 2007;46(4):281-90. doi: 10.2165/00003088-200746040-00002. [PubMed:17375980]
  5. Flockhart Table of Drug Interactions [Link]
  6. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
  7. FDA Approved Drug Products: Lexapro (escitalopram) for oral use [Link]
  8. DPD Approved Drugs: Escitalopram [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Bishop JR, Najjar F, Rubin LH, Guter SJ, Owley T, Mosconi MW, Jacob S, Cook EH: Escitalopram pharmacogenetics: CYP2C19 relationships with dosing and clinical outcomes in autism spectrum disorder. Pharmacogenet Genomics. 2015 Nov;25(11):548-54. doi: 10.1097/FPC.0000000000000173. [PubMed:26313485]
  2. Flockhart Table of Drug Interactions [Link]
  3. FDA Approved Drug Products: Lexapro (escitalopram) for oral use [Link]
  4. DPD Approved Drugs: Escitalopram [Link]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Serotonin binding
Specific Function
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...

Components:
References
  1. Rao N: The clinical pharmacokinetics of escitalopram. Clin Pharmacokinet. 2007;46(4):281-90. doi: 10.2165/00003088-200746040-00002. [PubMed:17375980]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Nikisch G, Eap CB, Baumann P: Citalopram enantiomers in plasma and cerebrospinal fluid of ABCB1 genotyped depressive patients and clinical response: a pilot study. Pharmacol Res. 2008 Nov-Dec;58(5-6):344-7. doi: 10.1016/j.phrs.2008.09.010. Epub 2008 Sep 30. [PubMed:18940259]

Drug created on June 13, 2005 07:24 / Updated on October 27, 2020 11:13

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