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Identification
NameEscitalopram
Accession NumberDB01175  (APRD00683)
TypeSmall Molecule
GroupsApproved, Investigational
Description

Escitalopram, the S-enantiomer of citalopram, belongs to a class of antidepressant agents known as selective serotonin-reuptake inhibitors (SSRIs). Despite distinct structural differences between compounds in this class, SSRIs possess similar pharmacological activity. As with other antidepressant agents, several weeks of therapy may be required before a clinical effect is seen. SSRIs are potent inhibitors of neuronal serotonin reuptake. They have little to no effect on norepinephrine or dopamine reuptake and do not antagonize α- or β-adrenergic, dopamine D2 or histamine H1 receptors. During acute use, SSRIs block serotonin reuptake and increase serotonin stimulation of somatodendritic 5-HT1A and terminal autoreceptors. Chronic use leads to desensitization of somatodendritic 5-HT1A and terminal autoreceptors. The overall clinical effect of increased mood and decreased anxiety is thought to be due to adaptive changes in neuronal function that leads to enhanced serotonergic neurotransmission. Side effects include dry mouth, nausea, dizziness, drowsiness, sexual dysfunction and headache. Side effects generally occur within the first two weeks of therapy and are usually less severe and frequent than those observed with tricyclic antidepressants. Escitalopram may be used to treat major depressive disorder (MDD) and generalized anxiety disorder (GAD).

Structure
Thumb
Synonyms
SynonymLanguageCode
(+)-CitalopramNot AvailableNot Available
(S)-CitalopramNot AvailableNot Available
Escitalopram OxalateNot AvailableNot Available
EscitalopramumNot AvailableNot Available
EsertiaNot AvailableNot Available
S-(+)-CitalopramNot AvailableNot Available
S(+)-CitalopramNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Escitalopram Oxalatetablet, film coated5 mgoralMylan Pharmaceuticals Inc.2012-02-29Not AvailableUs
Escitalopram Oxalatetablet, film coated10 mgoralMylan Pharmaceuticals Inc.2012-02-29Not AvailableUs
Escitalopram Oxalatetablet, film coated20 mgoralMylan Pharmaceuticals Inc.2012-02-29Not AvailableUs
Lexaprotablet, film coated5 mgoralForest Laboratories, Inc.2002-08-14Not AvailableUs
Lexaprotablet, film coated10 mgoralForest Laboratories, Inc.2002-08-14Not AvailableUs
Lexaprotablet, film coated20 mgoralForest Laboratories, Inc.2002-08-14Not AvailableUs
Lexaprosolution5 mg/5mLoralForest Laboratories, Inc.2002-11-26Not AvailableUs
Lexaprotablet, film coated10 mgoralSTAT Rx USA LLC2002-08-14Not AvailableUs
Lexaprotablet, film coated5 mgoralSTAT Rx USA LLC2002-08-14Not AvailableUs
Lexaprotablet, film coated20 mgoralREMEDYREPACK INC.2013-03-18Not AvailableUs
Lexaprotablet, film coated20 mgoralAidarex Pharmaceuticals LLC2002-08-14Not AvailableUs
Lexaprotablet, film coated10 mgoralAidarex Pharmaceuticals LLC2002-08-14Not AvailableUs
Lexaprotablet, film coated10 mgoralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2011-12-14Not AvailableUs
Lexaprotablet, film coated20 mgoralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2011-12-14Not AvailableUs
Lexaprotablet, film coated10 mgoralUnit Dose Services2002-08-14Not AvailableUs
Escitalopram Oxalatetablet, film coated10 mgoralMylan Institutional Inc.2012-02-29Not AvailableUs
Escitalopram Oxalatetablet, film coated20 mgoralMylan Institutional Inc.2012-02-29Not AvailableUs
Lexaprotablet10 mgoralPhysicians Total Care, Inc.2005-12-28Not AvailableUs
Lexaprotablet20 mgoralPhysicians Total Care, Inc.2009-04-15Not AvailableUs
Lexaprotablet5 mgoralPhysicians Total Care, Inc.2009-11-30Not AvailableUs
Escitalopram Oxalatetablet, film coated10 mgoralPhysicians Total Care, Inc.2012-10-16Not AvailableUs
Escitalopram Oxalatetablet, film coated20 mgoralPhysicians Total Care, Inc.2012-10-16Not AvailableUs
Lexaprotablet, film coated10 mgoralCardinal Health2002-08-14Not AvailableUs
Lexaprotablet, film coated20 mgoralCardinal Health2002-08-14Not AvailableUs
Lexaprotablet10 mgoralCardinal Health2002-08-14Not AvailableUs
Lexaprotablet20 mgoralCardinal Health2002-08-14Not AvailableUs
Escitalopram Oxalatetablet, film coated10 mgoralCardinal Health2002-08-14Not AvailableUs
Escitalopram Oxalatetablet, film coated20 mgoralCardinal Health2002-08-14Not AvailableUs
Lexaprotablet, film coated10 mgoralPd Rx Pharmaceuticals, Inc.2002-08-14Not AvailableUs
Lexaprotablet, film coated20 mgoralPd Rx Pharmaceuticals, Inc.2002-08-14Not AvailableUs
Lexaprotablet, film coated20 mgoralbryant ranch prepack2002-08-14Not AvailableUs
Lexaprotablet, film coated10 mgoralbryant ranch prepack2002-08-14Not AvailableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Escitalopramtablet, film coated5 mgoralTeva Pharmaceuticals USA Inc2012-03-14Not AvailableUs
Escitalopramtablet, film coated10 mgoralTeva Pharmaceuticals USA Inc2012-03-14Not AvailableUs
Escitalopramtablet, film coated20 mgoralTeva Pharmaceuticals USA Inc2012-03-14Not AvailableUs
Escitalopramtablet, film coated20 mgoralWest ward Pharmaceutical Corp2012-09-11Not AvailableUs
Escitalopramtablet, film coated10 mgoralWest ward Pharmaceutical Corp2012-09-11Not AvailableUs
Escitalopramtablet, film coated5 mgoralWest ward Pharmaceutical Corp2012-09-11Not AvailableUs
Escitalopramtablet, film coated10 mgoralNcs Health Care Of Ky, Inc Dba Vangard Labs2012-03-14Not AvailableUs
Escitalopramtablet, film coated20 mgoralNcs Health Care Of Ky, Inc Dba Vangard Labs2012-03-14Not AvailableUs
Escitalopramtablet, film coated10 mgoralMajor Pharmaceuticals2012-09-11Not AvailableUs
Escitalopramtablet, film coated20 mgoralMajor Pharmaceuticals2012-09-11Not AvailableUs
Escitalopram Oxalatetablet10 mgoralMajor Pharmaceuticals2014-10-15Not AvailableUs
Escitalopram Oxalatetablet20 mgoralMajor Pharmaceuticals2014-10-15Not AvailableUs
Escitalopram Oxalatetablet5 mgoralBlenheim Pharmacal, Inc.2013-11-15Not AvailableUs
Escitalopram Oxalatetablet10 mgoralBlenheim Pharmacal, Inc.2013-11-15Not AvailableUs
Escitalopram Oxalatetablet20 mgoralBlenheim Pharmacal, Inc.2013-11-15Not AvailableUs
Escitalopram Oxalatetablet5 mgoralTorrent Pharmaceuticals Limited2012-09-11Not AvailableUs
Escitalopram Oxalatetablet10 mgoralTorrent Pharmaceuticals Limited2012-09-11Not AvailableUs
Escitalopram Oxalatetablet20 mgoralTorrent Pharmaceuticals Limited2012-09-11Not AvailableUs
Escitalopramtablet, film coated5 mgoralAccord Healthcare Inc.2013-01-15Not AvailableUs
Escitalopramtablet, film coated10 mgoralAccord Healthcare Inc.2013-01-15Not AvailableUs
Escitalopramtablet, film coated20 mgoralAccord Healthcare Inc.2013-01-15Not AvailableUs
Escitalopramtablet, film coated20 mgoralRebel Distributors Corp2012-03-14Not AvailableUs
Escitalopramtablet5 mgoralCamber Pharmaceuticals2012-09-11Not AvailableUs
Escitalopramtablet10 mgoralCamber Pharmaceuticals2012-09-11Not AvailableUs
Escitalopramtablet20 mgoralCamber Pharmaceuticals2012-09-11Not AvailableUs
Escitalopram Oxalatesolution5 mg/5mLoralCamber Pharmaceuticals, Inc.2012-06-12Not AvailableUs
Escitalopramtablet, film coated10 mgoralAidarex Pharmaceuticals LLC2012-03-14Not AvailableUs
Escitalopram Oxalatetablet20 mgoralAidarex Pharmaceuticals LLC2012-09-11Not AvailableUs
Escitalopram Oxalatetablet, film coated5 mgoralMacleods Pharmaceuticals Limited2012-09-11Not AvailableUs
Escitalopram Oxalatetablet, film coated10 mg/21oralMacleods Pharmaceuticals Limited2012-09-11Not AvailableUs
Escitalopram Oxalatetablet, film coated20 mg/21oralMacleods Pharmaceuticals Limited2012-09-11Not AvailableUs
Escitalopramtablet, film coated20 mgoralLake Erie Medical DBA Quality Care Products LLC2013-05-08Not AvailableUs
Escitalopramtablet, film coated10 mgoralLake Erie Medical DBA Quality Care Products LLC2013-05-02Not AvailableUs
Escitalopramtablet, film coated10 mgoralRebel Distributors Corp2012-03-14Not AvailableUs
Escitalopramtablet, film coated20 mgoralSTAT Rx USA LLC2012-03-14Not AvailableUs
Escitalopramtablet, film coated10 mgoralPd Rx Pharmaceuticals, Inc.2012-03-14Not AvailableUs
Escitalopramtablet, film coated10 mgoralPd Rx Pharmaceuticals, Inc.2012-09-11Not AvailableUs
Escitalopramtablet, film coated20 mgoralPd Rx Pharmaceuticals, Inc.2012-09-11Not AvailableUs
Escitalopramtablet, film coated20 mgoralPd Rx Pharmaceuticals, Inc.2012-03-14Not AvailableUs
Escitalopramtablet, film coated10 mgoralREMEDYREPACK INC.2013-02-20Not AvailableUs
Escitalopramtablet, film coated10 mgoralREMEDYREPACK INC.2013-02-18Not AvailableUs
Escitalopramtablet, film coated20 mgoralREMEDYREPACK INC.2013-02-13Not AvailableUs
Escitalopramtablet, film coated20 mgoralREMEDYREPACK INC.2013-04-08Not AvailableUs
Escitalopramtablet, film coated10 mgoralUnit Dose Services2012-03-14Not AvailableUs
Escitalopramtablet, film coated20 mgoralUnit Dose Services2012-09-11Not AvailableUs
Escitalopramtablet, film coated10 mgoralUnit Dose Services2012-09-11Not AvailableUs
Escitalopramtablet, film coated20 mgoralNorthwind Pharmaceuticals2014-03-21Not AvailableUs
Escitalopramsolution5 mg/5mLoralTaro Pharmaceuticals U.S.A., Inc.2012-05-03Not AvailableUs
Escitalopramtablet, film coated10 mgoralREMEDYREPACK INC.2013-05-02Not AvailableUs
Escitalopramtablet, film coated20 mgoralREMEDYREPACK INC.2013-05-08Not AvailableUs
Escitalopramtablet, film coated20 mgoralREMEDYREPACK INC.2013-05-28Not AvailableUs
Escitalopramtablet, film coated20 mgoralREMEDYREPACK INC.2013-09-04Not AvailableUs
Escitalopramtablet, film coated10 mgoralREMEDYREPACK INC.2013-09-05Not AvailableUs
Escitalopramtablet20 mgoralREMEDYREPACK INC.2014-02-28Not AvailableUs
Escitalopramtablet, film coated20 mgoralInternational Labs, Inc.2013-09-20Not AvailableUs
Escitalopramtablet, film coated10 mgoralInternational Labs, Inc.2013-09-19Not AvailableUs
Escitalopram Oxalatesolution5 mg/5mLoralSilarx Pharmaceuticals, Inc2013-06-12Not AvailableUs
Escitalopramtablet, film coated5 mgoralSTI Pharma LLC2013-09-12Not AvailableUs
Escitalopramtablet, film coated10 mgoralSTI Pharma LLC2013-09-12Not AvailableUs
Escitalopramtablet, film coated20 mgoralSTI Pharma LLC2013-09-12Not AvailableUs
Escitalopramtablet, film coated10 mgoralCardinal Health2013-07-01Not AvailableUs
Escitalopramtablet, film coated10 mgoralLake Erie Medical DBA Quality Care Products LLC2012-03-14Not AvailableUs
Escitalopramtablet, film coated5 mgoralCitron Pharma LLC2012-09-11Not AvailableUs
Escitalopramtablet, film coated10 mgoralCitron Pharma LLC2012-09-11Not AvailableUs
Escitalopramtablet, film coated20 mgoralCitron Pharma LLC2012-09-11Not AvailableUs
Escitalopram Oxalatesolution5 mg/5mLoralCitron Pharma LLC2012-04-03Not AvailableUs
Escitalopramtablet, film coated5 mgoralHikma Pharmaceutical2012-09-11Not AvailableUs
Escitalopramtablet, film coated10 mgoralHikma Pharmaceutical2012-09-11Not AvailableUs
Escitalopramtablet, film coated20 mgoralHikma Pharmaceutical2012-09-11Not AvailableUs
Escitalopramtablet, film coated5 mgoralJubilant Cadista Pharmaceuticals Inc.2012-09-14Not AvailableUs
Escitalopramtablet, film coated10 mgoralJubilant Cadista Pharmaceuticals Inc.2012-09-14Not AvailableUs
Escitalopramtablet, film coated20 mgoralJubilant Cadista Pharmaceuticals Inc.2012-09-14Not AvailableUs
Escitalopramtablet, film coated5 mgoralApotex Corp.2012-09-11Not AvailableUs
Escitalopramtablet, film coated10 mgoralApotex Corp.2012-09-11Not AvailableUs
Escitalopramtablet, film coated20 mgoralApotex Corp.2012-09-11Not AvailableUs
Escitalopramtablet, film coated10 mgoralREMEDYREPACK INC.2014-11-26Not AvailableUs
Escitalopramtablet, film coated20 mgoralREMEDYREPACK INC.2014-11-28Not AvailableUs
Escitalopramtablet, film coated20 mgoralREMEDYREPACK INC.2014-12-24Not AvailableUs
Escitalopram Oxalatetablet20 mgoralDIRECT RX2014-01-01Not AvailableUs
Escitalopram Oxalatetablet10 mgoralDIRECT RX2014-01-01Not AvailableUs
Escitalopramtablet, film coated10 mgoralProficient Rx LP2012-03-14Not AvailableUs
Escitalopramtablet, film coated10 mgoralbryant ranch prepack2012-03-14Not AvailableUs
Escitalopramtablet, film coated20 mgoralbryant ranch prepack2012-03-14Not AvailableUs
Escitalopramtablet, film coated5 mgoralbryant ranch prepack2012-03-14Not AvailableUs
Escitalopramtablet, film coated10 mgoralReady Meds2012-03-14Not AvailableUs
Escitalopramtablet10 mgoralTYA Pharmaceuticals2012-09-11Not AvailableUs
Escitalopramtablet20 mgoralTYA Pharmaceuticals2012-09-11Not AvailableUs
Escitalopram Oxalatesolution5 mg/5mLoralAmneal Pharmaceuticals of New York, LLC2011-09-03Not AvailableUs
Escitalopram Oxalatesolution5 mg/5mLoralAurobindo Pharma Limited2012-04-03Not AvailableUs
Escitalopramtablet, film coated5 mgoralAurobindo Pharma Limited2012-09-11Not AvailableUs
Escitalopramtablet, film coated10 mgoralAurobindo Pharma Limited2012-09-11Not AvailableUs
Escitalopramtablet, film coated20 mgoralAurobindo Pharma Limited2012-09-11Not AvailableUs
Escitalopramtablet, film coated5 mgoralBlue Point Laboratories2014-02-06Not AvailableUs
Escitalopramtablet, film coated10 mgoralBlue Point Laboratories2014-02-06Not AvailableUs
Escitalopramtablet, film coated20 mgoralBlue Point Laboratories2014-02-06Not AvailableUs
Escitalopramtablet, film coated10 mgoralAmerican Health Packaging2013-07-01Not AvailableUs
Escitalopramtablet, film coated20 mgoralAmerican Health Packaging2013-07-01Not AvailableUs
Escitalopramtablet10 mgoralLupin Pharmaceuticals, Inc.2012-09-10Not AvailableUs
Escitalopramtablet20 mgoralLupin Pharmaceuticals, Inc.2012-09-10Not AvailableUs
Escitalopramtablet5 mgoralLupin Pharmaceuticals, Inc.2012-09-10Not AvailableUs
Escitalopramtablet, film coated10 mgoralDispensing Solutions, Inc.2012-09-11Not AvailableUs
Escitalopramtablet20 mgoralLegacy Pharmaceutical Packaging2012-09-11Not AvailableUs
Escitalopramtablet10 mgoralLegacy Pharmaceutical Packaging2012-09-11Not AvailableUs
Escitalopramtablet, film coated20 mgoralPreferred Pharmaceuticals, Inc.2014-09-25Not AvailableUs
Escitalopramtablet, film coated10 mgoralPreferred Pharmaceuticals, Inc.2013-01-18Not AvailableUs
Escitalopram Oxalatetablet, film coated5 mgoralExelan Pharmaceuticals Inc.2012-10-01Not AvailableUs
Escitalopram Oxalatetablet, film coated10 mgoralExelan Pharmaceuticals Inc.2012-10-01Not AvailableUs
Escitalopram Oxalatetablet, film coated20 mgoralExelan Pharmaceuticals Inc.2012-10-01Not AvailableUs
Escitalopramtablet10 mgoralPro Doc LimiteeNot AvailableNot AvailableCanada
Escitalopramtablet20 mgoralPro Doc LimiteeNot AvailableNot AvailableCanada
Escitalopramtablet10 mgoralSivem Pharmaceuticals UlcNot AvailableNot AvailableCanada
Escitalopramtablet20 mgoralSivem Pharmaceuticals UlcNot AvailableNot AvailableCanada
Escitalopramtablet10 mgoralSanis Health IncNot AvailableNot AvailableCanada
Escitalopramtablet20 mgoralSanis Health IncNot AvailableNot AvailableCanada
Over the Counter ProductsNot Available
International Brands
NameCompany
CipralexNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number128196-01-0
WeightAverage: 324.3919
Monoisotopic: 324.163791509
Chemical FormulaC20H21FN2O
InChI KeyWSEQXVZVJXJVFP-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[C@]1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylbutylamines
Direct ParentPhenylbutylamines
Alternative Parents
Substituents
  • Phenylbutylamine
  • Benzonitrile
  • Aralkylamine
  • Halobenzene
  • Fluorobenzene
  • Aryl halide
  • Aryl fluoride
  • Tertiary aliphatic amine
  • Tertiary amine
  • Oxacycle
  • Organoheterocyclic compound
  • Nitrile
  • Carbonitrile
  • Ether
  • Dialkyl ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
  • 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile (CHEBI:36791 )
Pharmacology
IndicationLabeled indications include major depressive disorder (MDD) and generalized anxiety disorder (GAD). Unlabeled indications include treatment of mild dementia-associated agitation in nonpsychotic patients.
PharmacodynamicsEscitalopram is one of a class of antidepressants known as selective serotonin reuptake inhibitors (SSRIs). It is used to treat the depression associated with mood disorders. It is also used on occassion in the treatment of body dysmorphic disorder and anxiety. The antidepressant, antiobsessive-compulsive, and antibulimic actions of escitalopram are presumed to be linked to its inhibition of CNS neuronal uptake of serotonin. In vitro studies show that escitalopram is a potent and selective inhibitor of neuronal serotonin reuptake and has only very weak effects on norepinephrine and dopamine neuronal reuptake. Escitalopram has no significant affinity for adrenergic (alpha1, alpha2, beta), cholinergic, GABA, dopaminergic, histaminergic, serotonergic (5HT1A, 5HT1B, 5HT2), or benzodiazepine receptors; antagonism of such receptors has been hypothesized to be associated with various anticholinergic, sedative, and cardiovascular effects for other psychotropic drugs. The chronic administration of escitalopram was found to downregulate brain norepinephrine receptors, as has been observed with other drugs effective in the treatment of major depressive disorder. Escitalopram does not inhibit monoamine oxidase.
Mechanism of actionThe antidepressant, antiobsessive-compulsive, and antibulimic actions of escitalopram are presumed to be linked to its inhibition of CNS neuronal uptake of serotonin. Escitalopram blocks the reuptake of serotonin at the serotonin reuptake pump of the neuronal membrane, enhancing the actions of serotonin on 5HT1A autoreceptors. SSRIs bind with significantly less affinity to histamine, acetylcholine, and norepinephrine receptors than tricyclic antidepressant drugs.
AbsorptionThe absolute bioavailability of citalopram is about 80% relative to an intravenous dose.
Volume of distribution
  • 12 L/kg
Protein binding~56%
Metabolism

Mainly hepatic. Escitalopram undergoes N-demethylation to S-demethylcitalopram (S-DCT) and S-didemethylcitalopram (S-DDCT). CYP3A4 and CYP2C19 are the enzymes responsible for this N-demethylation reaction.

Route of eliminationFollowing oral administrations of escitalopram, the fraction of drug recovered in the urine as escitalopram and S-demethylcitalopram (S-DCT) is about 8% and 10%, respectively. The oral clearance of escitalopram is 600 mL/min, with approximately 7% of that due to renal clearance. Escitalopram is metabolized to S-DCT and S-didemethylcitalopram (S-DDCT).
Half life27-32 hours
Clearance
  • oral cl=600 mL/min [Following oral administrations]
ToxicitySigns of overdose include convulsions, coma, dizziness, hypotension, insomnia, nausea, vomiting, sinus tachycardia, somnolence, and ECG changes (including QT prolongation).
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Escitalopram Action PathwayDrug actionSMP00425
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug Reactions
Interacting Gene/EnzymeSNP RS IDAllele nameDefining changeAdverse ReactionReference(s)
Sodium-dependent serotonin transporter
Gene symbol: SLC6A4
UniProt: P31645
rs25531 Not AvailableA alleleIncrease risk of side effects (ie. headaches)19272758
ADMET
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 substrateInhibitor0.8949
CYP450 2D6 substrateNon-inhibitor0.5054
CYP450 2C19 substrateInhibitor0.8994
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Solutionoral5 mg/5mL
Tabletoral10 mg
Tabletoral20 mg
Tabletoral5 mg
Tablet, film coatedoral10 mg
Tablet, film coatedoral10 mg/21
Tablet, film coatedoral20 mg
Tablet, film coatedoral20 mg/21
Tablet, film coatedoral5 mg
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
CountryPatent NumberApprovedExpires (estimated)
Canada13394521997-09-092014-09-09
Canada23737572010-01-052020-07-07
United States69169412003-02-122023-02-12
United StatesRE347121994-09-142011-09-14
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP3.5Not Available
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
Polarizability35.21 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

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

US20040167209
General Reference
  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
  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
  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
  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
  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
External Links
ATC CodesN06AB10
AHFS Codes
  • 28:16.04.20
PDB EntriesNot Available
FDA labelDownload (1.09 MB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AlmotriptanIncreased risk of CNS adverse effects
ArtemetherAdditive QTc-prolongation may occur. Concomitant therapy should be avoided.
CarvedilolThe SSRI, escitalopram, may increase the bradycardic effect of the beta-blocker, carvedilol.
DesvenlafaxineIncreased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
EletriptanIncreased risk of CNS adverse effects
FrovatriptanIncreased risk of CNS adverse effects
Ginkgo bilobaAdditive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
IsocarboxazidPossible severe adverse reaction with this combination
KetoprofenConcomitant therapy may result in additive antiplatelet effects and increase the risk of bleeding. Monitor for increased risk of bleeding during concomitant therapy.
LinezolidCombination associated with possible serotoninergic syndrome
LumefantrineAdditive QTc-prolongation may occur. Concomitant therapy should be avoided.
MetoprololThe SSRI, escitalopram, may increase the bradycardic effect of the beta-blocker, metoprolol.
NaratriptanIncreased risk of CNS adverse effects
OxycodoneIncreased risk of serotonin syndrome
PhenelzinePossible severe adverse reaction with this combination
PimozideThe SSRI, escitalopram, increases the effect and toxicity of pimozide.
PropranololThe SSRI, escitalopram, may increase the bradycardic effect of the beta-blocker, propranolol.
RasagilinePossible severe adverse reaction with this combination
RizatriptanIncreased risk of CNS adverse effects
SelegilinePossible severe adverse reaction with this combination
SibutramineRisk of serotoninergic syndrome
St. John's WortSt. John's Wort increases the effect and toxicity of the SSRI, escitalopram.
SumatriptanIncreased risk of CNS adverse effects
TelaprevirTelaprevir decreases Cmax, Cmin, and AUC of escitalopram however the mechanism of this interaction is unknown. Concomitant therapy may call for dose adjustment.
TelithromycinTelithromycin may reduce clearance of Escitalopram. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Escitalopram if Telithromycin is initiated, discontinued or dose changed.
Tiaprofenic acidAdditive antiplatelet effects increase the risk of bleeding. Consider alternate therapy or monitor for increased bleeding.
TiclopidineTiclopidine may decrease the metabolism and clearance of Escitalopram. Consider alternate therapy or monitor for adverse/toxic effects of Ambrisentan if Escitalopram is initiated, discontinued or dose changed.
TolmetinIncreased antiplatelet effects may enhance the risk of bleeding. Alternate therapy may be considered or monitor for inreased bleeding during concomitant therapy.
TramadolTramadol may increase the risk of serotonin syndrome and seizures.
TranylcypromineIncreased risk of serotonin syndrome. Concomitant therapy should be avoided. A significant washout period, dependent on the half-lives of the agents, should be employed between therapies.
TrazodoneIncreased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
TreprostinilThe prostacyclin analogue, Treprostinil, increases the risk of bleeding when combined with the antiplatelet agent, Escitalopram. Monitor for increased bleeding during concomitant thearpy.
TrimipramineThe SSRI, Escitalopram, may decrease the metabolism and clearance of Trimipramine. Increased risk of serotonin syndrome. Monitor for changes in Trimipramine efficacy and toxicity if Escitalopram is initiated, discontinued or dose changed.
TriprolidineThe CNS depressants, Triprolidine and Escitalopram, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
VenlafaxineIncreased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
VoriconazoleVoriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of escitalopram by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of escitalopram if voriconazole is initiated, discontinued or dose changed.
ZiprasidoneAdditive QTc-prolongation may occur increasing the risk of life-threatening ventricular arrhythmias and torsade de pointes. Concomitant therapy should be avoided.
ZolmitriptanUse of two serotonin modulators, such as zolmitriptan and escitalopram, may increase the risk of serotonin syndrome. Consider alternate therapy or monitor for serotonin syndrome during concomitant therapy.
ZuclopenthixolAdditive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Food Interactions
  • Take without regard to meals.

Targets

1. Sodium-dependent serotonin transporter

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Sodium-dependent serotonin transporter P31645 Details

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
  2. Owens JM, Knight DL, Nemeroff CB: [Second generation SSRIS: human monoamine transporter binding profile of escitalopram and R-fluoxetine] Encephale. 2002 Jul-Aug;28(4):350-5. Pubmed
  3. Burke WJ: Escitalopram. Expert Opin Investig Drugs. 2002 Oct;11(10):1477-86. Pubmed
  4. 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
  5. 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
  6. 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
  7. Fabre V, Hamon M: [Mechanisms of action of antidepressants: new data from Escitalopram] Encephale. 2003 May-Jun;29(3 Pt 1):259-65. Pubmed
  8. 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. Epub 2009 Jul 16. Pubmed

2. Sodium-dependent dopamine transporter

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Sodium-dependent dopamine transporter Q01959 Details

References:

  1. 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

3. Sodium-dependent noradrenaline transporter

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Sodium-dependent noradrenaline transporter P23975 Details

References:

  1. 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

4. Alpha-1A adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Alpha-1A adrenergic receptor P35348 Details

References:

  1. 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
  2. Fabre V, Hamon M: [Mechanisms of action of antidepressants: new data from Escitalopram] Encephale. 2003 May-Jun;29(3 Pt 1):259-65. Pubmed

5. Muscarinic acetylcholine receptor M1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M1 P11229 Details

References:

  1. 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

6. Histamine H1 receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Histamine H1 receptor P35367 Details

References:

  1. 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
  2. Fabre V, Hamon M: [Mechanisms of action of antidepressants: new data from Escitalopram] Encephale. 2003 May-Jun;29(3 Pt 1):259-65. Pubmed

Enzymes

1. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 2C19

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C19 P33261 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

3. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

References:

  1. Baumann P: Pharmacokinetic-pharmacodynamic relationship of the selective serotonin reuptake inhibitors. Clin Pharmacokinet. 1996 Dec;31(6):444-69. Pubmed
  2. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:13