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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H21FN2O
Molecular Weight 324.3919
Optical Activity ( + )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESCITALOPRAM

SMILES

CN(C)CCC[C@]1(OCC2=CC(=CC=C12)C#N)C3=CC=C(F)C=C3

InChI

InChIKey=WSEQXVZVJXJVFP-FQEVSTJZSA-N
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

HIDE SMILES / InChI
Molecular Formula C20H21FN2O
Molecular Weight 324.3919
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Escitalopram is one of a class of antidepressants known as selective serotonin reuptake inhibitors (SSRIs). Escitalopram, also known by the brand names Lexapro and Cipralex among others, is an antidepressant. The mechanism of antidepressant action of escitalopram, the S-enantiomer of racemic citalopram, is presumed to be linked to potentiation of serotonergic activity in the central nervous system (CNS) resulting from its inhibition of CNS neuronal reuptake of serotonin (5-HT). In vitro and in vivo studies in animals suggest that escitalopram is a highly selective serotonin reuptake inhibitor (SSRI) with minimal effects on norepinephrine and dopamine neuronal reuptake. Escitalopram is at least 100-fold more potent than the R-enantiomer with respect to inhibition of 5-HT reuptake and inhibition of 5-HT neuronal firing rate. LEXAPRO (escitalopram) is indicated for the treatment of major depressive disorder and generalized anxiety disorder .

CNS Activity

Originator

Approval Year

2002
144
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 2.6 µM [IC50]
Inhibitor
8504
 1.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
LEXAPRO

Approved Use

INDICATIONS & USAGE Escitalopram is a selective serotonin reuptake inhibitor (SSRI) indicated for: Acute and Maintenance Treatment of Major Depressive Disorder (MDD) in adults and adolescents aged 12 to 17 years (1.1) Acute Treatment of Generalized Anxiety Disorder (GAD) in adults (1.2) Escitalopram tablets USP are indicated for the acute and maintenance treatment of major depressive disorder in adults and in adolescents 12 to 17 years of age.

Launch Date

2002
Primary
Approved
8583
LEXAPRO

Approved Use

Lexapro® is a selective serotonin reuptake inhibitor (SSRI) indicated for: Acute and Maintenance Treatment of Major Depressive Disorder (MDD) in adults and adolescents aged 12-17 years (1.1) Acute Treatment of Generalized Anxiety Disorder (GAD) in adults (1.2)

Launch Date

2002
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
58.6 nM
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/16291715
10 mg single, intravenous
dose: 10 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ESCITALOPRAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
58 nM
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/16291715
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ESCITALOPRAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
63.4 nM
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/16291715
10 mg 1 times / day multiple, oral
dose: 10 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ESCITALOPRAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
198.4 nM
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/16291715
30 mg 1 times / day multiple, oral
dose: 30 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ESCITALOPRAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1102 nM × h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/16291715
10 mg single, intravenous
dose: 10 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ESCITALOPRAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1964 nM × h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/16291715
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ESCITALOPRAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1109 nM × h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/16291715
10 mg 1 times / day multiple, oral
dose: 10 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ESCITALOPRAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
3391 nM × h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/16291715
30 mg 1 times / day multiple, oral
dose: 30 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ESCITALOPRAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
26.6 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/16291715
10 mg single, intravenous
dose: 10 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ESCITALOPRAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
26.7 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/16291715
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ESCITALOPRAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
29 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/16291715
10 mg 1 times / day multiple, oral
dose: 10 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ESCITALOPRAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
32.5 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/16291715
30 mg 1 times / day multiple, oral
dose: 30 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ESCITALOPRAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
44%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021323s047lbl.pdf
ESCITALOPRAM plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1946

inhibitor
2252
inhibitor
2438
inhibitor
2507

substrate
1388
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
2153

CYP2C19
2057

CYP2E1
1060

K+ channels
73

Ca2+ channels
59
CYP2C19
1119

P-gp
2052
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
2333
 no [IC50 >100 uM]
CYP2C19
2141
 no [IC50 >100 uM]
CYP2C9
2497
 no [IC50 >100 uM]
CYP2E1
1146
 no [IC50 >100 uM]
CYP3A4
2633
 no [IC50 >100 uM]
Ca2+ channels
62
 no
K+ channels
73
 no
CYP2D6
2546
 yes [IC50 70 uM]
yes (co-administration study)
Comment: coadministration of metoprolol with escitalopram increased concetrations of metoprolol (p50 of clinical pharmacology review)
Page: 70.0
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP2D6
1388
 yes [Km 29 uM]
yes (co-administration study)
Comment: coadministration of escitalopram with desipramine resulted in a 50% increase in desipramine concentraitons
Page: 70.0
CYP3A4
1946
 yes [Km 588 uM]
CYP2C19
1119
 yes [Km 69 uM]
P-gp
2052
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:36791
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:36791
MolPort
MolPort-006-167-729
https://www.molport.com/shop/molecule-link/MolPort-006-167-729
ZINC
ZINC000003800706
http://zinc15.docking.org/substances/ZINC000003800706
PubMed

PubMed

TitleDatePubMed
Newer antidepressants in pregnancy and rates of major malformations: a meta-analysis of prospective comparative studies.
2005-12
Effects of acute and long-term administration of escitalopram and citalopram on serotonin neurotransmission: an in vivo electrophysiological study in rat brain.
2005-07
Evidence-based pharmacotherapy of Generalized Anxiety Disorder.
2005-06
Treatment of Raynaud's phenomenon with escitalopram.
2005-06
Escitalopram and suicidality in adult depression and anxiety.
2005-05
Prospective, multicentre, randomized, double-blind study of the efficacy of escitalopram versus citalopram in outpatient treatment of major depressive disorder.
2005-05
An open-label trial of escitalopram in pervasive developmental disorders.
2005-04
Escitalopram in the treatment of social anxiety disorder: randomised, placebo-controlled, flexible-dosage study.
2005-03
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.
2005-03
A cost-effectiveness model of escitalopram, citalopram,and venlafaxine as first-line treatment for major depressive disorder in Belgium.
2005-01
Escitalopram intoxication.
2005-01
Quetiapine-induced weight gain and escitalopram.
2005-01
Use of selective serotonin-reuptake inhibitors in the treatment of depression in adults with HIV.
2005-01
Escitalopram in clinical practice: results of an open-label trial in a naturalistic setting.
2005
Evaluation of the cost effectiveness of escitalopram versus venlafaxine XR in major depressive disorder.
2005
Generalised anxiety disorder in elderly patients : epidemiology, diagnosis and treatment options.
2005
The safety of newer antidepressants in pregnancy and breastfeeding.
2005
Gateways to clinical trials.
2004-12
A case of hyponatremia associated with escitalopram.
2004-12
Liquid chromatography--electrospray ionisation mass spectrometry method for the determination of escitalopram in human plasma and its application in bioequivalence study.
2004-11-25
Antidepressant-associated mania with escitalopram.
2004-11
The effect of escitalopram, desipramine, electroconvulsive seizures and lithium on brain-derived neurotrophic factor mRNA and protein expression in the rat brain and the correlation to 5-HT and 5-HIAA levels.
2004-10-22
Gateways to clinical trials.
2004-10
Gateways to clinical trials.
2004-09-07
Reformulation of consumer health queries with professional terminology: a pilot study.
2004-09-03
A double-blind comparison of escitalopram and venlafaxine extended release in the treatment of major depressive disorder.
2004-09
Escitalopram dose-response revisited: an alternative psychometric approach to evaluate clinical effects of escitalopram compared to citalopram and placebo in patients with major depression.
2004-09
Evidence based review of escitalopram in treating major depressive disorder in primary care.
2004-09
[Escitalopram--second generation of serotonin transporter inhibitors?].
2004-08-17
"Dopamine-dependent" side effects of selective serotonin reuptake inhibitors: a clinical review.
2004-08
Selective binding of 2-[125I]iodo-nisoxetine to norepinephrine transporters in the brain.
2004-07
Escitalopram versus citalopram: the surprising role of the R-enantiomer.
2004-07
Cost-effectiveness analysis of escitalopram: a new SSRI in the first-line treatment of major depressive disorder in Austria.
2004-06
Escitalopram in trichotillomania.
2004-06
Effects of chronic treatment with escitalopram or citalopram on extracellular 5-HT in the prefrontal cortex of rats: role of 5-HT1A receptors.
2004-06
[Escitalopram: a chiral agent for treatment of depression].
2004-05
Venous thromboembolism and escitalopram.
2004-04-12
Improved potency of escitalopram on the human serotonin transporter: demonstration of an ex vivo assay technique.
2004-04
Escitalopram in the treatment of social anxiety disorder: analysis of efficacy for different clinical subgroups and symptom dimensions.
2004
A comparison of the direct costs and cost effectiveness of serotonin reuptake inhibitors and associated adverse drug reactions.
2004
Efficacy and tolerability of escitalopram in 12- and 24-week treatment of social anxiety disorder: randomised, double-blind, placebo-controlled, fixed-dose study.
2004
Escitalopram in the treatment of generalized anxiety disorder: double-blind, placebo controlled, flexible-dose study.
2004
New formulations of existing antidepressants: advantages in the management of depression.
2004
A randomised study comparing escitalopram with venlafaxine XR in primary care patients with major depressive disorder.
2004
Spotlight on the pharmacoeconomics of escitalopram in depression.
2004
A pharmacoeconomic evaluation of escitalopram, a new selective serotonin reuptake inhibitor. Comparison of cost-effectiveness between escitalopram, citalopram, fluoxetine, and venlafaxine for the treatment of depression in Norway.
2003
New single-isomer compounds on the horizon.
2002-04
Efficacy comparison of escitalopram and citalopram in the treatment of major depressive disorder: pooled analysis of placebo-controlled trials.
2002-04
Escitalopram: a second-generation SSRI.
2002-04
Great expectations in stereochemistry: focus on antidepressants.
2002-04
Patents

Patents

07723533
3
JP2007500238A
3

Sample Use Guides

In Vivo Use Guide
Lexapro (escitalopram) should generally be administered once daily, morning or evening with or without food. Initial: 10 mg once daily Recommended: 10 mg once daily Maximum: 20 mg once daily
Route of Administration: Oral
In Vitro Use Guide
Escitalopram blocked human hERG currents expressed in human embryonic kidney cells in a concentration-dependent manner with an IC50 value of 2.6 uM
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:03:19 GMT 2025
Edited
by admin
on Mon Mar 31 18:03:19 GMT 2025
Record UNII
4O4S742ANY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CIPRALEX
Preferred Name English
ESCITALOPRAM
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
ESCITALOPRAM [VANDF]
Common Name English
(+)-(S)-1-(3-(DIMETHYLAMINO)PROPYL)-1-(P-FLUOROPHENYL)-5-PHTHALANCARBONITRILE
Common Name English
ESCITALOPRAM [EP MONOGRAPH]
Common Name English
S-(+)-5-ISOBENZOFURANCARBONITRILE, 1-(3-(DIMETHYLAMINO)PROPYL)-1-(4-FLUOROPHENYL)-1,3-DIHYDRO-
Common Name English
ESITOL
Brand Name English
S-(+)-1-(3-(DIMETHYLAMINO)PROPYL)-1-(P-FLUOROPHENYL)-5-PHTHALANCARBONITRILE
Common Name English
ESCITALOPRAM [MI]
Common Name English
escitalopram [INN]
Common Name English
Escitalopram [WHO-DD]
Common Name English
LU-26-054
Code English
ESERTIA
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C265
Created by admin on Mon Mar 31 18:03:19 GMT 2025 , Edited by admin on Mon Mar 31 18:03:19 GMT 2025
WHO-ATC N06AB10
Created by admin on Mon Mar 31 18:03:19 GMT 2025 , Edited by admin on Mon Mar 31 18:03:19 GMT 2025
LIVERTOX 368
Created by admin on Mon Mar 31 18:03:19 GMT 2025 , Edited by admin on Mon Mar 31 18:03:19 GMT 2025
NCI_THESAURUS C94725
Created by admin on Mon Mar 31 18:03:19 GMT 2025 , Edited by admin on Mon Mar 31 18:03:19 GMT 2025
NDF-RT N0000175696
Created by admin on Mon Mar 31 18:03:19 GMT 2025 , Edited by admin on Mon Mar 31 18:03:19 GMT 2025
NDF-RT N0000000109
Created by admin on Mon Mar 31 18:03:19 GMT 2025 , Edited by admin on Mon Mar 31 18:03:19 GMT 2025
WHO-VATC QN06AB10
Created by admin on Mon Mar 31 18:03:19 GMT 2025 , Edited by admin on Mon Mar 31 18:03:19 GMT 2025
Code System Code Type Description
DAILYMED
4O4S742ANY
Created by admin on Mon Mar 31 18:03:19 GMT 2025 , Edited by admin on Mon Mar 31 18:03:19 GMT 2025
PRIMARY
DRUG CENTRAL
1053
Created by admin on Mon Mar 31 18:03:19 GMT 2025 , Edited by admin on Mon Mar 31 18:03:19 GMT 2025
PRIMARY
ChEMBL
CHEMBL1508
Created by admin on Mon Mar 31 18:03:19 GMT 2025 , Edited by admin on Mon Mar 31 18:03:19 GMT 2025
PRIMARY
SMS_ID
100000078580
Created by admin on Mon Mar 31 18:03:19 GMT 2025 , Edited by admin on Mon Mar 31 18:03:19 GMT 2025
PRIMARY
CHEBI
36791
Created by admin on Mon Mar 31 18:03:19 GMT 2025 , Edited by admin on Mon Mar 31 18:03:19 GMT 2025
PRIMARY
LACTMED
Escitalopram
Created by admin on Mon Mar 31 18:03:19 GMT 2025 , Edited by admin on Mon Mar 31 18:03:19 GMT 2025
PRIMARY
DRUG BANK
DB01175
Created by admin on Mon Mar 31 18:03:19 GMT 2025 , Edited by admin on Mon Mar 31 18:03:19 GMT 2025
PRIMARY
EVMPD
SUB44650
Created by admin on Mon Mar 31 18:03:19 GMT 2025 , Edited by admin on Mon Mar 31 18:03:19 GMT 2025
PRIMARY
WIKIPEDIA
ESCITALOPRAM
Created by admin on Mon Mar 31 18:03:19 GMT 2025 , Edited by admin on Mon Mar 31 18:03:19 GMT 2025
PRIMARY
RXCUI
321988
Created by admin on Mon Mar 31 18:03:19 GMT 2025 , Edited by admin on Mon Mar 31 18:03:19 GMT 2025
PRIMARY RxNorm
FDA UNII
4O4S742ANY
Created by admin on Mon Mar 31 18:03:19 GMT 2025 , Edited by admin on Mon Mar 31 18:03:19 GMT 2025
PRIMARY
EVMPD
SUB16425MIG
Created by admin on Mon Mar 31 18:03:19 GMT 2025 , Edited by admin on Mon Mar 31 18:03:19 GMT 2025
PRIMARY
INN
7953
Created by admin on Mon Mar 31 18:03:19 GMT 2025 , Edited by admin on Mon Mar 31 18:03:19 GMT 2025
PRIMARY
NCI_THESAURUS
C61754
Created by admin on Mon Mar 31 18:03:19 GMT 2025 , Edited by admin on Mon Mar 31 18:03:19 GMT 2025
PRIMARY
PUBCHEM
146570
Created by admin on Mon Mar 31 18:03:19 GMT 2025 , Edited by admin on Mon Mar 31 18:03:19 GMT 2025
PRIMARY
IUPHAR
7177
Created by admin on Mon Mar 31 18:03:19 GMT 2025 , Edited by admin on Mon Mar 31 18:03:19 GMT 2025
PRIMARY
CAS
128196-01-0
Created by admin on Mon Mar 31 18:03:19 GMT 2025 , Edited by admin on Mon Mar 31 18:03:19 GMT 2025
PRIMARY
EPA CompTox
DTXSID8048440
Created by admin on Mon Mar 31 18:03:19 GMT 2025 , Edited by admin on Mon Mar 31 18:03:19 GMT 2025
PRIMARY
MERCK INDEX
m3587
Created by admin on Mon Mar 31 18:03:19 GMT 2025 , Edited by admin on Mon Mar 31 18:03:19 GMT 2025
PRIMARY Merck Index
Related Record Type Details
SODIUM-DEPENDENT SEROTONIN TRANSPORTER
TARGET -> INHIBITOR
CYTOCHROME P450 2C19
METABOLIC ENZYME -> SUBSTRATE
Structure of CITALOPRAM
RACEMATE -> ENANTIOMER
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
Structure of ESCITALOPRAM OXALATE
SALT/SOLVATE -> PARENT
Structure of ESCITALOPRAM HYDROBROMIDE
SALT/SOLVATE -> PARENT
CYTOCHROME P450 2D6
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
Structure of DIDESMETHYLESCITALOPRAM
METABOLITE INACTIVE -> PARENT
The principal metabolite of escitalopram is Sdemethylcitalopram (S-DCT), which may be further metabolized to S-didemethylcitalopram (S-DDCT) in small quantities.
Structure of DESMETHYLESCITALOPRAM
METABOLITE INACTIVE -> PARENT
The principal metabolite of escitalopram is Sdemethylcitalopram (S-DCT), which may be further metabolized to S-didemethylcitalopram (S-DDCT) in small quantities.
MAJOR
Related Record Type Details
Structure of ESCITALOPRAM
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC ESCITALOPRAM OXALATE (ELDERLY)
PHARMACOKINETIC
CITALOPRAM, REDUCED HEPATIC FUNCITON
PHARMACOKINETIC
BIOAVAILABILITY PHARMACOKINETIC
Tmax PHARMACOKINETIC
MAXIMUM TOLERATED DOSE TOXICITY
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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