ESCITALOPRAM

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H21FN2O
Molecular Weight	324.3927
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN(C)CCC[C@]1(c2ccc(cc2)F)c3ccc(cc3CO1)C#N

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	324.3927
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021323s047lbl.pdf | https://www.drugbank.ca/drugs/DB01175 | https://www.ncbi.nlm.nih.gov/pubmed/21901317

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

Targets

Primary Target	Pharmacology	Condition	Potency
HERG 90 Target ID: CHEMBL240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24045971	Inhibitor 7701		2.60000000000000009 µM [IC50]
Serotonin transporter 163 Target ID: CHEMBL228 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19720528 \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021323s047lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/19616061 \| https://www.ncbi.nlm.nih.gov/pubmed/20597489	Inhibitor 7701	Major depressive disorder Generalized anxiety disorder	1 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Major depressive disorder 170 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12387707 https://www.fda.gov/ohrms/dockets/ac/04/briefing/2004-4065b1-22-tab11C-Lexapro-Tabs-SLR015.pdf	Primary	Serotonin transporter	Approved 7997	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 1029283200000
Generalized anxiety disorder 27 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12387707 https://www.fda.gov/ohrms/dockets/ac/04/briefing/2004-4065b1-22-tab11C-Lexapro-Tabs-SLR015.pdf	Primary	Serotonin transporter	Approved 7997	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 1029283200000

C_max

Value	Dose	Analyte	Population
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
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

AUC

Value	Dose	Analyte	Population
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
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

T_1/2

Value	Dose	Analyte	Population
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
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

F_unbound

Value	Dose	Co-administered	Analyte	Population
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

Doses

Dose	Population	Adverse events
332 mg single, oral Overdose Dose: 332 mg Route: oral Route: single Dose: 332 mg Sources: https://pubmed.ncbi.nlm.nih.gov/20170390/	unknown, 16 - 84 years Health Status: unknown Age Group: 16 - 84 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/20170390/	Disc. AE: Coma, Dizziness... AEs leading to discontinuation/dose reduction: Coma (grade 3-4, 1 patient) Dizziness (grade 1-2, 2 patients) Restlessness (grade 1-2, 2 patients) Agitation (grade 3-4, 4 patients) Convulsion (grade 3-4, 1 patient) Tremor (grade 1-2, 8 patients) Mydriasis (grade 1-2, 3 patients) Tachycardia (grade 1-2, 7 patients) Change in ECG (grade 1-2, 4 patients) Change in ECG (grade 3-4, 1 patient) Nausea (grade 1-2, 4 patients) Vomiting (grade 1-2, 8 patients) Vomiting (grade 3-4, 1 patient) Intestinal atony (grade 3-4, 1 patient) Urinary retention (grade 3-4, 1 patient) Somnolence (grade 1-2, 25 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/20170390/
140 mg single, oral Overdose Dose: 140 mg Route: oral Route: single Dose: 140 mg Sources: https://pubmed.ncbi.nlm.nih.gov/19556032/	unknown, 18 - 36 years Health Status: unknown Age Group: 18 - 36 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/19556032/	Disc. AE: Clonus, Clonus... AEs leading to discontinuation/dose reduction: Clonus (12 patients) Clonus (2 patients) Hyperreflexia (21 patient) Myoclonus (3 patients) Eyelid myoclonus (2 patients) Hunter's syndrome (7 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/19556032/
140 mg single, oral Overdose Dose: 140 mg Route: oral Route: single Dose: 140 mg Sources: https://pubmed.ncbi.nlm.nih.gov/19556032/	unknown, 24 - 43 years Health Status: unknown Age Group: 24 - 43 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/19556032/	Disc. AE: Clonus, Hyperreflexia... AEs leading to discontinuation/dose reduction: Clonus (3 patients) Hyperreflexia (9 patients) Eyelid myoclonus (2 patients) Hunter's syndrome (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/19556032/
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/27736049/	unhealthy, 46.2 years Health Status: unhealthy Age Group: 46.2 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/27736049/	Disc. AE: Coronary heart disease... AEs leading to discontinuation/dose reduction: Coronary heart disease (10.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/27736049/
33.8 mg 1 times / day steady, oral Highest studied dose Dose: 33.8 mg, 1 times / day Route: oral Route: steady Dose: 33.8 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/18090508/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/18090508/	Other AEs: Dry mouth, Sexual desire decreased... Other AEs: Dry mouth (8 patients) Sexual desire decreased (21 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/18090508/

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1470 inhibitor 1172	inhibitor 1318	inhibitor 1421 substrate 1038	inhibitor 1360

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1268 CYP2C19 1215 CYP2E1 761 K+ channels 50 Ca2+ channels 40	CYP2C19 830 P-gp 1223

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 1406	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-323.pdf_Lexapro_BioPharmr.pdf Page: 70	no [IC50 >100 uM]
CYP2C19 1277	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-323.pdf_Lexapro_BioPharmr.pdf Page: 70	no [IC50 >100 uM]
CYP2C9 1362	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-323.pdf_Lexapro_BioPharmr.pdf Page: 70	no [IC50 >100 uM]
CYP2E1 841	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-323.pdf_Lexapro_BioPharmr.pdf Page: 70	no [IC50 >100 uM]
CYP3A4 1462	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-323.pdf_Lexapro_BioPharmr.pdf Page: 70	no [IC50 >100 uM]
Ca2+ channels 43	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-365_Lexapro_BioPharmr.pdf Page: 11	no
K+ channels 50	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-365_Lexapro_BioPharmr.pdf Page: 11	no
CYP2D6 1455	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-323.pdf_Lexapro_BioPharmr.pdf Page: 70	yes [IC50 70 uM]	yes (co-administration study) Comment: coadministration of metoprolol with escitalopram increased concetrations of metoprolol (p50 of clinical pharmacology review) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-323.pdf_Lexapro_BioPharmr.pdf Page: 70

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP2D6 1038	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-323.pdf_Lexapro_BioPharmr.pdf Page: 70	yes [Km 29 uM]	yes (co-administration study) Comment: coadministration of escitalopram with desipramine resulted in a 50% increase in desipramine concentraitons Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-323.pdf_Lexapro_BioPharmr.pdf Page: 70
CYP3A4 1470	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-323.pdf_Lexapro_BioPharmr.pdf Page: 70	yes [Km 588 uM]
CYP2C19 830	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-323.pdf_Lexapro_BioPharmr.pdf Page: 70	yes [Km 69 uM]
P-gp 1223	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/23670590/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1392	inhibitor 1374 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-323.pdf_Lexapro_Pharmr_P1.pdf Page: 16

Sourcing

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
New single-isomer compounds on the horizon.	2002 Apr	15131493
Efficacy comparison of escitalopram and citalopram in the treatment of major depressive disorder: pooled analysis of placebo-controlled trials.	2002 Apr	15131492
Escitalopram: a second-generation SSRI.	2002 Apr	15131491
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	15609164
Immediate-release versus controlled-release formulations: pharmacokinetics of newer antidepressants in relation to nausea.	2003	14700450
Escitalopram: a pharmacoeconomic review of its use in depression.	2003	14594439
Escitalopram in the treatment of panic disorder: a randomized, double-blind, placebo-controlled trial.	2003 Nov	14658946
Efficacy and tolerability of escitalopram in 12- and 24-week treatment of social anxiety disorder: randomised, double-blind, placebo-controlled, fixed-dose study.	2004	15274173
Escitalopram in the treatment of generalized anxiety disorder: double-blind, placebo controlled, flexible-dose study.	2004	15274172
New formulations of existing antidepressants: advantages in the management of depression.	2004	15182220
Spotlight on the pharmacoeconomics of escitalopram in depression.	2004	15139801
Treatment of anxiety and depression in transplant patients: pharmacokinetic considerations.	2004	15086275
Single-enantiomer drugs: elegant science, disappointing effects.	2004	15080762
Newer antidepressants: review of efficacy and safety of escitalopram and duloxetine.	2004	15046541
Improved potency of escitalopram on the human serotonin transporter: demonstration of an ex vivo assay technique.	2004 Apr	15206668
"Dopamine-dependent" side effects of selective serotonin reuptake inhibitors: a clinical review.	2004 Aug	15323590
A case of hyponatremia associated with escitalopram.	2004 Dec	15641882
Metabolism of the newest antidepressants: comparisons with related predecessors.	2004 Feb	15057659
Anxiolytic-like effects of escitalopram, citalopram, and R-citalopram in maternally separated mouse pups.	2004 Feb	14593091
Selective binding of 2-[125I]iodo-nisoxetine to norepinephrine transporters in the brain.	2004 Jul	15219270
Escitalopram versus citalopram: the surprising role of the R-enantiomer.	2004 Jul	15160261
Gateways to clinical trials.	2004 Jul-Aug	15349141
Cost-effectiveness analysis of escitalopram: a new SSRI in the first-line treatment of major depressive disorder in Austria.	2004 Jun	15200745
Escitalopram in trichotillomania.	2004 Jun	15196611
Effects of chronic treatment with escitalopram or citalopram on extracellular 5-HT in the prefrontal cortex of rats: role of 5-HT1A receptors.	2004 Jun	15148253
[Escitalopram--second generation of serotonin transporter inhibitors?].	2004 Mar-Apr	15307289
[Escitalopram is more effective than citalopram for the treatment of severe major depressive disorder].	2004 Mar-Apr	15107719
[Escitalopram: a chiral agent for treatment of depression].	2004 May	15171592
Liquid chromatography--electrospray ionisation mass spectrometry method for the determination of escitalopram in human plasma and its application in bioequivalence study.	2004 Nov 25	15522722
Venous thromboembolism and escitalopram.	2004 Nov-Dec	15567215
Gateways to clinical trials.	2004 Oct	15605126
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 Sep	15320956
Evidence based review of escitalopram in treating major depressive disorder in primary care.	2004 Sep	15289704
Comparison of the effects of citalopram and escitalopram on 5-Ht-mediated neuroendocrine responses.	2004 Sep	15127082
Reformulation of consumer health queries with professional terminology: a pilot study.	2004 Sep 3	15471753
Escitalopram in clinical practice: results of an open-label trial in a naturalistic setting.	2005	15786487
Evaluation of the cost effectiveness of escitalopram versus venlafaxine XR in major depressive disorder.	2005	15748090
Generalised anxiety disorder in elderly patients : epidemiology, diagnosis and treatment options.	2005	15733018
An open-label trial of escitalopram in pervasive developmental disorders.	2005 Apr	15782081
Newer antidepressants in pregnancy and rates of major malformations: a meta-analysis of prospective comparative studies.	2005 Dec	15742359
A cost-effectiveness model of escitalopram, citalopram,and venlafaxine as first-line treatment for major depressive disorder in Belgium.	2005 Jan	15763612
Escitalopram intoxication.	2005 Jan	15642453
Quetiapine-induced weight gain and escitalopram.	2005 Jan	15625223
Use of selective serotonin-reuptake inhibitors in the treatment of depression in adults with HIV.	2005 Jan	15562140
Effects of acute and long-term administration of escitalopram and citalopram on serotonin neurotransmission: an in vivo electrophysiological study in rat brain.	2005 Jul	15702136
Evidence-based pharmacotherapy of Generalized Anxiety Disorder.	2005 Jun	15576000
Treatment of Raynaud's phenomenon with escitalopram.	2005 Jun	15569398
Escitalopram in the treatment of social anxiety disorder: randomised, placebo-controlled, flexible-dosage study.	2005 Mar	15738503
Escitalopram and suicidality in adult depression and anxiety.	2005 May	15812263
Prospective, multicentre, randomized, double-blind study of the efficacy of escitalopram versus citalopram in outpatient treatment of major depressive disorder.	2005 May	15812262

Patents

Sample Use Guides

In Vivo Use Guide

Lexapro (escitalopram) should generally be administered once daily, morning

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 `Fri Jun 25 21:08:15 UTC 2021` Edited by `admin` on `Fri Jun 25 21:08:15 UTC 2021`
Record UNII	4O4S742ANY
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ESCITALOPRAM

Official Name

English

ESCITALOPRAM [VANDF]

Common Name

English

CIPRALEX

Brand 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