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

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

Targets

Primary Target	Pharmacology	Condition	Potency
HERG 89 Target ID: CHEMBL240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24045971	Inhibitor 7728		2.6 µM [IC50]
Serotonin transporter 164 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 7728		1.0 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		Approved 8043	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 1.02928318E12
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		Approved 8043	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 1.02928318E12

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 (mean) Overdose Dose: 332 mg Route: oral Route: single Dose: 332 mg Sources: https://pubmed.ncbi.nlm.nih.gov/20170390/	unknown, 16 - 84 years n = 63 Health Status: unknown Age Group: 16 - 84 years Sex: M+F Population Size: 63 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 (median) Overdose Dose: 140 mg Route: oral Route: single Dose: 140 mg Sources: https://pubmed.ncbi.nlm.nih.gov/19556032/	unknown, 18 - 36 years n = 46 Health Status: unknown Age Group: 18 - 36 years Sex: M+F Population Size: 46 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 (median) Overdose Dose: 140 mg Route: oral Route: single Dose: 140 mg Co-administed with:: coingested drugs Sources: https://pubmed.ncbi.nlm.nih.gov/19556032/	unknown, 24 - 43 years n = 33 Health Status: unknown Age Group: 24 - 43 years Sex: M+F Population Size: 33 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 n = 4185 Health Status: unhealthy Condition: Psychiatric diagnoses Age Group: 46.2 years Sex: M+F Population Size: 4185 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 (mean) 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 n = 64 Health Status: unhealthy Condition: obsessive-compulsive disorder Age Group: adult Sex: M+F Population Size: 64 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 1601 inhibitor 1467	inhibitor 1604	inhibitor 1702 substrate 1118	inhibitor 1475

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1383 CYP2C19 1325 CYP2E1 790 K+ channels 50 Ca2+ channels 40	CYP2C19 910 P-gp 1400

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 1532	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-323.pdf_Lexapro_BioPharmr.pdf Page: 70.0	no [IC50 >100 uM]
CYP2C19 1392	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-323.pdf_Lexapro_BioPharmr.pdf Page: 70.0	no [IC50 >100 uM]
CYP2C9 1648	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-323.pdf_Lexapro_BioPharmr.pdf Page: 70.0	no [IC50 >100 uM]
CYP2E1 871	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-323.pdf_Lexapro_BioPharmr.pdf Page: 70.0	no [IC50 >100 uM]
CYP3A4 1772	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-323.pdf_Lexapro_BioPharmr.pdf Page: 70.0	no [IC50 >100 uM]
Ca2+ channels 43	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-365_Lexapro_BioPharmr.pdf Page: 11.0	no
K+ channels 50	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-365_Lexapro_BioPharmr.pdf Page: 11.0	no
CYP2D6 1738	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-323.pdf_Lexapro_BioPharmr.pdf Page: 70.0	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: 70.0

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP2D6 1118	substrate 3113 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-323.pdf_Lexapro_BioPharmr.pdf Page: 70.0	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: 70.0
CYP3A4 1601	substrate 3113 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-323.pdf_Lexapro_BioPharmr.pdf Page: 70.0	yes [Km 588 uM]
CYP2C19 910	substrate 3113 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-323.pdf_Lexapro_BioPharmr.pdf Page: 70.0	yes [Km 69 uM]
P-gp 1400	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/23670590/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1507	inhibitor 1489 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-323.pdf_Lexapro_Pharmr_P1.pdf Page: 16.0

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
Escitalopram (S-citalopram) and its metabolites in vitro: cytochromes mediating biotransformation, inhibitory effects, and comparison to R-citalopram.	2001 Aug	11454728
Second-generation SSRIs: human monoamine transporter binding profile of escitalopram and R-fluoxetine.	2001 Sep 1	11543737
Gateways to clinical trials.	2002 Dec	12616965
[Misleading basis for marketing of Cipralex].	2002 Jul 11	12170524
[Second generation SSRIS: human monoamine transporter binding profile of escitalopram and R-fluoxetine].	2002 Jul-Aug	12232544
Escitalopram 10 mg/day is effective and well tolerated in a placebo-controlled study in depression in primary care.	2002 May	11981349
Gateways to clinical trials.	2002 Nov	12616707
Escitalopram: efficacy and tolerability in the treatment of depression.	2002 Nov	12474611
Escitalopram.	2002 Oct	12387707
Enantiomers' potential in psychopharmacology--a critical analysis with special emphasis on the antidepressant escitalopram.	2002 Oct	12208561
Escitalopram (lexapro) for depression.	2002 Sep 30	12360121
[Effects of escitalopram on anxiety symptoms in depression].	2002 Sep-Oct	12386549
Escitalopram: a pharmacoeconomic review of its use in depression.	2003	14594439
Escitalopram : a review of its use in the management of major depressive and anxiety disorders.	2003	12665392
An evaluation of the potential for pharmacokinetic interaction between escitalopram and the cytochrome P450 3A4 inhibitor ritonavir.	2003 Apr	12809966
The R-enantiomer of citalopram counteracts escitalopram-induced increase in extracellular 5-HT in the frontal cortex of freely moving rats.	2003 Aug	12842122
The development of new antidepressants: focus on duloxetine and escitalopram.	2003 Jan-Feb	12866739
R-citalopram counteracts the effect of escitalopram in a rat conditioned fear stress model of anxiety.	2003 Jul	12957234
Escitalopram (10-20 mg/day) is effective and well tolerated in a placebo-controlled study in depression in primary care.	2003 Jul	12817155
Escitalopram, the S-(+)-enantiomer of citalopram, is a selective serotonin reuptake inhibitor with potent effects in animal models predictive of antidepressant and anxiolytic activities.	2003 Jun	12719960
R-citalopram attenuates anxiolytic effects of escitalopram in a rat ultrasonic vocalisation model.	2003 Mar 19	12620508
Escitalopram in the treatment of panic disorder: a randomized, double-blind, placebo-controlled trial.	2003 Nov	14658946
Gateways to clinical trials.	2003 Sep	14571286
Treatment of anxiety and depression in transplant patients: pharmacokinetic considerations.	2004	15086275
Improved potency of escitalopram on the human serotonin transporter: demonstration of an ex vivo assay technique.	2004 Apr	15206668
A case of hyponatremia associated with escitalopram.	2004 Dec	15641882
Metabolism of the newest antidepressants: comparisons with related predecessors.	2004 Feb	15057659
Escitalopram continuation treatment prevents relapse of depressive episodes.	2004 Jan	14744167
Escitalopram: superior to citalopram or a chiral chimera?	2004 Jan-Feb	14665791
Reversal of fluoxetine-induced sexual dysfunction by switching to escitalopram.	2004 Jan-Feb	14660288
Mechanisms for the inhibition of genital vascular responses by antidepressants in a female rabbit model.	2004 Jul	15034084
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
Gateways to clinical trials.	2004 Mar	15071612
Do equivalent doses of escitalopram and citalopram have similar efficacy? A pooled analysis of two positive placebo-controlled studies in major depressive disorder.	2004 May	15107657
Gateways to clinical trials.	2004 Oct	15605126
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 Oct 22	15451381
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
The safety of newer antidepressants in pregnancy and breastfeeding.	2005	15691224
An open-label trial of escitalopram in pervasive developmental disorders.	2005 Apr	15782081
Use of selective serotonin-reuptake inhibitors in the treatment of depression in adults with HIV.	2005 Jan	15562140
Treatment of Raynaud's phenomenon with escitalopram.	2005 Jun	15569398
Escitalopram and suicidality in adult depression and anxiety.	2005 May	15812263

Patents

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 `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