ESCITALOPRAM OXALATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H21FN2O.C2H2O4
Molecular Weight	414.4268
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=KTGRHKOEFSJQNS-BDQAORGHSA-N

InChI=1S/C20H21FN2O.C2H2O4/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;3-1(4)2(5)6/h4-9,12H,3,10-11,14H2,1-2H3;(H,3,4)(H,5,6)/t20-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	C2H2O4
Molecular Weight	90.0349
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
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 99 Target ID: CHEMBL240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24045971	Inhibitor 8504		2.6 µM [IC50]
Serotonin transporter 183 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 8504		1.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Major depressive disorder 179 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 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
Generalized anxiety disorder 32 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 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

C_max

Value	Dose	Analyte	Population
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

Value	Dose	Analyte	Population
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

T_1/2

Value	Dose	Analyte	Population
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

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

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252	inhibitor 2438	inhibitor 2507 substrate 1388	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2C19 2057 CYP2E1 1060 K+ channels 73 Ca2+ channels 59	CYP2C19 1119 P-gp 2052

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-323.pdf_Lexapro_BioPharmr.pdf Page: 70.0	no [IC50 >100 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-323.pdf_Lexapro_BioPharmr.pdf Page: 70.0	no [IC50 >100 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-323.pdf_Lexapro_BioPharmr.pdf Page: 70.0	no [IC50 >100 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-323.pdf_Lexapro_BioPharmr.pdf Page: 70.0	no [IC50 >100 uM]
CYP3A4 2633	inhibitor 4027 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 62	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-365_Lexapro_BioPharmr.pdf Page: 11.0	no
K+ channels 73	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-365_Lexapro_BioPharmr.pdf Page: 11.0	no
CYP2D6 2546	inhibitor 4027 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 1388	substrate 4014 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 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-323.pdf_Lexapro_BioPharmr.pdf Page: 70.0	yes [Km 588 uM]
CYP2C19 1119	substrate 4014 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 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23670590/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 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
Newer antidepressants in pregnancy and rates of major malformations: a meta-analysis of prospective comparative studies.	2005-12	15742359
Effects of acute and long-term administration of escitalopram and citalopram on serotonin neurotransmission: an in vivo electrophysiological study in rat brain.	2005-07	15702136
Evidence-based pharmacotherapy of Generalized Anxiety Disorder.	2005-06	15576000
Treatment of Raynaud's phenomenon with escitalopram.	2005-06	15569398
Escitalopram and suicidality in adult depression and anxiety.	2005-05	15812263
Prospective, multicentre, randomized, double-blind study of the efficacy of escitalopram versus citalopram in outpatient treatment of major depressive disorder.	2005-05	15812262
An open-label trial of escitalopram in pervasive developmental disorders.	2005-04	15782081
Escitalopram in the treatment of social anxiety disorder: randomised, placebo-controlled, flexible-dosage study.	2005-03	15738503
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	15695064
A cost-effectiveness model of escitalopram, citalopram,and venlafaxine as first-line treatment for major depressive disorder in Belgium.	2005-01	15763612
Escitalopram intoxication.	2005-01	15642453
Quetiapine-induced weight gain and escitalopram.	2005-01	15625223
Use of selective serotonin-reuptake inhibitors in the treatment of depression in adults with HIV.	2005-01	15562140
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
The safety of newer antidepressants in pregnancy and breastfeeding.	2005	15691224
Gateways to clinical trials.	2004-12	15672123
A case of hyponatremia associated with escitalopram.	2004-12	15641882
Liquid chromatography--electrospray ionisation mass spectrometry method for the determination of escitalopram in human plasma and its application in bioequivalence study.	2004-11-25	15522722
Antidepressant-associated mania with escitalopram.	2004-11	15504660
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	15451381
Gateways to clinical trials.	2004-10	15605126
Gateways to clinical trials.	2004-09-07	15349141
Reformulation of consumer health queries with professional terminology: a pilot study.	2004-09-03	15471753
A double-blind comparison of escitalopram and venlafaxine extended release in the treatment of major depressive disorder.	2004-09	15367045
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	15320956
Evidence based review of escitalopram in treating major depressive disorder in primary care.	2004-09	15289704
[Escitalopram--second generation of serotonin transporter inhibitors?].	2004-08-17	15307289
"Dopamine-dependent" side effects of selective serotonin reuptake inhibitors: a clinical review.	2004-08	15323590
Selective binding of 2-[125I]iodo-nisoxetine to norepinephrine transporters in the brain.	2004-07	15219270
Escitalopram versus citalopram: the surprising role of the R-enantiomer.	2004-07	15160261
Cost-effectiveness analysis of escitalopram: a new SSRI in the first-line treatment of major depressive disorder in Austria.	2004-06	15200745
Escitalopram in trichotillomania.	2004-06	15196611
Effects of chronic treatment with escitalopram or citalopram on extracellular 5-HT in the prefrontal cortex of rats: role of 5-HT1A receptors.	2004-06	15148253
[Escitalopram: a chiral agent for treatment of depression].	2004-05	15171592
Venous thromboembolism and escitalopram.	2004-04-12	15567215
Improved potency of escitalopram on the human serotonin transporter: demonstration of an ex vivo assay technique.	2004-04	15206668
Escitalopram in the treatment of social anxiety disorder: analysis of efficacy for different clinical subgroups and symptom dimensions.	2004	15643634
A comparison of the direct costs and cost effectiveness of serotonin reuptake inhibitors and associated adverse drug reactions.	2004	15521793
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
A randomised study comparing escitalopram with venlafaxine XR in primary care patients with major depressive disorder.	2004	15179022
Spotlight on the pharmacoeconomics of escitalopram in depression.	2004	15139801
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
New single-isomer compounds on the horizon.	2002-04	15131493
Efficacy comparison of escitalopram and citalopram in the treatment of major depressive disorder: pooled analysis of placebo-controlled trials.	2002-04	15131492
Escitalopram: a second-generation SSRI.	2002-04	15131491
Great expectations in stereochemistry: focus on antidepressants.	2002-04	15131490

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 `Mon Mar 31 18:11:45 GMT 2025` Edited by `admin` on `Mon Mar 31 18:11:45 GMT 2025`
Record UNII	5U85DBW7LO
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LEXAPRO

Preferred Name

English

ESCITALOPRAM OXALATE

Official Name

English

ESCITALOPRAM OXALATE [USAN]

Common Name

English

LU-26-054-O

Code

English

S-(+)-1-(3-(DIMETHYLAMINO)PROPYL)-1-(P-FLUOROPHENYL)-5-PHTHALANCARBONITRILE OXALATE

Common Name

English

LU-26-054-0

Code

English

ESCITALOPRAM (AS OXALATE)

Common Name

English

ESCITALOPRAM OXALATE [EP MONOGRAPH]

Common Name

English

ESCITALOPRAM OXALATE [MART.]

Common Name

English

ESCITALOPRAM OXALATE [VANDF]

Common Name

English

ESCITALOPRAM OXALATE [MI]

Common Name

English

LU 26-054-0

Code

English

ESCITALOPRAM OXALATE [USP-RS]

Common Name

English

CITALOPRAM OXALATE, (S)-

Common Name

English

ESCITALOPRAM OXALATE [USP MONOGRAPH]

Common Name

English

ESCITALOPRAM OXALATE [JAN]

Common Name

English

Escitalopram oxalate [WHO-DD]

Common Name

English

ESCITALOPRAM OXALATE [ORANGE BOOK]

Common Name

English

NSC-758934

Code

English

S-(+)-5-ISOBENZOFURANCARBONITRILE, 1-(3-(DIMETHYLAMINO)PROPYL)-1-(4-FLUOROPHENYL)-1,3-DIHYDRO-, OXALATE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C265