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=C1C=CC(=C2)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 92 Target ID: CHEMBL240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24045971	Inhibitor 8297		2.6 µM [IC50]
Serotonin transporter 178 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 8297		1.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Major depressive disorder 173 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 8429	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 8429	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
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 1737 inhibitor 1587	inhibitor 1767	inhibitor 1852 substrate 1217	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2C19 1478 CYP2E1 882 K+ channels 70 Ca2+ channels 57	CYP2C19 991 P-gp 1537

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-323.pdf_Lexapro_BioPharmr.pdf Page: 70.0	no [IC50 >100 uM]
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-323.pdf_Lexapro_BioPharmr.pdf Page: 70.0	no [IC50 >100 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-323.pdf_Lexapro_BioPharmr.pdf Page: 70.0	no [IC50 >100 uM]
CYP2E1 970	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-323.pdf_Lexapro_BioPharmr.pdf Page: 70.0	no [IC50 >100 uM]
CYP3A4 1925	inhibitor 3277 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 60	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-365_Lexapro_BioPharmr.pdf Page: 11.0	no
K+ channels 70	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-365_Lexapro_BioPharmr.pdf Page: 11.0	no
CYP2D6 1891	inhibitor 3277 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 1217	substrate 3367 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 1737	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-323.pdf_Lexapro_BioPharmr.pdf Page: 70.0	yes [Km 588 uM]
CYP2C19 991	substrate 3367 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 1537	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/23670590/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 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-enantiomer of citalopram): clinical efficacy and onset of action predicted from a rat model.	2001 May	11393591
Great expectations in stereochemistry: focus on antidepressants.	2002 Apr	15131490
Escitalopram H Lundbeck.	2002 Aug	12211420
Gateways to clinical trials.	2002 Dec	12616965
[Who does need Cipralex and why?].	2002 May 16	12082954
Gateways to clinical trials.	2002 Nov	12616707
[Effects of escitalopram on anxiety symptoms in depression].	2002 Sep-Oct	12386549
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
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
Therapeutic drug monitoring of 13 antidepressant and five neuroleptic drugs in serum with liquid chromatography-electrospray ionization mass spectrometry.	2003 Dec	14708881
R-citalopram counteracts the effect of escitalopram in a rat conditioned fear stress model of anxiety.	2003 Jul	12957234
There is a new antidepressant escitalopram (Lexapro) that is a cousin of citalopram (Celexa). How are these two different and does the newer drug have any advantages?	2003 Jul	12888468
R-citalopram attenuates anxiolytic effects of escitalopram in a rat ultrasonic vocalisation model.	2003 Mar 19	12620508
Gateways to clinical trials.	2003 Sep	14571286
R-citalopram counteracts the antidepressant-like effect of escitalopram in a rat chronic mild stress model.	2003 Sep	14501259
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
"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
Escitalopram.	2004 Feb	15045034
R-citalopram inhibits functional and 5-HTP-evoked behavioural responses to the SSRI, escitalopram.	2004 Feb	14751469
Escitalopram continuation treatment prevents relapse of depressive episodes.	2004 Jan	14744167
Gateways to clinical trials.	2004 Jan-Feb	14988742
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
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
Gateways to clinical trials.	2004 Mar	15071612
[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
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
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
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
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
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
Escitalopram intoxication.	2005 Jan	15642453
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 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 Dec 15 15:52:32 GMT 2023` Edited by `admin` on `Fri Dec 15 15:52:32 GMT 2023`
Record UNII	5U85DBW7LO
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

LEXAPRO

Brand 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