U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C20H21FN2O.BrH
Molecular Weight 405.304
Optical Activity ( + )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESCITALOPRAM HYDROBROMIDE

SMILES

Br.CN(C)CCC[C@]1(OCC2=C1C=CC(=C2)C#N)C3=CC=C(F)C=C3

InChI

InChIKey=WIHMBLDNRMIGDW-BDQAORGHSA-N
InChI=1S/C20H21FN2O.BrH/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;1H/t20-;/m0./s1

HIDE SMILES / InChI
Molecular Formula BrH
Molecular Weight 80.912
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

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
8297
 2.6 µM [IC50]
Inhibitor
8297
 1.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
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
Doses

Doses

DosePopulationAdverse 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

AEs

AESignificanceDosePopulation
Dizziness grade 1-2, 2 patients
Disc. AE
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/
Restlessness grade 1-2, 2 patients
Disc. AE
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/
Somnolence grade 1-2, 25 patients
Disc. AE
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/
Mydriasis grade 1-2, 3 patients
Disc. AE
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/
Change in ECG grade 1-2, 4 patients
Disc. AE
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/
Nausea grade 1-2, 4 patients
Disc. AE
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/
Tachycardia grade 1-2, 7 patients
Disc. AE
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/
Tremor grade 1-2, 8 patients
Disc. AE
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/
Vomiting grade 1-2, 8 patients
Disc. AE
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/
Change in ECG grade 3-4, 1 patient
Disc. AE
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/
Coma grade 3-4, 1 patient
Disc. AE
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/
Convulsion grade 3-4, 1 patient
Disc. AE
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/
Intestinal atony grade 3-4, 1 patient
Disc. AE
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/
Urinary retention grade 3-4, 1 patient
Disc. AE
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/
Vomiting grade 3-4, 1 patient
Disc. AE
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/
Agitation grade 3-4, 4 patients
Disc. AE
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/
Clonus 12 patients
Disc. AE
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/
Clonus 2 patients
Disc. AE
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/
Eyelid myoclonus 2 patients
Disc. AE
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/
Hyperreflexia 21 patient
Disc. AE
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/
Myoclonus 3 patients
Disc. AE
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/
Hunter's syndrome 7 patients
Disc. AE
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/
Hunter's syndrome 1 patient
Disc. AE
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/
Eyelid myoclonus 2 patients
Disc. AE
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/
Clonus 3 patients
Disc. AE
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/
Hyperreflexia 9 patients
Disc. AE
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/
Coronary heart disease 10.7%
Disc. AE
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/
Sexual desire decreased 21 patient
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/
Dry mouth 8 patients
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/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1737

inhibitor
1587
inhibitor
1767
inhibitor
1852

substrate
1217
inhibitor
1612

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
1524

CYP2C19
1478

CYP2E1
882

K+ channels
70

Ca2+ channels
57
CYP2C19
991

P-gp
1537
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
1692
 no [IC50 >100 uM]
CYP2C19
1553
 no [IC50 >100 uM]
CYP2C9
1819
 no [IC50 >100 uM]
CYP2E1
970
 no [IC50 >100 uM]
CYP3A4
1925
 no [IC50 >100 uM]
Ca2+ channels
60
 no
K+ channels
70
 no
CYP2D6
1891
 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
1217
 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
1737
 yes [Km 588 uM]
CYP2C19
991
 yes [Km 69 uM]
P-gp
1537
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1647
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
Efficacy comparison of escitalopram and citalopram in the treatment of major depressive disorder: pooled analysis of placebo-controlled trials.
2002 Apr
Escitalopram: a second-generation SSRI.
2002 Apr
Escitalopram H Lundbeck.
2002 Aug
The preclinical observation that escitalopram possesses a faster time to onset of efficacy than citalopram.
2002 Jan
[Who does need Cipralex and why?].
2002 May 16
Escitalopram: efficacy and tolerability in the treatment of depression.
2002 Nov
Escitalopram.
2002 Oct
Escitalopram (lexapro) for depression.
2002 Sep 30
Therapeutic drug monitoring of 13 antidepressant and five neuroleptic drugs in serum with liquid chromatography-electrospray ionization mass spectrometry.
2003 Dec
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
R-citalopram attenuates anxiolytic effects of escitalopram in a rat ultrasonic vocalisation model.
2003 Mar 19
Treatment of anxiety and depression in transplant patients: pharmacokinetic considerations.
2004
Single-enantiomer drugs: elegant science, disappointing effects.
2004
Newer antidepressants: review of efficacy and safety of escitalopram and duloxetine.
2004
"Dopamine-dependent" side effects of selective serotonin reuptake inhibitors: a clinical review.
2004 Aug
Metabolism of the newest antidepressants: comparisons with related predecessors.
2004 Feb
Gateways to clinical trials.
2004 Jan-Feb
Escitalopram: superior to citalopram or a chiral chimera?
2004 Jan-Feb
Gateways to clinical trials.
2004 Jul-Aug
Cost-effectiveness of escitalopram versus citalopram in the treatment of severe depression.
2004 Jun
Gateways to clinical trials.
2004 Mar
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
Antidepressant-associated mania with escitalopram.
2004 Nov
Venous thromboembolism and escitalopram.
2004 Nov-Dec
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
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
Reformulation of consumer health queries with professional terminology: a pilot study.
2004 Sep 3
Evaluation of the cost effectiveness of escitalopram versus venlafaxine XR in major depressive disorder.
2005
A cost-effectiveness model of escitalopram, citalopram,and venlafaxine as first-line treatment for major depressive disorder in Belgium.
2005 Jan
Escitalopram intoxication.
2005 Jan
Use of selective serotonin-reuptake inhibitors in the treatment of depression in adults with HIV.
2005 Jan
Treatment of Raynaud's phenomenon with escitalopram.
2005 Jun
Escitalopram in the treatment of social anxiety disorder: randomised, placebo-controlled, flexible-dosage study.
2005 Mar
Prospective, multicentre, randomized, double-blind study of the efficacy of escitalopram versus citalopram in outpatient treatment of major depressive disorder.
2005 May
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 Sat Dec 16 19:10:15 GMT 2023
Edited
by admin
on Sat Dec 16 19:10:15 GMT 2023
Record UNII
SS9JTY593K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ESCITALOPRAM HYDROBROMIDE
Common Name English
5-ISOBENZOFURANCARBONITRILE, 1-(3-(DIMETHYLAMINO)PROPYL)-1-(4-FLUOROPHENYL)-1,3-DIHYDRO-, MONOHYDROBROMIDE, (1S)-
Systematic Name English
(S)-CITALOPRAM HYDROBROMIDE
Common Name English
5-ISOBENZOFURANCARBONITRILE, 1-(3-(DIMETHYLAMINO)PROPYL)-1-(4-FLUOROPHENYL)-1,3-DIHYDRO-, HYDROBROMIDE (1:1), (1S)-
Systematic Name English
Code System Code Type Description
CAS
481047-50-1
Created by admin on Sat Dec 16 19:10:15 GMT 2023 , Edited by admin on Sat Dec 16 19:10:15 GMT 2023
PRIMARY
SMS_ID
300000015326
Created by admin on Sat Dec 16 19:10:15 GMT 2023 , Edited by admin on Sat Dec 16 19:10:15 GMT 2023
PRIMARY
FDA UNII
SS9JTY593K
Created by admin on Sat Dec 16 19:10:15 GMT 2023 , Edited by admin on Sat Dec 16 19:10:15 GMT 2023
PRIMARY
PUBCHEM
9844182
Created by admin on Sat Dec 16 19:10:15 GMT 2023 , Edited by admin on Sat Dec 16 19:10:15 GMT 2023
PRIMARY
Related Record Type Details
Structure of ESCITALOPRAM
PARENT -> SALT/SOLVATE
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