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Compound Detail

CHEMBL1508

ESCITALOPRAM
💊 Approved Drug
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💊 Approved Drug
CN(C)CCC[C@@]1(c2ccc(F)cc2)OCc2cc(C#N)ccc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1508
Name ESCITALOPRAM
Phase Approved
Structure Type MOL
InChI Key WSEQXVZVJXJVFP-FQEVSTJZSA-N
Therapeutic ✓ Yes

Known Names

Cipralex Escitalopram Esertia Esitol LU-26-054
5
Targets
18
Activities
4
Assay Types
19
PK Parameters
20
Publications
5
Known Names
20
Indications

Molecular Properties

324.4
MW (Da)
3.81
ALogP
3
HBA
0
HBD
36.3
PSA (Ų)
0.84
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2002
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Chemical Probe
USAN Year 2000

Extended Properties

Molecular Formula C20H21FN2O
MW 324.40
Aromatic Rings 2
Heavy Atoms 24
NP-Likeness -0.47

Indications

Depressive Disorder Depressive Disorder Depressive Disorder, Major Anxiety Anxiety Disorders Arthritis, Rheumatoid Bipolar Disorder Bipolar Disorder Burning Mouth Syndrome Carcinoma Dementia Hypertension, Pulmonary Neoplasms Obsessive-Compulsive Disorder Schizophrenia Aphasia Borderline Personality Disorder Cocaine-Related Disorders Cocaine-Related Disorders Digestive System Diseases

ATC Classification

N06AB10
escitalopram
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Activity Summary

Ki 10 meas. best 9.05
IC50 5 meas. best 8.68
EC50 2 meas. best 5.29
Kd 1 meas. best 8.59

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent serotonin transporter
CHEMBL313
 Ki 9.05 9.05 0.9 1
Sodium-dependent serotonin transporter
CHEMBL228
 Ki 9.0 8.1067 1.0 6
5-hydroxytryptamine receptor 6
CHEMBL3371
 Ki 9.0 9.0 1.0 1
Sodium-dependent serotonin transporter
CHEMBL228
 IC50 8.68 7.34 2.1 3
Sodium-dependent serotonin transporter
CHEMBL228
 Kd 8.59 8.59 2.6 1
5-hydroxytryptamine receptor 6
CHEMBL3371
 IC50 7.26 7.26 55.0 1
Sodium-dependent serotonin transporter
CHEMBL228
 EC50 5.29 5.265 5100.0 2
Sodium-dependent dopamine transporter
CHEMBL338
 Ki 5.09 5.09 8150.0 1
Transporter
CHEMBL6184
 Ki 4.98 4.98 10500.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 63.87 ng.hr.mL-1 Rattus norvegicus
CL 0.16 mL.min-1.g-1 Rattus norvegicus
CL 0.19 mL.min-1.g-1 Rattus norvegicus
CL 117.0 mL.min-1.kg-1 Rattus norvegicus
CL 277.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 62.0 nM Rattus norvegicus
F 80.0 % Homo sapiens
F 80.0 % Homo sapiens
Fu 0.5 - Rattus norvegicus
ka 0.02 /min Rattus norvegicus
Ke 0.015 /min Rattus norvegicus
T1/2 0.4683 hr Homo sapiens
T1/2 1.133 hr Homo sapiens
T1/2 0.9 hr Rattus norvegicus
Tmax 2.0 hr Rattus norvegicus
Tmax 0.4333 hr Rattus norvegicus
Vd 18.0 L.kg-1 Rattus norvegicus
Vd 17.0 L.kg-1 Rattus norvegicus
Vd 4.1 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent serotonin transporter Ki = 0.89 nM 9.05 Displacement of [3H]citalopram from SERT in rat brain stem by scintillation coun... 20672825
Sodium-dependent serotonin transporter Ki = 1.0 nM 9.0 Displacement of [3H]citalopram from human serotonin transporter expressed in HEK... 19720528
Sodium-dependent serotonin transporter Ki = 1.0 nM 9.0 Displacement of [3H]citalopram form human SRET by liquid scintillation counting 20347298
5-hydroxytryptamine receptor 6 Ki = 1.0 nM 9.0 Displacement of [3H]-Citalopram from human SERT extracted from HEK293 cell membr... 38901106
Sodium-dependent serotonin transporter Ki = 1.77 nM 8.75 Displacement of [125I]-RTI-55 from human SERT expressed in HEK293 cell membranes... 30266542
Sodium-dependent serotonin transporter IC50 = 2.1 nM 8.68 Inhibition of [3H]5-HT uptake by SERT primary site (S1) (unknown origin) express... 28041833
Sodium-dependent serotonin transporter Ki = 2.2 nM 8.66 Inhibition of wild type human SERT expressed in HEK293 GripTite cells pre-incuba... 26153715
Sodium-dependent serotonin transporter Kd = 2.6 nM 8.59 Binding affinity to human SERT expressed in African green monkey COS7 cells afte... 24944746
Sodium-dependent serotonin transporter Ki = 7.4 nM 8.13 Inhibition of 5-hydroxy[3H]tryptamine uptake at human SERT expressed in African ... 24944746
Sodium-dependent serotonin transporter IC50 = 10.0 nM 8.0 Displacement of [3H]-S-citalopram from human SERT primary site (S1) expressed in... 28041833
5-hydroxytryptamine receptor 6 IC50 = 55.0 nM 7.26 Inhibition of human SERT extracted from HEK293 cell membrane assessed as inhibit... 38901106
Sodium-dependent serotonin transporter IC50 = 4600.0 nM 5.34 Allosteric modulation at wild-type human SERT site S2 expressed in african green... 24237160
Sodium-dependent serotonin transporter EC50 = 5100.0 nM 5.29 Inhibition of [3H]-S-citalopram dissociation from SERT allosteric modulator site... 28041833
Sodium-dependent serotonin transporter EC50 = 5800.0 nM 5.24 Inhibition of [3H]-S-citalopram dissociation from human SERT allosteric modulato... 28041833
Sodium-dependent serotonin transporter Ki = 7879.0 nM 5.1 Inhibition of human SERT S438T mutant expressed in HEK293 GripTite cells pre-inc... 26153715
Sodium-dependent dopamine transporter Ki = 8150.0 nM 5.09 Displacement of [3H]WIN-35428 from DAT in rat caudate-putamen by scintillation c... 20672825
Transporter Ki = 10500.0 nM 4.98 Displacement of [3H]nisoxetine from NET in rat frontal cortex by scintillation c... 20672825

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5303304 Fibroblast 10
22736307 10.1124/dmd.112.045682 ADMET 8
- 10.6019/CHEMBL5303304 HEK-293T 8
22736307 10.1124/dmd.112.045682 Plasma 6
22736307 10.1124/dmd.112.045682 Rattus norvegicus 5
38901106 10.1016/j.ejmech.2024.116601 5-hydroxytryptamine receptor 6 5
28391970 10.1016/j.bmc.2017.03.057 Mus musculus 5
24237160 10.1021/jm4014136 Sodium-dependent serotonin transporter 4
28041833 10.1016/j.bmcl.2016.12.037 Sodium-dependent serotonin transporter 4
- 10.6019/CHEMBL5303304 U2OS 4
37468498 10.1038/s41467-023-40064-9 Histamine H1 receptor 3
20672825 10.1021/jm1005034 Unchecked 3
32673902 10.1016/j.ejmech.2020.112437 ADMET 3
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
24944746 10.1021/ml5000806 Sodium-dependent serotonin transporter 2
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 2
26153715 10.1021/acs.jmedchem.5b00682 Sodium-dependent serotonin transporter 2

Data from ChEMBL 36 via Core Engine