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Compound Detail

CHEMBL549

CITALOPRAM
💊 Approved Drug
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💊 Approved Drug
CN(C)CCCC1(c2ccc(F)cc2)OCc2cc(C#N)ccc21

Basic Information

ChEMBL ID CHEMBL549
Name CITALOPRAM
Phase Approved
Structure Type MOL
InChI Key WSEQXVZVJXJVFP-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Citadur Citalopram
26
Targets
75
Activities
3
Assay Types
29
PK Parameters
20
Publications
2
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 1998
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Black Box Warning
USAN Year 1998

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 Burning Mouth Syndrome Dementia Obsessive-Compulsive Disorder Psychomotor Agitation Schizophrenia Stroke Alcoholism Alcoholism Bipolar Disorder Cocaine-Related Disorders Cocaine-Related Disorders Irritable Bowel Syndrome Opioid-Related Disorders Panic Disorder Parkinson Disease Acute Coronary Syndrome

ATC Classification

N06AB04
citalopram
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Activity Summary

IC50 37 meas. best 9.04
Ki 33 meas. best 9.32
EC50 5 meas. best 5.06

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent serotonin transporter
CHEMBL228
Ki 9.32 8.3 0.5 8
Sodium-dependent serotonin transporter
CHEMBL228
IC50 9.04 8.008 0.9 10
Sodium-dependent serotonin transporter
CHEMBL313
Ki 8.82 8.7767 1.5 3
Sodium-dependent serotonin transporter
CHEMBL313
IC50 8.74 8.5425 1.8 4
Sodium-dependent serotonin transporter
CHEMBL4642
Ki 8.54 8.54 2.9 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 8.0 5.73 10.0 6
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 6.81 6.81 156.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
Ki 6.78 6.78 167.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL3602
Ki 6.54 6.54 292.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
IC50 6.53 6.53 297.0 1
Histamine H1 receptor
CHEMBL231
Ki 6.43 6.43 371.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
IC50 6.4 6.4 398.0 1
Alpha-1A adrenergic receptor
CHEMBL319
Ki 6.15 6.15 711.0 1
Unchecked
CHEMBL612545
Ki 6.0 5.8067 996.0 3
Unchecked
CHEMBL612545
IC50 5.99 5.7733 1025.0 3
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 5.93 5.93 1171.0 1
Alpha-1D adrenergic receptor
CHEMBL223
Ki 5.79 5.79 1617.0 1
Alpha-1A adrenergic receptor
CHEMBL319
IC50 5.75 5.75 1756.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 5.74 5.74 1839.0 1
Alpha-1B adrenergic receptor
CHEMBL315
Ki 5.74 5.74 1820.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
IC50 5.66 5.66 2196.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 5.66 5.435 2178.0 2
Histamine H1 receptor
CHEMBL231
IC50 5.5 5.5 3194.0 1
Alpha-1D adrenergic receptor
CHEMBL223
IC50 5.48 5.48 3289.0 1
Alpha-1B adrenergic receptor
CHEMBL315
IC50 5.48 5.48 3288.0 1
Sigma intracellular receptor 2
CHEMBL4105864
Ki 5.27 5.27 5410.0 1
Transporter
CHEMBL6184
Ki 5.22 5.22 5950.0 1
Norepinephrine transporter
CHEMBL304
Ki 5.21 5.21 6190.0 1
Sodium-dependent serotonin transporter
CHEMBL228
EC50 5.06 5.06 8700.0 1
Norepinephrine transporter
CHEMBL304
IC50 5.06 5.06 8800.0 1
Sodium-dependent dopamine transporter
CHEMBL338
Ki 5.03 4.905 9270.0 2
DG-75
CHEMBL2366199
EC50 4.9 4.9 12589.2 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
Ki 4.86 4.86 13661.8 1
HEK293
CHEMBL614818
EC50 4.8 4.8 15848.9 1
Sodium-dependent dopamine transporter
CHEMBL238
Ki 4.78 4.78 16540.0 1
Solute carrier family 22 member 1
CHEMBL5685
IC50 4.73 4.73 18800.0 1
SH-SY5Y
CHEMBL614910
EC50 4.6 4.6 25118.9 1
Sodium-dependent dopamine transporter
CHEMBL338
IC50 4.39 4.39 41000.0 1
5-hydroxytryptamine receptor 1A
CHEMBL273
Ki 4.3 4.3 50118.7 1
Voltage-dependent L-type calcium channel subunit alpha-1C
CHEMBL3762
IC50 4.19 4.19 64500.0 1
Acetylcholinesterase
CHEMBL220
IC50 4.13 4.13 73300.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 12900.0 ng.hr.mL-1 Rattus norvegicus
AUC 12500.0 ng.hr.mL-1 Rattus norvegicus
AUC 421.0 ng.hr.mL-1 Rattus norvegicus
AUC 401.0 ng.hr.mL-1 Rattus norvegicus
AUC 958.0 ng.hr.mL-1 Rattus norvegicus
AUC 930.0 ng.hr.mL-1 Rattus norvegicus
CL 36.0 mL.min-1.g-1 Homo sapiens
CL 4.3 mL.min-1.kg-1 Homo sapiens
CL 3.8 mL.min-1.kg-1 Homo sapiens
CL 4.3 mL.min-1.kg-1 Homo sapiens
CL 39.0 mL.min-1.kg-1 Macaca
CL 82.0 mL.min-1.kg-1 Rattus norvegicus
CL 4.3 mL.min-1.kg-1 Homo sapiens
CL 5.0 mL.min-1.kg-1 Homo sapiens
CL 14.0 mL.min-1.kg-1 Canis lupus familiaris
F 80.0 % Homo sapiens
Fu 0.2 - Homo sapiens
Fu 0.2 - Homo sapiens
Fu 0.2 - Homo sapiens
Fu 0.81 - Homo sapiens
Fu 0.047 - Homo sapiens
Fu 0.061 - Macaca fascicularis
Fu 0.057 - Canis lupus familiaris
Fu 0.038 - Cavia porcellus
Fu 0.06 - Mus musculus
Fu 0.03 - Rattus norvegicus
Fu 0.05 - Rattus norvegicus
MRT 47.0 hr Homo sapiens
T1/2 33.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent serotonin transporter Ki = 0.479 nM 9.32 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
Sodium-dependent serotonin transporter IC50 = 0.902 nM 9.04 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
Sodium-dependent serotonin transporter Ki = 1.5 nM 8.82 Inhibition of [3H]citalopram binding to Serotonin transporter of rat cerebral co... 10915050
Sodium-dependent serotonin transporter Ki = 1.6 nM 8.8 Displacement of [3H]paroxetine from serotonin transporter of rat cerebral cortex 15686927
Sodium-dependent serotonin transporter Ki = 1.6 nM 8.8 Inhibition of SERT (unknown origin) 33111525
Sodium-dependent serotonin transporter Ki = 1.6 nM 8.8 Inhibition of [125I]RTI-55 binding to human serotonin transporter expressed in h... 14971892
Sodium-dependent serotonin transporter IC50 = 1.8 nM 8.74 Inhibition of 5-HT uptake in rat synaptosomal fraction 2999402
Sodium-dependent serotonin transporter Ki = 1.94 nM 8.71 Displacement of [3H]citalopram from SERT in rat brain stem by scintillation coun... 20672825
Sodium-dependent serotonin transporter Ki = 2.9 nM 8.54 Tested in vitro for serotonin(5-HT) neuronal uptake inhibition 2213832
Sodium-dependent serotonin transporter IC50 = 3.0 nM 8.52 Displacement of [3H]paroxetine from SERT in rat cortical membranes after 6 mins ... 24262884
Sodium-dependent serotonin transporter IC50 = 3.0 nM 8.52 Displacement of [3H]paroxetine from human SERT expressed in human HEK293 cells i... 32388114
Sodium-dependent serotonin transporter IC50 = 3.17 nM 8.5 Inhibition of [3H]5-HT reuptake at rat SERT expressed in HEK293 cells after 2 mi... 19717215
Sodium-dependent serotonin transporter IC50 = 3.9 nM 8.41 Inhibition of SERT-mediated [3H]5HT uptake in rat synaptosomes by scintillation ... 21486038
Sodium-dependent serotonin transporter Ki = 4.38 nM 8.36 Displacement of [3H]citalopram from human SERT expressed in HEK293 cells 18644726
Sodium-dependent serotonin transporter Ki = 4.38 nM 8.36 Displacement of [3H]citalopram from human SERT expressed in HEK293 cells 18487050
Sodium-dependent serotonin transporter IC50 = 5.81 nM 8.24 Inhibition of SERT (unknown origin) in HEK293 cells assessed as inhibition of 5-... 34922191
Sodium-dependent serotonin transporter IC50 = 6.27 nM 8.2 Inhibition of SERT (unknown origin) expressed in HEK293 cells assessed as reduct... 29729987
Sodium-dependent serotonin transporter IC50 = 6.7 nM 8.17 Inhibition of [3H]5-HT uptake by SERT primary site (S1) (unknown origin) express... 28041833
Sodium-dependent serotonin transporter IC50 = 9.2 nM 8.04 Inhibition of human SERT expressed in HEK293 cells assessed as reduction in 5-HT... 38552597
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 10.0 nM 8.0 Inhibition of human ERG 23919353

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 461
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 63
17870537 10.1016/j.bmc.2007.08.055 Mus musculus 17
26698537 10.1016/j.ejmech.2015.11.040 Mus musculus 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
20070106 10.1021/jm901371v Homo sapiens 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
15920768 10.1002/jps.20373 ADMET 8
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 6
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 5
21474681 10.1124/dmd.111.038778 Brain 5
- 10.6019/CHEMBL3301361 ADMET 5
18426954 10.1124/dmd.108.020479 ADMET 4
31358468 10.1016/j.bmcl.2019.07.030 Mus musculus 4
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 4
28763213 10.1021/acs.jmedchem.7b00839 Mus musculus 4
23043306 10.1021/jm300975f Rattus norvegicus 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4

Data from ChEMBL 36 via Core Engine