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Compound Detail

CHEMBL1200781

CITALOPRAM HYDROBROMIDE
💊 Approved Drug
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💊 Approved Drug
Br.CN(C)CCCC1(c2ccc(F)cc2)OCc2cc(C#N)ccc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1200781
Name CITALOPRAM HYDROBROMIDE
Phase Approved
Structure Type MOL
InChI Key WIHMBLDNRMIGDW-UHFFFAOYSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL549
Active Moiety CHEMBL549

Known Names

Celexa Cipramil Citalopram (as hydrobromide) Citalopram hbr Citalopram hydrobromide LU 10-171-B LU-10-171-B NSC-758684 Paxoran
2
Targets
5
Activities
2
Assay Types
4
PK Parameters
16
Publications
9
Known Names
5
Indications
1
Mechanisms

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 C20H22BrFN2O
MW 405.31
Aromatic Rings 2
Heavy Atoms 24
NP-Likeness -0.47

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Serotonin transporter inhibitor INHIBITOR Sodium-dependent serotonin transporter ✓ ✓

Indications

Depressive Disorder Depressive Disorder, Major Hot Flashes Autistic Disorder Panic Disorder

Drug Warnings

Black Box Warning
psychiatric toxicity
Country: United States

Activity Summary

IC50 4 meas. best 6.1
Ki 1 meas. best 9.11

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent serotonin transporter
CHEMBL228
 Ki 9.11 9.11 0.8 1
Plasmodium falciparum
CHEMBL364
 IC50 6.1 5.5 794.3 4

Pharmacokinetic Data

Parameter Value Units Species
Fu 0.035 - Mus musculus
Fu 0.32 - Mus musculus
Fu 0.031 - Rattus norvegicus
Fu 0.5 - Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent serotonin transporter Ki = 0.78 nM 9.11 Inhibition of [125I]IDAM uptake at SERT (unknown origin) expressed in LLC-PK1 ce... 23265880
Plasmodium falciparum IC50 = 794.33 nM 6.1 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 1995.26 nM 5.7 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
Plasmodium falciparum IC50 = 6309.57 nM 5.2 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g... 19734910

Literature References

PubMed DOI Target Context # Activities
22112383 10.1124/dmd.111.043083 ADMET 8
22112383 10.1124/dmd.111.043083 Plasma 6
19734910 10.1038/nchembio.215 Plasmodium falciparum 4
22112383 10.1124/dmd.111.043083 Brain 4
22112383 10.1124/dmd.111.043083 Molecular identity unknown 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
17417631 10.1038/nchembio873 Unchecked 1
23265880 10.1016/j.bmcl.2012.11.043 Sodium-dependent serotonin transporter 1
- 10.1101/2020.04.03.023846 SARS-CoV-2 1
- 10.6019/CHEMBL4513141 Candida albicans 1
- 10.6019/CHEMBL4513141 Cryptococcus neoformans 1
- 10.6019/CHEMBL4513141 Escherichia coli 1
- 10.6019/CHEMBL4513141 Klebsiella pneumoniae 1
- 10.6019/CHEMBL4513141 Pseudomonas aeruginosa 1
- 10.6019/CHEMBL4513141 Acinetobacter baumannii 1
- 10.6019/CHEMBL4513141 Staphylococcus aureus 1

Data from ChEMBL 36 via Core Engine