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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL549
CHEMBL549
Compound Name CITALOPRAM
ChEMBL Synonyms CITALOPRAM | Celexa | [3H]-Citalopram | CELEXA | LU-10-171-B | CIPRAMIL | CITALOPRAM HYDROBROMIDE | PAXORAN
Max Phase 4 (Approved)
Trade Names PAXORAN | CIPRAMIL | CELEXA | CITALOPRAM HYDROBROMIDE
Molecular Formula C20H21FN2O

Additional synonyms for CHEMBL549 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CN(C)CCCC1(OCc2cc(ccc12)C#N)c3ccc(F)cc3
Standard InChI InChI=1S/C20H21FN2O/c1-23(2)11-3-10-20(17-5-7-18(21)8-6-17)1 ...
Download InChI
Standard InChI Key WSEQXVZVJXJVFP-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • Curated Drug Metabolism Pathways
  • DrugMatrix
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL549

Molecule Features

CHEMBL549 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Racemic Mixture Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Serotonin transporter inhibitor Serotonin transporter FDA

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Obsessive-Compulsive DisorderD009771EFO:0004242obsessive-compulsive disorder3ClinicalTrials
StrokeD020521EFO:0000712stroke2ClinicalTrials
Cocaine-Related DisordersD019970EFO:0002610cocaine dependence2ClinicalTrials
DementiaD003704HP:0000726dementia3ClinicalTrials
Depressive Disorder, MajorD003865EFO:0003761unipolar depression4DailyMed
Acute Coronary SyndromeD054058EFO:0005672acute coronary syndrome1ClinicalTrials
AnxietyD001007EFO:0005230anxiety3ClinicalTrials
SchizophreniaD012559EFO:0000692schizophrenia3ClinicalTrials
Panic DisorderD016584EFO:0004262panic disorder2ClinicalTrials
ClinicalTrials
Irritable Bowel SyndromeD043183EFO:0000555irritable bowel syndrome2ClinicalTrials
Autistic DisorderD001321EFO:0003758autism2ClinicalTrials
AlcoholismD000437EFO:0003829alcohol dependence2ClinicalTrials
Child Development Disorders, PervasiveD002659EFO:0003756autism spectrum disorder1ClinicalTrials
Opioid-Related DisordersD009293EFO:0005611opioid dependence2ClinicalTrials
Bipolar DisorderD001714EFO:0000289bipolar disorder2ClinicalTrials
Depressive DisorderD003866EFO:0003761unipolar depression4DailyMed
ATC
ClinicalTrials

Clinical Data

ClinicalTrials.gov CITALOPRAM
The Cochrane Collaboration CITALOPRAM

Metabolites for CHEMBL549

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Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL549. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL313 Serotonin transporter Rattus norvegicus 1.000
CHEMBL228 Serotonin transporter Homo sapiens 1.000
CHEMBL231 Histamine H1 receptor Homo sapiens 0.997
CHEMBL240 HERG Homo sapiens 0.993
CHEMBL208 Progesterone receptor Homo sapiens 0.992
CHEMBL4822 Beta-secretase 1 Homo sapiens 0.611
CHEMBL1994 Mineralocorticoid receptor Homo sapiens 0.586
CHEMBL222 Norepinephrine transporter Homo sapiens 0.322



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL6184 Transporter Rattus norvegicus 1.000
CHEMBL313 Serotonin transporter Rattus norvegicus 1.000
CHEMBL228 Serotonin transporter Homo sapiens 1.000
CHEMBL240 HERG Homo sapiens 0.999
CHEMBL231 Histamine H1 receptor Homo sapiens 0.998
CHEMBL208 Progesterone receptor Homo sapiens 0.998
CHEMBL222 Norepinephrine transporter Homo sapiens 0.958
CHEMBL4822 Beta-secretase 1 Homo sapiens 0.861
CHEMBL315 Alpha-1b adrenergic receptor Rattus norvegicus 0.823
CHEMBL1994 Mineralocorticoid receptor Homo sapiens 0.691
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.520
CHEMBL338 Dopamine transporter Rattus norvegicus 0.283
CHEMBL2799 Dopamine transporter Mus musculus 0.282
CHEMBL344 Melanin-concentrating hormone receptor 1 Homo sapiens 0.260

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
324.4 324.1638 3.81 5 36.26 BASE


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
3 0 0 3 0 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 9.57 3.48 1.35 2 24 0.84

Structural Alerts

There are no structural alerts for CHEMBL549

Compound Cross References

ATC N - NERVOUS SYSTEM
N06 - PSYCHOANALEPTICS
N06A - ANTIDEPRESSANTS
N06AB - Selective serotonin reuptake inhibitors
N06AB04 - citalopram

ChemSpider ChemSpider:WSEQXVZVJXJVFP-UHFFFAOYSA-N
DailyMed citalopram hydrobromide
PubChem SID: 174007166 SID: 50104852 SID: 90340852
Wikipedia Citalopram

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL549



ACToR 59729-33-8
BindingDB 25870
Brenda 75639
ChEBI 77397
ChemicalBook CB5244937
DrugBank DB00215
DrugCentral 663
eMolecules 901656
EPA CompTox Dashboard DTXSID8022826
Guide to Pharmacology 7547 4621
Human Metabolome Database HMDB0005038
IBM Patent System 8B7A18F18379443A8753B5BA897B49D7
KEGG Ligand C07572
LINCS LSM-1585
Mcule MCULE-5882770916
MolPort MolPort-003-666-794
NIH Clinical Collection SAM002589960
Nikkaji J18.081E
NMRShiftDB 20182136
PharmGKB PA449015
PubChem 2771
PubChem: Thomson Pharma 14826333
SureChEMBL SCHEMBL946

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/WSEQXVZVJXJVFP-UHFFFAOYSA-N spacer
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