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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL809
CHEMBL809
Compound Name SERTRALINE
ChEMBL Synonyms SERTRALINE HYDROCHLORIDE | CP-51974-1 | BESITRON | AREMIS | ZOLOFT | SERTRALINE | LUSTRAL | CP-51,974-1
Max Phase 4 (Approved)
Trade Names LUSTRAL | AREMIS | BESITRON | SERTRALINE HYDROCHLORIDE | ZOLOFT
Molecular Formula C17H17Cl2N

Additional synonyms for CHEMBL809 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CN[C@H]1CC[C@@H](c2ccc(Cl)c(Cl)c2)c3ccccc13
Standard InChI InChI=1S/C17H17Cl2N/c1-20-17-9-7-12(13-4-2-3-5-14(13)17)11-6 ...
Download InChI
Standard InChI Key VGKDLMBJGBXTGI-SJCJKPOMSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • DrugMatrix
  • Drugs for Neglected Diseases Initiative (DNDi)
  • 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


CHEMBL809

Molecule Features

CHEMBL809 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:N First In Class:N Chirality:Single Stereoisomer 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
AlcoholismD000437EFO:0003829alcohol dependence2ClinicalTrials
Depression, PostpartumD019052EFO:0007453postpartum depression2ClinicalTrials
SchizophreniaD012559EFO:0000692schizophrenia3ClinicalTrials
Substance-Related DisordersD019966EFO:0003890drug dependence2ClinicalTrials
Wounds and InjuriesD014947EFO:0000546injury2ClinicalTrials
Depressive DisorderD003866EFO:0003761unipolar depression4ATC
ClinicalTrials
ClinicalTrials
Child Development Disorders, PervasiveD002659EFO:0003756autism spectrum disorder2ClinicalTrials
Leukemia, Myeloid, AcuteD015470EFO:0000222acute myeloid leukemia1ClinicalTrials
PruritusD011537HP:0000989Pruritus2ClinicalTrials
Bipolar DisorderD001714EFO:0000289bipolar disorder3ClinicalTrials
ObesityD009765EFO:0001073obesity1ClinicalTrials
Sleep Initiation and Maintenance DisordersD007319EFO:0004698insomnia3ClinicalTrials
GlioblastomaD005909EFO:0000519glioblastoma multiforme1ClinicalTrials
Mood DisordersD019964EFO:0004247mood disorder2ClinicalTrials
Stress Disorders, Post-TraumaticD013313EFO:0001358post-traumatic stress disorder3ClinicalTrials
ClinicalTrials
Cocaine-Related DisordersD019970EFO:0002610cocaine dependence2ClinicalTrials
CoccidioidomycosisD003047EFO:0007211coccidioidomycosis2ClinicalTrials
Meningitis, CryptococcalD016919EFO:0007228cryptococcal meningitis3ClinicalTrials
Panic DisorderD016584EFO:0004262panic disorder2ClinicalTrials
ClinicalTrials
Intellectual DisabilityD008607EFO:0003847mental retardation2ClinicalTrials
Autistic DisorderD001321EFO:0003758autism3ClinicalTrials
Fragile X SyndromeD005600Orphanet:908Fragile X syndrome2ClinicalTrials
Hepatitis CD006526EFO:0003047hepatitis C infection1ClinicalTrials
Myelodysplastic SyndromesD009190EFO:0000198myelodysplastic syndrome1ClinicalTrials
AnxietyD001007EFO:0005230anxiety3ClinicalTrials
DementiaD003704HP:0000726dementia3ClinicalTrials
Meningitis, FungalD016921EFO:1000942fungal meningitis3ClinicalTrials
Obsessive-Compulsive DisorderD009771EFO:0004242obsessive-compulsive disorder3ClinicalTrials
Phobia, SocialD000072861EFO:1001917social anxiety disorder3ClinicalTrials

Clinical Data

ClinicalTrials.gov SERTRALINE
The Cochrane Collaboration SERTRALINE

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 CHEMBL809. 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
CHEMBL238 Dopamine transporter Homo sapiens 1.000
CHEMBL304 Norepinephrine transporter Rattus norvegicus 1.000
CHEMBL222 Norepinephrine transporter Homo sapiens 1.000
CHEMBL228 Serotonin transporter Homo sapiens 1.000
CHEMBL313 Serotonin transporter Rattus norvegicus 1.000
CHEMBL338 Dopamine transporter Rattus norvegicus 1.000
CHEMBL6184 Transporter Rattus norvegicus 1.000
CHEMBL2370 Norepinephrine transporter Mus musculus 1.000
CHEMBL2799 Dopamine transporter Mus musculus 0.991
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.965
CHEMBL2327 Neurokinin 2 receptor Homo sapiens 0.928
CHEMBL287 Sigma opioid receptor Homo sapiens 0.862
CHEMBL1942 Alpha-2b adrenergic receptor Homo sapiens 0.845
CHEMBL1075228 Melanin-concentrating hormone receptor 1 Rattus norvegicus 0.456
CHEMBL2781 Sodium/hydrogen exchanger 1 Homo sapiens 0.450
CHEMBL340 Cytochrome P450 3A4 Homo sapiens 0.258
CHEMBL4306 Voltage-gated potassium channel subunit Kv1.5 Homo sapiens 0.258



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL222 Norepinephrine transporter Homo sapiens 1.000
CHEMBL238 Dopamine transporter Homo sapiens 1.000
CHEMBL304 Norepinephrine transporter Rattus norvegicus 1.000
CHEMBL228 Serotonin transporter Homo sapiens 1.000
CHEMBL338 Dopamine transporter Rattus norvegicus 1.000
CHEMBL313 Serotonin transporter Rattus norvegicus 1.000
CHEMBL2370 Norepinephrine transporter Mus musculus 1.000
CHEMBL6184 Transporter Rattus norvegicus 1.000
CHEMBL2799 Dopamine transporter Mus musculus 0.999
CHEMBL2327 Neurokinin 2 receptor Homo sapiens 0.951
CHEMBL287 Sigma opioid receptor Homo sapiens 0.892
CHEMBL1075228 Melanin-concentrating hormone receptor 1 Rattus norvegicus 0.691
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.451
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.406
CHEMBL1942 Alpha-2b adrenergic receptor Homo sapiens 0.296

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
306.2 305.0738 5.18 2 12.03 BASE


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
1 1 1 1 1 1


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 9.47 5.08 3.04 2 20 0.81

Structural Alerts

There are no structural alerts for CHEMBL809

Compound Cross References

ATC N - NERVOUS SYSTEM
N06 - PSYCHOANALEPTICS
N06A - ANTIDEPRESSANTS
N06AB - Selective serotonin reuptake inhibitors
N06AB06 - sertraline

ChemSpider ChemSpider:VGKDLMBJGBXTGI-SJCJKPOMSA-N
DailyMed sertraline hydrochloride
PubChem SID: 26753299 SID: 29215139 SID: 49665783 SID: 50105682 SID: 50105683 SID: 50105684 SID: 50105685 SID: 90341218
Wikipedia Sertraline

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL809



ACToR 79617-96-2
BindingDB 50028094 79021
Brenda 145083 145997 10052
ChEBI 9123
ChemicalBook CB5157644
DrugBank DB01104
DrugCentral 2436
eMolecules 29542786
EPA CompTox Dashboard DTXSID6023577
FDA SRS QUC7NX6WMB
Guide to Pharmacology 4798
Human Metabolome Database HMDB0005010
IBM Patent System 496EBCD735AEA519FE91BF467A47857F
KEGG Ligand C07246
LINCS LSM-3843
Mcule MCULE-4360779618
Nikkaji J33.072H
PDBe SRE
PharmGKB PA451333
PubChem 68617
PubChem: Thomson Pharma 14923174 14776364
SureChEMBL SCHEMBL28701
ZINC ZINC000001853550

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