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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1535
CHEMBL1535
Compound Name HYDROXYCHLOROQUINE
ChEMBL Synonyms HYDROXYCHLOROQUINE | Quensyl | OXICHLOROCHINE SULFATE | Oxichlorochine | Ercoquin | HYDROXYCHLOROQUINE SULFATE | PLAQUENIL
Max Phase 4 (Approved)
Trade Names Ercoquin | Oxichlorochine | PLAQUENIL | Hydroxychloroquine sulfate | Quensyl
Molecular Formula C18H26ClN3O

Additional synonyms for CHEMBL1535 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CCN(CCO)CCCC(C)Nc1ccnc2cc(Cl)ccc12
Standard InChI InChI=1S/C18H26ClN3O/c1-3-22(11-12-23)10-4-5-14(2)21-17-8-9- ...
Download InChI
Standard InChI Key XXSMGPRMXLTPCZ-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • DrugMatrix
  • GSK Malaria Screening
  • Manually Added Drugs
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • St Jude Leishmania Screening
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL1535

Molecule Features

CHEMBL1535 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
Ferriprotoporphyrin IX inhibitor Ferriprotoporphyrin IX PubMed
Toll-like receptor 7 antagonist Toll-like receptor 7 DailyMed FDA PubMed PubMed
Toll-like receptor 9 antagonist Toll-like receptor 9 DailyMed FDA PubMed PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
LUNG DISEASES, INTERSTITIALD017563EFO:0004244INTERSTITIAL LUNG DISEASE2ClinicalTrials

Clinical Data

ClinicalTrials.gov HYDROXYCHLOROQUINE
The Cochrane Collaboration HYDROXYCHLOROQUINE

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 CHEMBL1535. 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
CHEMBL1923 Histidine-rich protein Plasmodium falciparum 1.000

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL1923 Histidine-rich protein Plasmodium falciparum 1.000
CHEMBL2535 Glucose transporter Homo sapiens 0.969
CHEMBL2414 C-C chemokine receptor type 4 Homo sapiens 0.960
CHEMBL4697 Hexose transporter 1 Plasmodium falciparum 0.902
CHEMBL3721 Cytochrome P450 2C8 Homo sapiens 0.737
CHEMBL3241 Histamine N-methyltransferase Rattus norvegicus 0.647
CHEMBL5903 Activin receptor type-1 Homo sapiens 0.596

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
335.9 335.1764 3.46 9 48.39 BASE


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
4 2 0 4 2 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 8.87 3.53 2 2 23 0.74

Structural Alerts

There are 1 structural alerts for CHEMBL1535. To view alerts please click here.

Compound Cross References

ATC P - ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
P01 - ANTIPROTOZOALS
P01B - ANTIMALARIALS
P01BA - Aminoquinolines
P01BA02 - hydroxychloroquine

ChemSpider ChemSpider:XXSMGPRMXLTPCZ-UHFFFAOYSA-N
DailyMed hydroxychloroquine sulfate
PubChem SID: 29215442
Wikipedia Hydroxychloroquine

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1535



ACToR 118-42-3
Brenda 38397
ChEBI 5801
DrugBank DB01611
DrugCentral 1395
eMolecules 901965
EPA CompTox Dashboard DTXSID8023135
Guide to Pharmacology 7198
Human Metabolome Database HMDB0015549
IBM Patent System 4B4D95C1EEEB46C7328034CC06C58CC3
KEGG Ligand C07043
LINCS LSM-5193
Mcule MCULE-6282304706
Nikkaji J5.298A
PharmGKB PA164777036
PubChem 3652
PubChem: Thomson Pharma 14777730
SureChEMBL SCHEMBL8170

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