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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL76
CHEMBL76
Compound Name CHLOROQUINE
ChEMBL Synonyms Chloroquine [3H] | NSC-187208 | Chloroquine Diphosphate | Chloroquine Phosphate | CHLOROCHINE | Aralen | Chloroquine | CHLOROQUINE PHOSPHATE | CHLOROQUINE DIPHOSPHATE | ARALEN HYDROCHLORIDE | CHLOROQUINE HYDROCHLORIDE | ARALEN
Max Phase 4 (Approved)
Trade Names ARALEN | ARALEN HYDROCHLORIDE | CHLOROQUINE PHOSPHATE
Molecular Formula C18H26ClN3

Additional synonyms for CHEMBL76 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CCN(CC)CCCC(C)Nc1ccnc2cc(Cl)ccc12
Standard InChI InChI=1S/C18H26ClN3/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-1 ...
Download InChI
Standard InChI Key WHTVZRBIWZFKQO-UHFFFAOYSA-N

Sources

  • British National Formulary
  • Drugs for Neglected Diseases Initiative (DNDi)
  • GSK Malaria Screening
  • Gene Expression Atlas Compounds
  • Manually Added Drugs
  • Novartis Malaria Screening
  • Open Source Malaria Screening
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • St Jude Leishmania Screening
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL76

Molecule Features

CHEMBL76 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Racemic Mixture Prodrug:N Oral:Y Parenteral:Y Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Ferriprotoporphyrin IX inhibitor Ferriprotoporphyrin IX PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
GLIOBLASTOMAD005909EFO:0000519GLIOBLASTOMA MULTIFORME2ClinicalTrials
SMALL CELL LUNG CARCINOMAD055752EFO:0000702SMALL CELL LUNG CARCINOMA1ClinicalTrials
MALARIAD008288EFO:0001068MALARIA4DailyMed
ATC
DailyMed
DailyMed
DailyMed
DailyMed
DailyMed
DailyMed
DailyMed
ClinicalTrials
DailyMed
DailyMed
DailyMed
HIV INFECTIONSD015658EFO:0000764HIV INFECTION2ClinicalTrials
ClinicalTrials
MALARIA, FALCIPARUMD016778EFO:0007444PLASMODIUM FALCIPARUM MALARIA3ClinicalTrials
MALARIA, VIVAXD016780EFO:0007445PLASMODIUM VIVAX MALARIA3ClinicalTrials
ANEMIA, SICKLE CELLD000755Orphanet:232SICKLE CELL ANEMIA2ClinicalTrials
BRAIN DISEASESD001927EFO:0005774BRAIN DISEASE2ClinicalTrials
BREAST NEOPLASMSD001943EFO:0000305BREAST CARCINOMA2ClinicalTrials
INFLUENZA, HUMAND007251EFO:0001669INFLUENZA INFECTION2ClinicalTrials
ATRIAL FIBRILLATIOND001281EFO:0000275ATRIAL FIBRILLATION2ClinicalTrials

Clinical Data

ClinicalTrials.gov CHLOROQUINE
The Cochrane Collaboration CHLOROQUINE

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 CHEMBL76. 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
CHEMBL2414 C-C chemokine receptor type 4 Homo sapiens 1.000
CHEMBL3241 Histamine N-methyltransferase Rattus norvegicus 0.988
CHEMBL2535 Glucose transporter Homo sapiens 0.950
CHEMBL4697 Hexose transporter 1 Plasmodium falciparum 0.815
CHEMBL5903 Activin receptor type-1 Homo sapiens 0.709
CHEMBL1919 Voltage-gated calcium channel alpha2/delta subunit 1 Homo sapiens 0.591
CHEMBL3721 Cytochrome P450 2C8 Homo sapiens 0.336
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.294
CHEMBL5131 Trypanothione reductase Trypanosoma cruzi 0.277

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
319.9 319.1815 4.35 8 28.16 BASE


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
3 1 0 3 1 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 10.47 4.41 1.59 2 22 0.78

Structural Alerts

There are 1 structural alerts for CHEMBL76. To view alerts please click here.

Compound Cross References

ATC P - ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
P01 - ANTIPROTOZOALS
P01B - ANTIMALARIALS
P01BA - Aminoquinolines
P01BA01 - chloroquine

ChemSpider ChemSpider:WHTVZRBIWZFKQO-UHFFFAOYSA-N
DailyMed chloroquine phosphate
PubChem SID: 124879700 SID: 124879705 SID: 174006958 SID: 50111008 SID: 90340711
Wikipedia Chloroquine

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL76



ACToR 56598-66-4 54-05-7 58175-86-3 58175-87-4
BindingDB 22985
Brenda 1439 29852 66870
ChEBI 3638
DrugBank DB00608
DrugCentral 607
eMolecules 740214
EPA CompTox Dashboard DTXSID2040446
Guide to Pharmacology 5535
Human Metabolome Database HMDB0014746
IBM Patent System C022EF9F97B38221EA6B97CFA5858E5B
KEGG Ligand C07625
LINCS LSM-1901
Mcule MCULE-3610827164
Nikkaji J107.997B
NMRShiftDB 10019311
PharmGKB PA448948
PubChem 2719
PubChem: Thomson Pharma 14776983
SureChEMBL SCHEMBL8933

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