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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1535
CHEMBL1535
Compound Name HYDROXYCHLOROQUINE
ChEMBL Synonyms Oxichlorochine | Quensyl | PLAQUENIL | OXICHLOROCHINE SULFATE | Hydroxychloroquine | Ercoquin | HYDROXYCHLOROQUINE SULFATE | QUINORIC
Max Phase 4 (Approved)
Trade Names Ercoquin | HYDROXYCHLOROQUINE SULFATE | Oxichlorochine | PLAQUENIL | QUINORIC | 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 FDA PubMed PubMed
Toll-like receptor 9 antagonist Toll-like receptor 9 FDA PubMed PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Carcinoma, Non-Small-Cell LungD002289EFO:0003060non-small cell lung carcinoma2ClinicalTrials
Crohn DiseaseD003424EFO:0000384Crohn's disease2ClinicalTrials
Cystic FibrosisD003550Orphanet:586Cystic fibrosis1ClinicalTrials
Diabetes Mellitus, Type 1D003922EFO:0001359type I diabetes mellitus2ClinicalTrials
Graft vs Host DiseaseD006086EFO:0004599acute graft vs. host disease3ClinicalTrials
Hepatitis C, ChronicD019698EFO:0004220Chronic Hepatitis C infection1ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-CellD015451EFO:0000095chronic lymphocytic leukemia2ClinicalTrials
MalariaD008288EFO:0001068malaria4ATC
Small Cell Lung CarcinomaD055752EFO:0000702small cell lung carcinoma2ClinicalTrials
Lung Diseases, InterstitialD017563EFO:0004244interstitial lung disease2ClinicalTrials
Rheumatic DiseasesD012216EFO:0005755rheumatic disease1ClinicalTrials
Diabetes Mellitus, Type 2D003924EFO:0001360type II diabetes mellitus2ClinicalTrials
Giant Cell ArteritisD013700EFO:1001209temporal arteritis3ClinicalTrials
GliomaD005910EFO:0000326central nervous system cancer1ClinicalTrials
LeukemiaD007938EFO:0000565leukemia2ClinicalTrials
Multiple MyelomaD009101EFO:0001378multiple myeloma1ClinicalTrials
Ovarian NeoplasmsD010051EFO:0001075ovarian carcinoma1ClinicalTrials
Sarcoidosis, PulmonaryD017565DOID:13406pulmonary sarcoidosis3ClinicalTrials
Sjogren's SyndromeD012859EFO:0000699Sjogren syndrome3ClinicalTrials
Abortion, HabitualD000026EFO:1000954habitual abortion3ClinicalTrials
Arthritis, RheumatoidD001172EFO:0000685rheumatoid arthritis3ClinicalTrials
Carcinoma, Renal CellD002292EFO:0000349clear cell renal carcinoma1ClinicalTrials
Insulin ResistanceD007333EFO:0002614insulin resistance1ClinicalTrials
Osteoarthritis, KneeD020370EFO:0004616osteoarthritis, knee2ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma2ClinicalTrials
GlioblastomaD005909EFO:0000519glioblastoma multiforme2ClinicalTrials
Lichen PlanusD008010EFO:1000726lichen planus2ClinicalTrials
Lung NeoplasmsD008175EFO:0001071lung carcinoma1ClinicalTrials
Lupus Erythematosus, SystemicD008180EFO:0002690systemic lupus erythematosus2ClinicalTrials
ClinicalTrials
MelanomaD008545EFO:0000756melanoma1ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm1ClinicalTrials
Carcinoma, Renal CellD002292EFO:0000681renal cell carcinoma1ClinicalTrials
MelanomaD008545EFO:0000389cutaneous melanoma1ClinicalTrials
OsteoarthritisD010003EFO:0002506osteoarthritis3ClinicalTrials
Prostatic NeoplasmsD011471EFO:0001663prostate carcinoma2ClinicalTrials
Hidradenitis SuppurativaD017497EFO:1000710hidradenitis suppurativa1ClinicalTrials
LymphangioleiomyomatosisD018192Orphanet:538Lymphangioleiomyomatosis1ClinicalTrials
Multiple Sclerosis, Chronic ProgressiveD020528EFO:0003840chronic progressive multiple sclerosis2ClinicalTrials
Antiphospholipid SyndromeD016736EFO:0002689antiphospholipid syndrome3ClinicalTrials
Carcinoma, HepatocellularD006528EFO:0000182hepatocellular carcinoma2ClinicalTrials
Hepatitis CD006526EFO:0003047hepatitis C infection1ClinicalTrials
Leukemia, Myeloid, AcuteD015470EFO:0000222acute myeloid leukemia1ClinicalTrials
NeoplasmsD009369EFO:0000311cancer1ClinicalTrials
PregnancyD011247EFO:0002950pregnancy3ClinicalTrials
SarcomaD012509EFO:0000691sarcoma2ClinicalTrials
AdenocarcinomaD000230EFO:0000228adenocarcinoma1ClinicalTrials
Colorectal NeoplasmsD015179EFO:1001951colorectal carcinoma2ClinicalTrials
HIV InfectionsD015658EFO:0000764HIV infection2ClinicalTrials
Multiple SclerosisD009103EFO:0003885multiple sclerosis1ClinicalTrials
Pancreatic NeoplasmsD010190EFO:0002618pancreatic carcinoma2ClinicalTrials
Porphyria Cutanea TardaD017119Orphanet:101330Porphyria cutanea tarda2ClinicalTrials
ThrombocytopeniaD013921HP:0001873thrombocytopenia3ClinicalTrials

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
CHEMBL2414 C-C chemokine receptor type 4 Homo sapiens 0.963

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
CHEMBL4697 Hexose transporter 1 Plasmodium falciparum 0.956
CHEMBL2535 Glucose transporter Homo sapiens 0.742
CHEMBL3241 Histamine N-methyltransferase Rattus norvegicus 0.603
CHEMBL3721 Cytochrome P450 2C8 Homo sapiens 0.346

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
335.9 335.1764 3.78 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 0.73

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
MolPort MolPort-003-847-792
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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