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Compound Detail

CHEMBL1690

HYDROXYCHLOROQUINE SULFATE
💊 Approved Drug
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💊 Approved Drug
CCN(CCO)CCCC(C)Nc1ccnc2cc(Cl)ccc12.O=S(=O)(O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1690
Name HYDROXYCHLOROQUINE SULFATE
Phase Approved
Structure Type MOL
InChI Key JCBIVZZPXRZKTI-UHFFFAOYSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL1535
Active Moiety CHEMBL1535

Known Names

Ercoquin Hydroxychloroquine sulfate Hydroxychloroquine sulphate NSC-4375 Oxiklorin Plaquenil Plaquenil sulfate Quensyl Quinoric Sovuna TCMDC-123987
1
Targets
4
Activities
2
Assay Types
0
PK Parameters
20
Publications
11
Known Names
15
Indications
3
Mechanisms

Molecular Properties

335.9
MW (Da)
3.78
ALogP
4
HBA
2
HBD
48.4
PSA (Ų)
0.73
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1955
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Extended Properties

Molecular Formula C18H28ClN3O5S
MW 433.96
Aromatic Rings 2
Heavy Atoms 23
NP-Likeness -1.23

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Ferriprotoporphyrin IX inhibitor INHIBITOR Ferriprotoporphyrin IX ✓ ✓
Toll-like receptor 7 antagonist ANTAGONIST Toll-like receptor 7 ✓ ✓
Toll-like receptor 9 antagonist ANTAGONIST Toll-like receptor 9 ✓ ✓

Indications

Arthritis, Rheumatoid Malaria Coronavirus Infections Lung Diseases Lupus Erythematosus, Cutaneous Lupus Erythematosus, Systemic Severe Acute Respiratory Syndrome Antiphospholipid Syndrome Cholangiocarcinoma Lung Diseases, Interstitial Melanoma Melanoma Nephritis, Hereditary Pancreatic Neoplasms Rheumatic Diseases

Activity Summary

EC50 2 meas. best 5.38
IC50 2 meas. best 5.04

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
SARS-CoV-2
CHEMBL4303835
 EC50 5.38 5.335 4170.0 2
SARS-CoV-2
CHEMBL4303835
 IC50 5.04 4.995 9210.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
SARS-CoV-2 EC50 = 4170.0 nM 5.38 Antiviral efficacy against SARS-CoV-2 (strain BavPat1) in Vero E6 cells assessed... -
SARS-CoV-2 EC50 = 5090.0 nM 5.29 Antiviral activity against SARS-CoV-2 infected in Vero E6 cells assessed as vira... 34875467
SARS-CoV-2 IC50 = 9210.0 nM 5.04 IC50 determination at MOI 0.004 using CellTiter- Glo (CTG) assay, performed 3 da... -
SARS-CoV-2 IC50 = 11170.0 nM 4.95 IC50 determination at MOI 0.01 using CellTiter- Glo (CTG) assay, performed 3 day... -

Literature References

PubMed DOI Target Context # Activities
- 10.1101/2020.03.25.008482 SARS-CoV-2 7
20485427 10.1038/nature09107 Plasmodium falciparum 4
- 10.1101/2020.04.03.023846 SARS-CoV-2 3
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.1101/2020.04.21.054387 SARS-CoV-2 2
34875467 10.1016/j.bmc.2021.116523 SARS-CoV-2 2
- 10.1101/2020.03.25.008482 ADMET 2
- 10.1101/2020.03.25.008482 Vero C1008 2
23956101 10.1093/toxsci/kft176 Bile salt export pump 1
23956101 10.1093/toxsci/kft176 ATP-binding cassette sub-family C member 2 1
23956101 10.1093/toxsci/kft176 ATP-binding cassette sub-family C member 3 1
23956101 10.1093/toxsci/kft176 ATP-binding cassette sub-family C member 4 1
- 10.6019/CHEMBL3433997 Glucose transporter 1
- 10.6019/CHEMBL3433997 Hexose transporter 1 1
- 10.6019/CHEMBL3433997 Solute carrier family 2, facilitated glucose transporter member 1 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B1 1
34875467 10.1016/j.bmc.2021.116523 ADMET 1
- 10.1101/2020.04.03.023846 ADMET 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B3 1
20485427 10.1038/nature09107 HepG2 1

Data from ChEMBL 36 via Core Engine