General
Preferred name
HYDROXYCHLOROQUINE
Synonyms
HYDROXYCHLOROQUINE SULFATE ()
HCQ sulfate ()
Acidum iopanoicum ()
Hydroxychloroquine (sulfate) ()
Hydroxychloroquine sulfate ()
HCQ (sulfate) ()
Hydroxychloroquine Sulfate (NSC 4375) ()
HCQ ()
Oxichlorochine Sulfate ()
TCMDC-123987 ()
Hydroxychloroquine sulphate ()
Quinoric ()
Plaquenil ()
Ercoquin ()
NSC-4375 ()
Oxiklorin ()
Oxichlorochine ()
Quensyl ()
Polirreumin ()
Hydroxychloroquine-d4 (sulfate) ()
P&D ID
PD009448
CAS
747-36-4
118-42-3
1854126-45-6
Tags
nuisance
natural product
drug
available
Approved by
FDA
First approval
1955
Drug Status
approved
Drug indication
Coronavirus Disease 2019 (COVID-19)
Antimalarial
Suppressant (lupus erythematosus)
Malaria
Max Phase
Phase 4
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
DESCRIPTION
Although this drug has direct effects on survival of the malaria parasite it also appears to be an antagonist of two of the human TOLL-like receptors (TLR7 and TLR9). Antagonism of these receptors is likely related to the anti-inflammatory action of this drug in some auto-immune diseases.
DESCPRITION
A chemotherapeutic agent that acts against erythrocytic forms of malarial parasites. Hydroxychloroquine appears to concentrate in food vacuoles of affected protozoa. It inhibits plasmodial heme polymerase. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p970)
DESCRIPTION
Hydroxychloroquine is a 4-aminoquinoline and used primarily as an antimalarial drug.
The approved drug is a racemic mixture and we show the chemical structure without stereochemistry to represent the mixture. The non-isomeric structure is also represented in the PubChem, ChEMBL and ChEBI entries listed in the links table below, while the two enantiomers forming the racemate are represented by PubChem CID 178395 and PubChem CID 178396.
The marketed formulations contain hydroxychloroquine sulfate (PubChem CID 3044369).
Potential Target/Mechanism Of Action: Although this drug has direct effects on survival of the malaria parasite it also appears to be an antagonist of two of the human TOLL-like receptors (TLR7 and TLR9). Antagonism of these receptors is likely related to the anti-inflammatory action of this drug in some auto-immune diseases.
The approved drug is a racemic mixture and we show the chemical structure without stereochemistry to represent the mixture. The non-isomeric structure is also represented in the PubChem, ChEMBL and ChEBI entries listed in the links table below, while the two enantiomers forming the racemate are represented by PubChem CID 178395 and PubChem CID 178396.
The marketed formulations contain hydroxychloroquine sulfate (PubChem CID 3044369).
Potential Target/Mechanism Of Action: Although this drug has direct effects on survival of the malaria parasite it also appears to be an antagonist of two of the human TOLL-like receptors (TLR7 and TLR9). Antagonism of these receptors is likely related to the anti-inflammatory action of this drug in some auto-immune diseases.
DESCRIPTION
Hydroxychloroquine (HCQ) is a 4-aminoquinoline and used primarily as an antimalarial drug.
The approved drug is a racemic mixture and we show the chemical structure without stereochemistry to represent the mixture. The non-isomeric structure is also represented in the PubChem, ChEMBL and ChEBI entries listed in the links table below, while the two enantiomers forming the racemate are represented by PubChem CID 178395 and PubChem CID 178396.
The marketed formulations contain hydroxychloroquine sulfate (PubChem CID 3044369).
Activity at non-malarial protein targets:
Although this drug has direct effects on survival of the malaria parasite it also appears to be an antagonist of two of the human TOLL-like receptors (TLR7 and TLR9). Antagonism of these receptors is likely related to the anti-inflammatory action of this drug in auto-immune diseases. Some patients with systemic lupus erythematosus (SLE) and rheumatoid arthritis are prescribed HCQ .
Activity against SARS-CoV-2:
Hydroxychloroquine exhibits in vitro antiviral activity against both the original SARS coronavirus (SARS-CoV) and SARS-CoV-2 which emerged in 2019 . Extreme caution must be taken when condisering using hydroxychloroquine (HCQ) as it has severe cardiac adverse effects, and in addition its distribution to lung tissue is unknown. There was much hype around repositioning HCQ to treat COVID-19. But this was based on preliminary evidence from a cohort of COVID-19 patients in a VERY small study and anecdotal evidence that patients taking HCQ for other diseases fared better if they developed COVID-19. There was also a lot of controversy around some of the larger scale trials, particularly of how they were carried out, and/or how they were reported or published. Results from subsequent well run, well powered, large scale RCTs does not support any clinical benefit from HCQ in COVID-19 patients. HCQ may even pose an acceptable risk of harm in COVID19 patients . Derek Lowe's 'In the PIPELINE' blog (https://bit.ly/31C7DT1) provides a systematic and considered anaylsis of the (lack of) potential for hydroxychloroquine/chloroquine for COVID-19. (GtoPdb)
The approved drug is a racemic mixture and we show the chemical structure without stereochemistry to represent the mixture. The non-isomeric structure is also represented in the PubChem, ChEMBL and ChEBI entries listed in the links table below, while the two enantiomers forming the racemate are represented by PubChem CID 178395 and PubChem CID 178396.
The marketed formulations contain hydroxychloroquine sulfate (PubChem CID 3044369).
Activity at non-malarial protein targets:
Although this drug has direct effects on survival of the malaria parasite it also appears to be an antagonist of two of the human TOLL-like receptors (TLR7 and TLR9). Antagonism of these receptors is likely related to the anti-inflammatory action of this drug in auto-immune diseases. Some patients with systemic lupus erythematosus (SLE) and rheumatoid arthritis are prescribed HCQ .
Activity against SARS-CoV-2:
Hydroxychloroquine exhibits in vitro antiviral activity against both the original SARS coronavirus (SARS-CoV) and SARS-CoV-2 which emerged in 2019 . Extreme caution must be taken when condisering using hydroxychloroquine (HCQ) as it has severe cardiac adverse effects, and in addition its distribution to lung tissue is unknown. There was much hype around repositioning HCQ to treat COVID-19. But this was based on preliminary evidence from a cohort of COVID-19 patients in a VERY small study and anecdotal evidence that patients taking HCQ for other diseases fared better if they developed COVID-19. There was also a lot of controversy around some of the larger scale trials, particularly of how they were carried out, and/or how they were reported or published. Results from subsequent well run, well powered, large scale RCTs does not support any clinical benefit from HCQ in COVID-19 patients. HCQ may even pose an acceptable risk of harm in COVID19 patients . Derek Lowe's 'In the PIPELINE' blog (https://bit.ly/31C7DT1) provides a systematic and considered anaylsis of the (lack of) potential for hydroxychloroquine/chloroquine for COVID-19. (GtoPdb)
DESCRIPTION
Wnt pathway inhibitor
(Tocris Bioactive Compound Library)
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Cell lines
0
Organisms
3
Compound Sets
32
AdooQ Bioactive Compound Library
Axon Medchem Screening Library
CeMM library of unique drugs (CLOUD)
ChEMBL Approved Drugs
ChEMBL Drugs
Concise Guide to Pharmacology 2017/18
Concise Guide to Pharmacology 2019/20
Concise Guide to Pharmacology 2021/22
Concise Guide to Pharmacology 2023/24
Drug Repurposing Hub
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMAP Approved Drugs
DrugMatrix
Enamine BioReference Compounds
EU-OPENSCREEN Bioactive Compound Library
Guide to Pharmacology
LSP-MoA library (Laboratory of Systems Pharmacology)
MedChem Express Bioactive Compound Library
NCATS Inxight Approved Drugs
NPC Screening Collection
Nuisance compounds in cellular assays
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
TargetMol Bioactive Compound Library
The Spectrum Collection
Tocris Bioactive Compound Library
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
65
Molecular Weight
335.18
Hydrogen Bond Acceptors
4
Hydrogen Bond Donors
2
Rotatable Bonds
9
Ring Count
2
Aromatic Ring Count
2
cLogP
3.78
TPSA
48.39
Fraction CSP3
0.5
Chiral centers
1.0
Largest ring
6.0
QED
0.73
Structural alerts
1
CAD
Nuisance compounds in cellular assays
Related compounds
Custom attributes
(extracted from source data)
Target
Toll-like receptor 7
Toll-like receptor 9
Ferriprotoporphyrin IX
DNA
TLR9
TLR7, TLR9
Antimalarial drug
Parasite
SARS-CoV
Toll-like Receptor (TLR)
Anti-infection,Autophagy,COVID-19,TLR
MOA
toll-like receptor antagonist
DNA Alkylation inhibitor
Inhibitor
antimalarial agent
Pathway
DNA Damage/DNA Repair
Immunology/Inflammation
Anti-infection
Primary Target
Autophagy
Indication
malaria
Therapeutic Class
Antimalarials
Antiviral Agents
Source data
