General
Preferred name
CHLOROQUINE
Synonyms
CHLOROQUINE DIPHOSPHATE ()
Cloquinate ()
Aralen phosphate ()
Chingamin phosphate ()
Chloroquine (HCl) ()
Chloroquine Phosphate ()
CHLOROQUINE SULFATE MONOHYDRATE ()
Chloroquine phosphate ()
Chloroquine (phosphate) ()
chloroquine, DualTPharma ()
CHLOROQUINE SULPHATE ()
CHLOROQUINE HYDROCHLORIDE ()
Chloroquine (NSC-187208) ()
Aralen, CHQ, CQ ()
Malaquin ()
Chloroquini phosphas ()
Aralen ()
Resochin ()
Arechin ()
Malarivon ()
WR-1522 ()
SN-7618 ()
Chloroquine Diphosphate ()
NSC-14050 ()
Avloclor ()
NSC-187208 ()
Chlorochine ()
Chloroquine ()
Aralen HCl ()
Chloroquine HCl ()
NSC-292296 ()
Chloroquini sulfas ()
Chloroquine sulfate ()
Aralen hydrochloride ()
Chloroquine-d5 (phosphate) ()
P&D ID
PD009894
CAS
50-63-5
69698-56-2
54-05-7
58175-87-4
58175-86-3
56598-66-4
3545-67-3
1446-17-9
117399-83-4
1854126-42-3
Tags
obsolete probe
nuisance
natural product
drug
available
Approved by
FDA
First approval
1949
Drug Status
investigational
approved
vet_approved
Drug indication
Suppressant (lupus erythematosus)
Severe acute respiratory syndrome (SARS)
Antimalarial,Anti-Amebic
Antimalarial
Anti-Amebic
Malaria
Coronavirus Disease 2019 (COVID-19)
Middle East Respiratory Syndrome (MERS)
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
Chloroquine is primarily an antimalarial. In humans chloroquine inhibits thiamine uptake acting specifically on thiamine transporter 2 (SLC19A3). Other uses of chloroquine include treatment of autoimmune disorders (rheumatoid arthritis and lupus erythematosus), as an antiretroviral (HIV-1/AIDS and chikungunya fever) and as a radiosensitizing/chemosensitizing agent benefitting cancer therapies.
Marketed formulations may contain chloroquine phosphate (PubChem CID 64927).
Marketed formulations may contain chloroquine phosphate (PubChem CID 64927).
DESCRIPTION
Chloroquine is primarily an antimalarial drug. In humans chloroquine inhibits thiamine uptake acting specifically on thiamine transporter 2 (SLC19A3). Other uses of chloroquine include treatment of autoimmune disorders (rheumatoid arthritis and lupus erythematosus), as an antiretroviral (HIV-1/AIDS and chikungunya fever) and as a radiosensitizing/chemosensitizing agent benefitting cancer therapies.
Marketed formulations may contain chloroquine phosphate (PubChem CID 64927).
Chloroquine is one of the antimalarials listed in the WHO 20th Essential Medicines List (2017).
Marketed formulations may contain chloroquine phosphate (PubChem CID 64927).
Chloroquine is one of the antimalarials listed in the WHO 20th Essential Medicines List (2017).
MOA
The mechanism behind the plasmodicidal action of chloroquine is not completely certain. Like other quinoline derivatives, it is thought to inhibit the heme polymerase activity, resulting in an accumulation of free heme, which is toxic to the parasites. Inside red blood cells, the malarial parasite must degrade hemoglobin in vacuoles to acquire essential amino acids, which the parasite requires to construct its own protein and for energy metabolism. Degradation of hemoglobin involves the production of toxic heme, which consists of a porphyrin ring called Fe(II)-protoporphyrin IX (FP). To avoid destruction by this molecule, the parasite biocrystallizes heme to form hemosoin, which is non-toxic, which is collected in the digestive vacuole as insoluble crystals. Chloroquine enters the red blood cell, inhabiting parasite cell, and digestive vacuole by simple diffusion. Upon entry into the digestive vacuole, chloroquine become protonated due the acidic nature of the vacuole and this prevents chloroquine from leaving the vacuole via simple diffusion. The drug then mediates its plasmodicidal effect by capping hemozoin molecules to prevent further biocrystallization of heme, leading to heme buildup. Chloroquine can also bind to heme to form the toxic FP-Chloroquine complex, which is highly toxic to the cell. The complex disrupts the membrane function to promote cell lysis and ultimately, parasitic cell autodigestion.
DESCPRITION
The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.
DESCRIPTION
Chloroquine is a 4-aminoquinoline and used primarily as an antimalarial drug.
In humans, chloroquine inhibits thiamine uptake acting specifically on thiamine transporter 2 (SLC19A3). Other uses of chloroquine include treatment of autoimmune disorders (rheumatoid arthritis and lupus erythematosus), as an antiretroviral (HIV-1/AIDS and chikungunya fever) and as a radiosensitizing/chemosensitizing agent benefitting cancer therapies.
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 444810 and PubChem CID 639540.
Marketed formulations may contain chloroquine phosphate (PubChem CID 64927).
Chloroquine is one of the antimalarials listed in the WHO 20th Essential Medicines List (2017).
In humans, chloroquine inhibits thiamine uptake acting specifically on thiamine transporter 2 (SLC19A3). Other uses of chloroquine include treatment of autoimmune disorders (rheumatoid arthritis and lupus erythematosus), as an antiretroviral (HIV-1/AIDS and chikungunya fever) and as a radiosensitizing/chemosensitizing agent benefitting cancer therapies.
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 444810 and PubChem CID 639540.
Marketed formulations may contain chloroquine phosphate (PubChem CID 64927).
Chloroquine is one of the antimalarials listed in the WHO 20th Essential Medicines List (2017).
DESCRIPTION
Chloroquine 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 444810 and PubChem CID 639540. The PDB entry listed in the links table is for (R)-chloroquine.
Marketed formulations may contain chloroquine phosphate (PubChem CID 64927).
The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY. (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 444810 and PubChem CID 639540. The PDB entry listed in the links table is for (R)-chloroquine.
Marketed formulations may contain chloroquine phosphate (PubChem CID 64927).
The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY. (GtoPdb)
DESCRIPTION
Antimalarial
(Tocris Bioactive Compound Library)
DESCRIPTION
An antimalarial agent.
(BOC Sciences Bioactive Compounds)
DESCRIPTION
Antimalarial; anti-amoebic; anti-inflammatory; binds strongly to double-stranded DNA
(LOPAC library)
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Cell lines
36
Organisms
33
Compound Sets
35
AdooQ Bioactive Compound Library
Axon Medchem Screening Library
BOC Sciences Bioactive Compounds
CeMM library of unique drugs (CLOUD)
ChEMBL Approved Drugs
ChEMBL Drugs
Concise Guide to Pharmacology 2023/24
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMAP Approved Drugs
DrugMatrix
Enamine BioReference Compounds
Guide to Pharmacology
Ki Database
LINCS compound set
LOPAC library
LSP-MoA library (Laboratory of Systems Pharmacology)
NCATS Inxight Approved Drugs
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
Nuisance compounds in cellular assays
Obsolete Compounds
Other bioactive compounds
Pandemic Response Box
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
111
Molecular Weight
319.18
Hydrogen Bond Acceptors
3
Hydrogen Bond Donors
1
Rotatable Bonds
8
Ring Count
2
Aromatic Ring Count
2
cLogP
4.81
TPSA
28.16
Fraction CSP3
0.5
Chiral centers
1.0
Largest ring
6.0
QED
0.76
Structural alerts
2
CAD
Nuisance compounds in cellular assays
historic compounds (Chemical Probes.org)
Obsolete
Related compounds
Custom attributes
(extracted from source data)
Selectivity
DNA
MOA
Unknown molecular target
TLR
"Thiamine uptake inhibitor
Apoptosis Inducers"
Thiamine uptake inhibitor
Apoptosis Inducers
Target
Ferriprotoporphyrin IX
Hemoglobin subunit alpha
TLR7
TLR9
Antimalarial drug
antibiotic
HIV
Parasite
SARS-CoV
Toll-like Receptor (TLR)
Anti-infection,ATM/ATR,Autophagy,COVID-19,TLR
Autophagy,COVID-19,HIV Protease,TLR
Pathway
Autophagy
Immunology/Inflammation
Anti-infection
Primary Target
Antimalarials
Member status
member
Therapeutic Class
Antiviral Agents
Solubility
In Vitro:<br/>Ethanol : 100 mg/mL(312.63 mM
Need ultrasonic)<br/>DMSO : 50 mg/mL(156.31 mM
Need ultrasonic)<br/>In Vivo:<br/>1.Add each solvent one by one:10% DMSO >> 40%PEG300 >> 5%Tween-80 >> 45% saline<br/>Solubility: ≥ 2.5 mg/mL (7.82 mM)
Clear solution<br/>2.Add each solvent one by one:10% DMSO >> 90% (20%SBE-β-CDin saline)<br/>Solubility: ≥ 2.5 mg/mL (7.82 mM)
Clear solution<br/>3.Add each solvent one by one:10% DMSO >> 90%corn oil<br/>Solubility: ≥ 2.5 mg/mL (7.82 mM)
Clear solution
Source data
