Chloroquine (CED0001096)

Record Information
Version1.0
Creation Date2009-07-05 03:00:49 UTC
Update Date2026-05-14 16:43:53 UTC
Accession NumberCHEM002087
Identification
Common NameChloroquine
ClassSmall Molecule
Description
Chloroquine belongs to the aminoquinolines and derivatives, a subclass of quinolines and derivatives within the organic compounds. This exogenous compound has the formula C18H26ClN3 and an average molecular weight of 319.87 g/mol. At room temperature, it exists as a solid. It is utilized as a biological drug (PMC9311413) and a biological autophagy inhibitor (PMC10918910, PMC12157995, PMC12512164, PMC13211753, PMC5128862). Recorded exposure routes include oral administration. The compound is used as a treatment for malaria (PMC4621027), COVID-19 (PMC7284245, PMC7376526, PMC7381292, PMC7385928, PMC8243632, PMC8451976), rheumatoid arthritis (PMC8243632, PMC9340490), and leishmaniasis (PMC11943490). It has a therapeutic effect on glioblastoma (PMC12197219) and COVID-19 (PMC8879019). However, it is associated with cardiomyopathy (PMC8515266), hypoglycemia (PMC8515266), and acute renal failure (PMC7362872). Chloroquine targets eleven recorded proteins, including Hemoglobin subunit alpha (HBA1), Tumor necrosis factor (TNF), Toll-like receptor 9 (TLR9), and Glutathione S-transferase A2 (GSTA2). It also acts as an inhibitor or modulator of Cytochrome P450 3A4 (CYP3A4), the Voltage-gated inwardly rectifying potassium channel KCNH2, Glutathione S-transferase (GST), and High mobility group protein B1 (HMGB1), among three other proteins. Its plasmodicidal action is not completely certain, but like other quinoline derivatives, it is thought to inhibit heme polymerase activity, resulting in the accumulation of free heme which is toxic to parasites. Chloroquine is found in 18 recorded sources, including antiprotozoals within healthcare, pharmaceuticals and veterinary products; food preservation within food, food processing and cookware; as well as various household cleaning, consumer, and electrical products.
Contaminant Type
  • Amebicide
  • Amine
  • Antimalarial
  • Antirheumatic Agent
  • Drug
  • Human Neurotoxin
  • Metabolite
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
AralenChEBI
ArtrichinChEBI
BemaphateChEBI
CapquinChEBI
ChlorochinChEBI
ChloroquinumChEBI
CloroquinaChEBI
N(4)-(7-Chloro-4-quinolinyl)-N(1),N(1)-diethyl-1,4-pentanediamineChEBI
Nivaquine bChEBI
ResoquineChEBI
ReumachlorChEBI
SanoquinChEBI
Bemaphic acidGenerator
ChloraquineHMDB
ChlorochineHMDB
ChloroquinaHMDB
ChloroquiniumHMDB
ChlorquinHMDB
ClorochinaHMDB
ChingaminHMDB
ArechineHMDB
KhingaminHMDB
Sulphate, chloroquineHMDB
ArequinHMDB
Chloroquine sulfateHMDB
Chloroquine sulphateHMDB
NivaquineHMDB
Sulfate, chloroquineHMDB
Chemical FormulaC18H26ClN3
Average Molecular Mass319.872 g/mol
Monoisotopic Mass319.182 g/mol
CAS Registry Number54-05-7
IUPAC Name7-chloro-N-[5-(diethylamino)pentan-2-yl]quinolin-4-amine
Traditional Name7-chloro-N-[5-(diethylamino)pentan-2-yl]quinolin-4-amine
SMILESCCN(CC)CCCC(C)NC1=C2C=CC(Cl)=CC2=NC=C1
InChI IdentifierInChI=1S/C18H26ClN3/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21)
InChI KeyWHTVZRBIWZFKQO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 4-aminoquinolines. These are organic compounds containing an amino group attached to the 4-position of a quinoline ring system.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassAminoquinolines and derivatives
Direct Parent4-aminoquinolines
Alternative Parents
Substituents
  • 4-aminoquinoline
  • Haloquinoline
  • Chloroquinoline
  • Aminopyridine
  • Secondary aliphatic/aromatic amine
  • Aryl chloride
  • Aryl halide
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Secondary amine
  • Amine
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateSolid
AppearanceWhite to slightly yellow, crystalline powder (2).
Experimental Properties
PropertyValue
Melting Point289°C
Boiling PointNot Available
Solubility10.6 mg/L
Predicted Properties
PropertyValueSource
Water Solubility0.018 g/LALOGPS
logP5.28ALOGPS
logP3.93ChemAxon
logS-4.3ALOGPS
pKa (Strongest Basic)10.32ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area28.16 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity96.42 m³·mol⁻¹ChemAxon
Polarizability37.29 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-00di-0009000000-d54119d64cfc341cee7dNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00di-0009000000-d54119d64cfc341cee7dNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0pbi-9242000000-6cd79ce1c8a9ada4550dNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-002p-8920000000-552012cb889bf65320d8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0391000000-7360fd3b6728bd6574b8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0029000000-3ea9f3105801d7abf080Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0119000000-8f9d4513bf5993f3c9c4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dl-3957000000-e533e26da609c9329daeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00bc-9530000000-646244109f4c47e0c2a6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0009000000-d45e56a4f82a2d58657dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-1229000000-09769326d92e55dd78aaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00fu-9630000000-f2986e805921cc8d3a37Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0049000000-7e55e664b21e89ddbe44Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dj-0198000000-64a0ed0e3e428bf65cbbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004r-6950000000-75bff8c32e9dcca35dbfNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0009000000-b550e787bd639403cc76Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0109000000-3494d09f71ff43a3ce73Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-2910000000-efba909b8046e2bf2c67Not AvailableView Spectrum
MSMS Spectrumsplash10-000i-9320000000-2663c398ede2e502ca34Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityThe mechanism of plasmodicidal action of chloroquine is not completely certain. Like other quinoline derivatives, it is thought to inhibit heme polymerase activity. This results in accumulation of free heme, which is toxic to the parasites. nside red blood cells, the malarial parasite must degrade hemoglobin to acquire essential amino acids, which the parasite requires to construct its own protein and for energy metabolism. Digestion is carried out in a vacuole of the parasite cell. During this process, the parasite produces the toxic and soluble molecule heme. The heme moiety consists of a porphyrin ring called Fe(II)-protoporphyrin IX (FP). To avoid destruction by this molecule, the parasite biocrystallizes heme to form hemozoin, a non-toxic molecule. Hemozoin collects in the digestive vacuole as insoluble crystals. Chloroquine enters the red blood cell, inhabiting parasite cell, and digestive vacuole by simple diffusion. Chloroquine then becomes protonated (to CQ2+), as the digestive vacuole is known to be acidic (pH 4.7); chloroquine then cannot leave by diffusion. Chloroquine caps hemozoin molecules to prevent further biocrystallization of heme, thus leading to heme buildup. Chloroquine binds to heme (or FP) to form what is known as the FP-Chloroquine complex; this complex is highly toxic to the cell and disrupts membrane function. Action of the toxic FP-Chloroquine and FP results in cell lysis and ultimately parasite cell autodigestion. In essence, the parasite cell drowns in its own metabolic products.
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (4)
Minimum Risk LevelNot Available
SymptomsConvulsive seizures. Mild and transient headache.
TreatmentTreatment is symptomatic and must be prompt with immediate evacuation of the stomach by emesis (at home, before transportation to the hospital) or gastric lavage until the stomach is completely emptied. If finely powdered, activated charcoal is introduced by stomach tube, after lavage, and within 30 minutes after ingestion of the antimalarial, it may inhibit further intestinal absorption of the drug. To be effective, the dose of activated charcoal should be at least five times the estimated dose of chloroquine ingested. Convulsions, if present, should be controlled before attempting gastric lavage. (5)
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
695.0Log mg/kg[390:1200]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
malariais_treatment_forNot AvailablePMC4621027
leishmaniasisis_treatment_forNot AvailablePMC11943490
rheumatoid arthritisis_treatment_forNot AvailablePMC8243632 , PMC9340490
cardiomyopathyassociated_withNot AvailablePMC8515266
COVID-19is_treatment_forNot AvailablePMC7284245 , PMC7376526 , PMC7381292 , PMC7385928 , PMC8243632 , PMC8451976
COVID-19has_therapeutic_effect_onNot AvailablePMC8879019
glioblastomahas_therapeutic_effect_onNot AvailablePMC12197219
hypoglycemiaassociated_withNot AvailablePMC8515266
acute renal failureassociated_withNot AvailablePMC7362872
systemic lupus erythematosusis_treatment_forNot AvailablePMC9340490
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
385AntiprotozoalsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
597ChemosterilantsAgriculture & land managementNot Available
598Fertiliser DistributorsAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
620Card GamesRecreation & sports surfacesNot Available
630ToysRecreation & sports surfacesNot Available
631Anthraquinone DyesTextiles, leather & furnishingsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
Pathways
2 pathways
Chloroquine Action Pathway
Chloroquine Action Pathway
Chloroquine Drug Metabolism Action Pathway
Chloroquine Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureHistidine-rich protein PFHRP-IIP05227Plasmodium falciparumPredicted (SEA)0.0778492
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)2.17978
Muscarinic acetylcholine receptor M2 structureClick to view 3D structureMuscarinic acetylcholine receptor M2P08172HumansPredicted (SEA)1.32344
Muscarinic acetylcholine receptor M3 structureClick to view 3D structureMuscarinic acetylcholine receptor M3P20309HumansPredicted (SEA)1.63483
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)9.10836
Muscarinic acetylcholine receptor M4 structureClick to view 3D structureMuscarinic acetylcholine receptor M4P08173HumansPredicted (SEA)1.40129
Sigma non-opioid intracellular receptor 1 structureClick to view 3D structureSigma non-opioid intracellular receptor 1Q99720HumansPredicted (SEA)5.83869
Click to view 3D structureSigma intracellular receptor 2Q5BJF2HumansPredicted (SEA)3.42537
Muscarinic acetylcholine receptor M1 structureClick to view 3D structureMuscarinic acetylcholine receptor M1P11229HumansPredicted (SEA)6.92858
Histamine N-methyltransferase structureClick to view 3D structureHistamine N-methyltransferaseP50135HumansPredicted (SEA)0.0778492
Alpha-2C adrenergic receptor structureClick to view 3D structureAlpha-2C adrenergic receptorP18825HumansPredicted (SEA)12.2223
Angiotensin-converting enzyme 2 structureClick to view 3D structureAngiotensin-converting enzyme 2Q9BYF1HumansPredicted (SEA)1.63483
Click to view 3D structureRiboflavin-binding proteinP02752Gallus gallusPredicted (SEA)0.0778492
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)74.1125
Amyloid-beta precursor protein structureClick to view 3D structureAmyloid-beta precursor proteinP05067HumansPredicted (SEA)17.4382
Major prion protein structureClick to view 3D structureMajor prion proteinP04156HumansPredicted (SEA)0.233548
Click to view 3D structureAlpha-1D adrenergic receptorP25100HumansPredicted (SEA)32.0739
Serine/threonine-protein kinase mTOR structureClick to view 3D structureSerine/threonine-protein kinase mTORP42345HumansPredicted (SEA)84.9335
Ribosyldihydronicotinamide dehydrogenase [quinone] structureClick to view 3D structureRibosyldihydronicotinamide dehydrogenase [quinone]P16083HumansPredicted (SEA)4.12601
Beta-secretase 1 structureClick to view 3D structureBeta-secretase 1P56817HumansPredicted (SEA)61.0338
Alpha-2B adrenergic receptor structureClick to view 3D structureAlpha-2B adrenergic receptorP18089HumansPredicted (SEA)53.4046
Cytochrome P450 2C8 structureClick to view 3D structureCytochrome P450 2C8P10632HumansPredicted (SEA)43.2842
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)203.809
Replicase polyprotein 1ab structureClick to view 3D structureReplicase polyprotein 1abP0DTD1SARS-CoV-2Predicted (SEA)59.7882
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)343.393
Toll-like receptor 9 structureClick to view 3D structureToll-like receptor 9Q9NR96HumansKnownThe mechanism of plasmodicidal action of chloroquine is not completely certain. Like other quinoline derivatives, it is thought to inhibit heme polymerase activity. This results in accumulation of free heme, which is toxic to the parasites.
Tumor necrosis factor structureClick to view 3D structureTumor necrosis factorP01375HumansKnownThe mechanism of plasmodicidal action of chloroquine is not completely certain. Like other quinoline derivatives, it is thought to inhibit heme polymerase activity. This results in accumulation of free heme, which is toxic to the parasites.
Hemoglobin subunit alpha structureClick to view 3D structureHemoglobin subunit alphaP69905HumansKnownThe mechanism of plasmodicidal action of chloroquine is not completely certain. Like other quinoline derivatives, it is thought to inhibit heme polymerase activity. This results in accumulation of free heme, which is toxic to the parasites.
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansKnownNot Available
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansKnownNot Available
Glutathione S-transferase A2 structureClick to view 3D structureGlutathione S-transferase A2P09210HumansKnownThe mechanism of plasmodicidal action of chloroquine is not completely certain. Like other quinoline derivatives, it is thought to inhibit heme polymerase activity. This results in accumulation of free heme, which is toxic to the parasites.
Concentrations
Not Available
External Links
DrugBank IDDB00608
HMDB IDHMDB0014746
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkChloroquine
Chemspider ID2618
ChEBI ID3638
PubChem Compound ID2719
Kegg Compound IDC07625
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Andersag, H., Breitner, S.and Jung, H.; U S . Patent 2,233,970; March 4,1941; assigned to
Winthrop Chemical Company, Inc.

MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11198399
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17594118
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=18052874
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19426658
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23288916
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23580861
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23635029
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23644906
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23706562
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23852712
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=23891850
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=25285162