1.0 2009-07-05 03:00:49 UTC 2026-05-14 16:43:53 UTC T3D2561 Chloroquine SmallMolecule 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. Drug Synthetic Toxin Organic Compound Organochloride Amine Drug Antimalarial Antirheumatic Agent Amebicide Metabolite Synthetic Compound Human Neurotoxin Aralen Artrichin Bemaphate Capquin Chloraquine Chlorochin Chlorochine Chloroquina Chloroquinium Chloroquinum Chlorquin Clorochina Cloroquina Malarex N(4)-(7-chloro-4-Quinolinyl)-N(1),N(1)-diethyl-1,4-pentanediamine Nivaquine b Resochin Resoquine Reumachlor Sanoquin C18H26ClN3 319.872 319.181525554 7-chloro-N-[5-(diethylamino)pentan-2-yl]quinolin-4-amine 7-chloro-N-[5-(diethylamino)pentan-2-yl]quinolin-4-amine 54-05-7 CCN(CC)CCCC(C)NC1=C2C=CC(Cl)=CC2=NC=C1 InChI=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) WHTVZRBIWZFKQO-UHFFFAOYSA-N Organic compounds Organoheterocyclic compounds Quinolines and derivatives Aminoquinolines and derivatives 4-aminoquinolines Aminopyridines and derivatives Aryl chlorides Azacyclic compounds Benzenoids Chloroquinolines Heteroaromatic compounds Hydrocarbon derivatives Organochlorides Organopnictogen compounds Secondary alkylarylamines Trialkylamines 4-aminoquinoline Amine Aminopyridine Aromatic heteropolycyclic compound Aryl chloride Aryl halide Azacycle Benzenoid Chloroquinoline Haloquinoline Heteroaromatic compound Hydrocarbon derivative Organic nitrogen compound Organochloride Organohalogen compound Organonitrogen compound Organopnictogen compound Pyridine Secondary aliphatic/aromatic amine Secondary amine Tertiary aliphatic amine Tertiary amine Aromatic heteropolycyclic compounds aminoquinoline organochlorine compound secondary amino compound tertiary amino compound Detected and Not Quantified Exogenous Cytoplasm Extracellular Membrane Chloroquine Action Pathway SMP0125864 Chloroquine Drug Metabolism Action Pathway SMP0143056 Solid White to slightly yellow, crystalline powder (A619). melting_point 289°C solubility 10.6 mg/L logp 4.63 logp 5.28 ALOGPS logs -4.26 ALOGPS solubility 1.75e-02 g/l ALOGPS logp 3.93 ChemAxon pka_strongest_basic 10.32 ChemAxon iupac 7-chloro-N-[5-(diethylamino)pentan-2-yl]quinolin-4-amine ChemAxon average_mass 319.872 ChemAxon mono_mass 319.181525554 ChemAxon smiles CCN(CC)CCCC(C)NC1=C2C=CC(Cl)=CC2=NC=C1 ChemAxon formula C18H26ClN3 ChemAxon inchi InChI=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) ChemAxon inchikey WHTVZRBIWZFKQO-UHFFFAOYSA-N ChemAxon polar_surface_area 28.16 ChemAxon refractivity 96.42 ChemAxon polarizability 37.29 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge 2 ChemAxon formal_charge 0 ChemAxon Inhalation Completely absorbed from gastrointestinal tract The 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. Completely absorbed from gastrointestinal tract. Chloroquine is partially metabolized; the major metabolite is desethylchloroquine. Desethylchloroquine also has antiplasmodial activity, but is slightly less active than chloroquine. Bisdesethylchloroquine, which is a carboxylic acid derivative, and several other unidentified metabolites are also formed in small amounts (A625). Route of Elimination: Excretion of chloroquine is quite slow, but is increased by acidification of the urine. Half Life: 1-2 months 3, not classifiable as to its carcinogenicity to humans. (L135) For the suppressive treatment and for acute attacks of malaria due to P. vivax, P.malariae, P. ovale, and susceptible strains of P. falciparum, Second-line agent in treatment of Rheumatoid Arthritis (A308). #<HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f727323ea78> Convulsive seizures. Mild and transient headache. Treatment 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. (L1712) DB00608 HMDB14746 2719 CHEMBL76 2618 C07625 3638 D002738 Chloroquine CLQ Chloroquine 18048412 16886665 12480170 Osol A, Hoover JE, et al. (eds) (1975). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co. McEvoy GK (ed) (2006). American Hospital Formulary Service - Drug Information 2006. Bethesda, MD: American Society of Health-System Pharmacists. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. : http://monographs.iarc.fr/index.php Drugs.com: http://www.drugs.com/cons/Chloroquine.html RxList: The Internet Drug Index (2009).: http://www.rxlist.com/ BE0001171 The 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. BE0000704 The 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. BE0000130 The 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. BE0000090 IC50 2.5 uM BindingDB 22985 BE0002638 IC50 350 uM BindingDB 22985 BE0002189 The 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. BE0002659 BE0003428 BE0000807 BE0000982 BE0015068