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Chloroquine is a medication used to prevent and to treat malaria in areas where malaria is known to be sensitive to its effects.
Common side effects include muscle problems, loss of appetite, diarrhea, and skin rash.
Chloroquine was discovered in 1934 by Hans Andersag.
Contents
1 Medical uses
1.1 Malaria
1.2 Amebiasis
1.3 Rheumatic disease
2 Adverse effects
2.1 Pregnancy
2.2 Elderly
3 Drug interactions
4 Overdose
5 Resistance in malaria
6 Pharmacology
7 Mechanism of action
7.1 Antimalarial
7.2 Other
8 Names
9 History
9.1 Research
10 See also
11 References
12 External links
Medical uses
Resochin tablet package
Malaria
Chloroquine has long been used in the treatment or prevention of malaria from Plasmodium vivax, P. ovale, and P. malariae, excluding the malaria parasite Plasmodium falciparum, for it started to develop widespread resistance to it.
Chloroquine has been extensively used in mass drug administrations, which may have contributed to the emergence and spread of resistance. It is recommended to check if chloroquine is still effective in the region prior to using it.
Amebiasis
In treatment of amoebic liver abscess, chloroquine may be used instead of or in addition to other medications in the event of failure of improvement with metronidazole or another nitroimidazole within 5 days or intolerance to metronidazole or a nitroimidazole.
Rheumatic disease
As it mildly suppresses the immune system, it is used in some autoimmune disorders, such as rheumatoid arthritis and lupus erythematosus.
Adverse effects
Side effects include neuromuscular, hearing, gastrointestinal, brain, skin, eye, cardiovascular (rare), and blood reactions.
Seizures
Deafness or tinnitus.
Nausea, vomiting, diarrhea, abdominal cramps, and anorexia.
Mild and transient headache.
Skin itchiness, skin color changes, hair loss, and skin rashes.
Chloroquine-induced itching is very common among black Africans (70%), but much less common in other races. It increases with age, and is so severe as to stop compliance with drug therapy. It is increased during malaria fever; its severity is correlated to the malaria parasite load in blood. Some evidence indicates it has a genetic basis and is related to chloroquine action with opiate receptors centrally or peripherally.
Unpleasant metallic taste
This could be avoided by ‘taste-masked and controlled release’ formulations such as multiple emulsions.
Chloroquine retinopathy
May be irreversible.
Hypotension and electrocardiographic changes
This manifests itself as either conduction disturbances (bundle-branch block, atrioventricular block) or cardiomyopathy – often with hypertrophy, restrictive physiology, and congestive heart failure. The changes may be irreversible. Only two cases have been reported requiring heart transplantation, suggesting this particular risk is very low. Electron microscopy of cardiac biopsies show pathognomonic cytoplasmic inclusion bodies.
Pancytopenia, aplastic anemia, reversible agranulocytosis, low blood platlets, neutropenia.
Pregnancy
Chloroquine has not been shown to have any harmful effects on the fetus when used for malarial prophylaxis.
Elderly
There is not enough evidence to determine whether chloroquine is safe to be given to people aged 65 and older. However, the drug is cleared by the kidneys and toxicity should be monitored carefully in people with poor kidney functions.
Drug interactions
Antacids – may reduce absorption of chloroquine; take 4 hours apart
Kaolin- may reduce absorption of chloroquine; take 4 hours apart
Cimetidine – may inhibit metabolism of chloroquine; increasing levels of chloroquine in the body
Ampicillin – levels may be reduced by chloroquine; take 2 hours apart
Cyclosporine – levels may be increased by chloroquine
Mefloquine – may increase risk of convulsions
Overdose
Chloroquine is very dangerous in overdose. It is rapidly absorbed from the gut. In 1961, published studies showed three children who took overdoses died within 2.5 hours of taking the drug. While the amount of the overdose was not cited, the therapeutic index for chloroquine is known to be small.
A metabolite of chloroquine – hydroxychloroquine – has a long half-life (32–56 days) in blood and a large volume of distribution (580–815 L/kg).
Resistance in malaria
Since the first documentation of P. falciparum chloroquine resistance in the 1950s, resistant strains have appeared throughout East and West Africa, Southeast Asia, and South America. The effectiveness of chloroquine against P. falciparum has declined as resistant strains of the parasite evolved. They effectively neutralize the drug via a mechanism that drains chloroquine away from the digestive vacuole. Chloroquine-resistant cells efflux chloroquine at 40 times the rate of chloroquine-sensitive cells; the related mutations trace back to transmembrane proteins of the digestive vacuole, including sets of critical mutations in the P. falciparum chloroquine resistance transporter ( PfCRT ) gene. The mutated protein, but not the wild-type transporter, transports chloroquine when expressed in Xenopus oocytes and is thought to mediate chloroquine leak from its site of action in the digestive vacuole.
Other agents which have been shown to reverse chloroquine resistance in malaria are chlorpheniramine, gefitinib, imatinib, tariquidar and zosuquidar.
Pharmacology
Absorption: Rapid and almost completely
Distribution: Widely distributed into body tissues
Protein binding: 55%
Metabolism: Partially hepatic to main metabolite, desethylchloroquine
Excretion: Urine (≥50% as unchanged drug); acidification of urine increases elimination
Chloroquine has a very high volume of distribution, as it diffuses into the body’s adipose tissue. Chloroquine and related quinines have been associated with cases of retinal toxicity, particularly when provided at higher doses for longer times. Accumulation of the drug may result in deposits that can lead to blurred vision and blindness. With long-term doses, routine visits to an ophthalmologist are recommended.
Chloroquine is also a lysosomotropic agent, meaning it accumulates preferentially in the lysosomes of cells in the body. The pK a for the quinoline nitrogen of chloroquine is 8.5, meaning it is about 10% deprotonated at physiological pH as calculated by the Henderson-Hasselbalch equation. This decreases to about 0.2% at a lysosomal pH of 4.6. Because the deprotonated form is more membrane-permeable than the protonated form, a quantitative “trapping” of the compound in lysosomes results. (A quantitative treatment of this phenomenon involves the pK a s of all nitrogens in the molecule; this treatment, however, suffices to show the principle.)
The lysosomotropic character of chloroquine is believed to account for much of its antimalarial activity; the drug concentrates in the acidic food vacuole of the parasite and interferes with essential processes. Its lysosomotropic properties further allow for its use for in vitro experiments pertaining to intracellular lipid related diseases,
Mechanism of action
Antimalarial
Hemozoin formation in P. falciparum : many antimalarials are strong inhibitors of hemozoin crystal growth.
Inside red blood cells, the malarial parasite, which is then in its asexual lifecycle stage, 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 parasitic cell.
Hemoglobin is composed of a protein unit (digested by the parasite) and a heme unit (not used by the parasite). During this process, the parasite releases 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 nontoxic molecule. Hemozoin collects in the digestive vacuole as insoluble crystals.
Chloroquine enters the red blood cell, inhibiting the 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 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.
Other
Chloroquine inhibits thiamine uptake. It acts specifically on the transporter SLC19A3.
Against rheumatoid arthritis, it operates by inhibiting lymphocyte proliferation, phospholipase A2, antigen presentation in dendritic cells, release of enzymes from lysosomes, release of reactive oxygen species from macrophages, and production of IL-1.
Names
Brand names include Chloroquine FNA, Resochin, and Dawaquin.
History
Chloroquine was discovered in 1934 by Hans Andersag and coworkers at the Bayer laboratories, who named it “Resochin”.
Research
Chloroquine is in clinical trials as an investigational antiretroviral in humans with HIV-1/AIDS and is being considered in pre-clinical models as a potential antiviral agent against chikungunya fever.
The radiosensitizing and chemosensitizing properties of chloroquine are beginning to be exploited in anticancer strategies in humans.
In biomedicinal science, chloroquine is used for in vitro experiments to inhibit lysosomal degradation of protein products.
See also
History of malaria
Quinine
Artemether

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