|1: 1 mixture of
( R ) -form (top) and ( S ) -form (bottom)
|Molecular formula||C 18 H 26 ClN 3|
white to almost white, crystalline, hygroscopic powder (diphosphate)
|External identifiers / databases|
|Molar mass||319.87 g · mol -1|
214–221 ° C (27 Pa, free base)
|pK s value||
|As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .|
Chloroquine , trade name Resochin , is a mixture of two enantiomeric chemical compounds , some of which are structurally related to quinine . Hydroxychloroquine is an analog preparation to chloroquine .
Chloroquine and hydroxychloroquine can be used as drugs for therapy and chemoprophylaxis of malaria . However, widespread pathogen resistance severely restrict the application for these indications . In addition, chloroquine is used as an agent in the treatment of rheumatic diseases such as lupus erythematosus and rheumatoid arthritis , porphyria cutanea tarda and the rare form of extraintestinal amoebiasis .
Chloroquine was synthesized in 1934 by Hans Andersag at IG Farbenindustrie in Elberfeld. However, this agent called Resochin was initially of no importance, since the German Wehrmacht used the closely related Sontochin (methylated chloroquine), which was invented at the same time, for malaria prophylaxis during World War II . Samples from Sontochin were found in German prisoners of war in North Africa and analyzed in the USA. Analogous substances were also examined there, showing the superior effect and tolerability of chloroquine in comparison to other drugs such as atebrine , the malaria drug used by the Allies in the Pacific War under the name of quinacrine. After the Second World War, chloroquine was a highly effective agent for a long time; In the meantime, many malaria parasites have developed resistance to the drug.
In July 2019, Bayer AG stopped selling its Resochin product . It was the only product available in Germany with the active ingredient chloroquine phosphate. According to the company, it was no longer possible to manufacture the drug in the required quality. However, Bayer continued to sell the product in Pakistan , where, according to the company, production of Resochin was " restarted" as part of the 2020 COVID-19 pandemic . In the event that it is effective against COVID-19, the German government has reserved “larger quantities” of the drug at Bayer.
Chloroquine is a colorless to yellowish, odorless and almost water-insoluble compound. Due to the basic properties of the substance, it dissolves well in acids . The much more water-soluble salts chloroquine diphosphate (50 g / l) and chloroquine sulfate are used as medicinal substances . The free base decomposes on contact with daylight and atmospheric oxygen; the salts are mostly stable in air.
Mode of action
Chloroquine inhibits the crystallization of hemozoin , a breakdown product of heme . Hemozoin is produced when the malaria pathogen breaks down the hemoglobin in infected red blood cells in order to obtain proteins for its metabolism. If the hemozoin can no longer be crystallized, this leads to the death of the parasite.
Chloroquine has a blood schizontocidal effect, that is, it leads to an inhibition in the later erythrocytic stage of the pathogen. Chloroquine was once the most widely used drug in the world for the therapy and prevention of malaria, but it is now increasingly ineffective due to resistant pathogens.
As a preventive measure against malaria, the recommended (oral) dose for adults is 500 mg chloroquine phosphate per week, starting 1 to 2 weeks before departure and continuing up to four weeks after the end of the journey. Due to the frequent resistance, chloroquine was often used in combination with other active ingredients, especially proguanil . Effectiveness and tolerance are mostly rated negatively. The combination is therefore usually no longer common in German-speaking countries today - also due to the existence of alternatives with a better risk-benefit ratio. Exceptions to this are considered in children and during pregnancy. Chloroquine requires a prescription. In the case of chloroquine poisoning, diazepam can be administered i.v. be used as an antidote . The biological half-life of the substance increases significantly with continued intake of initially a few days due to considerable accumulation in the tissue (up to 30-60 days; according to other sources, to 40 to 50 days or two to three weeks.)
Side effects and contraindications
Chloroquine can have various side effects, including clouding of the cornea and changes in the retina in the eye , gastrointestinal complaints, sleep disorders, neuropsychiatric symptoms and reddened skin. Chloroquine must not be used, particularly in the case of severe liver and kidney damage . The combination of chloroquine together with drugs that damage the liver or MAO inhibitors (see monoamine oxidase inhibitors ) must not be used. Chloroquine must not be used if there are diseases of the eye and the blood-forming system. If there is a hypersensitivity to quinine or mefloquine , chloroquine must not be used for therapy.
In some patients, chloroquine can cause a dose-dependent prolongation of the QT interval . In patients with pre-existing cardiac diseases or with simultaneous use of substances that prolong the QT interval, the risk of cardiac arrhythmias - sometimes with fatal outcome - is increased. An overdose of the drug was reported in 2012 by the association SterbeHilfeDeutschland e. V. used as a means of killing in the context of euthanasia .
The weekly intake of chloroquine is permitted for pregnant women and nursing mothers, but should be avoided for long-term use with daily intake (as in the treatment of rheumatoid arthritis). Otherwise there is a risk of eye defects in the unborn or infant. Chloroquine can also be used in children, but long-term treatment should not be used.
Overdosing leads to pigmentation disorders that make hair bleach.
According to a study from 2008, chloroquine has also been linked to inducing antibiotic resistance (to fluoroquinolones ).
Rheumatic form circle
Chloroquine is also used for the therapy of rheumatoid arthritis . Severe courses of Porphyria cutanea tarda are treated with low-dose chloroquine or hydroxychloroquine (for example 200 mg twice a week).
After chloroquine had already shown effectiveness against the first SARS coronavirus in an in vitro study in cell culture , it was considered for the treatment of COVID-19 . Here, too, promising results were shown in cell culture with a mean effective concentration in the micromolar range for both chloroquine and hydroxychloroquine.
A review from March 10, 2020 concludes that high quality clinical data from different geographic regions is urgently needed. The Institute for Tropical Medicine at the Tübingen University Hospital announced an application for approval for a clinical study on March 18, 2020 . This was advocated by the Paul Ehrlich Institute and the Federal Institute for Drugs and Medical Devices (BfArM). The study, in which the Bernhard Nocht Institute for Tropical Medicine is also involved, is to take place in a placebo-controlled manner and begin on March 23, 2020. Further clinical trials have been announced by the University of Oxford and the University of Queensland . On March 20, 2020, the World Health Organization started the SOLIDARITY study, which aims to evaluate chloroquine and other active ingredients on thousands of patients worldwide.
A short scientific article from China reported good experiences in treating COVID-19 patients with chloroquine, but did not quantify these results. In contrast, a clinical pilot study carried out in Shanghai found no advantage for hydroxychloroquine over conventional treatment . A clinical study by a hospital in Marseille came to positive results with the use of hydroxychloroquine, but was widely criticized for its methodology. Based on some data, the BfArM sees a possible benefit of chloroquine, especially if it is used early.
Chloroquine and hydroxychloroquine are recommended in the Belgian provisional treatment guidelines and the South Korean guidelines for COVID-19 patients.
In the United States, the drug attracted a lot of public attention after President Donald Trump expressed high expectations of its effectiveness at a press conference and in a tweet . And even if it shouldn't be effective, it won't kill anyone (Trump on March 19, 2020: " But the nice part is, it's been around for a long time, so we know that if it - if things don't go as planned, it's not going to kill anybody. ").
Stephen Hahn, head of the Food and Drug Administration (FDA), warned that the drug may do more harm than good. In France, people died after uncontrolled self-administration as a result of serious interactions with other drugs. As the US Department of Health announced on March 30, 2020, the FDA had issued an Emergency Use Authorization (EUA) that allows the dispensing or prescription of chloroquine and hydroxychloroquine in emergencies "by doctors to adolescent and adult patients with Covid in hospital -19 “and revoked it on June 15, 2020. The European Medicines Agency said on 1 April 2020 that patients and healthcare professionals chloroquine and hydroxychloroquine may use only for their approved applications, or likely to be used but maximum in clinical trials or national emergency treatment programs for COVID-19th
In Brazil, a clinical study began on March 23, 2020 in a hospital in Manaus . In the double-blind , randomized , adaptive, two-arm phase IIb study , one group of Covid-19 patients received 600 mg of chloroquine twice daily for ten days (high dose) and the other group received 450 mg once daily for five days with a double dose Day 1. A total of 440 people should be enrolled in the study. However, after 81 patients were enrolled, the high-dose arm of the study was stopped after several of those patients suffered fatal arrhythmias or cardiac muscle damage.
On April 24, 2020, the FDA issued a Drug Safety Communication warning of complications that may be associated with the use of chloroquine and hydroxychloroquine. There have been reports of serious heart rhythm problems in Covid 19 patients treated with these substances. Those affected were often treated in combination with azithromycin or other QT-prolonging drugs. When using hydroxychloroquine or chloroquine in the context of emergency programs or clinical studies, she recommended an initial evaluation and monitoring of the therapy with, for example, ECG , electrolytes, as well as kidney function and liver tests.
A study by the Irving Medical Center in Manhattan published on May 7th in The New England Journal of Medicine came to the conclusion that hydroxychloroquine is neither harmful nor beneficial in Covid-19 diseases. The drug was used in 811 patients (control group: 565 patients), which makes it supposedly the largest series of treatments in the world to date. According to the Deutsches Ärzteblatt , the experience "will probably lead to hydroxychloroquine no longer being used to treat COVID-19."
Medicinal products containing chloroquine and hydroxychloroquine are part of a series of drugs, of which the German Federal Ministry of Health will purchase millions of packs from April 2020 to be used as an alternative in the event of severe courses against Covid-19.
Biochemical use and importance
Chloroquine is also used in cell culture for transfection used to increase the efficiency of transfection. It inhibits the lysosomal DNases by neutralizing the pH within the vesicles . Chloroquine inhibits also the endocytosis . Since it also inhibits autophagy , it is being discussed as a potential chemotherapeutic agent . Clinical studies are carried out worldwide with chloroquine in combination with classic chemotherapeutic agents.
Use in the aquarium hobby
Outside of human medicine, chloroquine phosphate is recommended to combat certain parasites in aquarium fish . The FDA recently warned against the human medical use of these products after a serious illness and death became known in the United States.
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Chloroquin (CH), Nivaquine (CH), Resochin (D, A), Weimer quin (D)