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Artemisinin 3,12-epoxy-12h-pyranol(4,3-j)-1,2-benzodioxepin-10(3h)-one,octahydro-3,6,9-tr ;octahydro-3,6,9-trimethyl-3,12-epoxy-12h-pyrano(4,3-j)-1,2-benzodioxepin-10
Artemisinin Basic information |
Artemisinin Chemical Properties |
Melting point | 156-157 °C(lit.) |
alpha | 76 º (c=0.5,MeOH) |
refractive index | 75 ° (C=0.5, MeOH) |
storage temp. | Store at +4°C |
solubility | Soluble to 100mM in DMSO and to 75mM in ethanol |
Merck | 14,817 |
Stability: | Stable. Combustible. Incompatible with strong oxidizing agents, acids, acid chlorides, acid anhydrides. May absorb, and react with, carbon dioxide from the air. |
Safety Information |
Safety Statements | 22-24/25 |
WGK Germany | 2 |
RTECS | KD4170000 |
HS Code | 29322985 |
MSDS Information |
Provider | Language |
---|---|
(+)-Arteannuin | English |
SigmaAldrich | English |
Artemisinin Usage And Synthesis |
Drugs for treatment of malaria |
Artemisinin is the drug for the treatment of malaria with the most excellent efficacy, being a kind of sesquiterpene lactone containing peroxide group extracted from the traditional Chinese medicine Artemisia annua. It is characterized with high efficiency, rapid efficacy, clearing summer-heat, clearing deficiency heat, protozoa-killing effect and low toxicity. Currently, the efficacy of the artemisinin-based combination therapy (ACT) for the treatment of malaria worldwide has reached over 90%. ACT has been already widely applied to the treatment of malaria in many countries around the world. It has a strong and rapid killing effect on the erythrocytic stage of plasmodium, being able to rapidly control the clinical seizures and symptoms. Meanwhile, it also has prominent efficacy in the treatment of chicken coccidiosis, Mycoplasma Suis, toxoplasmosis, weakness and fever, damp heat jaundice, tertian malaria, falciparum malaria, cerebral malaria and chloroquine malaria. Artemisinin was first successfully developed by Chinese scientists, being effective monomer originated from the folk malaria-treatment herbs Artemisia annua. China is one of the major resource countries for the growth of such plants. The demands for research and development originated from the Vietnam War in 1960s when Malaria parasites had been resistant to special drug chloroquine at that time. In Vietnam War, many soldiers are not killed in the war, but instead died of malaria. Because of the presence of artemisinin resistance in the border areas of Cambodia and Thailand, the World Health Organization advocates the use of combinations rather than monomeric formulation. In this environment, the world's first artemisinin-based compound antimalarial drug-compound artemether has been successfully developed in China. However, due to the lack of attention on the importance of intellectual property of Chinese pharmaceutical companies, currently in the world, only Novartis Company has the authority of foreign selling of artemether compound that has been recognized by the World Health Organization. The Novartis Company has offered the drug to the WHO at the cost price, wining the wide acclaim from international community. However, in this trade war, China can only play a role of major drug producing countries. |
Chemical properties | It appears as colorless needle crystal with a melting point being156-157 °C. It is easily soluble in chloroform, acetone, ethyl acetate and benzene, being soluble in methanol, ethanol and insoluble in water. |
Uses |
Artemisia annua is used as antimalarial drugs. Clinical application has shown that artemisinin and its derivatives have special effects on treating the malaria and falciparum malaria, especially artemisinin which has stronger killing effect on Plasmodium falciparum intracellular phorozoon than other artemisinin drugs, characterized by high efficiency, rapid efficacy, low toxicity and no cross-resistance with chloroquine, etc. It can be not only used for treatment, but also for emergency treatment. It is applicable to a variety of malaria such as falciparum malaria, vivax malaria, anti-chloroquine malaria and cerebral malaria, including dangerous type. The most notable drug is dihydroartemisinin and its tablets. This drug has its antimalarial effect be 10 times as strong as artemisinin with the recurrence rate of only 1.95%, thus having been rated as China's top ten scientific and technological achievements in 1992. Artemisinin and its derivatives not only are excellent antimalarial drugs, but also have potentially attractive prospect in the treatment of other diseases. Animal experiments have found that artemisinin treatment of Clonorchis sinensis can achieve a rate of pest control being up to 100%; treatment of animal schistosomiasis can achieve a pest control rate of 33.8-99.3%. Application of artemisinin treatment of discoid lupus erythematosus can achieve a total effective rate of 90%. Its efficacy in the treatment of dengue fever is significantly better than morphine biguanide and other western medicines. Immunologists have also found that artemisinin can significantly improve the lymphocyte transformation rate and enhance the immune function of antibodies. People haven’t found toxic effect of this product on the heart, liver and kidney. People haven’t observed any significant side effects in clinical practice. |
Production method | It can be extracted from the leaves of Artemisia annua L. (Compositae). In addition to artemisinin, China also produces both artemether and sodium artemisinin. |
Category | Toxic substances |
Toxic grading | Poisoning |
Acute toxicity | Intraperitoneal-rat LD50: 2571 mg/kg; Abdominal-mouse LD50: 1558 mg/kg |
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