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Artemisinin information


Artemisinin
Clinical data
Pronunciation/ɑːrtɪˈmɪsɪnɪn/
Other namesArtemisinine, qinghaosu
Routes of
administration
Oral
ATC code
  • P01BE01 (WHO)
Identifiers
IUPAC name
  • (3R,5aS,6R,8aS,9R,12S,12aR)-Octahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10(3H)-one
CAS Number
  • 63968-64-9 checkY
PubChem CID
  • 68827
ChemSpider
  • 62060 checkY
UNII
  • 9RMU91N5K2
KEGG
  • D02481 checkY
ChEBI
  • CHEBI:223316 checkY
ChEMBL
  • ChEMBL567597 ☒N
CompTox Dashboard (EPA)
  • DTXSID2040652 Edit this at Wikidata
ECHA InfoCard100.110.458 Edit this at Wikidata
Chemical and physical data
FormulaC15H22O5
Molar mass282.336 g·mol−1
3D model (JSmol)
  • Interactive image
Density1.24 ± 0.1 g/cm3
Melting point152 to 157 °C (306 to 315 °F)
Boiling pointdecomposes
SMILES
  • O=C3O[C@@H]4O[C@@]1(OO[C@@]42[C@@H](CC1)[C@H](C)CC[C@H]2[C@H]3C)C
InChI
  • InChI=1S/C15H22O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-11,13H,4-7H2,1-3H3/t8-,9-,10+,11+,13-,14-,15-/m1/s1 checkY
  • Key:BLUAFEHZUWYNDE-NNWCWBAJSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Artemisinin (/ˌɑːrtɪˈmsɪnɪn/) and its semisynthetic derivatives are a group of drugs used in the treatment of malaria due to Plasmodium falciparum.[1] It was discovered in 1972 by Tu Youyou, who shared the 2015 Nobel Prize in Physiology or Medicine for her discovery.[2] Artemisinin-based combination therapies (ACTs) are now standard treatment worldwide for P. falciparum malaria as well as malaria due to other species of Plasmodium.[3] Artemisinin is extracted from the plant Artemisia annua (sweet wormwood) a herb employed in Chinese traditional medicine. A precursor compound can be produced using a genetically engineered yeast, which is much more efficient than using the plant.[4]

Artemisinin and its derivatives are all sesquiterpene lactones containing an unusual peroxide bridge. This endoperoxide 1,2,4-trioxane ring is responsible for their antimalarial properties. Few other natural compounds with such a peroxide bridge are known.[5]

Artemisinin and its derivatives have been used for the treatment of malarial and parasitic worm (helminth) infections. Advantages of such treatments over other anti-parasitics include faster parasite elimination and broader efficacy across the parasite life-cycle; disadvantages include their low bioavailability, poor pharmacokinetic properties, and high cost.[6][7] Moreover, use of the drug by itself as a monotherapy is explicitly discouraged by the World Health Organization,[8] as there have been signs that malarial parasites are developing resistance to the drug. Combination therapies, featuring artemisinin or its derivatives alongside some other antimalarial drug, constitute the contemporary standard-of-care treatment regimen for malaria.[9]

  1. ^ Wang J, Xu C, Wong YK, Li Y, Liao F, Jiang T, et al. (2019). "Artemisinin, the Magic Drug Discovered from Traditional Chinese Medicine". Engineering. 5 (1): 32–9. Bibcode:2019Engin...5...32W. doi:10.1016/j.eng.2018.11.011.
  2. ^ Cite error: The named reference nobel-2015 was invoked but never defined (see the help page).
  3. ^ WHO 2015, pp. 9–11.
  4. ^ Arsenault PR, Wobbe KK, Weathers PJ (2008). "Recent advances in artemisinin production through heterologous expression". Current Medicinal Chemistry. 15 (27): 2886–96. doi:10.2174/092986708786242813. PMC 2821817. PMID 18991643.
  5. ^ Brown G (2006). "Artemisinin and a new generation of antimalarial drugs". Education in Chemistry. 43 (4). Royal Society of Chemistry: 97–9. Retrieved 2018-03-09.
  6. ^ Whirl-Carrillo M, McDonagh EM, Hebert JM, Gong L, Sangkuhl K, Thorn CF, et al. (2012). "Pharmacogenomics knowledge for personalized medicine". Clinical Pharmacology and Therapeutics. 92 (4): 414–7. doi:10.1038/clpt.2012.96. PMC 3660037. PMID 22992668.
  7. ^ "Development of Novel Antimalarials". MalariaWorld. September 6, 2010. Retrieved 2016-10-22.
  8. ^ "WHO calls for an immediate halt to provision of single-drug artemisinin malaria pills". WHO. 19 January 2006. Archived from the original on November 16, 2006.
  9. ^ Pelfrene E, Pinheiro MH, Cavaleri M (2015). "Artemisinin-based combination therapy in the treatment of uncomplicated malaria: review of recent regulatory experience at the European Medicines Agency". International Health. 7 (4): 239–46. doi:10.1093/inthealth/ihv017. PMC 4492341. PMID 25855638.

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Artemisinin

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Artemisinin (/ˌɑːrtɪˈmiːsɪnɪn/) and its semisynthetic derivatives are a group of drugs used in the treatment of malaria due to Plasmodium falciparum....

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Artemisia annua

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extract of A. annua, called artemisinin (or artesunate), is a medication used to treat malaria. Discovery of artemisinin and its antimalarial properties...

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Antimalarial medication

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in the malaria parasite—including for combination therapies featuring artemisinin, a drug of last resort, where resistance has now been observed in Southeast...

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PfATP6

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of artemisinin (a potent antimalarial drug). It was observed that single amino acid mutations in PfATP6 could abolish sensitivity to artemisinin compounds...

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Project 523

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and led to the development of a class of new antimalarial drugs called artemisinins. Launched during and lasting throughout the Cultural Revolution, Project...

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Malaria

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Artemisinin drugs are effective and safe in treating uncomplicated malaria. Artemisinin in combination with other antimalarials (known as artemisinin-combination...

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Tu Youyou

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is a Chinese malariologist and pharmaceutical chemist. She discovered artemisinin (also known as qīnghāosù, 青蒿素) and dihydroartemisinin, used to treat...

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Dihydroartemisinin

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malaria. Dihydroartemisinin is the active metabolite of all artemisinin compounds (artemisinin, artesunate, artemether, etc.) and is also available as a...

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Jay Keasling

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developing synthetic biology tools to engineer the antimalarial drug artemisinin. Keasling received his bachelor's degree at the University of Nebraska-Lincoln...

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Artemether

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Organization (WHO) therefore recommends its use during pregnancy. It is in the artemisinin class of medication. Artemether has been studied since at least 1981...

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History of malaria

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therapeutic drugs, including chloroquine and artemisinins, were used to resist the scourge. Today, artemisinin is present in every remedy applied in the...

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Artesunate

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harm to the baby. Use is likely fine during breastfeeding. It is in the artemisinin class of medication. Artesunate was developed by Liu Xu in 1977. It is...

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Secondary metabolite

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metabolites. The two most commonly known terpenoids are artemisinin and paclitaxel. Artemisinin was widely used in Traditional Chinese medicine and later...

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Herbal medicine

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into modern remedies, such as the anti-malarial group of drugs called artemisinin isolated from Artemisia annua, a herb that was known in Chinese medicine...

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Artemisia japonica

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about artemisinin production in Artemisia species, A. japonica had around average levels compared to other species (0.05% to 0.15% artemisinin). It also...

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Omeprazole

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Constitutive androstane receptor Agonists: 6,7-Dimethylesculetin Amiodarone Artemisinin Benfuracarb Carbamazepine Carvedilol Chlorpromazine Chrysin CITCO Clotrimazole...

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ATC code P01

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Mefloquine P01BD01 Pyrimethamine P01BD51 Pyrimethamine, combinations P01BE01 Artemisinin P01BE02 Artemether P01BE03 Artesunate P01BE04 Artemotil P01BE05 Artenimol...

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Pharmacognosy

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into modern remedies, such as the anti-malarial group of drugs called artemisinin isolated from Artemisia annua herb, a herb that was known in Chinese...

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Fentanyl

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Constitutive androstane receptor Agonists: 6,7-Dimethylesculetin Amiodarone Artemisinin Benfuracarb Carbamazepine Carvedilol Chlorpromazine Chrysin CITCO Clotrimazole...

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Permethrin

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Constitutive androstane receptor Agonists: 6,7-Dimethylesculetin Amiodarone Artemisinin Benfuracarb Carbamazepine Carvedilol Chlorpromazine Chrysin CITCO Clotrimazole...

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Loratadine

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Constitutive androstane receptor Agonists: 6,7-Dimethylesculetin Amiodarone Artemisinin Benfuracarb Carbamazepine Carvedilol Chlorpromazine Chrysin CITCO Clotrimazole...

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Multiple drug resistance

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sulfadoxine-pyrimethamine resistant a few decades ago, and as of 2012 artemisinin-resistant Plasmodium falciparum has emerged in western Cambodia and western...

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Piperaquine

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out of use as a monotherapy, and is instead used as a partner drug for artemisinin combination therapy. Piperaquine kills parasites by disrupting the detoxification...

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Zhou Yiqing

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under Chairman Mao Zedong. The project resulted in the discovery of artemisinins, a class of antimalarial drugs, from the medicinal plant Artemisia annua...

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Clotrimazole

Last Update:

Constitutive androstane receptor Agonists: 6,7-Dimethylesculetin Amiodarone Artemisinin Benfuracarb Carbamazepine Carvedilol Chlorpromazine Chrysin CITCO Clotrimazole...

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Ketoconazole

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Constitutive androstane receptor Agonists: 6,7-Dimethylesculetin Amiodarone Artemisinin Benfuracarb Carbamazepine Carvedilol Chlorpromazine Chrysin CITCO Clotrimazole...

Word Count : 4374

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