Artemisinin

Artemisinin
Clinical data
Pronunciation	⫽ɑːrtɪˈmɪsɪnɪn⫽
Other names	Artemisinine, 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 ;
PubChem CID	68827;
ChemSpider	62060 ;
UNII	9RMU91N5K2;
KEGG	D02481 ;
ChEBI	CHEBI:223316 ;
ChEMBL	ChEMBL567597 ;
CompTox Dashboard (EPA)	DTXSID2040652 ;
ECHA InfoCard	100.110.458
Chemical and physical data
Formula	C15H22O5
Molar mass	282.336 g·mol−1
3D model (JSmol)	Interactive image;
Density	1.24 ± 0.1 g/cm3
Melting point	152 to 157 °C (306 to 315 °F)
Boiling point	decomposes
	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 ; Key:BLUAFEHZUWYNDE-NNWCWBAJSA-N ;
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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.^[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]

^ 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.
^ Cite error: The named reference nobel-2015 was invoked but never defined (see the help page).
^ WHO 2015, pp. 9–11.
^ 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.
^ 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.
^ 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.
^ "Development of Novel Antimalarials". MalariaWorld. September 6, 2010. Retrieved 2016-10-22.
^ "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.
^ 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.

[Wang2019-1] 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.

[nobel-2015-2] Cite error: The named reference nobel-2015 was invoked but never defined (see the help page).

[FOOTNOTEWHO20159–11-3] WHO 2015, pp. 9–11.

[arsenault-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.

[eic-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.

[whirl-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.

[Pelfrene-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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