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361593 Sigma

Artemisinin

98%

Synonym: Arteannuin, Qinghaosu

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Properties

Related Categories Antibiotics, Antiviral, Biochemicals and Reagents, Cell Biology, Nutrition Research,
assay   98%
optical activity   [α]20/D +76°, c = 0.5 in methanol
mp   156-157 °C(lit.)

Description

Frequently Asked Questions

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Packaging

100 mg in glass bottle

Biochem/physiol Actions

Artemisinin (Qinghaosu), a sesquiterpene lactone, is a highly active anti-malarial (falciparum malaria) drug. Artemisinin is also an anthelmintic (parasitic worm) effective against the blood fluke, schistosomiasis.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 361593.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Price and Availability

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Safety & Documentation

Safety Information

WGK Germany 
2
RTECS 
KD4170000

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

Chiral 2,2’-Bipyrrolidines

C2-symmetrical, chiral 2,2’-bipyrrolidines have recently emerged as interesting structural chiral motifs in a number of ligands for asymmetric transformations (Figure 1). When the two nitrogen atoms ...
Daniel Weibel
ChemFiles Volume 10 Article 4
Keywords: Asymmetric synthesis, Catalysis, Dihydroxylations, Ligands, Oxidations, Preferential Oxidation, Type

Traditional Medicinals and Cancer

Traditional Chinese Medicine (TCM) is a healing art that has been practiced for thousands of years. The practice of TCM is a holistic approach that includes the use of herbal preparations, acupunctur...
Lynn Stephenson, Product Specialist, Sigma® Life Science and Chloe McClanahan, Product Manager, Sigma Life Science
Biofiles Vol. 8, No. 6
Keywords: Analgesics, Antitumor agents, Apoptosis, Biofiles, Cancer, Drug discovery, Formulations, Fractionation, High performance liquid chromatography, Metabolites, Metabolomics, Methods, Nuclear magnetic resonance spectroscopy, Pharmaceutical

Peer-Reviewed Papers

References

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Multiple populations of artemisinin-resistant Plasmodium falciparum in Cambodia. Miotto O, Almagro-Garcia J, Manske M, et al. Nat. Genet. 45(6), 648-55, (2013)

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Mitigating the threat of artemisinin resistance in Africa: improvement of drug-resistance surveillance and response systems. Talisuna AO, Karema C, Ogutu B, et al. Lancet Infect. Dis. 12(11), 888-96, (2012)

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Recent clinical and molecular insights into emerging artemisinin resistance in Plasmodium falciparum. O'Brien C, Henrich PP, Passi N, et al. Curr. Opin. Infect. Dis. 24(6), 570-7, (2011)

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Early parasitological response following artemisinin-containing regimens: a critical review of the literature. Das D, Price RN, Bethell D, et al. Malaria Journal 12, 125, (2013)

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Artemisone and Artemiside Control Acute and Reactivated Toxoplasmosis in a Murine Model Ildiko R. Dunay, Wing Chi Chan, et al. Antimicrob. Agents Chemother. 53, 4450-4456, (2009)

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Synthesis and antimalarial efficacy of two-carbon-linked, artemisinin-derived trioxane dimers in combination with known antimalarial drugs. Mott BT, Tripathi A, Siegler MA, et al. J. Med. Chem. 56(6), 2630-41, (2013)

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Defining the timing of action of antimalarial drugs against Plasmodium falciparum. Wilson DW, Langer C, Goodman CD, et al. Antimicrob. Agents Chemother. 57(3), 1455-67, (2013)

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Metabolic engineering for the production of clinically important molecules: Omega-3 fatty acids, artemisinin, and taxol. Ye VM and Bhatia SK Biotechnol. J. 7(1), 20-33, (2012)

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Fighting drug-resistant Plasmodium falciparum: the challenge of artemisinin resistance. Wongsrichanalai C and Sibley CH Clin. Microbiol. Infect. 19(10), 908-16, (2013)

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Antidogmatic approaches to artemisinin resistance: reappraisal as treatment failure with artemisinin combination therapy. Krishna S and Kremsner PG Trends Parasitol. 29(7), 313-7, (2013)

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In vitro interaction of artemisinin derivatives or the fully synthetic peroxidic anti-malarial OZ277 with thapsigargin in Plasmodium falciparum strains. Abiodun OO, Brun R, and Wittlin S Malaria Journal 12, 43, (2013)

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Wacker-type oxidation of internal alkenes using Pd(Quinox) and TBHP. DeLuca RJ, Edwards JL, Steffens LD, et al. J. Org. Chem. 78(4), 1682-6, (2013)

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The pharmacogenetics of antimalaria artemisinin combination therapy. Piedade R, Gil JP. Expert Opin. Drug Metab. Toxicol. 7, 1185-1200, (2011)

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Artemisinin derivatives: a patent review (2006 - present). Njuguna NM, Ongarora DS, and Chibale K Expert Opin. Ther. Pat. 22(10), 1179-203, (2012)

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Effects of transferrin conjugates of artemisinin and artemisinin dimer on breast cancer cell lines. Gong Y, Gallis BM, Goodlett DR, et al. Anticancer Res. 33(1), 123-32, (2013)

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Rational engineering of plasticity residues of sesquiterpene synthases from Artemisia annua: product specificity and catalytic efficiency. Li JX, Fang X, Zhao Q, et al. Biochem. J. 451(3), 417-26, (2013)

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Infectious diseases. Understanding artemisinin resistance. Sibley CH Science 347(6220), 373-4, (2015)

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Infectious diseases. The genetics of resistant malaria. Vogel G Science 346(6215), 1276-7, (2014)

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Drug resistance. Population transcriptomics of human malaria parasites reveals the mechanism of artemisinin resistance. Mok S, Ashley EA, Ferreira PE, et al. Science 347(6220), 431-5, (2015)

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Drug resistance. K13-propeller mutations confer artemisinin resistance in Plasmodium falciparum clinical isolates. Straimer J, Gnädig NF, Witkowski B, et al. Science 347(6220), 428-31, (2015)

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Malaria: an update on current chemotherapy. Visser BJ, van Vugt M, and Grobusch MP Expert Opin. Pharmacother. 15(15), 2219-54, (2014)

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Molecular surveillance for artemisinin resistance in Africa. Roper C, Alifrangis M, Ariey F, et al. Lancet Infect. Dis. 14(8), 668-70, (2014)

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Synergic effects of artemisinin and resveratrol in cancer cells. Li P, Yang S, Dou M, et al. J. Cancer Res. Clin. Oncol. 140(12), 2065-75, (2014)

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Directional selection at the pfmdr1, pfcrt, pfubp1, and pfap2mu loci of Plasmodium falciparum in Kenyan children treated with ACT. Henriques G, Hallett RL, Beshir KB, et al. J. Infect. Dis. 210(12), 2001-8, (2014)

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Neuroauditory toxicity of artemisinin combination therapies-have safety concerns been addressed? Ramos-Martín V, González-Martínez C, Mackenzie I, et al. Am. J. Trop. Med. Hyg. 91(1), 62-73, (2014)

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Malaria: a molecular marker of artemisinin resistance. White NJ Lancet 383(9927), 1439-40, (2014)

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Time to contain artemisinin resistance. Lancet 383(9927), 1438, (2014)

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Artemisinin combination therapies and malaria parasite drug resistance: the game is afoot. Taylor SM and Juliano JJ J. Infect. Dis. 210(3), 335-7, (2014)

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[Artemisinin: a natural product for fighting against cancer]. Takatani-Nakase T Nippon. Yakurigaku Zasshi. 143(2), 61-4, (2014)

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[Determination of chrysosplenetin, metabolic inhibitor of artemisinin, in rat plasma by UPLC-ms/MS and study on its pharmacokinetics]. Chen J, Ji HY, Wei SJ, et al. Zhongguo Zhong Yao Za Zhi 38(19), 3363-7, (2013)

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Vector control to eliminate artemisinin resistant malaria in the Greater Mekong subregion. Kolaczinski J, Macdonald M, and Meek S Lancet Infect. Dis. 14(1), 9-11, (2014)

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Malaria: Resistance nailed. Plowe CV Nature 505(7481), 30-1, (2014)

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Trends in antimalarial drug use in Africa. Flegg JA, Metcalf CJ, Gharbi M, et al. Am. J. Trop. Med. Hyg. 89(5), 857-65, (2013)

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[Research advance in antitumor activities of artemisinin and its derivatives]. Yang H and Tan XJ Zhongguo Yi Xue Ke Xue Yuan Xue Bao. 35(4), 466-71, (2013)

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Malaria. White NJ, Pukrittayakamee S, Hien TT, et al. Lancet 383(9918), 723-35, (2014)

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Artemisinin therapy and severe delayed haemolysis. Jarvis JN, Coltart CE, Pule M, et al. Lancet 382(9887), 180, (2013)

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Epidemiology: resistance mapping in malaria. Bright AT and Winzeler EA Nature 498(7455), 446-7, (2013)

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Genome sequencing sheds light on emerging drug resistance in malaria parasites. Neafsey DE Nat. Genet. 45(6), 589-90, (2013)

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[Research progresses in synthetic biology of artemisinin]. Kong JQ, Wang W, Cheng KD, et al. Yao Xue Xue Bao 48(2), 193-205, (2013)

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The quest for affordable artemisinin. Cook SP Future Med. Chem. 5(3), 233-6, (2013)

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[Determination of artemisinin in rat plasma with HPLC-mS and its application]. Fu C, Yu J, Zou J, et al. Zhongguo Zhong Yao Za Zhi 37(19), 2964-7, (2012)

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Artemisinin-resistant malaria: research challenges, opportunities, and public health implications. Fairhurst RM, Nayyar GM, Breman JG, et al. Am. J. Trop. Med. Hyg. 87(2), 231-41, (2012)

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Artemisinin: discovery from the chinese herbal garden. Miller LH, Su X. Cell 146, 855-858, (2011)

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High-level semi-synthetic production of the potent antimalarial artemisinin. Paddon CJ, Westfall PJ, Pitera DJ, et al. Nature 496(7446), 528-32, (2013)

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Effects of artemisinin and Artemisia extracts on Haemonchus contortus in gerbils (Meriones unguiculatus). Squires JM, Ferreira JF, et al. Vet. Parasitol. 175, 103-108, (2011)

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The effect of an anti-malarial subsidy programme on the quality of service provision of artemisinin-based combination therapy in Kenya: a cluster-randomized, controlled trial. Kangwana BP, Kedenge SV, Noor AM, et al. Malaria Journal 12, 81, (2013)

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The pharmacokinetic evaluation of artemisinin drugs for the treatment of malaria in paediatric populations. Mercer AE and Sarr Sallah M Expert Opin. Drug Metab. Toxicol. 7(4), 427-39, (2011)

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Understanding the impact of subsidizing artemisinin-based combination therapies (ACTs) in the retail sector--results from focus group discussions in rural Kenya. Kedenge SV, Kangwana BP, Waweru EW, et al. PLoS ONE 8(1), e54371, (2013)

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Safety monitoring of artemisinin combination therapy through a national pharmacovigilance system in an endemic malaria setting. Thiam S, Ndiaye JL, Diallo I, et al. Malaria Journal 12, 54, (2013)

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in vitro and in vivo properties of ellagic acid in malaria treatment. Patrice Njomnang Soh et al Antimicrob. Agents Chemother. 53, 1100-6, (2009)

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Genetic analysis in mice identifies cysteamine as a novel partner for artemisinin in the treatment of malaria. Min-Oo G and Gros P Mamm. Genome 22(7-8), 486-94, (2011)

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Molecular monitoring of antimalarial drug resistance among Plasmodium falciparum field isolates from Odisha, India. Das Sutar SK, Dhangadamajhi G, Kar SK, et al. Acta Trop. 126(1), 84-7, (2013)

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Evolution of Plasmodium falciparum drug resistance: implications for the development and containment of artemisinin resistance. Mita T and Tanabe K Jpn. J. Infect. Dis. 65(6), 465-75, (2012)

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Qinghaosu (artemisinin): chemistry and pharmacology. Li Y Acta Pharmacol. Sin. 33(9), 1141-6, (2012)

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Metabolic engineering of plants for artemisinin synthesis. Farhi M, Kozin M, Duchin S, et al. Biotechnol. Genet. Eng. Rev. 29, 135-48, (2013)

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Searching for artemisinin production improvement in plants and microorganisms. Barbacka K and Baer-Dubowska W Curr. Pharm. Biotechnol. 12(11), 1743-51, (2011)

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Dried whole plant Artemisia annua as an antimalarial therapy. Elfawal MA, Towler MJ, Reich NG, et al. PLoS ONE 7(12), e52746, (2012)

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Artemisinin-based combination therapy availability and use in the private sector of five AMFm phase 1 countries. Davis B, Ladner J, Sams K, et al. Malaria Journal 12, 135, (2013)

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A molecular marker of artemisinin-resistant Plasmodium falciparum malaria. Ariey F, Witkowski B, Amaratunga C, et al. Nature 505(7481), 50-5, (2014)

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Artemisinins for schistosomiasis and beyond. Utzinger J, Xiao SH, et al. Curr. Opin. Investig. Drugs 8, 105-116, (2007)

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Protein complex directs hemoglobin-to-hemozoin formation in Plasmodium falciparum. Chugh M, Sundararaman V, Kumar S, et al. Proc. Natl. Acad. Sci. U. S. A. 110(14), 5392-7, (2013)

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Cholesterol-reducer, antioxidant and liver protective effects of Thymbra spicata L. var. spicata. Akkol, E.K., et al. J. Ethnopharmacol. 126, 314-9, (2009)

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Protein-based signatures of functional evolution in Plasmodium falciparum. Gardner KB, Sinha I, et al. BMC Evol. Biol. 11, 257, (2011)

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Preparation and characterization of anti-algal sustained-release granules and their inhibitory effects on algae. Ni L, Acharya K, Ren G, et al. Chemosphere 91(5), 608-15, (2013)

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Schistosoma mansoni: N-acetylcysteine downregulates oxidative stress and enhances the antischistosomal activity of artemether in mice. Seif el-Din SH, Al-Hroob AM, Ebeid FA. Exp. Parasitol. 128, 230-235, (2011)

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Increasing incidence of malaria in children despite insecticide-treated bed nets and prompt anti-malarial therapy in Tororo, Uganda. Jagannathan P, Muhindo MK, Kakuru A, et al. Malaria Journal 11, 435, (2012)

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Malaria and artemisinin derivatives: an updated review. Ansari MT, Saify ZS, Sultana N, et al. Mini Rev. Med. Chem. 13(13), 1879-902, (2013)

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Mutation analysis in pfmdr1 and pfmrp1 as potential candidate genes for artemisinin resistance in Plasmodium falciparum clinical isolates 4years after implementation of artemisinin combination therapy in Iran. Pirahmadi S, Zakeri S, Afsharpad M, et al. Infect. Genet. Evol. 14, 327-34, (2013)

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Pro-oxidant properties of indolone-N-oxides in relation to their antimalarial properties. Yen NT, Ibrahim H, Reybier K, et al. J. Inorg. Biochem. 126, 7-16, (2013)

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Chemosensitization potential of P-glycoprotein inhibitors in malaria parasites. Alcantara LM, Kim J, Moraes CB, et al. Exp. Parasitol. 134(2), 235-43, (2013)

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Artemisinin based combination therapy in travel medicine. Jelinek T Travel Med. Infect. Dis. 11(1), 23-8, (2013)

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Systematic review and meta-analysis of artemisinin based therapies for the treatment and prevention of schistosomiasis. Pérez del Villar L, Burguillo FJ, López-Abán J, et al. PLoS ONE 7(9), e45867, (2012)

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Bioassay of Artemisia annua leaf extracts and artemisinin against larvae of Culex quinquefasciatus and Culex tritaeniorhynchus. Sharma G, Kumar K, Sharma A, et al. J. Am. Mosq. Control Assoc. 28(4), 317-9, (2012)

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Genetic ablation of plasmoDJ1, a multi-activity enzyme, attenuates parasite virulence and reduces oocyst production. Singhal N, Atul, Mastan BS, et al. Biochem. J. 461(2), 189-203, (2014)

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Comparative impacts over 5 years of artemisinin-based combination therapies on Plasmodium falciparum polymorphisms that modulate drug sensitivity in Ugandan children. Conrad MD, LeClair N, Arinaitwe E, et al. J. Infect. Dis. 210(3), 344-53, (2014)

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Fast and reliable artemisinin determination from different Artemisia annua leaves based alimentary products by high performance liquid chromatography-tandem mass spectrometry. Carrà A, Bagnati R, Fanelli R, et al. Food Chem. 142, 114-20, (2014)

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Merck 14,817

Beil. 19,11,690

FT-IR 2 (1), 1200:B / FT-NMR 1 (1), 1163:B / RegBook 1 (1), 819:K / Structure Index 1, 128:C:8

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