artemisinin

(1S,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one

CAS: 63968-64-9 C15 H22 O5 MW: 282.33634000

Identification

Nameartemisinin
CAS Number63968-64-9
FDA UNII9RMU91N5K2
Molecular FormulaC15 H22 O5
Molecular Weight282.33634000
MDL NumberMFCD00081057
Beilstein4194670

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 389.00 to 390.00 °C. @ 760.00 mm Hg (est)
Flash Point 342.00 °F. TCC ( 172.00 °C. ) (est)
logP (o/w) 2.900
Soluble in water, 51.85 mg/L @ 25 °C (est)

Cosmetic Information

CosIngcosmetic data
Cosmetic Usesantimicrobial agents

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityoral-rat LD50 5576 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements', 'BEHAVIORAL: TREMOR\nBEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)\nBEHAVIORAL: ATAXIA', 'BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)\nBEHAVIORAL: ATAXIA\nBEHAVIORAL: TREMOR', 'BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)\nBEHAVIORAL: ATAXIA\nBEHAVIORAL: TREMOR']

Safety in Use

Categoryantimicrobial, skin conditioning
Recommendation for artemisinin usage levels up tonot for fragrance use.
Recommendation for artemisinin flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

Artemisia annua

Synonyms

artemisine artemisinine artemisininum huanghuahaosu (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 qing hau sau qinghaosu 1,5,9- trimethyl-(1R,4S,5R,8S,9R,12S,13R)-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one 1,5,9- trimethyl-(1R,4S,5R,9R,12S,13R)-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one 1,5,9- trimethyl-(1S,4S,5R,8S,9R,12S,13S)-11,15,16-trioxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one (1R,4S,5R,8S,9R,12S,13R)-1,5,9- trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one (1S,4S,5R,8S,9R,12S,13R)-1,5,9- trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one Info: Artemisinin PubMed: Engineering a mevalonate pathway in Escherichia coli for production of terpenoids. PubMed: Metabolic engineering of plants for artemisinin synthesis. PubMed: Regulation of 3β-hydroxysteroid dehydrogenase and sulphotransferase 2A1 gene expression in primary porcine hepatocytes by selected sex-steroids and plant secondary metabolites from chicory (Cichorium intybus L.) and wormwood (Artemisia sp.). PubMed: Pumped up: reflections on PfATP6 as the target for artemisinins. PubMed: Regulation of cytochrome P450 mRNA expression in primary porcine hepatocytes by selected secondary plant metabolites from chicory (Cichorium intybus L.). PubMed: Artemisinin rewires the protein interaction network in cancer cells: network analysis, pathway identification, and target prediction. PubMed: Fast and reliable artemisinin determination from different Artemisia annua leaves based alimentary products by high performance liquid chromatography-tandem mass spectrometry. PubMed: Dihydroartemisinin promotes angiogenesis during the early embryonic development of zebrafish. PubMed: Toxic essential oils. Part II: chemical, toxicological, pharmacological and microbiological profiles of Artemisia annua L. volatiles. PubMed: Protein complex directs hemoglobin-to-hemozoin formation in Plasmodium falciparum. PubMed: Inhibitory effect of dihydroartemisinin against phorbol ester-induced cyclooxygenase-2 expression in macrophages. PubMed: Use of artemether-lumefantrine to treat malaria during pregnancy: what do we know and need to know? PubMed: Defining the timing of action of antimalarial drugs against Plasmodium falciparum. PubMed: Artemisinin production and precursor ratio in full grown Artemisia annua L. plants subjected to external stress. PubMed: Management of imported malaria in Europe. PubMed: Effect of external stress on density and size of glandular trichomes in full-grown Artemisia annua, the source of anti-malarial artemisinin. PubMed: Awareness of anti-malarial policy and malaria treatment practices of patent medicine vendors in three Nigerian states. PubMed: Artemether-lumefantrine: an option for malaria. PubMed: Pyronaridine-artesunate combination therapy for the treatment of malaria. PubMed: Monitoring of artemisinin, dihydroartemisinin, and artemether in environmental matrices using high-performance liquid chromatography-tandem mass spectrometry (LC-MS/MS). PubMed: In vitro trematocidal effects of crude alcoholic extracts of Artemisia annua, A. absinthium, Asimina triloba, and Fumaria officinalis: trematocidal plant alcoholic extracts. PubMed: Artemisinin reduces the level of antibodies to gliadin in schizophrenia. PubMed: Millet-porridge with Artemisia annua as first aid for African children with malaria? PubMed: Genotoxicity assessment of the antimalarial compound artesunate in somatic cells of mice. PubMed: Artemisia annua extracts, artemisinin and 1,8-cineole, prevent fruit infestation by a major, cosmopolitan pest of apples. PubMed: Malaria: severe, life-threatening. PubMed: Update on the diagnosis and treatment of food-borne trematode infections. PubMed: Intravenous artesunate for the treatment of severe malaria. PubMed: Effect of artemisinin on oocyst wall formation and sporulation during Eimeria tenella infection. PubMed: Single-dose safety, pharmacokinetics, and food effects studies of compound naphthoquine phosphate tablets in healthy volunteers. PubMed: Merging traditional Chinese medicine with modern drug discovery technologies to find novel drugs and functional foods. PubMed: Drying affects artemisinin, dihydroartemisinic acid, artemisinic acid, and the antioxidant capacity of Artemisia annua L. leaves. PubMed: Dispersible formulation of artemether/lumefantrine: specifically developed for infants and young children. PubMed: Progress in the development of piperaquine combinations for the treatment of malaria. PubMed: Treatment of malaria from monotherapy to artemisinin-based combination therapy by health professionals in urban health facilities in Yaoundé, central province, Cameroon. PubMed: A stratified random survey of the proportion of poor quality oral artesunate sold at medicine outlets in the Lao PDR - implications for therapeutic failure and drug resistance. PubMed: Artemisinin-dipeptidyl vinyl sulfone hybrid molecules: design, synthesis and preliminary SAR for antiplasmodial activity and falcipain-2 inhibition. PubMed: First artemisinin-based antimalarial combination approved for U.S. market. PubMed: [Pregnancy and traveling]. PubMed: Willingness and ability to pay for artemisinin-based combination therapy in rural Tanzania. PubMed: Artemether-lumefantrine versus dihydroartemisinin-piperaquine for treating uncomplicated malaria: a randomized trial to guide policy in Uganda. PubMed: Artemether + lumefantrine: new drug. An alternative to atovaquone + proguanil. PubMed: Household burden of malaria in South Africa and Mozambique: is there a catastrophic impact? PubMed: Artemisinins and synthetic trioxolanes in the treatment of helminth infections. PubMed: [The treatment of falciparum malaria]. PubMed: How much fat is necessary to optimize lumefantrine oral bioavailability? PubMed: Nutrient deficiency in the production of artemisinin, dihydroartemisinic acid, and artemisinic acid in Artemisia annua L. PubMed: Malaria: uncomplicated, caused by Plasmodium falciparum. PubMed: Pharmacovigilance and new essential drugs in Africa: Zambia draws lessons from its own experiences and beyond. PubMed: Mechanism of antimalarial action of the synthetic trioxolane RBX11160 (OZ277). PubMed: Genetic linkage of pfmdr1 with food vacuolar solute import in Plasmodium falciparum. PubMed: Modeling the decomposition mechanism of artemisinin. PubMed: Oral artemisinin prevents and delays the development of 7,12-dimethylbenz[a]anthracene (DMBA)-induced breast cancer in the rat. PubMed: Analysis of artemisinin in Artemisia annua L. by LC-MS with selected ion monitoring. PubMed: ATPase activity of purified plasma membranes and digestive vacuoles from Plasmodium falciparum. PubMed: Artemisinin-based combination therapies for uncomplicated malaria. PubMed: Characterization of the effect of retinol on Plasmodium falciparum in vitro. PubMed: Reaction of artemisinin with haemoglobin: implications for antimalarial activity. PubMed: Antimalarial quinolines and artemisinin inhibit endocytosis in Plasmodium falciparum. PubMed: Artemisinins target the SERCA of Plasmodium falciparum. PubMed: Safety evaluations of drugs containing artemisinin derivatives for the treatment of malaria. PubMed: Mechanism-based design of parasite-targeted artemisinin derivatives: synthesis and antimalarial activity of new diamine containing analogues. PubMed: Effects of arteether on an auditory radial-arm maze task in rats. PubMed: Studies of the neurotoxicity of oral artemisinin derivatives in mice. PubMed: Arteether toxicokinetics and pharmacokinetics in rats after 25 mg/kg/day single and multiple doses. PubMed: Antiparasitic agents. PubMed: The Plasmodium falciparum translationally controlled tumor protein: subcellular localization and calcium binding. PubMed: Pharmacokinetics of mefloquine combined with artesunate in children with acute falciparum malaria. PubMed: Effect of food intake on pharmacokinetics of oral artemisinin in healthy Vietnamese subjects. PubMed: Artemisinin enhances heme-catalysed oxidation of lipid membranes. PubMed: Oxidative stress in malaria; implications for prevention and therapy. PubMed: Morphologic effects of artemisinin in Plasmodium falciparum.