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
 
Notes:
sesquiterpene lactone from chinese medicinal herb artemisia annua
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      ARTEMISININ WORMWOOD EXTRACT (WORLD WAY)
       
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CAS Number: 63968-64-9Picture of molecule
FDA UNII: 9RMU91N5K2
Beilstein Number: 4194670
MDL: MFCD00081057
XlogP3-AA: 2.80 (est)
Molecular Weight: 282.33634000
Formula: C15 H22 O5
BioActivity Summary: listing
Category: antimicrobial, skin conditioning
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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IBM Patents: Obtain
Pubchem Patents: Search
PubMed: Search
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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)
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Organoleptic Properties:
  
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: antimicrobial agents
skin conditioning
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Suppliers:
Charkit Chemical
ARTEMISININ WORMWOOD EXTRACT (WORLD WAY)
Coompo
For experimental / research use only.
Artemisinin from Plants ≥96%
Odor: characteristic
Use: Active antimalarial constituent of the tradional Chinese medicinal herb Artemisia annua L., Compositae, which has been known for almost 2000 years as Qinghao. Antimalarial.
Qingdao Dacon Trading
Artemisinin
Santa Cruz Biotechnology
For experimental / research use only.
Artemisinin >98%
Sigma-Aldrich: Sigma
For experimental / research use only.
Artemisinin 98%
Sinoway Industrial
For experimental / research use only.
Artemisinin
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50  5576 mg/kg
BEHAVIORAL: TREMOR BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: ATAXIA
Journal of Traditional Chinese Medicine Vol. 2, Pg. 31, 1982.

oral-mouse LD50  4228 mg/kg
BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: ATAXIA BEHAVIORAL: TREMOR
Journal of Traditional Chinese Medicine Vol. 2, Pg. 31, 1982.

intraperitoneal-mouse LD50  1558 mg/kg
Chinese Medical Journal Vol. 92, Pg. 811, 1979.

intramuscular-dog LD  > 800 mg/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Journal of Traditional Chinese Medicine Vol. 2, Pg. 31, 1982.

unreported-mouse LD  > 2000 mg/kg
Antimicrobial Agents and Chemotherapy. Vol. 37, Pg. 1108, 1993.

intramuscular-mouse LD50  2800 mg/kg
Chinese Medical Journal Vol. 92, Pg. 811, 1979.

intramuscular-rat LD50  2571 mg/kg
BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: ATAXIA BEHAVIORAL: TREMOR
Journal of Traditional Chinese Medicine Vol. 2, Pg. 31, 1982.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: antimicrobial, skin conditioning
Recommendation for artemisinin usage levels up to:
 not for fragrance use.
 
Recommendation for artemisinin flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
ClinicalTrials.gov: search
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
Env. Mutagen Info. Center: Search
NLM Developmental and Reproductive Toxicity: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 68827
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 2
Chemidplus: 0063968649
RTECS: KD4170000 for cas# 63968-64-9
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References:
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 68827
Pubchem (sid): 135028424
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
Golm Metabolome Database: Search
KEGG (GenomeNet): C09538
HMDB (The Human Metabolome Database): Search
Export Tariff Code: 2932.29.5050
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 Artemisia annua
Search Trop  Picture
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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
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Articles:
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.
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