361593
Artemisinin
98%
Synonym(s):
Arteannuin, Qinghaosu
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About This Item
Empirical Formula (Hill Notation):
C15H22O5
CAS Number:
Molecular Weight:
282.33
NACRES:
NA.79
PubChem Substance ID:
UNSPSC Code:
12352205
MDL number:
Quality Level
assay
98%
form
solid
optical activity
[α]20/D +76°, c = 0.5 in methanol
mp
156-157 °C (lit.)
antibiotic activity spectrum
parasites, viruses
application(s)
metabolomics
vitamins, nutraceuticals, and natural products
mode of action
enzyme | inhibits
SMILES string
C[C@@H]1CC[C@H]2[C@@H](C)C(=O)O[C@@H]3OC4(C)CC[C@@H]1[C@@]23OO4
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
InChI key
BLUAFEHZUWYNDE-NNWCWBAJSA-N
General description
Artemisinin is extracted from sweet wormwood (Artemisia annua). It has anticancer, antiprotozoal and antiviral activities. Artemisinin is associated with brainstem encephalopathy.
Application
Artemisinin has been used:
- in drug susceptibility assays
- as a standard for its quantification from artemisinin from hairy roots
- to check cell viability using 3-(4, 5-dimethylthiazol-2yl)-2,5-diphenyl tetrazolium bromide (MTT) assay
- as an antimalarial agent to investigate the role of autophagy-related (ATG) genes throughout the P. falciparum asexual and sexual blood stages
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.
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Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Olivo Miotto et al.
Nature genetics, 45(6), 648-655 (2013-04-30)
We describe an analysis of genome variation in 825 P. falciparum samples from Asia and Africa that identifies an unusual pattern of parasite population structure at the epicenter of artemisinin resistance in western Cambodia. Within this relatively small geographic area
C J Paddon et al.
Nature, 496(7446), 528-532 (2013-04-12)
In 2010 there were more than 200 million cases of malaria, and at least 655,000 deaths. The World Health Organization has recommended artemisinin-based combination therapies (ACTs) for the treatment of uncomplicated malaria caused by the parasite Plasmodium falciparum. Artemisinin is a
The multifunctional autophagy pathway in the human malaria parasite, Plasmodium falciparum
Cervantes S, et al.
Autophagy, 10(1), 80-92 (2014)