artemisinin   Click here for help

GtoPdb Ligand ID: 9954

Synonyms: qinghaosu
Antimalarial Ligand
Comment: Artemisinin is a sesquiterpene lactone with an unusual endoperoxide bridge, believed to be responsible for the antimalarial activity of the compound. It is a natural product, isolated from the qinghao or sweet wormwood plant (Artemisia annua) and used in Chinese traditional medicine to treat fever.
Artemisinin is a prodrug that is converted to the active metabolite artenimol (dihydroartemisinin).
We show one representation of artemisinin here. As with other natural products, there are alternative chemical structures due to the complex stereochemistry.

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 0
Rotatable bonds 0
Topological polar surface area 53.99
Molecular weight 282.15
XLogP 3.04
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES O=C1OC2OC3(C)CCC4C2(C(C1C)CCC4C)OO3
Isomeric SMILES O=C1O[C@@H]2O[C@@]3(C)CC[C@@H]4[C@]2([C@H]([C@H]1C)CC[C@H]4C)OO3
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
InChI Key BLUAFEHZUWYNDE-NNWCWBAJSA-N
Guide to Malaria Pharmacology Comments
Artemisinin was first isolated in the early 1970s during antimalarial research initiated by the Chinese military (Project 523) and led to one half of the 2015 Nobel Prize in Physiology or Medicine being awarded to Tu Youyou for her work on the discovery and isolation of the compound [3].
A number of semisynthetic artemisinin derivatives have been developed that have an improved pharmacokinetic profile, these include artemether, artesunate, and artemotil.
Artemisinin and derivatives have potent activity against the asexual blood stage of P. falciparum (including chloroquine-resistant strains) and are characterised by an extremely rapid parasitemia clearance and a short terminal half-life of elimination. Combination therapies, containing an artemisinin derivative (artemisinin-combination therapies, ACTs), are recommended by the World Health Organization as the standard treatment for uncomplicated P. falciparum malaria [4].

Potential Target/Mechanism Of Action: As the precise mechanism of action of artemisinin is not yet known, we do not have a molecular target for this compound.