artemisinin

Ligand id: 9954

Name: artemisinin

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
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

Molecular properties generated using the CDK

Classification
Compound class Natural product or derivative
Ligand families/groups Antimalarial ligands
International Nonproprietary Names
INN number INN
5954 artemisinin
Comments
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 quinghaosu 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). 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 [3].
We show one representation of artemisinin here. As with other natural products, there are alternative chemical structures due to the complex stereochemistry.

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.
Database Links
CAS Registry No. 63968-64-9 (source: Scifinder)
ChEBI CHEBI:223316
ChEMBL Ligand CHEMBL269671
PubChem CID 68827
Search Google for chemical match using the InChIKey BLUAFEHZUWYNDE-NNWCWBAJSA-N
Search Google for chemicals with the same backbone BLUAFEHZUWYNDE
Search PubMed clinical trials artemisinin
Search PubMed titles artemisinin
Search PubMed titles/abstracts artemisinin
Search UniChem for chemical match using the InChIKey BLUAFEHZUWYNDE-NNWCWBAJSA-N
Search UniChem for chemicals with the same backbone BLUAFEHZUWYNDE
Wikipedia Artemisinin