artesunate   Click here for help

GtoPdb Ligand ID: 9956

Approved drug PDB Ligand Antimalarial Ligand
artesunate is an approved drug (FDA (2020), EMA (2021))
Compound class: Synthetic organic
Comment: Artesunate is a semisynthetic derivative of artemisinin, a natural product isolated from the qinghao or sweet wormwood plant (Artemisia annua). It contains an unusual endoperoxide bridge, believed to be responsible for the antimalarial activity of artemisinin and its derivatives.
Artesunate is a prodrug that is converted to the active metabolite artenimol (dihydroartemisinin).

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.

artesunate is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 8
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 100.52
Molecular weight 384.18
XLogP 2.92
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES OC(=O)CCC(=O)OC1OC2OC3(C)CCC4C2(C(C1C)CCC4C)OO3
Isomeric SMILES OC(=O)CCC(=O)O[C@@H]1O[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/C19H28O8/c1-10-4-5-13-11(2)16(23-15(22)7-6-14(20)21)24-17-19(13)12(10)8-9-18(3,25-17)26-27-19/h10-13,16-17H,4-9H2,1-3H3,(H,20,21)/t10-,11-,12+,13+,16-,17-,18-,19-/m1/s1
InChI Key FIHJKUPKCHIPAT-AHIGJZGOSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Guide to Malaria Pharmacology Comments
Artesunate has potent antimalarial activity against the asexual blood stage of P. falciparum (including chloroquine-resistant strains) and is characterised by an extremely rapid parasitemia clearance.

Artesunate is listed in the World Health Organization's Model List of Essential Medicines as an antimalarial for use in the management of severe malaria. It is also listed as an antimalarial for curative treatment in combination with either amodiaquine, mefloquine or sulfadoxine + pyrimethamine (SP). These are three of the artemisinin-based combination therapies (ACTs) recommended in the WHO's Guidelines for the treatment of malaria [4].

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