artesunate   

GtoPdb Ligand ID: 9956

artesunate is an approved drug (FDA (2020))
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.
2D Structure
Click here for structure editor
Physico-chemical Properties
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
SMILES / InChI / InChIKey
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
No information available.
Summary of Clinical Use
Intravenous or intramuscular artesunate is one of the recommended treatments for children and adults with severe malaria [3]. As part of an artemisinin-based combination therapy (ACT), artesunate is also a highly effective treatment for uncomplicated malaria caused by all species of the malaria parasite.
Pharmacokinetics
Elimination
The elimination half-life is between 15-45 minutes depending on route of administration [2].