Artemisinin

Artemisinin

Clinical data
Pronunciation	/ɑːrtᵻˈmɪsᵻnᵻn/
Routes of administration	Oral
ATC code	P01BE01 (WHO)
Identifiers
IUPAC name (3R,5aS,6R,8aS,9R,12S,12aR)-Octahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10(3H)-one
Synonyms	Artemisinine, qinghaosu
CAS Number	63968-64-9 Y
PubChem CID	68827
ChemSpider	62060 Y
UNII	9RMU91N5K2
KEGG	D02481 Y
ChEBI	CHEBI:223316 Y
ChEMBL	CHEMBL567597 N
ECHA InfoCard	100.110.458
Chemical and physical data
Formula	C15H22O5
Molar mass	282.332 g/mol
3D model (Jmol)	Interactive image
Density	1.24 ± 0.1 g/cm3
Melting point	152 to 157 °C (306 to 315 °F)
Boiling point	decomposes
SMILES O=C3O[C@@H]4O[C@@]1(OO[C@@]42[C@@H](CC1)[C@H](C)CC[C@H]2[C@H]3C)C
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 Y Key:BLUAFEHZUWYNDE-NNWCWBAJSA-N Y
NY (what is this?)

Artemisinin, also known as qinghao su (Chinese: 青蒿素), and its semi-synthetic derivatives are a group of drugs used against Plasmodium falciparum malaria. It was discovered by Tu Youyou, a Chinese scientist, who was awarded half of the 2015 Nobel Prize in Medicine for her discovery. Treatments containing an artemisinin derivative (artemisinin-combination therapies, ACTs) are now standard treatment worldwide for P. falciparum malaria. Artemisinin is isolated from the plant Artemisia annua, sweet wormwood, an herb employed in Chinese traditional medicine. A precursor compound can be produced using genetically engineered yeast.

Chemically, artemisinin is a sesquiterpene lactone containing an unusual peroxide bridge. This peroxide is believed to be responsible for the drug's mechanism of action. Few other natural compounds with such a peroxide bridge are known.

Artemisinin and its endoperoxides derivatives have been used for the treatment of P. falciparum related infections but low bioavailability, poor pharmacokinetic properties and high cost of the drugs are a major drawback of their use. Use of the drug by itself as a monotherapy is explicitly discouraged by the World Health Organization, as there have been signs that malarial parasites are developing resistance to the drug. Therapies that combine artemisinin or its derivatives with some other antimalarial drug are the preferred treatment for malaria and are both effective and well tolerated in patients.