Structure via PubChem · Public domain (PubChem)
artemisinin
Sign in to saveAlso known as artemisinine
Artemisinin () and its semisynthetic derivatives are a group of drugs used in the treatment of malaria due to Plasmodium falciparum. It was discovered in 1972 by Tu Youyou, who shared the 2015 Nobel Prize in Physiology or Medicine for her discovery. Artemisinin-based combination therapies (ACTs) have become standard treatment worldwide for P. falciparum malaria as well as malaria due to other species of Plasmodium. Artemisinin can be extracted from the herb Artemisia annua (sweet wormwood), which is used in traditional Chinese medicine. Alternatively, it can be prepared by a semi-synthetic met
Key facts
- Drug.Verifiedfields
- changed
- Drug.verifiedrevid
- 671166811
- Drug.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
- Drug.image
- Artemisinin skeletal.svg
- Drug.image_class
- skin-invert-image
- Drug.image2
- Artemisinin 3D balls 2.png
- Drug.image_class2
- bg-transparent
- Drug.routes_of_administration
- Oral
- Drug.CAS_number
- 63968-64-9
- Drug.ATC_prefix
- P01
- Drug.ATC_suffix
- BE01
- Drug.PubChem
- 68827
- Drug.ChemSpiderID
- 62060
- Drug.UNII
- 9RMU91N5K2
- Drug.KEGG
- D02481
- Drug.ChEBI
- 223316
- Drug.ChEMBL
- 567597
- Drug.C
- 15
via Wikipedia infobox
Chemical data
- Formula
- C15H22O5
- Molecular weight
- 282.33 g/mol
- IUPAC name
- (1R,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one
- SMILES
- C[C@@H]1CC[C@H]2[C@H](C(=O)O[C@H]3[C@@]24[C@H]1CC[C@](O3)(OO4)C)C
- InChIKey
- BLUAFEHZUWYNDE-NNWCWBAJSA-N
- XLogP
- 2.8
- Polar surface area
- 54 Ų
- H-bond donors
- 0
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Research
13,626 papers- The birth of artemisinin.Pharmacology & therapeutics · 2020
- Artemisinin-resistant malaria.Clinical microbiology reviews · 2024
- Artemisinin and Its Derivatives as Potential Anticancer Agents.Molecules (Basel, Switzerland) · 2024
- Artemisinin: mechanisms of action, resistance and toxicity.International journal for parasitology · 2002
- Artemisinin-A Gift from Traditional Chinese Medicine to the World (Nobel Lecture).Angewandte Chemie (International ed. in English) · 2016
via PubMed
~25 min read
Encyclopedic overview
25 sectionsContents
- Medical use
- Contraindications
- Adverse effects
- Chemistry
- Mechanism of action
- Resistance
- Synthesis
- Biosynthesis in ''Artemisia annua''
- Chemical synthesis
- Synthesis in engineered organisms
- Production and price
- Metabolism
- History
- Etymology
- Discovery
- Research
- New artemisinin-based combination therapies
- Helminthiasis
- Cancer
- Autoimmune disease
- Polycystic ovary syndrome
- See also
- References
- Further reading
- External links
Artemisinin () and its semisynthetic derivatives are a group of drugs used in the treatment of malaria due to Plasmodium falciparum. It was discovered in 1972 by Tu Youyou, who shared the 2015 Nobel Prize in Physiology or Medicine for her discovery. Artemisinin-based combination therapies (ACTs) have become standard treatment worldwide for P. falciparum malaria as well as malaria due to other species of Plasmodium. Artemisinin can be extracted from the herb Artemisia annua (sweet wormwood), which is used in traditional Chinese medicine. Alternatively, it can be prepared by a semi-synthetic method from a precursor compound that can be produced using a genetically engineered yeast, which is much more efficient than extraction from the plant.
Artemisinin and its derivatives are all sesquiterpene lactones containing an unusual peroxide bridge. This endoperoxide 1,2,4-trioxane ring is responsible for their antimalarial properties. Few other natural compounds with such a peroxide bridge are known.
Excerpted from Wikipedia’s “artemisinin” article, available under the CC BY-SA 4.0 licence.