Structure via PubChem · Public domain (PubChem)
artemisinin
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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
OverviewAI-generated
Artemisinin is a chemical compound with the formula C₁₅H₂₂O₅. Its IUPAC name is (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. The molecule has a mass of 282.146723804 and a weight of 282.33.
Physicochemical properties include an xlogp of 2.8 and a topological polar surface area of 54. The compound features five hydrogen bond acceptors and zero hydrogen bond donors, with a charge of 0. It is referenced by 450 other encyclopedia articles and has 13626 associated PubMed entries.
Synthesized by Vinony from 18 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
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.