Grundinformationen
- Standard-SMILES
C[C@@H]1CC[C@H]2[C@@H](C)C(=O)O[C@@H]3O[C@@]4(C)CC[C@@H]1[C@]32OO4- InChIKey
BLUAFEHZUWYNDE-NNWCWBAJSA-N- Summenformel
- C15H22O5
- Durchschnittliche Molmasse
- 282,33 g/mol
Überblick
(+)-artemisinin is a sesquiterpene lactone obtained from sweet wormwood, Artemisia annua, which is used as an antimalarial for the treatment of multi-drug resistant strains of falciparum malaria. It has a role as an antimalarial and a plant metabolite. It is an organic peroxide and a sesquiterpene lactone.
Namen und Bezeichner
- Bevorzugter Name
- Artemisinin
- IUPAC
- (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
Namen und Synonyme
artemisinin63968-64-9QinghaosuHuanghuahaosu(+)-ArtemisininArtemisinineArtemisininumArtemisininaquinghaosuDTXSID2040652GNF-Pf-53419RMU91N5K2
Weitere Namen anzeigen
CHEBI:223316(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-oneNSC-369397DTXCID40819890qing hao su2-azanyl-5-methylsulfanyl-pentanoic acid1,5,9-trimethyl-(1R,4S,5R,9R,12S,13R)-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one(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
Datenbank-Bezeichner
- CAS
119241-68-8、63968-64-9- PubChem CID
- 68827
- DTXSID
DTXSID2040652- ChEMBL
CHEMBL269671- ChEBI
CHEBI:223316- UNII
- 9RMU91N5K2
- EC Number
- 700-290-5
- Nikkaji
- J86.051D
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2,8
- Polarare Oberfläche (TPSA)
- 54 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 5
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 20
- Formalladung
- 0
- Komplexität
- 452
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C15 isoprenoids (sesquiterpenes) [PR0103]
LogP2.9
Collision Cross Section
168.1 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
167.28 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 5.6% (2 of 36) of reports.
Danger
H242 (91.7%): Heating may cause a fire [Danger Self-reactive substances and mixtures; Organic peroxides]
P210, P234, P235, P240, P273, P280, P370+P378, P391, P403, P410, P411, P420, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 36 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory InformationStatus: Active Update: 15-11-2012 https://echa.europa.eu/registration-dossier/-/registered-dossier/1057
Hazard Classes and CategoriesOrg. Perox. D (91.7%)
Toxikologische Informationen
Toxicity Summary
A 2025 systematic review notes that although Artemisinin is generally regarded as being well-tolerated, ico-administration with other pharmacological agents should be carefully monitored. In animal-focused studies, Artemisinin led to neurotoxicity (affecting brain matter and nuclei), cardiotoxicity (slower heart rate and prolonged QTc interval), hematotoxicity (low counts of white blood cells and platelets), and genotoxicity, embryotoxicity, and nephrotoxicity.
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Artemisinin
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Chemie und Industrie
Pharmakologische Informationen
ATC CodeP - Antiparasitic products, insecticides and repellents
Mechanism of ActionA 2025 systematic review notes that Artemisinin decreases lipid accumulation in hepatocytes by inhibiting CD36 expression and reducing TAG content.
MeSH Pharmacological ClassificationSubstances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.
Zugehörige Reaktionen
4
Verknüpfte Notizen
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