Artesunate (CHEM017845)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:41:22 UTC
Update Date2016-11-09 01:15:41 UTC
Accession NumberCHEM017845
Identification
Common NameArtesunate
ClassSmall Molecule
DescriptionArtesunate (AS) is a medication used to treat malaria. The intravenous form is preferred to quinidine for severe malaria. Often it is used as part of combination therapy, such as artesunate plus mefloquine. It is not used for the prevention of malaria. Artesunate can be given by injection into a vein, injection into a muscle, by mouth, and by rectum.Artesunate is generally well tolerated. Side effects may include a slow heartbeat, allergic reaction, dizziness, and low white blood cell levels. During pregnancy it appears to be a safer option, even though animal studies have found harm to the baby. Use is likely okay during breastfeeding. It is in the artemisinin class of medication.Artesunate is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. The wholesale cost in the developing world is US$2.09 to US$2.57 a dose. It is not commercially available in the United States; however, it can be obtained via the Centers for Disease Control. It was originally made from the sweet wormwood plant.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Artesunic acidGenerator
Dihydroartemisinine-12-alpha-succinateMeSH
Sodium artesunateMeSH
Dihydroartemisinine 12 alpha succinateMeSH
Succinyl dihydroartemisininMeSH
Dihydroartemisinin, succinylMeSH
MalartinMeSH
MalacefMeSH
ArtesunateMeSH
4-oxo-4-{[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0⁴,¹³.0⁸,¹³]hexadecan-10-yl]oxy}butanoateGenerator
Chemical FormulaC19H28O8
Average Molecular Mass384.425 g/mol
Monoisotopic Mass384.178 g/mol
CAS Registry Number88495-63-0
IUPAC Name4-oxo-4-{[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0⁴,¹³.0⁸,¹³]hexadecan-10-yl]oxy}butanoic acid
Traditional Name4-oxo-4-{[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0⁴,¹³.0⁸,¹³]hexadecan-10-yl]oxy}butanoic acid
SMILES[H][C@@]1(C)CC[C@@]2([H])[C@@]([H])(C)[C@@]([H])(OC(=O)CCC(O)=O)O[C@]3([H])O[C@@]4(C)CC[C@]1([H])[C@@]23OO4
InChI IdentifierInChI=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 KeyFIHJKUPKCHIPAT-NKHDUEHSSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as artemisinins. These are sesquiterpenoids originally isolated from the herb Artemisia annua. Their structure is based on artemisinin, a tetracyclic compound that contains a 1,2-dioxepane fused to an octahydrobenzopyran moiety. The internal peroxide bridge is believed to be a key to the mode of action of artemisinins.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentArtemisinins
Alternative Parents
Substituents
  • Artemisinin skeleton
  • Fatty acid ester
  • Heterocyclic fatty acid
  • Oxepane
  • Dicarboxylic acid or derivatives
  • Oxane
  • Fatty acyl
  • 1,2,4-trioxane
  • Carboxylic acid ester
  • Dialkyl peroxide
  • Oxacycle
  • Carboxylic acid
  • Acetal
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.68 g/LALOGPS
logP2.35ALOGPS
logP3.1ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.77ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area100.52 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity89.95 m³·mol⁻¹ChemAxon
Polarizability38.91 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-2459000000-709f5cba7340e7cb0802Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-7392000000-6aade85a0d3ce77db50eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9050000000-c432eeabf339e3f7593bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000t-9034000000-4fd3316b534c1c9695e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00m0-4191000000-c1b630ac82bbe1ed3eecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-8590000000-1aec7778a60c3c83b96fSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkArtesunate
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID65664
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available