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361593

Sigma-Aldrich

Artemisinin

98%

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Synonym(s):
Arteannuin, Qinghaosu
Empirical Formula (Hill Notation):
C15H22O5
CAS Number:
Molecular Weight:
282.33
MDL number:
PubChem Substance ID:
NACRES:
NA.79

Assay

98%

form

solid

optical activity

[α]20/D +76°, c = 0.5 in methanol

mp

156-157 °C (lit.)

antibiotic activity spectrum

parasites
viruses

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Mode of action

enzyme | inhibits

SMILES string

C[C@@H]1CC[C@H]2[C@@H](C)C(=O)O[C@@H]3OC4(C)CC[C@@H]1[C@@]23OO4

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

InChI key

BLUAFEHZUWYNDE-NNWCWBAJSA-N

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General description

Artemisinin is extracted from sweet wormwood (Artemisia annua). It has anticancer, antiprotozoal and antiviral activities. Artemisinin is associated with brainstem encephalopathy.

Application

Artemisinin has been used:
  • in drug susceptibility assays
  • as a standard for its quantification from artemisinin from hairy roots
  • to check cell viability using 3-(4, 5-dimethylthiazol-2yl)-2,5-diphenyl tetrazolium bromide (MTT) assay
  • as an antimalarial agent to investigate the role of autophagy-related (ATG) genes throughout the P. falciparum asexual and sexual blood stages

Biochem/physiol Actions

Artemisinin (Qinghaosu), a sesquiterpene lactone, is a highly active anti-malarial (falciparum malaria) drug. Artemisinin is also an anthelmintic (parasitic worm) effective against the blood fluke, schistosomiasis.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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  5. In what solvents is Product 361593, Artemisinin, soluble?

    According to the chemicals encyclopedia published by the Royal Society of Chemistry, artemisinin is expected to be soluble in most aprotic solvents and slightly soluble in oil. Sigma-Aldrich tests the solubility of this product in chloroform at 25 mg/mL. Our quality control is also able to prepare a 0.5% solution in methanol in order to measure the optical rotation.

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Artemether resistance in vitro is linked to mutations in PfATP6 that also interact with mutations in PfMDR1 in travellers returning with Plasmodium falciparum infections
Pillai DR, et al.
Malaria Journal, 11(1), 131-131 (2012)
Jürg Utzinger et al.
Current opinion in investigational drugs (London, England : 2000), 8(2), 105-116 (2007-03-03)
Schistosomiasis is a significant health issue caused by a blood fluke that affects more than 200 million individuals worldwide, over half of whom suffer from disease-associated symptoms. In areas of high burden, disease is mainly managed by controlling morbidity with
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Chakraborty B, et al.
EBioMedicine, 37, 442-452 (2018)
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Simooya OO
Side Effects of Drugs Annual, 30, 336-342 (2008)
Pierre-Eric Campos et al.
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Chemical study of the CH₂Cl₂-MeOH (1:1) extract of the sponge Fascaplysinopsis reticulata collected in Mayotte highlighted three new tryptophan derived alkaloids, 6,6'-bis-(debromo)-gelliusine F (1), 6-bromo-8,1'-dihydro-isoplysin A (2) and 5,6-dibromo-8,1'-dihydro-isoplysin A (3), along with the synthetically known 8-oxo-tryptamine (4) and the

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