An antimalarial compound
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Labeled Version(s)
28769Artesunate-d4
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Artesunate

Item No. 11817

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
butanedioic acid, 1-[(3R,5aS,6R,8aS,9R,10S,12R,12aR)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-yl] ester
CAS Number
88495-63-0
Synonyms
  • Artesunic Acid
  • NSC 712571
  • WR 256283
Molecular Formula
C19H28O8
Formula Weight
384.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 11 mg/mlDMSO: 14 mg/mlEthanol: 20 mg/mlEthanol:PBS (pH 7.2) (1:1): 0.5 mg/ml
SMILES
[H][C@]12[C@@H](C)[C@H](OC(CCC(O)=O)=O)O[C@@]3([H])[C@@]1(OO4)[C@](CC[C@]4(C)O3)([H])[C@H](C)CC2
InChi Code
InChI=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 Key
FIHJKUPKCHIPAT-AHIGJZGOSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Artesunate is a derivative of artemisinin (Item No. 11816) that is active against P. falciparum in vitro (IC50 = 1.28 nM).1 It is an iron(II) oxide-reactive endoperoxide that generates reactive oxygen species (ROS) upon cleavage of its endoperoxide bridge.2 It inhibits the activity of the P. falciparum EXP1, a glutathione S-transferase (GST) that degrades hematin, with an IC50 value of 2.05 nM.3 Artesunate inhibits proliferation of germinal center B cells in vitro and prevents development of arthritis via inhibition of germinal center formation and autoantibody production in the K/BxN mouse model of rheumatoid arthritis when administered at a dose of 100 mg/kg twice per day.4 It also inhibits alveolitis and pulmonary fibrosis induced by bleomycin (Item No. 13877) in rats.5 Artesunate increases the activity of GST in mice infected with P. berghei compared to uninfected and infected control animals.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Akoachere, M., Buchholz, K., Fischer, E., et al. In vitro assessment of methylene blue on chloroquine-sensitive and -resistant Plasmodium falciparum strains reveals synergistic action with artemisinins. Antimicrob. Agents Chemother. 49(11), 4592-4597 (2005).

    2. Ooko, E., Saeed, M.E.M., Kadioglu, O., et al. Artemisinin derivatives induce iron-dependent cell death (ferroptosis) in tumor cells. Phytomedicine 22(11), 1045-1054 (2015).

    3. Lisewski, A.M., Quiros, J.P., Ng, C.L., et al. Supergenomic network compression and the discovery of EXP1 as a glutathione transferase inhibited by artesunate. Cell 158(4), 916-928 (2014).

    4. Hou, L., Block, K.E., and Huang, H. Artesunate abolishes germinal center B cells and inhibits autoimmune arthritis. PloS One 9(8), e104762 (2014).

    5. Wang, Y., Huang, G., Mo, B., et al. Artesunate modulates expression of matrix metalloproteinases and their inhibitors as well as collagen-IV to attenuate pulmonary fibrosis in rats. Genet. Mol. Res. 15(2), (2016).

    6. Olanlokun, J.O., Balogun, F.A., and Olorunsogo, O.O. Chemotherapeutic and prophylactic antimalarial drugs induce cell death through mitochondrial-mediated apoptosis in murine models. Drug Chem. Toxicol. 44(1), 47-57 (2021).