Artemisone

• CAT Number: I002865
• CAS Number: 255730-18-8
• Molecular Formula: C19H31NO6S
• Molecular Weight: 401.51
• Purity: ≥95%
• Solubility: Soluble in DMSO
• Storage: 0 - 4°Cfor short term (days to weeks), or -20 °C for long term (months).
• IUPAC Name: 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]-1,4-thiazinane 1,1-dioxide
• InChI: InChI=1S/C19H31NO6S/c1-12-4-5-15-13(2)16(20-8-10-27(21,22)11-9-20)23-17-19(15)14(12)6-7-18(3,24-17)25-26-19/h12-17H,4-11H2,1-3H3/t12-,13-,14+,15+,16-,17-,18-,19-/m1/s1
• InChIKey: FDMUNKXWYMSZIR-NQWKWHCYSA-N
• SMILES: CC1CCC2C(C(OC3C24C1CCC(O3)(OO4)C)N5CCS(=O)(=O)CC5)C

Artemisone (Cat.No:I002865), also known as BAY-44-9585; BAY-449585, is potentially for the treatment of malaria. Artemisone inhibits in vitro and in vivo propagation of Babesia bovis and B. bigemina parasites. Artemisone showed MIC50 and MIC90 values of 0.25 mg/L and 0.5 mg/L, respectively, and an MBC50 value of 0.5 mg/L. Artemisone was synergistic with amoxicillin in 60% of strains, with clarithromycin in 40% and with metronidazole in 20%. Artemisone has the potential to be efficacious for the treatment of H. pylori infection, especially in combination with antibiotics. Artemisone is also active in cancer cell lines.

Reference

1:Elimination of Schistosoma mansoni in infected mice by slow release of artemisone. Gold D, Alian M, Domb A, Karawani Y, Jbarien M, Chollet J, Haynes RK, Wong HN, Buchholz V, Greiner A, Golenser J.Int J Parasitol Drugs Drug Resist. 2017 May 4;7(2):241-247. doi: 10.1016/j.ijpddr.2017.05.002. [Epub ahead of print] PMID: 28511056 Free Article2:Controlled release of artemisone for the treatment of experimental cerebral malaria. Golenser J, Buchholz V, Bagheri A, Nasereddin A, Dzikowski R, Guo J, Hunt NH, Eyal S, Vakruk N, Greiner A.Parasit Vectors. 2017 Mar 1;10(1):117. doi: 10.1186/s13071-017-2018-7. PMID: 28249591 Free PMC Article3:Methylene Homologues of Artemisone: An Unexpected Structure-Activity Relationship and a Possible Implication for the Design of C10-Substituted Artemisinins. Wu Y, Wu RW, Cheu KW, Williams ID, Krishna S, Slavic K, Gravett AM, Liu WM, Wong HN, Haynes RK.ChemMedChem. 2016 Jul 5;11(13):1469-79. doi: 10.1002/cmdc.201600011. Epub 2016 Jun 7. PMID: 27273875 4:In vitro activity of artemisone and artemisinin derivatives against extracellular and intracellular Helicobacter pylori. Sisto F, Scaltrito MM, Masia C, Bonomi A, Coccè V, Marano G, Haynes RK, Miani A, Farronato G, Taramelli D.Int J Antimicrob Agents. 2016 Jul;48(1):101-5. doi: 10.1016/j.ijantimicag.2016.03.018. Epub 2016 May 6. PMID: 27216383 5:In vitro skin permeation of artemisone and its nano-vesicular formulations. Dwivedi A, Mazumder A, Fox LT, Brümmer A, Gerber M, du Preez JL, Haynes RK, du Plessis J.Int J Pharm. 2016 Apr 30;503(1-2):1-7. doi: 10.1016/j.ijpharm.2016.02.041. Epub 2016 Feb 27. PMID: 26930566 6:In vitro anti-cancer effects of artemisone nano-vesicular formulations on melanoma cells. Dwivedi A, Mazumder A, du Plessis L, du Preez JL, Haynes RK, du Plessis J.Nanomedicine. 2015 Nov;11(8):2041-50. doi: 10.1016/j.nano.2015.07.010. Epub 2015 Aug 15. PMID: 26282380 7:Assessment of the induction of dormant ring stages in Plasmodium falciparum parasites by artemisone and artemisone entrapped in Pheroid vesicles in vitro. Grobler L, Chavchich M, Haynes RK, Edstein MD, Grobler AF.Antimicrob Agents Chemother. 2014 Dec;58(12):7579-82. doi: 10.1128/AAC.02707-14. Epub 2014 Oct 6. PMID: 25288088 Free PMC Article8:Ex vivo activity of endoperoxide antimalarials, including artemisone and arterolane, against multidrug-resistant Plasmodium falciparum isolates from Cambodia. Lanteri CA, Chaorattanakawee S, Lon C, Saunders DL, Rutvisuttinunt W, Yingyuen K, Bathurst I, Ding XC, Tyner SD.Antimicrob Agents Chemother. 2014 Oct;58(10):5831-40. doi: 10.1128/AAC.02462-14. Epub 2014 Jul 21. PMID: 25049252 Free PMC Article9:Treatment of murine cerebral malaria by artemisone in combination with conventional antimalarial drugs: antiplasmodial effects and immune responses. Guiguemde WA, Hunt NH, Guo J, Marciano A, Haynes RK, Clark J, Guy RK, Golenser J.Antimicrob Agents Chemother. 2014 Aug;58(8):4745-54. doi: 10.1128/AAC.01553-13. Epub 2014 Jun 9. PMID: 24913162 Free PMC Article10:The effect of the Pheroid delivery system on the in vitro metabolism and in vivo pharmacokinetics of artemisone. Grobler L, Grobler A, Haynes R, Masimirembwa C, Thelingwani R, Steenkamp P, Steyn HS.Expert Opin Drug Metab Toxicol. 2014 Mar;10(3):313-25. doi: 10.1517/17425255.2014.885503. Epub 2014 Feb 10. PMID: 24511903