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MedKoo Cat#: 326937 | Name: Artemisone

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Artemisone, 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.

Chemical Structure

Artemisone
CAS#255730-18-8

Theoretical Analysis

MedKoo Cat#: 326937

Name: Artemisone

CAS#: 255730-18-8

Chemical Formula: C19H31NO6S

Exact Mass: 401.1872

Molecular Weight: 401.52

Elemental Analysis: C, 56.84; H, 7.78; N, 3.49; O, 23.91; S, 7.98

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Artemisone; BAY-44-9585; BAY44-9585; BAY 44-9585; BAY-449585; BAY 449585; BAY449585.
IUPAC/Chemical Name
4-((3R,5aS,6R,8aS,9R,10R,12R,12aR)-3,6,9-Trimethyldecahydro-12H-3,12-epoxypyrano(4,3-j)(1,2)benzodioxepin-10-yl)thiomorpholine-1,1-dione
InChi Key
FDMUNKXWYMSZIR-NQWKWHCYSA-N
InChi Code
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
SMILES Code
O=S1(CCN([C@H]2[C@H](C)[C@]3([H])CC[C@@H](C)[C@]4([H])CC[C@@](O5)(C)OO[C@]43[C@]5([H])O2)CC1)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 401.52 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Wu Y, Wu RW, Cheu KW, Williams ID, Krishna S, Slavic K, Gravett AM, Liu WM, Wong HN, Haynes RK. Methylene Homologues of Artemisone: An Unexpected Structure-Activity Relationship and a Possible Implication for the Design of C10-Substituted Artemisinins. ChemMedChem. 2016 Jul 5;11(13):1469-79. doi: 10.1002/cmdc.201600011. Epub 2016 Jun 7. PubMed PMID: 27273875. 2: Sisto F, Scaltrito MM, Masia C, Bonomi A, Coccè V, Marano G, Haynes RK, Miani A, Farronato G, Taramelli D. In vitro activity of artemisone and artemisinin derivatives against extracellular and intracellular Helicobacter pylori. Int J Antimicrob Agents. 2016 Jul;48(1):101-5. doi: 10.1016/j.ijantimicag.2016.03.018. Epub 2016 May 6. PubMed PMID: 27216383. 3: Dwivedi A, Mazumder A, Fox LT, Brümmer A, Gerber M, du Preez JL, Haynes RK, du Plessis J. In vitro skin permeation of artemisone and its nano-vesicular formulations. Int J Pharm. 2016 Apr 30;503(1-2):1-7. doi: 10.1016/j.ijpharm.2016.02.041. Epub 2016 Feb 27. PubMed PMID: 26930566. 4: Dwivedi A, Mazumder A, du Plessis L, du Preez JL, Haynes RK, du Plessis J. In vitro anti-cancer effects of artemisone nano-vesicular formulations on melanoma cells. Nanomedicine. 2015 Nov;11(8):2041-50. doi: 10.1016/j.nano.2015.07.010. Epub 2015 Aug 15. PubMed PMID: 26282380. 5: Grobler L, Chavchich M, Haynes RK, Edstein MD, Grobler AF. Assessment of the induction of dormant ring stages in Plasmodium falciparum parasites by artemisone and artemisone entrapped in Pheroid vesicles in vitro. Antimicrob Agents Chemother. 2014 Dec;58(12):7579-82. doi: 10.1128/AAC.02707-14. Epub 2014 Oct 6. PubMed PMID: 25288088; PubMed Central PMCID: PMC4249507. 6: Lanteri CA, Chaorattanakawee S, Lon C, Saunders DL, Rutvisuttinunt W, Yingyuen K, Bathurst I, Ding XC, Tyner SD. Ex vivo activity of endoperoxide antimalarials, including artemisone and arterolane, against multidrug-resistant Plasmodium falciparum isolates from Cambodia. Antimicrob Agents Chemother. 2014 Oct;58(10):5831-40. doi: 10.1128/AAC.02462-14. Epub 2014 Jul 21. PubMed PMID: 25049252; PubMed Central PMCID: PMC4187925. 7: Guiguemde WA, Hunt NH, Guo J, Marciano A, Haynes RK, Clark J, Guy RK, Golenser J. Treatment of murine cerebral malaria by artemisone in combination with conventional antimalarial drugs: antiplasmodial effects and immune responses. Antimicrob Agents Chemother. 2014 Aug;58(8):4745-54. doi: 10.1128/AAC.01553-13. Epub 2014 Jun 9. PubMed PMID: 24913162; PubMed Central PMCID: PMC4135990. 8: Grobler L, Grobler A, Haynes R, Masimirembwa C, Thelingwani R, Steenkamp P, Steyn HS. The effect of the Pheroid delivery system on the in vitro metabolism and in vivo pharmacokinetics of artemisone. Expert Opin Drug Metab Toxicol. 2014 Mar;10(3):313-25. doi: 10.1517/17425255.2014.885503. Epub 2014 Feb 10. PubMed PMID: 24511903. 9: Mazuz ML, Golenser J, Fish L, Haynes RK, Wollkomirsky R, Leibovich B, Shkap V. Artemisone inhibits in vitro and in vivo propagation of Babesia bovis and B. bigemina parasites. Exp Parasitol. 2013 Dec;135(4):690-4. doi: 10.1016/j.exppara.2013.10.006. Epub 2013 Oct 30. PubMed PMID: 24184077. 10: Mazuz ML, Haynes R, Shkap V, Fish L, Wollkomirsky R, Leibovich B, Molad T, Savitsky I, Golenser J. Neospora caninum: in vivo and in vitro treatment with artemisone. Vet Parasitol. 2012 Jun 8;187(1-2):99-104. doi: 10.1016/j.vetpar.2011.12.020. Epub 2011 Dec 26. PubMed PMID: 22260899. 11: Steyn JD, Wiesner L, du Plessis LH, Grobler AF, Smith PJ, Chan WC, Haynes RK, Kotzé AF. Absorption of the novel artemisinin derivatives artemisone and artemiside: potential application of Pheroid™ technology. Int J Pharm. 2011 Jul 29;414(1-2):260-6. doi: 10.1016/j.ijpharm.2011.05.003. Epub 2011 May 7. PubMed PMID: 21596127. 12: Pooley S, Fatih FA, Krishna S, Gerisch M, Haynes RK, Wong HN, Staines HM. Artemisone uptake in Plasmodium falciparum-infected erythrocytes. Antimicrob Agents Chemother. 2011 Feb;55(2):550-6. doi: 10.1128/AAC.01216-10. Epub 2010 Dec 6. PubMed PMID: 21135191; PubMed Central PMCID: PMC3028811. 13: Waknine-Grinberg JH, Hunt N, Bentura-Marciano A, McQuillan JA, Chan HW, Chan WC, Barenholz Y, Haynes RK, Golenser J. Artemisone effective against murine cerebral malaria. Malar J. 2010 Aug 9;9:227. doi: 10.1186/1475-2875-9-227. PubMed PMID: 20691118; PubMed Central PMCID: PMC2928250. 14: Gravett AM, Liu WM, Krishna S, Chan WC, Haynes RK, Wilson NL, Dalgleish AG. In vitro study of the anti-cancer effects of artemisone alone or in combination with other chemotherapeutic agents. Cancer Chemother Pharmacol. 2011 Mar;67(3):569-77. doi: 10.1007/s00280-010-1355-4. Epub 2010 May 19. PubMed PMID: 20490800. 15: Dunay IR, Chan WC, Haynes RK, Sibley LD. Artemisone and artemiside control acute and reactivated toxoplasmosis in a murine model. Antimicrob Agents Chemother. 2009 Oct;53(10):4450-6. doi: 10.1128/AAC.00502-09. Epub 2009 Jul 27. PubMed PMID: 19635951; PubMed Central PMCID: PMC2764205. 16: Obaldia N 3rd, Kotecka BM, Edstein MD, Haynes RK, Fugmann B, Kyle DE, Rieckmann KH. Evaluation of artemisone combinations in Aotus monkeys infected with Plasmodium falciparum. Antimicrob Agents Chemother. 2009 Aug;53(8):3592-4. doi: 10.1128/AAC.00471-09. Epub 2009 Jun 8. PubMed PMID: 19506062; PubMed Central PMCID: PMC2715646. 17: Schmuck G, Klaus AM, Krötlinger F, Langewische FW. Developmental and reproductive toxicity studies on artemisone. Birth Defects Res B Dev Reprod Toxicol. 2009 Apr;86(2):131-43. doi: 10.1002/bdrb.20192. PubMed PMID: 19306395. 18: Nagelschmitz J, Voith B, Wensing G, Roemer A, Fugmann B, Haynes RK, Kotecka BM, Rieckmann KH, Edstein MD. First assessment in humans of the safety, tolerability, pharmacokinetics, and ex vivo pharmacodynamic antimalarial activity of the new artemisinin derivative artemisone. Antimicrob Agents Chemother. 2008 Sep;52(9):3085-91. doi: 10.1128/AAC.01585-07. Epub 2008 Jun 16. PubMed PMID: 18559649; PubMed Central PMCID: PMC2533467. 19: D'Alessandro S, Gelati M, Basilico N, Parati EA, Haynes RK, Taramelli D. Differential effects on angiogenesis of two antimalarial compounds, dihydroartemisinin and artemisone: implications for embryotoxicity. Toxicology. 2007 Nov 20;241(1-2):66-74. Epub 2007 Aug 19. PubMed PMID: 17897768. 20: Haynes RK, Chan WC, Lung CM, Uhlemann AC, Eckstein U, Taramelli D, Parapini S, Monti D, Krishna S. The Fe2+-mediated decomposition, PfATP6 binding, and antimalarial activities of artemisone and other artemisinins: the unlikelihood of C-centered radicals as bioactive intermediates. ChemMedChem. 2007 Oct;2(10):1480-97. PubMed PMID: 17768732.