Artemisinin | CAS#63968-64-9 | malaria and cancer drug

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

MedKoo CAT#: 317131

CAS#: 63968-64-9

Description: Artemisinin, also known as qinghaosu (Chinese: 青蒿素), and its semi-synthetic derivatives are a group of drugs that possess the most rapid action of all current drugs against Plasmodium falciparum malaria. It was discovered by Tu Youyou, a Chinese scientist, who was awarded half of the 2015 Nobel Prize in Medicine for her discovery. Treatments containing an artemisinin derivative (artemisinin-combination therapies, ACTs) are now standard treatment worldwide for P. falciparum malaria. Artemisinin is isolated from the plant Artemisia annua, sweet wormwood, an herb employed in Chinese traditional medicine. A precursor compound can be produced using genetically engineered yeast. Chemically, artemisinin is a sesquiterpene lactone containing an unusual peroxide bridge. This peroxide is believed to be responsible for the drug's mechanism of action. Few other natural compounds with such a peroxide bridge are known. The drug is also increasingly being used in Plasmodium vivax malaria, as well as being a topic of research in cancer treatment.

Chemical Structure

Artemisinin

CAS# 63968-64-9

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 317131
Name: Artemisinin
CAS#: 63968-64-9
Chemical Formula: C15H22O5
Exact Mass: 282.15
Molecular Weight: 282.340
Elemental Analysis: C, 63.81; H, 7.85; O, 28.33

Price and Availability

Size	Price	Availability
5g	USD 250	2 Weeks
25g	USD 650	2 Weeks
50g	USD 950	2 Weeks
100g	USD 1650	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Artemisinin, also known as qinghaosu (Chinese: 青蒿素); NSC 369397; NSC-369397; NSC-369397;

IUPAC/Chemical Name: (3R,5aS,6R,8aS,9R,12S,12aR)-3,6,9-trimethyloctahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10(3H)-one

InChi Key: BLUAFEHZUWYNDE-NNWCWBAJSA-N

InChi Code: 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

SMILES Code: O=C1[C@H](C)[C@]2([H])CC[C@@H](C)[C@]3([H])CC[C@@](O4)(C)OO[C@]32[C@]4([H])O1

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, not in water

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

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Product Data:

Product Data

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Biological target:	Artemisinin inhibits AKT signaling pathway by decreasing pAKT in a dose-dependent manner.
In vitro activity:	As shown in Figure 2, low concentrations of artemisinin promoted cell growth and induced cell death in a concentration-dependent manner at higher concentrations. Maximum cell viability significantly increased (p < 0.05) when pMECs were treated with 20 μM artemisinin for 12 h. According to these results, 20 μM artemisinin (treated with 12 h) was chosen to examine the protective effects of artemisinin against inflammatory injury in LPS-induced pMECs. Reference: Animals (Basel). 2021 Jun; 11(6): 1528. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8225056/
In vivo activity:	Recipients treated with ART (Artemisinin) had longer graft survival than controls (17.33 ± 4.89 vs 6.83 ± 0.75 days); approximately 66% of grafts in the ART rat group survived over 2 weeks, while survival time of grafts were less than 8 day in the control group (Figure 1A). Subsequently, allografts were harvested on day 5 after cardiac transplantation. As shown by representative H&E photomicrographs, the rejection area of the ART group was noticeably thinner than that of the control group. Interstitial vasculitis, hemorrhage, and edema were evident in the control group, which were significantly diminished by ART treatment (Figure 1B). Moreover, TUNEL staining revealed apoptotic cells (red) in the ART group were significantly less than that in the control group, especially in the rejection area. DAPI staining (blue) indicated that nuclei in the control group were deformed and broken, which indicated that more cells were in a state of apoptosis. Together, these data indicate that ART reduced rejection and protected cardiomyocytes (Figure 1C). Reference: Front Immunol. 2021; 12: 634368. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7943449/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	36.3	128.60
	DMF	20.0	70.84
	DMF:PBS (pH 7.2) (1:1)	0.5	1.77
	Ethanol	20.4	72.22

Preparing Stock Solutions

The following data is based on the product molecular weight 282.34 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.

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

Formulation protocol:	1. Zhang W, Xiong L, Chen J, Tian Z, Liu J, Chen F, Ren M, Guan W, Zhang S. Artemisinin Protects Porcine Mammary Epithelial Cells against Lipopolysaccharide-Induced Inflammatory Injury by Regulating the NF-κB and MAPK Signaling Pathways. Animals (Basel). 2021 May 24;11(6):1528. doi: 10.3390/ani11061528. PMID: 34073895; PMCID: PMC8225056. 2. Hu HM, Mao MH, Hu YH, Zhou XC, Li S, Chen CF, Li CN, Yuan QL, Li W. Artemisinin protects DPSC from hypoxia and TNF-α mediated osteogenesis impairments through CA9 and Wnt signaling pathway. Life Sci. 2021 Jul 15;277:119471. doi: 10.1016/j.lfs.2021.119471. Epub 2021 Mar 31. PMID: 33811898. 3. Lin SP, Wei JX, Hu JS, Bu JY, Zhu LD, Li Q, Liao HJ, Lin PY, Ye S, Chen SQ, Chen XH. Artemisinin improves neurocognitive deficits associated with sepsis by activating the AMPK axis in microglia. Acta Pharmacol Sin. 2021 Jul;42(7):1069-1079. doi: 10.1038/s41401-021-00634-3. Epub 2021 Mar 23. PMID: 33758353; PMCID: PMC8209200. 4. Yang Z, Han F, Liao T, Zheng H, Luo Z, Ma M, He J, Li L, Ye Y, Zhang R, Huang Z, Zhang Y, Sun Q. Artemisinin Attenuates Transplant Rejection by Inhibiting Multiple Lymphocytes and Prolongs Cardiac Allograft Survival. Front Immunol. 2021 Feb 24;12:634368. doi: 10.3389/fimmu.2021.634368. PMID: 33717174; PMCID: PMC7943449.
In vitro protocol:	1. Zhang W, Xiong L, Chen J, Tian Z, Liu J, Chen F, Ren M, Guan W, Zhang S. Artemisinin Protects Porcine Mammary Epithelial Cells against Lipopolysaccharide-Induced Inflammatory Injury by Regulating the NF-κB and MAPK Signaling Pathways. Animals (Basel). 2021 May 24;11(6):1528. doi: 10.3390/ani11061528. PMID: 34073895; PMCID: PMC8225056. 2. Hu HM, Mao MH, Hu YH, Zhou XC, Li S, Chen CF, Li CN, Yuan QL, Li W. Artemisinin protects DPSC from hypoxia and TNF-α mediated osteogenesis impairments through CA9 and Wnt signaling pathway. Life Sci. 2021 Jul 15;277:119471. doi: 10.1016/j.lfs.2021.119471. Epub 2021 Mar 31. PMID: 33811898.
In vivo protocol:	1. Lin SP, Wei JX, Hu JS, Bu JY, Zhu LD, Li Q, Liao HJ, Lin PY, Ye S, Chen SQ, Chen XH. Artemisinin improves neurocognitive deficits associated with sepsis by activating the AMPK axis in microglia. Acta Pharmacol Sin. 2021 Jul;42(7):1069-1079. doi: 10.1038/s41401-021-00634-3. Epub 2021 Mar 23. PMID: 33758353; PMCID: PMC8209200. 2. Yang Z, Han F, Liao T, Zheng H, Luo Z, Ma M, He J, Li L, Ye Y, Zhang R, Huang Z, Zhang Y, Sun Q. Artemisinin Attenuates Transplant Rejection by Inhibiting Multiple Lymphocytes and Prolongs Cardiac Allograft Survival. Front Immunol. 2021 Feb 24;12:634368. doi: 10.3389/fimmu.2021.634368. PMID: 33717174; PMCID: PMC7943449.

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1: Yakasai AM, Hamza M, Dalhat MM, Bello M, Gadanya MA, Yaqub ZM, Ibrahim DA, Hassan-Hanga F. Adherence to Artemisinin-Based Combination Therapy for the Treatment of Uncomplicated Malaria: A Systematic Review and Meta-Analysis. J Trop Med. 2015;2015:189232. doi: 10.1155/2015/189232. Epub 2015 May 28. Review. PubMed PMID: 26161095; PubMed Central PMCID: PMC4464595.

2: Shi C, Li H, Yang Y, Hou L. Anti-inflammatory and immunoregulatory functions of artemisinin and its derivatives. Mediators Inflamm. 2015;2015:435713. doi: 10.1155/2015/435713. Epub 2015 Apr 16. Review. PubMed PMID: 25960615; PubMed Central PMCID: PMC4415672.

3: Cravo P, Napolitano H, Culleton R. How genomics is contributing to the fight against artemisinin-resistant malaria parasites. Acta Trop. 2015 Aug;148:1-7. doi: 10.1016/j.actatropica.2015.04.007. Epub 2015 Apr 21. Review. PubMed PMID: 25910626.

4: Lussiana C. Towards subsidized malaria rapid diagnostic tests. Lessons learned from the global subsidy of artemisinin-based combination therapies: a review. Health Policy Plan. 2015 Apr 9. pii: czv028. [Epub ahead of print] Review. PubMed PMID: 25862732.

5: Das AK. Anticancer Effect of AntiMalarial Artemisinin Compounds. Ann Med Health Sci Res. 2015 Mar-Apr;5(2):93-102. doi: 10.4103/2141-9248.153609. Review. PubMed PMID: 25861527; PubMed Central PMCID: PMC4389338.

6: Pelfrene E, Pinheiro MH, Cavaleri M. Artemisinin-based combination therapy in the treatment of uncomplicated malaria: review of recent regulatory experience at the European Medicines Agency. Int Health. 2015 Jul;7(4):239-46. doi: 10.1093/inthealth/ihv017. Epub 2015 Apr 8. Review. PubMed PMID: 25855638; PubMed Central PMCID: PMC4492341.

7: Zhao SM, Wang MY. [Artemisinin resistance in Plasmodium falciparum: global status and basic research]. Zhongguo Ji Sheng Chong Xue Yu Ji Sheng Chong Bing Za Zhi. 2014 Oct;32(5):380-4. Review. Chinese. PubMed PMID: 25726605.

8: Isba R, Zani B, Gathu M, Sinclair D. Artemisinin-naphthoquine for treating uncomplicated Plasmodium falciparum malaria. Cochrane Database Syst Rev. 2015 Feb 23;2:CD011547. doi: 10.1002/14651858.CD011547. Review. PubMed PMID: 25702785; PubMed Central PMCID: PMC4453860.

9: George KW, Alonso-Gutierrez J, Keasling JD, Lee TS. Isoprenoid drugs, biofuels, and chemicals--artemisinin, farnesene, and beyond. Adv Biochem Eng Biotechnol. 2015;148:355-89. doi: 10.1007/10_2014_288. Review. Erratum in: Adv Biochem Eng Biotechnol. 2015;148:469. PubMed PMID: 25577395.

10: Winzeler EA, Manary MJ. Drug resistance genomics of the antimalarial drug artemisinin. Genome Biol. 2014 Nov 25;15(11):544. doi: 10.1186/s13059-014-0544-6. Review. PubMed PMID: 25470531; PubMed Central PMCID: PMC4283579.

11: Visser BJ, Wieten RW, Kroon D, Nagel IM, Bélard S, van Vugt M, Grobusch MP. Efficacy and safety of artemisinin combination therapy (ACT) for non-falciparum malaria: a systematic review. Malar J. 2014 Nov 26;13:463. doi: 10.1186/1475-2875-13-463. Review. PubMed PMID: 25428624; PubMed Central PMCID: PMC4258384.

12: Corsello MA, Garg NK. Synthetic chemistry fuels interdisciplinary approaches to the production of artemisinin. Nat Prod Rep. 2015 Mar;32(3):359-66. doi: 10.1039/c4np00113c. Review. Erratum in: Nat Prod Rep. 2015 Mar;32(3):504. PubMed PMID: 25342519.

13: Liu YX, Wu W, Liang YJ, Jie ZL, Wang H, Wang W, Huang YX. New uses for old drugs: the tale of artemisinin derivatives in the elimination of schistosomiasis japonica in China. Molecules. 2014 Sep 19;19(9):15058-74. doi: 10.3390/molecules190915058. Review. PubMed PMID: 25244286.

14: Kano S. Artemisinin-based combination therapies and their introduction in Japan. Kansenshogaku Zasshi. 2014 May;88(3 Suppl 9-10):18-25. Review. PubMed PMID: 24979951.

15: Ramos-Martín V, González-Martínez C, Mackenzie I, Schmutzhard J, Pace C, Lalloo DG, Terlouw DJ. Neuroauditory toxicity of artemisinin combination therapies-have safety concerns been addressed? Am J Trop Med Hyg. 2014 Jul;91(1):62-73. doi: 10.4269/ajtmh.13-0702. Epub 2014 May 27. Review. PubMed PMID: 24865683; PubMed Central PMCID: PMC4080570.

16: Goodrich SK, Schlegel CR, Wang G, Belinson JL. Use of artemisinin and its derivatives to treat HPV-infected/transformed cells and cervical cancer: a review. Future Oncol. 2014 Mar;10(4):647-54. doi: 10.2217/fon.13.228. Review. PubMed PMID: 24754594.

17: Okebe J, Bojang K, D'Alessandro U. Use of artemisinin and its derivatives for the treatment of malaria in children. Pediatr Infect Dis J. 2014 May;33(5):522-4. doi: 10.1097/INF.0000000000000306. Review. PubMed PMID: 24736442.

18: Paddon CJ, Keasling JD. Semi-synthetic artemisinin: a model for the use of synthetic biology in pharmaceutical development. Nat Rev Microbiol. 2014 May;12(5):355-67. doi: 10.1038/nrmicro3240. Epub 2014 Apr 1. Review. PubMed PMID: 24686413.

19: Farhi M, Kozin M, Duchin S, Vainstein A. Metabolic engineering of plants for artemisinin synthesis. Biotechnol Genet Eng Rev. 2013;29:135-48. doi: 10.1080/02648725.2013.821283. Epub 2013 Aug 2. Review. PubMed PMID: 24568277.

20: Takatani-Nakase T. [Artemisinin: a natural product for fighting against cancer]. Nihon Yakurigaku Zasshi. 2014 Feb;143(2):61-4. Review. Japanese. PubMed PMID: 24531897.

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