Artesunate | CAS#88495-63-0 | antimalarial | viral inhibitor | cell cycle arrestor

MedKoo Cat#: 540032 | Name: Artesunate

Description:

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

Artesunate is an antimalarial derived from Artemisia. It is also known to induce cell cycle arrest in breast cancer cells, inhibit replication of Polyoma virus and inhibit neovascularization and inflammation in corneas.

Chemical Structure

Artesunate

CAS#88495-63-0

Theoretical Analysis

MedKoo Cat#: 540032

Name: Artesunate

CAS#: 88495-63-0

Chemical Formula: C19H28O8

Exact Mass: 384.1784

Molecular Weight: 384.42

Elemental Analysis: C, 59.36; H, 7.34; O, 33.29

Price and Availability

Size	Price	Availability
1g	USD 110.00	Ready to ship
2g	USD 165.00	Ready to ship
5g	USD 325.00	Ready to ship
10g	USD 550.00	2 Weeks
25g	USD 950.00	2 Weeks

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Related CAS #

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Synonym

Artesunate; Armax 200; SM-804; WR-256283; HSDB-7458; SM804; WR256283; HSDB7458; SM 804; WR 256283; HSDB 7458

IUPAC/Chemical Name

4-oxo-4-(((3R,5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl)oxy)butanoic acid

InChi Key

FIHJKUPKCHIPAT-AHIGJZGOSA-N

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

SMILES Code

C[C@@H]1CC[C@H]2[C@@H](C)[C@H](OC(CCC(O)=O)=O)O[C@H]3[C@@]24[C@H]1CC[C@](OO4)(C)O3

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

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#T21C02I26

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Artesunate is an inhibitor of both STAT-3 and exported protein 1 (EXP1).

In vitro activity:

To broaden the testing of artesunate, a dose-response experiment was performed in 18 different B-cell lymphoma cell lines, representing various histological types. This revealed that artesunate exhibited broad activity across the lymphoma cell lines and potently affected cell growth, whereas it had limited effect in normal B-cells activated with CD40L alone or in combination with IL21(Fig. 2a). Artesunate reduced cell growth with IC50 values from 0.189 to 3.72 μM, and a high sensitivity to artesunate (IC50 < 1 μM) was observed in 11 out of 18 cell lines tested (Fig. 2a, Additional file 2: Figure S1). A pronounced cell death was detected with PI staining after 72 h, with only minor effects in normal B-cells (Additional file 2: Figure S1B). Detection of DNA fragmentation by TUNEL assay demonstrated potent artesunate-induced apoptosis with percentage apoptotic cells ranging from 55 to 96 after 72 h exposure to artesunate, whereas normal B-cells were not affected (Fig. 2b). Induction of apoptosis was an early event, with prominent increase of active caspase 3+ cells after 24 h of artesunate treatment (Additional file 2: Figure S1C). The increase of active caspase 3+ cells by artesunate was counteracted by the presence of the pan caspase inhibitor Z-VAD-FMK (Fig. 2c), indicating that artesunate induces apoptosis in tumor cells via a caspase-dependent pathway. Together, these results indicated that induction of apoptosis represents the main mechanism of the anti-lymphoma activity of artesunate. Reference: J Hematol Oncol. 2018; 11: 23. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5819282/

In vivo activity:

To test the efficacy of artesunate as a potent anti-lymphoma drug in vivo, NSG mice were subcutaneously inoculated with 2 × 106 BL41-luc lymphoma cells and subsequently treated with artesunate (200 mg/kg/day, n = 10) or left untreated (control, n = 10). Mice with varying tumor loads were evenly distributed among the groups (Additional file 4: Figure S3A and B), and treatment was initiated at day 4 after inoculation. Tumor growth was significantly reduced in mice treated with artesunate, and statistically significant differences were reached at day 12 and day 16 after start of treatment (P = .0045, day 12 and P < .0050, day 16; Fig. 3a). IVIS images of the mice at day 16 showed a distinct reduction in tumor growth in the artesunate-treated mice compared to the control group (Fig. 3b). In one of the artesunate-treated mice, the tumor was undetectable (Fig. 3b). At day 16, half of the control mice were euthanized due to maximum tumor size limitation (2 cm3). In comparison, the first artesunate-treated mouse was euthanized due to its tumor size 6 days later. All remaining mice were monitored after end of treatment (day 19), and a delayed tumor growth was observed in artesunate-treated mice. Survival analysis showed that the median time to reach maximum tumor size criteria was 17.5 versus 30.5 days for control and artesunate-treated mice, respectively (p < .0001; Fig. 3c). The artesunate dose (200 mg/kg/day) was well tolerated with no body weight loss during treatment (Additional file 4: Figure S3C). Taken together, artesunate showed potent anti-tumor response in an aggressive B-cell lymphoma xenograft model. Reference: J Hematol Oncol. 2018; 11: 23. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5819282/

	Solvent	mg/mL	mM
Solubility
	DMSO	53.0	137.87
	Ethanol	45.0	117.06

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 384.42 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. Våtsveen TK, Myhre MR, Steen CB, Wälchli S, Lingjærde OC, Bai B, Dillard P, Theodossiou TA, Holien T, Sundan A, Inderberg EM, Smeland EB, Myklebust JH, Oksvold MP. Artesunate shows potent anti-tumor activity in B-cell lymphoma. J Hematol Oncol. 2018 Feb 20;11(1):23. doi: 10.1186/s13045-018-0561-0. PMID: 29458389; PMCID: PMC5819282. 2. Zeng XZ, Zhang YY, Yang Q, Wang S, Zou BH, Tan YH, Zou M, Liu SW, Li XJ. Artesunate attenuates LPS-induced osteoclastogenesis by suppressing TLR4/TRAF6 and PLCγ1-Ca2+-NFATc1 signaling pathway. Acta Pharmacol Sin. 2020 Feb;41(2):229-236. doi: 10.1038/s41401-019-0289-6. Epub 2019 Aug 20. PMID: 31431733; PMCID: PMC7468527 3. Kong Z, Liu R, Cheng Y. Artesunate alleviates liver fibrosis by regulating ferroptosis signaling pathway. Biomed Pharmacother. 2019 Jan;109:2043-2053. doi: 10.1016/j.biopha.2018.11.030. Epub 2018 Nov 26. PMID: 30551460.

In vitro protocol:

In vivo protocol:

1. Kong Z, Liu R, Cheng Y. Artesunate alleviates liver fibrosis by regulating ferroptosis signaling pathway. Biomed Pharmacother. 2019 Jan;109:2043-2053. doi: 10.1016/j.biopha.2018.11.030. Epub 2018 Nov 26. PMID: 30551460. 2. Våtsveen TK, Myhre MR, Steen CB, Wälchli S, Lingjærde OC, Bai B, Dillard P, Theodossiou TA, Holien T, Sundan A, Inderberg EM, Smeland EB, Myklebust JH, Oksvold MP. Artesunate shows potent anti-tumor activity in B-cell lymphoma. J Hematol Oncol. 2018 Feb 20;11(1):23. doi: 10.1186/s13045-018-0561-0. PMID: 29458389; PMCID: PMC5819282.

1: Krishna S, Ganapathi S, Ster IC, Saeed ME, Cowan M, Finlayson C, Kovacsevics H, Jansen H, Kremsner PG, Efferth T, Kumar D. A Randomised, Double Blind, Placebo-Controlled Pilot Study of Oral Artesunate Therapy for Colorectal Cancer. EBioMedicine. 2014 Nov 15;2(1):82-90. doi: 10.1016/j.ebiom.2014.11.010. eCollection 2015 Jan. PubMed PMID: 26137537; PubMed Central PMCID: PMC4484515. 2: Okebe J, Eisenhut M. Pre-referral rectal artesunate for severe malaria. Cochrane Database Syst Rev. 2014 May 29;(5):CD009964. doi: 10.1002/14651858.CD009964.pub2. Review. PubMed PMID: 24869943; PubMed Central PMCID: PMC4463986. 3: Ravindra KC, Ho WE, Cheng C, Godoy LC, Wishnok JS, Ong CN, Wong WS, Wogan GN, Tannenbaum SR. Untargeted Proteomics and Systems-Based Mechanistic Investigation of Artesunate in Human Bronchial Epithelial Cells. Chem Res Toxicol. 2015 Oct 19;28(10):1903-13. doi: 10.1021/acs.chemrestox.5b00105. Epub 2015 Sep 21. PubMed PMID: 26340163. 4: Mori F, Pantano S, Rossi ME, Montagnani C, Chiappini E, Novembre E, Galli L, de Martino M. Skin prick test results to artesunate in children sensitized to Artemisia vulgaris L. Int J Immunopathol Pharmacol. 2015 Sep;28(3):411-4. doi: 10.1177/0394632015589518. Epub 2015 Jul 8. PubMed PMID: 26157064. 5: Wang C, Xuan X, Yao W, Huang G, Jin J. Anti-profibrotic effects of artesunate on bleomycin-induced pulmonary fibrosis in Sprague Dawley rats. Mol Med Rep. 2015 Jul;12(1):1291-7. doi: 10.3892/mmr.2015.3500. Epub 2015 Mar 17. PubMed PMID: 25816117. 6: Alzoubi K, Calabrò S, Bissinger R, Abed M, Faggio C, Lang F. Stimulation of suicidal erythrocyte death by artesunate. Cell Physiol Biochem. 2014;34(6):2232-44. doi: 10.1159/000369666. Epub 2014 Dec 8. PubMed PMID: 25562169. 7: Kloprogge F, McGready R, Phyo AP, Rijken MJ, Hanpithakpon W, Than HH, Hlaing N, Zin NT, Day NP, White NJ, Nosten F, Tarning J. Opposite malaria and pregnancy effect on oral bioavailability of artesunate - a population pharmacokinetic evaluation. Br J Clin Pharmacol. 2015 Oct;80(4):642-53. doi: 10.1111/bcp.12660. Epub 2015 Jul 22. PubMed PMID: 25877779; PubMed Central PMCID: PMC4594700. 8: Lee SH, Cho YC, Kim KH, Lee IS, Choi HJ, Kang BY. Artesunate inhibits proliferation of naïve CD4(+) T cells but enhances function of effector T cells. Arch Pharm Res. 2015 Jun;38(6):1195-203. doi: 10.1007/s12272-014-0491-5. Epub 2014 Nov 6. PubMed PMID: 25370606. 9: Bukirwa H, Unnikrishnan B, Kramer CV, Sinclair D, Nair S, Tharyan P. Artesunate plus pyronaridine for treating uncomplicated Plasmodium falciparum malaria. Cochrane Database Syst Rev. 2014 Mar 4;(3):CD006404. doi: 10.1002/14651858.CD006404.pub2. Review. PubMed PMID: 24596021; PubMed Central PMCID: PMC4448218. 10: Singh S, Giri A, Giri S. The antimalarial agent artesunate causes sperm DNA damage and hepatic antioxidant defense in mice. Mutat Res Genet Toxicol Environ Mutagen. 2015 Jan 1;777:1-6. doi: 10.1016/j.mrgentox.2014.11.001. Epub 2014 Nov 15. PubMed PMID: 25726169. 11: Hou L, Block KE, Huang H. Artesunate abolishes germinal center B cells and inhibits autoimmune arthritis. PLoS One. 2014 Aug 12;9(8):e104762. doi: 10.1371/journal.pone.0104762. eCollection 2014. PubMed PMID: 25116436; PubMed Central PMCID: PMC4130578. 12: Wang B, Hou D, Liu Q, Wu T, Guo H, Zhang X, Zou Y, Liu Z, Liu J, Wei J, Gong Y, Shao C. Artesunate sensitizes ovarian cancer cells to cisplatin by downregulating RAD51. Cancer Biol Ther. 2015;16(10):1548-56. doi: 10.1080/15384047.2015.1071738. Epub 2015 Jul 15. PubMed PMID: 26176175; PubMed Central PMCID: PMC5391513. 13: Olivera GC, Postan M, González MN. Effects of artesunate against Trypanosma cruzi. Exp Parasitol. 2015 Sep;156:26-31. doi: 10.1016/j.exppara.2015.05.014. Epub 2015 May 27. PubMed PMID: 26024969. 14: Vandewynckel YP, Laukens D, Geerts A, Vanhove C, Descamps B, Colle I, Devisscher L, Bogaerts E, Paridaens A, Verhelst X, Van Steenkiste C, Libbrecht L, Lambrecht BN, Janssens S, Van Vlierberghe H. Therapeutic effects of artesunate in hepatocellular carcinoma: repurposing an ancient antimalarial agent. Eur J Gastroenterol Hepatol. 2014 Aug;26(8):861-70. doi: 10.1097/MEG.0000000000000066. PubMed PMID: 24987823. 15: Ng DS, Liao W, Tan WS, Chan TK, Loh XY, Wong WS. Anti-malarial drug artesunate protects against cigarette smoke-induced lung injury in mice. Phytomedicine. 2014 Oct 15;21(12):1638-44. doi: 10.1016/j.phymed.2014.07.018. Epub 2014 Sep 1. PubMed PMID: 25442271. 16: Yuliang W, Zejian W, Hanlin S, Ming Y, Kexuan T. The hypolipidemic effect of artesunate and ursolic acid in rats. Pak J Pharm Sci. 2015 May;28(3):871-4. PubMed PMID: 26004719. 17: Cui C, Feng H, Shi X, Wang Y, Feng Z, Liu J, Han Z, Fu J, Fu Z, Tong H. Artesunate down-regulates immunosuppression from colorectal cancer Colon26 and RKO cells in vitro by decreasing transforming growth factor β1 and interleukin-10. Int Immunopharmacol. 2015 Jul;27(1):110-21. doi: 10.1016/j.intimp.2015.05.004. Epub 2015 May 12. PubMed PMID: 25978851. 18: Tan SS, Ong B, Cheng C, Ho WE, Tam JK, Stewart AG, Harris T, Wong WS, Tran T. The antimalarial drug artesunate inhibits primary human cultured airway smooth muscle cell proliferation. Am J Respir Cell Mol Biol. 2014 Feb;50(2):451-8. doi: 10.1165/rcmb.2013-0273OC. PubMed PMID: 24066853. 19: Okorji UP, Olajide OA. A semi-synthetic derivative of artemisinin, artesunate inhibits prostaglandin E2 production in LPS/IFNγ-activated BV2 microglia. Bioorg Med Chem. 2014 Sep 1;22(17):4726-34. doi: 10.1016/j.bmc.2014.07.007. Epub 2014 Jul 11. PubMed PMID: 25074847. 20: Luo Q, Lin J, Zhang L, Li H, Pan L. The anti-malaria drug artesunate inhibits cigarette smoke and ovalbumin concurrent exposure-induced airway inflammation and might reverse glucocorticoid insensitivity. Int Immunopharmacol. 2015 Dec;29(2):235-45. doi: 10.1016/j.intimp.2015.11.016. Epub 2015 Nov 14. PubMed PMID: 26590116.