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MedKoo Cat#: 329860 | Name: Artemotil
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Description:

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

Artemotil, also known as Arteether, is a fast acting blood schizonticide specifically indicated for the treatment of chloroquine-resistant Plasmodium falciparum malaria and cerebral malaria cases. It is a semi-synthetic derivative of artemisinin, a natural product of the Chinese plant Artemisia annua. It is currently only used as a second line drug in severe cases of malaria.

Chemical Structure

Artemotil
CAS#75887-54-6

Theoretical Analysis

MedKoo Cat#: 329860

Name: Artemotil

CAS#: 75887-54-6

Chemical Formula: C17H28O5

Exact Mass: 312.1937

Molecular Weight: 312.41

Elemental Analysis: C, 65.36; H, 9.03; O, 25.61

Price and Availability

Size Price Availability Quantity
10mg USD 350.00 2 Weeks
50mg USD 950.00 2 Weeks
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Related CAS #
75887-54-6 109716-83-8
Synonym
Arteether; Artemotil; beta-Arteether; beta-Dihydroartemisinin ethyl ether; Dihydroartemisinin ethyl ether; NSC 665971; SM 227;
IUPAC/Chemical Name
(3R,5aS,6R,8aS,9R,10S,12R,12aR)-10-Ethoxydecahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin
InChi Key
NLYNIRQVMRLPIQ-XQLAAWPRSA-N
InChi Code
InChI=1S/C17H28O5/c1-5-18-14-11(3)13-7-6-10(2)12-8-9-16(4)20-15(19-14)17(12,13)22-21-16/h10-15H,5-9H2,1-4H3/t10-,11-,12+,13+,14+,15-,16-,17-/m1/s1
SMILES Code
C[C@H]1[C@@H](OCC)O[C@@]2([H])[C@]34[C@@]([C@H](C)CC[C@]41[H])([H])CC[C@@](O2)(C)OO3
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 312.41 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: Looareesuwan S, Oosterhuis B, Schilizzi BM, Sollie FA, Wilairatana P, Krudsood S, Lugt ChB, Peeters PA, Peggins JO. Dose-finding and efficacy study for i.m. artemotil (beta-arteether) and comparison with i.m. artemether in acute uncomplicated P. falciparum malaria. Br J Clin Pharmacol. 2002 May;53(5):492-500. PubMed PMID: 11994055; PubMed Central PMCID: PMC1874374. 2: Thuma PE, Bhat GJ, Mabeza GF, Osborne C, Biemba G, Shakankale GM, Peeters PA, Oosterhuis B, Lugt CB, Gordeuk VR. A randomized controlled trial of artemotil (beta-arteether) in Zambian children with cerebral malaria. Am J Trop Med Hyg. 2000 Apr;62(4):524-9. PubMed PMID: 11220772. 3: Li Q, Lugt CB, Looareesuwan S, Krudsood S, Wilairatana P, Vannaphan S, Chalearmrult K, Milhous WK. Pharmacokinetic investigation on the therapeutic potential of artemotil (beta-arteether) in Thai patients with severe Plasmodium falciparum malaria. Am J Trop Med Hyg. 2004 Dec;71(6):723-31. PubMed PMID: 15642961. 4: Yeates RA. Artemotil Artecef. Curr Opin Investig Drugs. 2002 Apr;3(4):545-9. Review. PubMed PMID: 12090721. 5: Kager PA. [Three newly registered drugs in the Netherlands for the treatment and chemoprophylaxis of malaria: atovaquone-proguanil, artemether-lumefantrine and artemotil]. Ned Tijdschr Geneeskd. 2003 Feb 15;147(7):291-5. Review. Dutch. PubMed PMID: 12622006. 6: Ooko E, Saeed ME, Kadioglu O, Sarvi S, Colak M, Elmasaoudi K, Janah R, Greten HJ, Efferth T. Artemisinin derivatives induce iron-dependent cell death (ferroptosis) in tumor cells. Phytomedicine. 2015 Oct 15;22(11):1045-54. doi: 10.1016/j.phymed.2015.08.002. Epub 2015 Aug 18. PubMed PMID: 26407947. 7: Chandra R, Puri SK. Arteether resistance reversal by ketoconazole/fluconazole in rodent malaria parasite Plasmodium vinckei. Parasitol Res. 2015 Mar;114(3):1239-43. doi: 10.1007/s00436-015-4321-6. Epub 2015 Jan 25. PubMed PMID: 25616344. 8: Dende C, Meena J, Nagarajan P, Panda AK, Rangarajan PN, Padmanaban G. Simultaneously targeting inflammatory response and parasite sequestration in brain to treat Experimental Cerebral Malaria. Sci Rep. 2015 Jul 31;5:12671. doi: 10.1038/srep12671. PubMed PMID: 26227888; PubMed Central PMCID: PMC4521148. 9: Dhawan S, Gunjan S, Pal A, Tripathi R. Potentiation of antimalarial activity of arteether in combination with Vetiver root extract. Indian J Exp Biol. 2016 May;54(5):315-21. PubMed PMID: 27319050. 10: Ali Z, Mishra N, Baldi A. Development and characterization of arteether-loaded nanostructured lipid carriers for the treatment of malaria. Artif Cells Nanomed Biotechnol. 2016;44(2):545-9. doi: 10.3109/21691401.2014.968821. Epub 2014 Oct 23. PubMed PMID: 25340261. 11: Sunita K, Rajyalakshmi M, Kumar KK, Sowjanya M, Satish PV, Prasad DM. Human malaria in C57BL/6J mice: an in vivo model for chemotherapy studies. Indian J Exp Biol. 2014 Jan;52(1):67-72. PubMed PMID: 24617017. 12: Oyinloye OE, Kosoko AM, Emikpe B, Falade CO, Ademowo OG. Potential antimalarial activity of Methyl Jasmonate and its effect on lipid profiles in Plasmodium Berghei infected mice. Afr Health Sci. 2015 Sep;15(3):841-50. doi: 10.4314/ahs.v15i3.19. PubMed PMID: 26957973; PubMed Central PMCID: PMC4765454. 13: Dwivedi P, Khatik R, Chaturvedi P, Khandelwal K, Taneja I, Raju KS, Dwivedi H, Singh SK, Gupta PK, Shukla P, Tripathi P, Singh S, Tripathi R, Wahajuddin, Paliwal SK, Dwivedi AK, Mishra PR. Arteether nanoemulsion for enhanced efficacy against Plasmodium yoelii nigeriensis malaria: an approach by enhanced bioavailability. Colloids Surf B Biointerfaces. 2015 Feb 1;126:467-75. doi: 10.1016/j.colsurfb.2014.12.052. Epub 2015 Jan 7. PubMed PMID: 25616971. 14: Dwivedi H, Singh SK, Chauhan BS, Gunjan S, Tripathi R. Potential cerebral malaria therapy: intramuscular arteether and vitamin D co-administration. Parasitology. 2016 Oct;143(12):1557-68. doi: 10.1017/S0031182016001207. Epub 2016 Jul 21. PubMed PMID: 27440106. 15: Van der Meersch H. [Review of the use of artemisinin and its derivatives in the treatment of malaria]. J Pharm Belg. 2005;60(1):23-9. Review. French. Erratum in: J Pharm Belg. 2005;60(3):103. PubMed PMID: 15828489. 16: Memvanga PB, Mbinze JK, Rozet E, Hubert P, Préat V, Marini RD. Development of a liquid chromatographic method for the simultaneous quantification of curcumin, β-arteether, tetrahydrocurcumin and dihydroartemisinin. Application to lipid-based formulations. J Pharm Biomed Anal. 2014 Jan;88:447-56. doi: 10.1016/j.jpba.2013.09.009. Epub 2013 Oct 5. PubMed PMID: 24184380. 17: Gugulothu D, Patravale V. Stability-indicating HPLC method for arteether and application to nanoparticles of arteether. J Chromatogr Sci. 2014 Sep;52(8):831-6. doi: 10.1093/chromsci/bmt125. Epub 2013 Aug 26. PubMed PMID: 23983243. 18: Gaur R, Darokar MP, Ajayakumar PV, Shukla RS, Bhakuni RS. In vitro antimalarial studies of novel artemisinin biotransformed products and its derivatives. Phytochemistry. 2014 Nov;107:135-40. doi: 10.1016/j.phytochem.2014.08.004. Epub 2014 Aug 30. PubMed PMID: 25183484. 19: Hien TT, Turner GD, Mai NT, Phu NH, Bethell D, Blakemore WF, Cavanagh JB, Dayan A, Medana I, Weller RO, Day NP, White NJ. Neuropathological assessment of artemether-treated severe malaria. Lancet. 2003 Jul 26;362(9380):295-6. PubMed PMID: 12892962. 20: Dwivedi P, Khatik R, Khandelwal K, Taneja I, Raju KS, Wahajuddin, Paliwal SK, Dwivedi AK, Mishra PR. Pharmacokinetics study of arteether loaded solid lipid nanoparticles: an improved oral bioavailability in rats. Int J Pharm. 2014 May 15;466(1-2):321-7. doi: 10.1016/j.ijpharm.2014.03.036. Epub 2014 Mar 20. PubMed PMID: 24657144.