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MedKoo Cat#: 318170 | Name: Lumefantrine
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Description:

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

Lumefantrine, also known as HSDB 7210, is an antimalarial agent used to treat acute uncomplicated malaria. It is administered in combination with artemether for improved efficacy. This combination therapy exerts its effects against the erythrocytic stages of Plasmodium spp. and may be used to treat infections caused by P. falciparum and unidentified Plasmodium species, including infections acquired in chloroquine-resistant areas.

Chemical Structure

Lumefantrine
Lumefantrine
CAS#82186-77-4

Theoretical Analysis

MedKoo Cat#: 318170

Name: Lumefantrine

CAS#: 82186-77-4

Chemical Formula: C30H32Cl3NO

Exact Mass: 527.1550

Molecular Weight: 528.94

Elemental Analysis: C, 68.12; H, 6.10; Cl, 20.11; N, 2.65; O, 3.02

Price and Availability

Size Price Availability Quantity
1g USD 110.00 Ready to ship
2g USD 180.00 Ready to ship
5g USD 350.00 2 weeks
10g USD 550.00 2 weeks
25g USD 950.00 2 weeks
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Related CAS #
82186-77-4 120583-70-2 (+) 120583-71-3 (-)
Synonym
HSDB 7210; HSDB7210; HSDB-7210; Lumefantrine; Benflumetol.
IUPAC/Chemical Name
2-(dibutylamino)-1-[(9Z)-2,7-dichloro-9-[(4-chlorophenyl)methylidene]fluoren-4-yl]ethanol
InChi Key
DYLGFOYVTXJFJP-MYYYXRDXSA-N
InChi Code
InChI=1S/C30H32Cl3NO/c1-3-5-13-34(14-6-4-2)19-29(35)28-18-23(33)17-27-25(15-20-7-9-21(31)10-8-20)26-16-22(32)11-12-24(26)30(27)28/h7-12,15-18,29,35H,3-6,13-14,19H2,1-2H3/b25-15-
SMILES Code
CCCCN(CCCC)CC(C1=C2C3=C(C=C(C=C3)Cl)C(=CC4=CC=C(C=C4)Cl)C2=CC(=C1)Cl)O
Appearance
Yellow 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
More Info
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot#TC60705
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Lumefantrine is an antimalarial drug, used in combination with Artemether.
In vitro activity:
Based on the connection between Fli-1 expression and radio/TMZ resistance in GBM cells, Fli-1 inhibitors were screened for and identified an antimalarial FDA-approved drug, lumefantrine, as a putative therapeutic agent targeting radio/TMZ resistance in GBM. Phase-contrast microscopy images of lumefantrine-treated U87MG and T98G cells showed morphological changes suggestive of apoptotic cell death (SI Appendix, Fig. S2A, arrows). Lumefantrine inhibited wound healing, migration, infiltration, and anchorageindependent growth in U87MG and T98G cells (SI Appendix, Fig. S2 B–D). In addition, lumefantrine significantly reduced the enzymatic activity of MMP-2 and MMP-9 in U87MG and T98G cells (SI Appendix, Fig. S2E). A dose-dependent antiproliferative effect was also observed in lumefantrine-treated radio/TMZ-resistant cells (SI Appendix, Fig. S1 D and E). Half-maximal inhibitory concentration (IC50) values of lumefantrine were 137.2 μM in U87MG RR cells, 73.1 μM in T98G RR cells, 185.3 μM in U87MG TMZR cells, and 120.2 μM in T98G TMZR cells.A direct interaction between lumefantrine and Fli-1 was confirmed by docking of lumefantrine with the DNA-binding domain of the Fli-1 protein (Fig. 2 A–C) and ITC. The chemical structure of lumefantrine is shown in Fig. 2B. The ITC thermogram and fitted binding isotherm (Fig. 2D) displayed the following thermodynamic parameters of lumefantrine’s binding to Fli-1 protein: ΔH (enthalpy), −1.349E4 ± 1,349 cal/mol; ΔS (entropy), −27.8 cal/mol/degree; Kd (dissociation constant), 6.5 μM; and N (stoichiometry), 0.687 ± 0.0496. These studies confirm that lumefantrine affects the in vitro properties of GBM and radio/TMZ-resistant GBM, and that it directly binds to the Fli-1 protein. Proc Natl Acad Sci U S A. 2020 Jun 2; 117(22): 12324–12331. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7275698/
In vivo activity:
In order to determine whether lumefantrine treatment enhances Th1 or Th2 cytokine response, IFN-γ, IL-4 and IL-10 levels in the serum of mice were determined (Fig. 5). Significantly higher levels of IFN-γ were observed in mice treated with a high concentration lumefantrine compared to the negative control group (P ≤ 0.01), which indicated that high concentration lumefantrine could stimulate the hosts to produce IFN-γ to eliminate T. gondii. Meanwhile, IL-4 and IL-10 were significantly produced in mice treated with a low concentration lumefantrine compared to the negative control group (P ≤ 0.01). The results showed that lumefantrine could adjust the cytokines in hosts to eliminate parasites through the change of drug concentrations. Based on these results in this study, we speculate that lumefantrine may be used to treat toxoplasmosis patients or people who suffer combination infections of T. gondii and Plasmodium clinically. Parasitology. 2021 Jan; 148(1): 122–128. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7808861/
Solvent mg/mL mM
Solubility
DMSO 1.8 3.40
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 528.94 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
Formulation protocol:
1. Rajesh Y, Biswas A, Kumar U, Banerjee I, Das S, Maji S, Das SK, Emdad L, Cavenee WK, Mandal M, Fisher PB. Lumefantrine, an antimalarial drug, reverses radiation and temozolomide resistance in glioblastoma. Proc Natl Acad Sci U S A. 2020 Jun 2;117(22):12324-12331. doi: 10.1073/pnas.1921531117. Epub 2020 May 14. PMID: 32409605; PMCID: PMC7275698. 2. Wang D, Xing M, El-Ashram S, Ding Y, Zhang X, Sang X, Feng Y, Chen R, Wang X, Jiang N, Chen Q, Yang N. Determination of lumefantrine as an effective drug against Toxoplasma gondii infection - in vitro and in vivo study. Parasitology. 2021 Jan;148(1):122128. doi: 10.1017/S0031182020002036. Epub 2020 Oct 22. PMID: 33087183; PMCID: PMC7808861.
In vitro protocol:
1. Rajesh Y, Biswas A, Kumar U, Banerjee I, Das S, Maji S, Das SK, Emdad L, Cavenee WK, Mandal M, Fisher PB. Lumefantrine, an antimalarial drug, reverses radiation and temozolomide resistance in glioblastoma. Proc Natl Acad Sci U S A. 2020 Jun 2;117(22):12324-12331. doi: 10.1073/pnas.1921531117. Epub 2020 May 14. PMID: 32409605; PMCID: PMC7275698. 2. Wang D, Xing M, El-Ashram S, Ding Y, Zhang X, Sang X, Feng Y, Chen R, Wang X, Jiang N, Chen Q, Yang N. Determination of lumefantrine as an effective drug against Toxoplasma gondii infection - in vitro and in vivo study. Parasitology. 2021 Jan;148(1):122128. doi: 10.1017/S0031182020002036. Epub 2020 Oct 22. PMID: 33087183; PMCID: PMC7808861.
In vivo protocol:
1. Rajesh Y, Biswas A, Kumar U, Banerjee I, Das S, Maji S, Das SK, Emdad L, Cavenee WK, Mandal M, Fisher PB. Lumefantrine, an antimalarial drug, reverses radiation and temozolomide resistance in glioblastoma. Proc Natl Acad Sci U S A. 2020 Jun 2;117(22):12324-12331. doi: 10.1073/pnas.1921531117. Epub 2020 May 14. PMID: 32409605; PMCID: PMC7275698. 2. Wang D, Xing M, El-Ashram S, Ding Y, Zhang X, Sang X, Feng Y, Chen R, Wang X, Jiang N, Chen Q, Yang N. Determination of lumefantrine as an effective drug against Toxoplasma gondii infection - in vitro and in vivo study. Parasitology. 2021 Jan;148(1):122128. doi: 10.1017/S0031182020002036. Epub 2020 Oct 22. PMID: 33087183; PMCID: PMC7808861.
1: Gonçalves BP, Tiono AB, Ouédraogo A, Guelbéogo WM, Bradley J, Nebie I, Siaka D, Lanke K, Eziefula AC, Diarra A, Pett H, Bougouma EC, Sirima SB, Drakeley C, Bousema T. Single low dose primaquine to reduce gametocyte carriage and Plasmodium falciparum transmission after artemether-lumefantrine in children with asymptomatic infection: a randomised, double-blind, placebo-controlled trial. BMC Med. 2016 Mar 8;14(1):40. doi: 10.1186/s12916-016-0581-y. PubMed PMID: 26952094; PubMed Central PMCID: PMC4782330. 2: Mssusa AK, Fimbo AM, Nkayamba AF, Irunde HF, Sillo HB, Shewiyo DH, Hill G, Minzi OM. Safety Profile of Artemether-Lumefantrine: A Cohort Event Monitoring Study in Public Health Facilities in Tanzania. Clin Drug Investig. 2016 Mar 7. [Epub ahead of print] PubMed PMID: 26951203. 3: Barger-Kamate B, Forman M, Sangare CO, Haidara AS, Maiga H, Vaidya D, Djimde A, Arav-Boger R. Effect of artemether-lumefantrine (Coartem) on cytomegalovirus urine viral load during and following treatment for malaria in children. J Clin Virol. 2016 Apr;77:40-5. doi: 10.1016/j.jcv.2016.02.006. Epub 2016 Feb 11. PubMed PMID: 26895228. 4: Niaré K, Dara A, Sagara I, Sissoko MS, Guindo CO, Cissé NH, Coulibaly CO, Ringwald P, Benoit-Vical F, Berry A, Djimdé AA, Doumbo OK. In Vivo Efficacy and Parasite Clearance of Artesunate + Sulfadoxine-Pyrimethamine Versus Artemether-Lumefantrine in Mali. Am J Trop Med Hyg. 2016 Mar 2;94(3):634-9. doi: 10.4269/ajtmh.15-0503. Epub 2016 Jan 25. PubMed PMID: 26811430. 5: Yeka A, Kigozi R, Conrad MD, Lugemwa M, Okui P, Katureebe C, Belay K, Kapella BK, Chang MA, Kamya MR, Staedke SG, Dorsey G, Rosenthal PJ. Artesunate/Amodiaquine Versus Artemether/Lumefantrine for the Treatment of Uncomplicated Malaria in Uganda: A Randomized Trial. J Infect Dis. 2016 Apr 1;213(7):1134-42. doi: 10.1093/infdis/jiv551. Epub 2015 Nov 23. PubMed PMID: 26597254. 6: Saran I, Yavuz E, Kasozi H, Cohen J. Can Rapid Diagnostic Testing for Malaria Increase Adherence to Artemether-Lumefantrine?: A Randomized Controlled Trial in Uganda. Am J Trop Med Hyg. 2016 Feb 29. pii: 15-0420. [Epub ahead of print] PubMed PMID: 26928828. 7: Toure OA, Valecha N, Tshefu AK, Thompson R, Krudsood S, Gaye O, Rao BH, Sagara I, Bose TK, Mohanty S, Rao BS, Anvikar AR, Mwapasa V, Noedl H, Arora S, Roy A, Iyer SS, Sharma P, Saha N, Jalali RK; AM–PQP Study Team; AM-PQP Study Team. A Phase 3, Double-Blind, Randomized Study of Arterolane Maleate-Piperaquine Phosphate vs Artemether-Lumefantrine for Falciparum Malaria in Adolescent and Adult Patients in Asia and Africa. Clin Infect Dis. 2016 Feb 21. pii: ciw029. [Epub ahead of print] PubMed PMID: 26908796. 8: Maganda BA, Minzi OM, Ngaimisi E, Kamuhabwa AA, Aklillu E. CYP2B6*6 genotype and high efavirenz plasma concentration but not nevirapine are associated with low lumefantrine plasma exposure and poor treatment response in HIV-malaria-coinfected patients. Pharmacogenomics J. 2016 Feb;16(1):88-95. doi: 10.1038/tpj.2015.37. Epub 2015 May 12. PubMed PMID: 25963334. 9: Abuaku B, Duah N, Quaye L, Quashie N, Malm K, Bart-Plange C, Koram K. Therapeutic efficacy of artesunate-amodiaquine and artemether-lumefantrine combinations in the treatment of uncomplicated malaria in two ecological zones in Ghana. Malar J. 2016 Jan 5;15(1):6. doi: 10.1186/s12936-015-1080-x. PubMed PMID: 26728096; PubMed Central PMCID: PMC4700572. 10: Parashar D, N P A, R S R M. Development of artemether and lumefantrine co-loaded nanostructured lipid carriers: physicochemical characterization and in vivo antimalarial activity. Drug Deliv. 2016 Jan;23(1):123-9. doi: 10.3109/10717544.2014.905883. Epub 2014 Apr 30. PubMed PMID: 24786480. 11: Kredo T, Mauff K, Workman L, Van der Walt JS, Wiesner L, Smith PJ, Maartens G, Cohen K, Barnes KI. The interaction between artemether-lumefantrine and lopinavir/ritonavir-based antiretroviral therapy in HIV-1 infected patients. BMC Infect Dis. 2016 Jan 27;16(1):30. doi: 10.1186/s12879-016-1345-1. PubMed PMID: 26818566; PubMed Central PMCID: PMC4728832. 12: Abolaji AO, Adesanoye OA, Awogbindin I, Farombi EO. Endocrine disruption and oxidative stress implications of artemether-lumefantrine combination therapy in the ovary and uterus of rats. Hum Exp Toxicol. 2016 Jan 25. pii: 0960327115626580. [Epub ahead of print] PubMed PMID: 26811345. 13: Ogouyèmi-Hounto A, Azandossessi C, Lawani S, Damien G, de Tove YS, Remoue F, Gazard DK. Therapeutic efficacy of artemether-lumefantrine for the treatment of uncomplicated falciparum malaria in northwest Benin. Malar J. 2016 Jan 22;15(1):37. doi: 10.1186/s12936-016-1091-2. PubMed PMID: 26801767; PubMed Central PMCID: PMC4722724. 14: Nyunt MM, Nguyen VK, Kajubi R, Huang L, Ssebuliba J, Kiconco S, Mwima MW, Achan J, Aweeka F, Parikh S, Mwebaza N. Artemether-Lumefantrine Pharmacokinetics and Clinical Response Are Minimally Altered in Pregnant Ugandan Women Treated for Uncomplicated Falciparum Malaria. Antimicrob Agents Chemother. 2015 Dec 14;60(3):1274-82. doi: 10.1128/AAC.01605-15. PubMed PMID: 26666942. 15: Sow D, Ndiaye JL, Sylla K, Ba MS, Tine RC, Faye B, Pene M, Ndiaye M, Seck A, Lo AC, Abiola A, Dieng Y, Gaye O. Evaluation of the efficacy and safety of three 2-drug combinations for the treatment of uncomplicated Plasmodium falciparum malaria in Senegal: artesunate-amodiaquine, dihydroartemisinin-piperaquine, and artemether-lumefantrine. Med Sante Trop. 2015 Dec 5. [Epub ahead of print] PubMed PMID: 26644184. 16: Parikh S, Fehintola F, Huang L, Olson A, Adedeji WA, Darin KM, Morse GD, Murphy RL, Taiwo BO, Akinyinka OO, Adewole IF, Aweeka FT, Scarsi KK. Artemether-Lumefantrine Exposure in HIV-Infected Nigerian Subjects on Nevirapine-Containing Antiretroviral Therapy. Antimicrob Agents Chemother. 2015 Dec;59(12):7852-6. doi: 10.1128/AAC.01153-15. Epub 2015 Sep 21. PubMed PMID: 26392500; PubMed Central PMCID: PMC4649208. 17: Achieng AO, Muiruri P, Ingasia LA, Opot BH, Juma DW, Yeda R, Ngalah BS, Ogutu BR, Andagalu B, Akala HM, Kamau E. Temporal trends in prevalence of Plasmodium falciparum molecular markers selected for by artemether-lumefantrine treatment in pre-ACT and post-ACT parasites in western Kenya. Int J Parasitol Drugs Drug Resist. 2015 Jun 29;5(3):92-9. doi: 10.1016/j.ijpddr.2015.05.005. eCollection 2015 Dec. PubMed PMID: 26236581; PubMed Central PMCID: PMC4501530. 18: Kiaco K, Teixeira J, Machado M, do Rosário V, Lopes D. Evaluation of artemether-lumefantrine efficacy in the treatment of uncomplicated malaria and its association with pfmdr1, pfatpase6 and K13-propeller polymorphisms in Luanda, Angola. Malar J. 2015 Dec 16;14:504. doi: 10.1186/s12936-015-1018-3. PubMed PMID: 26670642; PubMed Central PMCID: PMC4681156. 19: Adeel AA, Saeed NA, Aljasari A, Almohager AM, Galab MH, AlMahdi A, Mahammed MH, AlDarsi M, Salaeah YA, Atta H, Zamani G, Warsame M, Barrette A, Mohammady HE, Nada RA. High efficacy of two artemisinin-based combinations: artesunate + sulfadoxine-pyrimethamine and artemether-lumefantrine for falciparum malaria in Yemen. Malar J. 2015 Nov 14;14(1):449. doi: 10.1186/s12936-015-0970-2. PubMed PMID: 26573814; PubMed Central PMCID: PMC4647513. 20: Pfeil J, Borrmann S, Bassat Q, Mulenga M, Talisuna A, Tozan Y. An Economic Evaluation of the Posttreatment Prophylactic Effect of Dihydroartemisinin-Piperaquine Versus Artemether-Lumefantrine for First-Line Treatment of Plasmodium falciparum Malaria Across Different Transmission Settings in Africa. Am J Trop Med Hyg. 2015 Nov;93(5):961-6. doi: 10.4269/ajtmh.15-0162. Epub 2015 Aug 3. PubMed PMID: 26240155; PubMed Central PMCID: PMC4703290.

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