Lumefantrine

Base Information

• Chemical Name: Lumefantrine
• CAS No.: 82186-77-4
• Deprecated CAS: 120583-69-9
• Molecular Formula: C₃₀H₃₂Cl₃NO
• Molecular Weight: 528.949
• Hs Code.: 29221950
• UNII: F38R0JR742,ZUV4B00D9P,01NP22J3SV
• DSSTox Substance ID: DTXSID3046663
• Nikkaji Number: J3.642.651I
• Wikipedia: Lumefantrine
• Wikidata: Q904464
• NCI Thesaurus Code: C81541
• RXCUI: 847728
• Pharos Ligand ID: LHD19CSBQ57X
• Metabolomics Workbench ID: 43688
• ChEMBL ID: CHEMBL38827
• Mol file: 82186-77-4.mol

Synonyms:9H-Fluorene-4-methanol, 2,7-dichloro-9-((4-chlorophenyl)methylene)-alpha-((dibutylamino)methyl)-, (Z)-;benflumetol;benflumetol, (+)-isomer;benflumetol, (+-)-isomer;benflumetol, (-)-isomer;lumefantrine

Chemical Property of Lumefantrine

Chemical Property:

• Appearance/Colour: Yellow solid
• Vapor Pressure: 2.2E-17mmHg at 25°C
• Melting Point: 129-131oC
• Refractive Index: 1.633
• Boiling Point: 642.5 °C at 760 mmHg
• PKA: 13.44±0.20(Predicted)
• Flash Point: 342.3 °C
• PSA: 23.47000
• Density: 1.252 g/cm³
• LogP: 9.15170
• Storage Temp.: Refrigerator
• Solubility.: DMSO: ≥20mg/mL
• XLogP3: 8.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 10
• Exact Mass: 527.154948
• Heavy Atom Count: 35
• Complexity: 671

Purity/Quality:

99% ^*data from raw suppliers

Lumefantrine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCN(CCCC)CC(C1=CC(=CC2=C1C3=C(C2=CC4=CC=C(C=C4)Cl)C=C(C=C3)Cl)Cl)O
• Isomeric SMILES: CCCCN(CCCC)CC(C1=CC(=CC\2=C1C3=C(/C2=C/C4=CC=C(C=C4)Cl)C=C(C=C3)Cl)Cl)O
• Recent ClinicalTrials: Drug-drug Interaction Study of Ganaplacide and Lumefantrine With Efavirenz
• Description: Lumefantrine is a derivative of halofantrine that has been reported to exhibit antimalarial activity when combined with artemether in the treatment of multidrug-resistant Plasmodium falciparium . No evidence of cardiotoxicity has been reported with this combination, which may offer promise for successful treatment of resistant organisms. Lumefantrine is an antimalarial drug that is used in combination with artemether . The pairing of lumefantrine and artemether is a major form of oral artemisinin combination therapy used against uncomplicated P. falciparum malaria. Lumefantrine also blocks the rapidly activating delayed-rectifier potassium channel (IKr; IC50 = 8.1 μM).
• Uses: Inhibits hemozoin formation. Antimalarial A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human. Lumefantrine has been used: to study its effect on ex-vivo?Plasmodium falciparum?sensitivity using the tritiated hypoxanthine-based assayas a standard in the quantification of combined tablet formulation using HPTLCas a drug molecule in in vitro growth inhibition assay for in vitro B. caballi?growth inhibition studies
• Clinical Use: Treatment of P. falciparum infections (including mixed infections) in a fixed-dose combination treatment with artemether.

Technology Process of Lumefantrine

There total 19 articles about Lumefantrine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2-(dibutylamino)-1-(2,7-dichloro-9H-fluoren-4-yl)ethanol + 4-chlorobenzaldehyde (104-88-1) → lumefantrine (82186-77-4)

Guidance literature:

2-(dibutylamino)-1-(2,7-dichloro-9H-fluoren-4-yl)ethanol; With sodium hydroxide; In ethanol; at 20 ℃; for 0.5h;

4-chlorobenzaldehyde; In ethanol; at 20 ℃; for 60h;

Reference yield:

2-dibutylamino-1-(2,7-dichloro-9H-fluoren-4-yl)ethanol (69759-61-1) + 4-chlorobenzaldehyde (104-88-1) → lumefantrine (204133-10-8,82186-77-4)

Guidance literature:

With sodium hydroxide; In ethanol; at 30 - 40 ℃; for 24h; Large scale;

Reference yield:

2-dibutylamino-1-(2,7-dichloro-9H-fluoren-4-yl)ethanol (69759-61-1) + 4-chlorobenzaldehyde (104-88-1) → 2-dibutylamino-1-{2,7-dichloro-9-[1-(4-chlorophenyl)meth-(E)-ylidene]-9H-fluoren-4-yl}ethanol (82186-77-4) + lumefantrine (82186-77-4)

Guidance literature:

With sodium hydroxide; In ethanol; at 23 - 70 ℃; for 6h;

DOI:10.1021/op060244p

upstream raw materials:

2-dibutylamino-1-(2,7-dichloro-9H-fluoren-4-yl)ethanol

4-chlorobenzaldehyde

2-(2,7-dichloro-9H-fluoren-4-yl)oxirane

2,7-dichloro-9H-fluorene

Refernces

• 1、 -. "Preparation method for benflumetol and matched system thereof". Paragraph 0041-0050; 0057-0058. . Retrieved 2020/05/02.
• 2、 -. "POLYMORPHIC FORM I OF LUMEFANTRINE AND PROCESSES FOR ITS PREPARATION". Page/Page column 7. . Retrieved 2010/11/24.