Table 1 Structural information for the observed and/or reported lumefantrine related impurities
From: Stability-indicating HPLC-DAD/UV-ESI/MS impurity profiling of the anti-malarial drug lumefantrine
# | Compound [formula, mono-isotopic mass] | Structure | Origin |
|---|---|---|---|
1 | Desbenzylketo N-oxide [C23H27NO3Cl2, MW 435.14] |
| Alkaline stress Oxidative stress |
2 | Lumefantrine (mono-)desbutyl derivative [C26H24NOCl3, MW 473.09] |
| Oxidative stress Metabolite |
3 | Lumefantrine N-oxide [C30H32NO2Cl3, MW 543.15] |
| Oxidative stress Degradation |
4 | 2,7-dichloro-4-[2-(di-n-butylamino)-1-hydroxyethyl]-9H-fluoren-9-one; Desbenzylketo derivative (DBK) [C23H27NO2Cl2, MW 419.14] |
| Oxidative stress Acidic stress Degradation |
5 | 2-(di-n-butylamino)-1-[2,7-dichloro-9H-fluoren-4-yl]ethanol; Desbenzyl derivative [C23H29NOCl2, 405.16] |
| Synthesis |
6 | Synthesis impurity found in lumefantrine API; Lumefantrine oxide [C30H32NO2Cl3, MW 543.14] |
| Synthesis |
7 | Synthesis impurity found in lumefantrine API; Lumefantrine oxide [C30H32NO2Cl3, MW 543.14] |
| Synthesis |
8 | (RS,Z)-2-(Dibutylamino)-2-(2,7-dichloro-9-(4-chloro-benzylidene)-9H-fluoren-4-yl)ethanol (isomeric compound); Impurity A (Ph. Int./USP Salmous) [C30H32NOCl3, MW 527.15] |
| Synthesis |
9 | Synthesis impurity found in lumefantrine API; Lumefantrine oxide [C30H32NO2Cl3, MW 543.14] |
| Synthesis |
10 | (1S,3R,5R)-1,3-bis((EZ)-2,7-Dichloro-9-(4-chlorobenzyl-idene)-9H-fluoren-4-yl)-2,6-dioxabicyclo[3.1.0]hexane; Impurity BA (USP Salmous) [C44H24Cl6O2, 797.39] |
| Synthesis |
11 | 2-((EZ)-2,6-Dichloro-9- (4-chlorobenzylidene)-9H-fluoren-4-yl)-3'-((EZ)-2,7-dichloro-9-(4-chlorobenzylidene)-9H-fluoren-4-yl)-2,2'-bioxirane; Impurity BB (USP Salmous) [C44H24Cl6O2, 797.39] |
| Synthesis |
