Lumefantrine

Structural formula
	Structural formula with incomplete stereochemistry
General
Non-proprietary name	Lumefantrine
other names	( RS ) -2- (Dibutylamino) -1 - [(9 Z ) -2,7-dichloro-9 - [(4-chlorophenyl) -methylidene] -fluoren-4-yl] ethanol ( IUPAC ) ; (±) -2- (Dibutylamino) -1 - [(9 Z ) -2,7-dichloro-9 - [(4-chlorophenyl) -methylidene] -fluoren-4-yl] ethanol; rac -2- (Dibutylamino) -1 - [(9 Z ) -2,7-dichloro-9 - [(4-chlorophenyl) -methylidene] -fluoren-4-yl] ethanol; DL -2- (Dibutylamino) -1 - [(9 Z ) -2,7-dichloro-9 - [(4-chlorophenyl) -methylidene] -fluoren-4-yl] ethanol;
Molecular formula	C 30 H 32 Cl 3 NO
External identifiers / databases
EC number	617-303-4
ECHA InfoCard	100.133.797
PubChem	6437380
DrugBank	DB06708
Wikidata	Q904464
Drug information
ATC code	P01
Drug class	Antiprotozoic
properties
Molar mass	528.94 g · mol -1
solubility	hardly soluble in water, oil and most organic solvents , soluble in unsaturated fatty acids
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: ?
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Lumefantrine is a substance that is toxic to plasmodia .

It is used as drug in a fixed combination with artemether for the treatment of by Plasmodium falciparum induced malaria used.

Pharmacological properties

Lumefantrine probably interferes in the plasmodia with the breakdown of haemin, which is toxic to the parasites, to form haemozoin . The absorption of the lipid-soluble substance is greatly facilitated in the case of oral administration by a meal that is as rich in fat as possible. Lumefantrine has a half-life of four to six days. Lumefantrine is metabolized in the liver by the enzyme cytochrome P450 3A4 .

Preparations and Uses

Lumefantrine is used exclusively as a combination preparation for the therapy of malaria. Lumefantrine monopreparations are not approved worldwide.

The main focus for the use of artemether-lumefantrine combination preparations is the treatment of uncomplicated tropic malaria , especially with plasmodia that are resistant to other drugs such as chloroquine .

Stereoisomerism

In addition to a Z -configured double bond, lumefantrine also has a chiral center, the configuration of which is not fixed. The racemate (1: 1 mixture of enantiomers ) is used as the medicinal substance .

Trade names

in a fixed combination (Lumefantrine 120 mg with Artemether 20 mg) as Riamet u. a. in D , A , CH , GB , F , S , NL and as Coartem u. a. in USA , ZA

Individual evidence

^ The Merck Index. An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 970, ISBN 978-0-911910-00-1 .
↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A label for 2- (dibutylamino) -1 - [(9Z) -2,7-dichloro-9 - [(4-chlorophenyl) methylidene] -9H-fluoren-4-yl] ethane is shown, which is derived from a self-classification by the distributor -1-ol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on July 7, 2020.

↑ ABDA database (as of December 4, 2009).

[MerckIndex-1] The Merck Index. An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 970, ISBN 978-0-911910-00-1 .

[2] Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A label for 2- (dibutylamino) -1 - [(9Z) -2,7-dichloro-9 - [(4-chlorophenyl) methylidene] -9H-fluoren-4-yl] ethane is shown, which is derived from a self-classification by the distributor -1-ol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on July 7, 2020.

[3] ABDA database (as of December 4, 2009).