lumefantrine   Click here for help

GtoPdb Ligand ID: 9969

Synonyms: benflumetol
Approved drug Antimalarial Ligand
lumefantrine is an approved drug (FDA (2009) in combination with artemether)
Compound class: Synthetic organic
Comment: Lumefantrine belongs to the aryl amino alcohols, a chemical class of antimalarial compounds that includes quinine, mefloquine and halofantrine.
Lumefantrine is a racemic mixture, with PubChem listing 9 stereoisotopes.

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.

lumefantrine is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 10
Topological polar surface area 23.47
Molecular weight 527.15
XLogP 10.14
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCCCN(CC(c1cc(Cl)cc2c1c1ccc(cc1C2=Cc1ccc(cc1)Cl)Cl)O)CCCC
Isomeric SMILES CCCCN(CC(c1cc(Cl)cc2c1c1ccc(cc1/C/2=C/c1ccc(cc1)Cl)Cl)O)CCCC
InChI 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-
InChI Key DYLGFOYVTXJFJP-MYYYXRDXSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Guide to Malaria Pharmacology Comments
Lumefantrine was first synthesized in the 1970s in China by the Academy of Military Medical Sciences as part of Project 523, an initiative to identify new antimalarial drugs [2]. The compound has activity against the asexual blood stages of P. falciparum and is used to treat malaria as part of an artemisinin-based combination therapy (ACT).
Lumefantrine is on the World Health Organisation's List of Essential Medicines. Click here to access the pdf version of the WHO's 21st Essential Medicines list (2019).

Potential Target/Mechanism Of Action: As the precise mechanism of action of lumefantrine is not yet known, we do not have a molecular target for this compound. Further information about possible mechanistic insights is provided under the Clinical data tab.