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.
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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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/)
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
Approved drug? Yes (FDA (2009) in combination with artemether)
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
2-(dibutylamino)-1-[(9Z)-2,7-dichloro-9-[(4-chlorophenyl)methylidene]fluoren-4-yl]ethanol
International Nonproprietary Names Click here for help
INN number INN
7610 lumefantrine
Synonyms Click here for help
benflumetol
Database Links Click here for help
CAS Registry No. 82186-77-4 (source: Scifinder)
ChEBI CHEBI:156095
ChEMBL Ligand CHEMBL38827
DrugBank Ligand DB06708
DrugCentral Ligand 1617
GtoPdb PubChem SID 374883856
PubChem CID 6437380
Search Google for chemical match using the InChIKey DYLGFOYVTXJFJP-MYYYXRDXSA-N
Search Google for chemicals with the same backbone DYLGFOYVTXJFJP
Search PubMed clinical trials lumefantrine
Search PubMed titles lumefantrine
Search PubMed titles/abstracts lumefantrine
UniChem Compound Search for chemical match using the InChIKey DYLGFOYVTXJFJP-MYYYXRDXSA-N
UniChem Connectivity Search for chemical match using the InChIKey DYLGFOYVTXJFJP-MYYYXRDXSA-N