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.
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2D Structure
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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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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
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 Model List of Essential Medicines (21st List, 2019). Access PDF version.
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
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