lumefantrine   

GtoPdb Ligand ID: 9969

Synonyms: benflumetol
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
Click here for structure editor
Physico-chemical Properties
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
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
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
2-(dibutylamino)-1-[(9Z)-2,7-dichloro-9-[(4-chlorophenyl)methylidene]fluoren-4-yl]ethanol
International Nonproprietary Names
INN number INN
7610 lumefantrine
Synonyms
benflumetol
Database Links
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
Search UniChem for chemical match using the InChIKey DYLGFOYVTXJFJP-MYYYXRDXSA-N
Search UniChem for chemicals with the same backbone DYLGFOYVTXJFJP