halofantrine

Ligand id: 10019

Name: halofantrine

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 11
Topological polar surface area 23.47
Molecular weight 499.17
XLogP 8.52
No. Lipinski's rules broken 2

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
Approved drug? Yes (FDA (1992))
IUPAC Name
3-(dibutylamino)-1-[1,3-dichloro-6-(trifluoromethyl)phenanthren-9-yl]propan-1-ol
International Nonproprietary Names
INN number INN
4749 halofantrine
Synonyms
Halfan® | WR-171669
Comments
Halofantrine is a phenanthrene class antimalarial drug. This chemical class includes quinine and lumefantrine. The INN record specifies that halofantrine is a racemic mixture of stereoisomers. We show the structure without specified stereochemistry to represent the mixture.
The marketed formulation contains halofantrine hydrochloride (PubChem CID 37392).

Potential Target/Mechanism Of Action: As the precise mechanism of action of halofantrine is not yet known, we do not have a molecular target for this compound. There is some evidence that suggests that halofantrine inhibits the haem detoxification pathway in the parasite, and that this action causes lethal haem toxicity [1-2].
Database Links
BindingDB Ligand 79214
CAS Registry No. 69756-53-2 (source: WHO INN record)
ChEMBL Ligand CHEMBL1107
DrugBank Ligand DB01218
GtoPdb PubChem SID 375973209
PubChem CID 37393
Search Google for chemical match using the InChIKey FOHHNHSLJDZUGQ-UHFFFAOYSA-N
Search Google for chemicals with the same backbone FOHHNHSLJDZUGQ
Search PubMed clinical trials halofantrine
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Search PubMed titles/abstracts halofantrine
Search UniChem for chemical match using the InChIKey FOHHNHSLJDZUGQ-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone FOHHNHSLJDZUGQ
Wikipedia Halofantrine