halofantrine   Click here for help

GtoPdb Ligand ID: 10019

Synonyms: Halfan® | WR-171669
Approved drug Antimalarial Ligand
halofantrine is an approved drug (FDA (1992))
Compound class: Synthetic organic
Comment: Halofantrine is a phenanthrene containing compound and belongs to the aryl amino alcohols, a chemical class of antimalarial drugs that includes quinine, mefloquine 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).

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 11
Topological polar surface area 23.47
Molecular weight 499.17
XLogP 8.93
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES CCCCN(CCC(c1cc2c(Cl)cc(cc2c2c1ccc(c2)C(F)(F)F)Cl)O)CCCC
Isomeric SMILES CCCCN(CCC(c1cc2c(Cl)cc(cc2c2c1ccc(c2)C(F)(F)F)Cl)O)CCCC
InChI InChI=1S/C26H30Cl2F3NO/c1-3-5-10-32(11-6-4-2)12-9-25(33)23-16-22-21(14-18(27)15-24(22)28)20-13-17(26(29,30)31)7-8-19(20)23/h7-8,13-16,25,33H,3-6,9-12H2,1-2H3
InChI Key FOHHNHSLJDZUGQ-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
Approved drug? Yes (FDA (1992))
IUPAC Name Click here for help
3-(dibutylamino)-1-[1,3-dichloro-6-(trifluoromethyl)phenanthren-9-yl]propan-1-ol
International Nonproprietary Names Click here for help
INN number INN
4749 halofantrine
Synonyms Click here for help
Halfan® | WR-171669
Database Links Click here for help
BindingDB Ligand 79214
CAS Registry No. 69756-53-2 (source: WHO INN record)
ChEMBL Ligand CHEMBL1107
DrugBank Ligand DB01218
DrugCentral Ligand 1350
GtoPdb PubChem SID 375973209
PubChem CID 37393
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Wikipedia Halofantrine