Human Metabolome Database Version 3.5

Showing metabocard for Halofantrine (HMDB15349)

Record Information
Version 3.5
Creation Date 2012-09-06 09:16:51 -0600
Update Date 2013-02-08 17:33:32 -0700
HMDB ID HMDB15349
Secondary Accession Numbers None
Metabolite Identification
Common Name Halofantrine
Description Halofantrine is a drug used to treat malaria. It belongs to the phenanthrene class of compounds that includes quinine and lumefantrine. It appears to inhibit polymerisation of heme molecules (by the parasite enzyme 'heme polymerase'), resulting in the parasite being poisoned by its own waste. Halofantrine has been shown to preferentially block open and inactivated HERG channels leading to some degree of cardiotoxicity.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Halofantrina [INN-Spanish]
  2. Halofantrine [Usan]
  3. Halofantrinum [INN-Latin]
Chemical Formula C26H30Cl2F3NO
Average Molecular Weight 500.424
Monoisotopic Molecular Weight 499.165654616
IUPAC Name 3-(dibutylamino)-1-[1,3-dichloro-6-(trifluoromethyl)phenanthren-9-yl]propan-1-ol
Traditional IUPAC Name halofantrine
CAS Registry Number 69756-53-2
SMILES CCCCN(CCCC)CCC(O)C1=C2C=CC(=CC2=C2C=C(Cl)C=C(Cl)C2=C1)C(F)(F)F
InChI Identifier 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
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Phenanthrenes and Derivatives
Sub Class N/A
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • Aromatic Homopolycyclic Compounds
Substituents
  • Aryl Chloride
  • Benzyl Alcohol Derivative
  • Chlorobenzene
  • Naphthalene
  • Organochloride
  • Organofluoride
  • Secondary Alcohol
  • Tertiary Aliphatic Amine (Trialkylamine)
Direct Parent Phenanthrenes and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Drug
Biofunction
  • Antimalarials
  • Antiprotozoals
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility 1.11e-04 g/L Not Available
LogP 8.9 Not Available
Predicted Properties
Property Value Source
Water Solubility 1.110E-04 g/L ALOGPS
LogP 7.34 ALOGPS
LogP 8.06 ChemAxon
LogS -6.66 ALOGPS
pKa (strongest acidic) 14.47 ChemAxon
pKa (strongest basic) 10.05 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 23.47 A2 ChemAxon
Rotatable Bond Count 11 ChemAxon
Refractivity 131.66 ChemAxon
Polarizability 51.53 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB01218
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB01218
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB01218 Link_out
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID Not Available
KNApSAcK ID Not Available
Chemspider ID 34303 Link_out
KEGG Compound ID C07634 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Halofantrine Link_out
NuGOwiki Link HMDB15349 Link_out
Metagene Link HMDB15349 Link_out
METLIN ID Not Available
PubChem Compound 37393 Link_out
PDB ID Not Available
ChEBI ID 252728 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available

Enzymes
Name: Cytochrome P450 3A4
Reactions: Not Available
Gene Name: CYP3A4
Uniprot ID: P08684 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2D6
Reactions: Not Available
Gene Name: CYP2D6
Uniprot ID: P10635 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A5
Reactions: Not Available
Gene Name: CYP3A5
Uniprot ID: P20815 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C8
Reactions: Not Available
Gene Name: CYP2C8
Uniprot ID: P10632 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Potassium voltage-gated channel subfamily H member 2
Reactions: Not Available
Gene Name: KCNH2
Uniprot ID: Q12809 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA