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Identification
NameHalofantrine
Accession NumberDB01218  (APRD00419)
TypeSmall Molecule
GroupsApproved
DescriptionHalofantrine 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
Synonyms
Halfan
Halofantrina
Halofantrine
Halofantrinum
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Halfan - Tab 250mgTablet250 mgOralSmithkline Beecham Pharma Division Of Smithkline Beecham Inc1996-07-161999-03-08Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
HalfanNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Halofantrine hydrochloride
ThumbNot applicableDBSALT001186
Categories
UNIIQ2OS4303HZ
CAS number69756-53-2
WeightAverage: 500.424
Monoisotopic: 499.165654616
Chemical FormulaC26H30Cl2F3NO
InChI KeyFOHHNHSLJDZUGQ-UHFFFAOYSA-N
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
IUPAC Name
3-(dibutylamino)-1-[1,3-dichloro-6-(trifluoromethyl)phenanthren-9-yl]propan-1-ol
SMILES
CCCCN(CCCC)CCC(O)C1=C2C=CC(=CC2=C2C=C(Cl)C=C(Cl)C2=C1)C(F)(F)F
Pharmacology
IndicationFor treatment of Severe malaria
Structured Indications Not Available
PharmacodynamicsHalofantrine is a synthetic antimalarial which acts as a blood schizonticide. It is effective against multi drug resistant (including mefloquine resistant) P. falciparum malaria.
Mechanism of actionThe mechanism of action of Halofantrine may be similar to that of chloroquine, quinine, and mefloquine; by forming toxic complexes with ferritoporphyrin IX that damage the membrane of the parasite.
TargetKindPharmacological actionActionsOrganismUniProt ID
Fe(II)-protoporphyrin IXSmall moleculeyes
antagonist
Plasmodium falciparumnot applicabledetails
Potassium voltage-gated channel subfamily H member 2Proteinyes
inhibitor
HumanQ12809 details
Plasmepsin-2Proteinunknown
inhibitor
Plasmodium falciparumP46925 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein binding60-70%;
Metabolism

Hepatic

SubstrateEnzymesProduct
Halofantrine
N-debutylhalofantrineDetails
Route of eliminationNot Available
Half life6-10 days
ClearanceNot Available
ToxicitySide effects incldue coughing noisy, rattling, troubled breathing, loss of appetite, aches and pain in joints, indigestion,and skin itching or rash.
Affected organisms
  • Plasmodium
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of Halofantrine can be increased when it is combined with Abiraterone.Approved
AcepromazineThe serum concentration of Acepromazine can be increased when it is combined with Halofantrine.Approved, Vet Approved
AceprometazineThe serum concentration of Aceprometazine can be increased when it is combined with Halofantrine.Approved
AlimemazineThe serum concentration of Alimemazine can be increased when it is combined with Halofantrine.Approved, Vet Approved
AmiodaroneThe serum concentration of Halofantrine can be increased when it is combined with Amiodarone.Approved, Investigational
AprepitantThe serum concentration of Halofantrine can be increased when it is combined with Aprepitant.Approved, Investigational
ArtemetherThe risk or severity of adverse effects can be increased when Artemether is combined with Halofantrine.Approved
AtazanavirThe serum concentration of Halofantrine can be increased when it is combined with Atazanavir.Approved, Investigational
AtomoxetineThe serum concentration of Halofantrine can be increased when it is combined with Atomoxetine.Approved
BetaxololThe metabolism of Halofantrine can be decreased when combined with Betaxolol.Approved
BexaroteneThe serum concentration of Halofantrine can be decreased when it is combined with Bexarotene.Approved, Investigational
BL-1020The serum concentration of BL-1020 can be increased when it is combined with Halofantrine.Investigational
BoceprevirThe serum concentration of Halofantrine can be increased when it is combined with Boceprevir.Approved
BortezomibThe serum concentration of Halofantrine can be increased when it is combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Halofantrine can be decreased when it is combined with Bosentan.Approved, Investigational
BupropionThe metabolism of Halofantrine can be decreased when combined with Bupropion.Approved
CarbamazepineThe metabolism of Halofantrine can be increased when combined with Carbamazepine.Approved, Investigational
CelecoxibThe metabolism of Halofantrine can be decreased when combined with Celecoxib.Approved, Investigational
CeritinibThe serum concentration of Halofantrine can be increased when it is combined with Ceritinib.Approved
ChloroquineThe metabolism of Halofantrine can be decreased when combined with Chloroquine.Approved, Vet Approved
ChlorpromazineThe serum concentration of Chlorpromazine can be increased when it is combined with Halofantrine.Approved, Vet Approved
CholecalciferolThe metabolism of Halofantrine can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CimetidineThe metabolism of Halofantrine can be decreased when combined with Cimetidine.Approved
CinacalcetThe metabolism of Halofantrine can be decreased when combined with Cinacalcet.Approved
CitalopramThe metabolism of Halofantrine can be decreased when combined with Citalopram.Approved
ClarithromycinThe serum concentration of Halofantrine can be increased when it is combined with Clarithromycin.Approved
ClemastineThe serum concentration of Halofantrine can be increased when it is combined with Clemastine.Approved
ClobazamThe metabolism of Halofantrine can be decreased when combined with Clobazam.Approved, Illicit
ClomipramineThe metabolism of Halofantrine can be decreased when combined with Clomipramine.Approved, Vet Approved
ClopidogrelThe metabolism of Halofantrine can be decreased when combined with Clopidogrel.Approved, Nutraceutical
ClotrimazoleThe serum concentration of Halofantrine can be increased when it is combined with Clotrimazole.Approved, Vet Approved
ClozapineThe metabolism of Halofantrine can be decreased when combined with Clozapine.Approved
CobicistatThe serum concentration of Halofantrine can be increased when it is combined with Cobicistat.Approved
CocaineThe metabolism of Halofantrine can be decreased when combined with Cocaine.Approved, Illicit
ConivaptanThe serum concentration of Halofantrine can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe serum concentration of Halofantrine can be increased when it is combined with Crizotinib.Approved
CyclosporineThe serum concentration of Halofantrine can be increased when it is combined with Cyclosporine.Approved, Investigational, Vet Approved
DabrafenibThe serum concentration of Halofantrine can be decreased when it is combined with Dabrafenib.Approved
DapsoneThe risk or severity of adverse effects can be increased when Halofantrine is combined with Dapsone.Approved, Investigational
DarifenacinThe metabolism of Halofantrine can be decreased when combined with Darifenacin.Approved, Investigational
DarunavirThe serum concentration of Halofantrine can be increased when it is combined with Darunavir.Approved
DasatinibThe serum concentration of Halofantrine can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Halofantrine can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe serum concentration of Halofantrine can be increased when it is combined with Delavirdine.Approved
DesipramineThe metabolism of Halofantrine can be decreased when combined with Desipramine.Approved
DexamethasoneThe serum concentration of Halofantrine can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DihydroergotamineThe serum concentration of Halofantrine can be increased when it is combined with Dihydroergotamine.Approved
DiltiazemThe serum concentration of Halofantrine can be increased when it is combined with Diltiazem.Approved
DiphenhydramineThe metabolism of Halofantrine can be decreased when combined with Diphenhydramine.Approved
DoxycyclineThe serum concentration of Halofantrine can be increased when it is combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe serum concentration of Halofantrine can be increased when it is combined with Dronedarone.Approved
DuloxetineThe metabolism of Halofantrine can be decreased when combined with Duloxetine.Approved
EfavirenzThe serum concentration of Halofantrine can be decreased when it is combined with Efavirenz.Approved, Investigational
EliglustatThe metabolism of Halofantrine can be decreased when combined with Eliglustat.Approved
EnzalutamideThe serum concentration of Halofantrine can be decreased when it is combined with Enzalutamide.Approved
ErythromycinThe serum concentration of Halofantrine can be increased when it is combined with Erythromycin.Approved, Vet Approved
Eslicarbazepine acetateThe serum concentration of Halofantrine can be decreased when it is combined with Eslicarbazepine acetate.Approved
EtravirineThe serum concentration of Halofantrine can be decreased when it is combined with Etravirine.Approved
FelodipineThe metabolism of Halofantrine can be decreased when combined with Felodipine.Approved, Investigational
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Halofantrine.Approved
FluconazoleThe serum concentration of Halofantrine can be increased when it is combined with Fluconazole.Approved
FluoxetineThe metabolism of Halofantrine can be decreased when combined with Fluoxetine.Approved, Vet Approved
FluphenazineThe serum concentration of Fluphenazine can be increased when it is combined with Halofantrine.Approved
FluvoxamineThe serum concentration of Halofantrine can be increased when it is combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe serum concentration of Halofantrine can be increased when it is combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Halofantrine can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Halofantrine can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Halofantrine can be increased when it is combined with Fusidic Acid.Approved
GemfibrozilThe metabolism of Halofantrine can be decreased when combined with Gemfibrozil.Approved
HaloperidolThe metabolism of Halofantrine can be decreased when combined with Haloperidol.Approved
IdelalisibThe serum concentration of Halofantrine can be increased when it is combined with Idelalisib.Approved
ImatinibThe serum concentration of Halofantrine can be increased when it is combined with Imatinib.Approved
ImipramineThe metabolism of Halofantrine can be decreased when combined with Imipramine.Approved
IndinavirThe serum concentration of Halofantrine can be increased when it is combined with Indinavir.Approved
IrbesartanThe metabolism of Halofantrine can be decreased when combined with Irbesartan.Approved, Investigational
IsavuconazoniumThe serum concentration of Halofantrine can be increased when it is combined with Isavuconazonium.Approved, Investigational
IsoniazidThe metabolism of Halofantrine can be decreased when combined with Isoniazid.Approved
IsradipineThe serum concentration of Halofantrine can be increased when it is combined with Isradipine.Approved
ItraconazoleThe serum concentration of Halofantrine can be increased when it is combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Halofantrine can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe serum concentration of Halofantrine can be increased when it is combined with Ketoconazole.Approved, Investigational
Lanthanum carbonateThe serum concentration of Halofantrine can be decreased when it is combined with Lanthanum carbonate.Approved
LapatinibThe metabolism of Halofantrine can be decreased when combined with Lapatinib.Approved, Investigational
LopinavirThe serum concentration of Halofantrine can be increased when it is combined with Lopinavir.Approved
LorcaserinThe metabolism of Halofantrine can be decreased when combined with Lorcaserin.Approved
LosartanThe metabolism of Halofantrine can be decreased when combined with Losartan.Approved
LovastatinThe serum concentration of Halofantrine can be increased when it is combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Halofantrine can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Halofantrine can be increased when it is combined with Lumacaftor.Approved
LumefantrineLumefantrine may increase the QTc-prolonging activities of Halofantrine.Approved
MefloquineMefloquine may increase the QTc-prolonging activities of Halofantrine.Approved
MesoridazineThe serum concentration of Mesoridazine can be increased when it is combined with Halofantrine.Approved
MethadoneThe metabolism of Halofantrine can be decreased when combined with Methadone.Approved
MethotrimeprazineThe metabolism of Halofantrine can be decreased when combined with Methotrimeprazine.Approved
Methylene blueThe serum concentration of Methylene blue can be increased when it is combined with Halofantrine.Investigational
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Halofantrine.Approved, Investigational
MifepristoneThe serum concentration of Halofantrine can be increased when it is combined with Mifepristone.Approved, Investigational
MirabegronThe metabolism of Halofantrine can be decreased when combined with Mirabegron.Approved
MitotaneThe serum concentration of Halofantrine can be decreased when it is combined with Mitotane.Approved
ModafinilThe serum concentration of Halofantrine can be decreased when it is combined with Modafinil.Approved, Investigational
MoricizineThe serum concentration of Moricizine can be increased when it is combined with Halofantrine.Approved, Withdrawn
NafcillinThe serum concentration of Halofantrine can be decreased when it is combined with Nafcillin.Approved
NefazodoneThe serum concentration of Halofantrine can be increased when it is combined with Nefazodone.Approved, Withdrawn
NelfinavirThe serum concentration of Halofantrine can be increased when it is combined with Nelfinavir.Approved
NetupitantThe serum concentration of Halofantrine can be increased when it is combined with Netupitant.Approved
NevirapineThe serum concentration of Halofantrine can be increased when it is combined with Nevirapine.Approved
NicardipineThe metabolism of Halofantrine can be decreased when combined with Nicardipine.Approved
NilotinibThe serum concentration of Halofantrine can be increased when it is combined with Nilotinib.Approved, Investigational
OlaparibThe serum concentration of Halofantrine can be increased when it is combined with Olaparib.Approved
OsimertinibThe serum concentration of Halofantrine can be increased when it is combined with Osimertinib.Approved
PalbociclibThe serum concentration of Halofantrine can be increased when it is combined with Palbociclib.Approved
PanobinostatThe serum concentration of Halofantrine can be increased when it is combined with Panobinostat.Approved, Investigational
ParoxetineThe metabolism of Halofantrine can be decreased when combined with Paroxetine.Approved, Investigational
Peginterferon alfa-2bThe serum concentration of Halofantrine can be decreased when it is combined with Peginterferon alfa-2b.Approved
PentobarbitalThe metabolism of Halofantrine can be increased when combined with Pentobarbital.Approved, Vet Approved
PerazineThe serum concentration of Perazine can be increased when it is combined with Halofantrine.Investigational
PerphenazineThe serum concentration of Perphenazine can be increased when it is combined with Halofantrine.Approved
PhenobarbitalThe metabolism of Halofantrine can be increased when combined with Phenobarbital.Approved
PhenytoinThe metabolism of Halofantrine can be increased when combined with Phenytoin.Approved, Vet Approved
PioglitazoneThe metabolism of Halofantrine can be decreased when combined with Pioglitazone.Approved, Investigational
PosaconazoleThe serum concentration of Halofantrine can be increased when it is combined with Posaconazole.Approved, Investigational, Vet Approved
PrimidoneThe metabolism of Halofantrine can be increased when combined with Primidone.Approved, Vet Approved
ProchlorperazineThe serum concentration of Prochlorperazine can be increased when it is combined with Halofantrine.Approved, Vet Approved
PromazineThe serum concentration of Promazine can be increased when it is combined with Halofantrine.Approved, Vet Approved
PromethazineThe serum concentration of Promethazine can be increased when it is combined with Halofantrine.Approved
PropiopromazineThe serum concentration of Propiopromazine can be increased when it is combined with Halofantrine.Vet Approved
QuinidineThe metabolism of Halofantrine can be decreased when combined with Quinidine.Approved
QuinineThe risk or severity of adverse effects can be increased when Quinine is combined with Halofantrine.Approved
RabeprazoleThe metabolism of Halofantrine can be decreased when combined with Rabeprazole.Approved, Investigational
RanolazineThe serum concentration of Halofantrine can be increased when it is combined with Ranolazine.Approved, Investigational
RifabutinThe metabolism of Halofantrine can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Halofantrine can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Halofantrine can be increased when combined with Rifapentine.Approved
RitonavirThe serum concentration of Halofantrine can be increased when it is combined with Ritonavir.Approved, Investigational
RolapitantThe metabolism of Halofantrine can be decreased when combined with Rolapitant.Approved
RopiniroleThe metabolism of Halofantrine can be decreased when combined with Ropinirole.Approved, Investigational
RosiglitazoneThe metabolism of Halofantrine can be decreased when combined with Rosiglitazone.Approved, Investigational
SaquinavirThe serum concentration of Halofantrine can be increased when it is combined with Saquinavir.Approved, Investigational
SecobarbitalThe metabolism of Halofantrine can be increased when combined with Secobarbital.Approved, Vet Approved
SertralineThe metabolism of Halofantrine can be decreased when combined with Sertraline.Approved
SildenafilThe serum concentration of Halofantrine can be increased when it is combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Halofantrine can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Halofantrine can be increased when it is combined with Simeprevir.Approved
St. John's WortThe serum concentration of Halofantrine can be decreased when it is combined with St. John's Wort.Nutraceutical
StiripentolThe serum concentration of Halofantrine can be increased when it is combined with Stiripentol.Approved
SulfamethoxazoleThe metabolism of Halofantrine can be decreased when combined with Sulfamethoxazole.Approved
SulfisoxazoleThe serum concentration of Halofantrine can be increased when it is combined with Sulfisoxazole.Approved, Vet Approved
TamoxifenThe metabolism of Halofantrine can be decreased when combined with Tamoxifen.Approved
TelaprevirThe serum concentration of Halofantrine can be increased when it is combined with Telaprevir.Approved
TelithromycinThe serum concentration of Halofantrine can be increased when it is combined with Telithromycin.Approved
TerbinafineThe metabolism of Halofantrine can be decreased when combined with Terbinafine.Approved, Investigational, Vet Approved
TeriflunomideThe metabolism of Halofantrine can be decreased when combined with Teriflunomide.Approved
ThiethylperazineThe serum concentration of Thiethylperazine can be increased when it is combined with Halofantrine.Withdrawn
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Halofantrine.Approved
TiclopidineThe serum concentration of Halofantrine can be increased when it is combined with Ticlopidine.Approved
TipranavirThe metabolism of Halofantrine can be decreased when combined with Tipranavir.Approved, Investigational
TocilizumabThe serum concentration of Halofantrine can be decreased when it is combined with Tocilizumab.Approved
TranylcypromineThe metabolism of Halofantrine can be decreased when combined with Tranylcypromine.Approved
TrifluoperazineThe serum concentration of Trifluoperazine can be increased when it is combined with Halofantrine.Approved
TriflupromazineThe serum concentration of Triflupromazine can be increased when it is combined with Halofantrine.Approved, Vet Approved
TrimethoprimThe metabolism of Halofantrine can be decreased when combined with Trimethoprim.Approved, Vet Approved
VenlafaxineThe serum concentration of Halofantrine can be increased when it is combined with Venlafaxine.Approved
VerapamilThe serum concentration of Halofantrine can be increased when it is combined with Verapamil.Approved
VoriconazoleThe serum concentration of Halofantrine can be increased when it is combined with Voriconazole.Approved, Investigational
ZiprasidoneThe serum concentration of Halofantrine can be increased when it is combined with Ziprasidone.Approved
Food Interactions
  • Take on an empty stomach, bioavailability is 6 times higher when drug is taken with high fat meals. Risks of cardiac toxicity are then increased.
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesP01BX01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (84 KB)
MSDSDownload (27.1 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.949
Caco-2 permeable+0.6485
P-glycoprotein substrateSubstrate0.74
P-glycoprotein inhibitor IInhibitor0.6857
P-glycoprotein inhibitor IIInhibitor0.6097
Renal organic cation transporterNon-inhibitor0.5267
CYP450 2C9 substrateNon-substrate0.8426
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateSubstrate0.6218
CYP450 1A2 substrateInhibitor0.5513
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8931
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorInhibitor0.7959
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5252
Ames testNon AMES toxic0.6185
CarcinogenicityNon-carcinogens0.6485
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6809 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.732
hERG inhibition (predictor II)Inhibitor0.9085
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
TabletOral250 mg
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP8.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000111 mg/mLALOGPS
logP7.34ALOGPS
logP8.06ChemAxon
logS-6.7ALOGPS
pKa (Strongest Acidic)14.47ChemAxon
pKa (Strongest Basic)10.05ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.47 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity131.66 m3·mol-1ChemAxon
Polarizability51.53 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenanthrenes and derivatives
Sub ClassNot Available
Direct ParentPhenanthrenes and derivatives
Alternative Parents
Substituents
  • Phenanthrene
  • Naphthalene
  • 1,3-dichlorobenzene
  • Aralkylamine
  • Chlorobenzene
  • Aryl halide
  • Aryl chloride
  • 1,3-aminoalcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organochloride
  • Organohalogen compound
  • Amine
  • Alkyl halide
  • Alkyl fluoride
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available

Targets

1. Fe(II)-protoporphyrin IX
Kind
Small molecule
Organism
Plasmodium falciparum
Pharmacological action
yes
Actions
antagonist
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Blauer G: Interaction of ferriprotoporphyrin IX with the antimalarials amodiaquine and halofantrine. Biochem Int. 1988 Oct;17(4):729-34. [PubMed:3240320 ]
  4. Egan TJ, Hempelmann E, Mavuso WW: Characterisation of synthetic beta-haematin and effects of the antimalarial drugs quinidine, halofantrine, desbutylhalofantrine and mefloquine on its formation. J Inorg Biochem. 1999 Jan-Feb;73(1-2):101-7. [PubMed:10212997 ]
  5. Famin O, Krugliak M, Ginsburg H: Kinetics of inhibition of glutathione-mediated degradation of ferriprotoporphyrin IX by antimalarial drugs. Biochem Pharmacol. 1999 Jul 1;58(1):59-68. [PubMed:10403519 ]
  6. de Villiers KA, Marques HM, Egan TJ: The crystal structure of halofantrine-ferriprotoporphyrin IX and the mechanism of action of arylmethanol antimalarials. J Inorg Biochem. 2008 Aug;102(8):1660-7. doi: 10.1016/j.jinorgbio.2008.04.001. Epub 2008 Apr 20. [PubMed:18508124 ]
  7. Fitch CD: Ferriprotoporphyrin IX, phospholipids, and the antimalarial actions of quinoline drugs. Life Sci. 2004 Mar 5;74(16):1957-72. [PubMed:14967191 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarization
Specific Function:
Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the delayed rectifying potassium current in heart (IKr). Isoforms USO have no channel activity by themself, but modulates channel characteristics by forming heterotetramers with other isoforms which are r...
Gene Name:
KCNH2
Uniprot ID:
Q12809
Molecular Weight:
126653.52 Da
References
  1. Tie H, Walker BD, Singleton CB, Valenzuela SM, Bursill JA, Wyse KR, Breit SN, Campbell TJ: Inhibition of HERG potassium channels by the antimalarial agent halofantrine. Br J Pharmacol. 2000 Aug;130(8):1967-75. [PubMed:10952689 ]
  2. Mbai M, Rajamani S, January CT: The anti-malarial drug halofantrine and its metabolite N-desbutylhalofantrine block HERG potassium channels. Cardiovasc Res. 2002 Sep;55(4):799-805. [PubMed:12176129 ]
Kind
Protein
Organism
Plasmodium falciparum
Pharmacological action
unknown
Actions
inhibitor
General Function:
Aspartic-type endopeptidase activity
Specific Function:
Not Available
Gene Name:
Not Available
Uniprot ID:
P46925
Molecular Weight:
51489.41 Da
References
  1. Friedman R, Caflisch A: Discovery of plasmepsin inhibitors by fragment-based docking and consensus scoring. ChemMedChem. 2009 Aug;4(8):1317-26. doi: 10.1002/cmdc.200900078. [PubMed:19472268 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular Weight:
57108.065 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular Weight:
55824.275 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23