Structure via PubChem · Public domain (PubChem)
halofantrine
Sign in to saveAlso known as Halfan, Halofantrina, Halofantrinum
Halofantrine is a drug used to treat malaria. Halofantrine's structure contains a substituted phenanthrene, and is related to the antimalarial drugs quinine and lumefantrine. Marketed as Halfan, halofantrine is never used to prevent malaria and its mode of action is unknown, although a crystallographic study showed that it binds to hematin in vitro, suggesting a possible mechanism of action. Halofantrine has also been shown to bind to plasmepsin, a haemoglobin degrading enzyme unique to the malarial parasites.
Key facts
- Drug.verifiedrevid
- 461766301
- Drug.IUPAC_name
- 3-(Dibutylamino)-1-[1,3-dichloro-6-(trifluoromethyl)-9-phenanthryl]-1-propanol
- Drug.image
- Halofantrine.svg
- Drug.image_class
- skin-invert-image
- Drug.tradename
- Halfan
- Drug.MedlinePlus
- a603030
- Drug.routes_of_administration
- Oral
- Drug.protein_bound
- 60–70%
- Drug.metabolism
- Hepatic (CYP3A4-mediated)
- Drug.elimination_half life
- 6–10 days
- Drug.CAS_number
- 69756-53-2
- Drug.ATC_prefix
- P01
- Drug.ATC_suffix
- BX01
- Drug.PubChem
- 37393
- Drug.DrugBank
- DB01218
- Drug.ChemSpiderID
- 34303
- Drug.UNII
- Q2OS4303HZ
- Drug.ChEMBL
- 1107
via Wikipedia infobox
Chemical data
- Formula
- C26H30Cl2F3NO
- Molecular weight
- 500.4 g/mol
- IUPAC name
- 3-(dibutylamino)-1-[1,3-dichloro-6-(trifluoromethyl)phenanthren-9-yl]propan-1-ol
- SMILES
- CCCCN(CCCC)CCC(C1=C2C=CC(=CC2=C3C=C(C=C(C3=C1)Cl)Cl)C(F)(F)F)O
- InChIKey
- FOHHNHSLJDZUGQ-UHFFFAOYSA-N
- XLogP
- 8.6
- Polar surface area
- 23.5 Ų
- H-bond donors
- 1
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1992
- Admin. routes
- oral
- Indications
- malaria
via ChEMBL · EBI
Research
693 papers- Halofantrine in the treatment of malaria.Lancet (London, England) · 1989
- Halofantrine.East African medical journal · 1989
- Halofantrine. A review of its antimalarial activity, pharmacokinetic properties and therapeutic potential.Drugs · 1992
- Clinical pharmacokinetics of halofantrine.Clinical pharmacokinetics · 1994
- Halofantrine sensitivity.Lancet (London, England) · 1993
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 499.165655
- Has use
- medication
Show 6 more facts
- significant drug interaction
- thioridazine
- Commons category
- Halofantrine
- chemical formula
- C₂₆H₃₀Cl₂F₃NO
- canonical SMILES
- CCCCN(CCCC)CCC(C1=C2C=CC(=CC2=C3C=C(C=C(C3=C1)Cl)Cl)C(F)(F)F)O
- defined daily dose
- 1.5
- subject has role
- antimalarial
Sources (6)
via Wikidata · CC0
~3 min read
Encyclopedic overview
7 sectionsContents
- Adverse reactions
- Other adverse reactions
- Pharmacology
- Uses
- Dosing
- Manufacturing information and availability
- References
Halofantrine is a drug used to treat malaria. Halofantrine's structure contains a substituted phenanthrene, and is related to the antimalarial drugs quinine and lumefantrine. Marketed as Halfan, halofantrine is never used to prevent malaria and its mode of action is unknown, although a crystallographic study showed that it binds to hematin in vitro, suggesting a possible mechanism of action. Halofantrine has also been shown to bind to plasmepsin, a haemoglobin degrading enzyme unique to the malarial parasites.
Halofantrine was developed at SRI International for the Walter Reed Army Institute of Research from 1965 to 1975 by a team led by medicinal chemist William Colwell.
Excerpted from Wikipedia’s “halofantrine” article, available under the CC BY-SA 4.0 licence.
Available in 13 languages
via Wikidata sitelinks · CC0