Tìm theo
Halofantrine
Các tên gọi khác (4 ) :
  • Halfan
  • Halofantrina
  • Halofantrine
  • Halofantrinum
antimalarials, antiprotozoal agents
Thuốc Gốc
Small Molecule
CAS: 69756-53-2
ATC: P01BX01
CTHH: C26H30Cl2F3NO
PTK: 500.424
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.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C26H30Cl2F3NO
Phân tử khối
500.424
Monoisotopic mass
499.165654616
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
InChIKey=FOHHNHSLJDZUGQ-UHFFFAOYSA-N
IUPAC Name
3-(dibutylamino)-1-[1,3-dichloro-6-(trifluoromethyl)phenanthren-9-yl]propan-1-ol
Traditional IUPAC Name
halofantrine
SMILES
CCCCN(CCCC)CCC(O)C1=C2C=CC(=CC2=C2C=C(Cl)C=C(Cl)C2=C1)C(F)(F)F
Độ hòa tan
1.11e-04 g/l
logP
8.9
logS
-6.7
pKa (strongest acidic)
14.47
pKa (Strongest Basic)
10.05
PSA
23.47 Å2
Refractivity
131.66 m3·mol-1
Polarizability
51.53 Å3
Rotatable Bond Count
11
H Bond Acceptor Count
2
H Bond Donor Count
1
Physiological Charge
1
Number of Rings
3
Bioavailability
0
MDDR-Like Rule
true
Dược Lực Học : Halofantrine is a synthetic antimalarial which acts as a blood schizonticide. It is effective against multi drug resistant (including mefloquine resistant) P. falciparum malaria.
Cơ Chế Tác Dụng : 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. The 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.
Dược Động Học :

▧ Protein binding :
60-70%;
▧ Metabolism :
Hepatic
▧ Half Life :
6-10 days
Độc Tính : Side effects incldue coughing noisy, rattling, troubled breathing, loss of appetite, aches and pain in joints, indigestion,and skin itching or rash.
Chỉ Định : For treatment of Severe malaria
Tương Tác Thuốc :
  • Artemether Halofantrine may increase the adverse effects of artemether. Combination therapy is contraindicated unless there are no other treatment options.
  • Bicalutamide CYP3A4 Inhibitors like bicalutamide may increase the serum concentration of halofantrine. Extreme caution, with possibly increased monitoring of cardiac status (e.g., ECG), should be used with concurrent use of halofantrine with any moderate CYP3A4 inhibitor(s).
  • Clotrimazole CYP3A4 Inhibitors (Moderate) such as clotrmazole may increase the serum concentration of halofantrine. Extreme caution, with possibly increased monitoring of cardiac status (e.g., ECG), should be used with concurrent use of halofantrine with any moderate CYP3A4 inhibitor(s).
  • Conivaptan CYP3A4 Inhibitors (Strong) may increase the serum concentration of Fluticasone (Oral Inhalation). Concurrent use of orally inhaled fluticasone with strong CYP3A4 inhibitors is not recommended.
  • Lumefantrine Halofantrine may increase the adverse effects of lumefantrine. Additive QTc-prolongation may occur. Combination therapy is contraindicated and therapies should not be administered within one month of each other due to the long half-life of lumefantrine.
  • Mefloquine Increased risk of cardiac toxicity
  • Mesoridazine Increased risk of cardiotoxicity and arrhythmias
  • Posaconazole Contraindicated co-administration
  • Quinupristin This combination presents an increased risk of toxicity
  • Tacrolimus Additive QTc-prolongation may occur increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
  • Telithromycin Telithromycin may reduce clearance of Halofantrine. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Halofantrine if Telithromycin is initiated, discontinued or dose changed.
  • Thioridazine Increased risk of cardiotoxicity and arrhythmias
  • Thiothixene May cause additive QTc-prolonging effects. Increased risk of ventricular arrhythmias. Consider alternate therapy. Thorough risk:benefit assessment is required prior to co-administration.
  • Toremifene Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Consider alternate therapy. A thorough risk:benefit assessment is required prior to co-administration.
  • Trimipramine Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
  • Verapamil Verapamil, a moderate CYP3A4 inhibitor, may increase the serum concentration of Halofantrine by decreasing its metabolism. Extreme caution with increased cardiac status monitoring should be used during concomitant therapy.
  • Voriconazole Voriconazole may increase the serum concentration of halofantrine by decreasing its metabolism by CYP3A4. Concomitant therapy should be avoided due to the concentration-dependent risk of QTc prolongation related to halofantrine.
  • Vorinostat Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
  • Ziprasidone Additive QTc-prolonging effects may increase the risk of severe arrhythmias. Concomitant therapy should be avoided.
  • Zuclopenthixol Additive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Dữ Kiện Thương Mại
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Halfan
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB01218
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=37393
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46506753
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07634
ChemSpider
http://www.chemspider.com/Chemical-Structure.34303.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50096846
PharmGKB
http://www.pharmgkb.org/drug/PA449839
Wikipedia
http://en.wikipedia.org/wiki/Halofantrine
Drugs.com
http://www.drugs.com/cdi/halofantrine.html
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