3-(dibutylamino)-1-[1,3-dichloro-6-(trifluoromethyl)phenanthren-9-yl]propan-1-ol

• ChemBase ID: 1088
• Molecular Formular: C26H30Cl2F3NO
• Molecular Mass: 500.4237096
• Monoisotopic Mass: 499.16565461
• SMILES: Clc1c2cc(C(O)CCN(CCCC)CCCC)c3c(c2cc(Cl)c1)cc(cc3)C(F)(F)F
• Canonical 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
• InChIKey: FOHHNHSLJDZUGQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(dibutylamino)-1-[1,3-dichloro-6-(trifluoromethyl)phenanthren-9-yl]propan-1-ol
• IUPAC Traditional name: halofantrine
• Brand Name: Halfan
• Synonyms: Halofantrina [INN-Spanish]; Halofantrine [Usan]; Halofantrinum [INN-Latin]; Halofantrine; 1,3-Dichloro-α-[2-(dibutylamino)ethyl]-6-(trifluoromethyl)-9-phenanthrenemethanol; (+/-)-Halofantrine Hydrochloride; Halfan Hydrochloride; SKF 102886; WR 171669; Halofantrine Hydrochloride

Database IDs

• CAS Number: 69756-53-2; 36167-63-2
• PubChem SID: 160964551; 46506753
• PubChem CID: 37393

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.470627
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.592538
• LogD (pH = 7.4): 5.4610047
• Log P: 8.056956
• Molar Refractivity: 131.6595 cm^3
• Polarizability: 52.36676 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 7.34
• LOG S: -6.66
• Solubility (Water): 1.11e-04 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 198-200°C
• Hydrophobicity(logP): 8.9

Safety Information

• Storage Condition: Refrigerator

DETAILS

DrugBank - DB01218

• Drug Groups: approved
• 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.
• Indication: For treatment of Severe malaria
• Pharmacology: Halofantrine is a synthetic antimalarial which acts as a blood schizonticide. It is effective against multi drug resistant (including mefloquine resistant) P. falciparum malaria.
• Toxicity: Side effects incldue coughing noisy, rattling, troubled breathing, loss of appetite, aches and pain in joints, indigestion,and skin itching or rash.
• Affected Organisms: Plasmodium
• Biotransformation: Hepatic
• Half Life: 6-10 days
• Protein Binding: 60-70%
• External Links: Wikipedia; Drugs.com

Toronto Research Chemicals - H102400

Antimalarial.

REFERENCES

• Schmidt, L.H., et al.: Antimicrob. Agents Chemother., 14, 292 (1978)
• Hines, J.W., et al.: J. Pharm. Sci., 74, 433 (1978)
• Bryson, H.M., et al.: Drugs, 43, 236 (1978)