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

• ChemBase编号: 1088
• 分子式: C26H30Cl2F3NO
• 平均质量: 500.4237096
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 3-(dibutylamino)-1-[1,3-dichloro-6-(trifluoromethyl)phenanthren-9-yl]propan-1-ol
• IUPAC传统名: halofantrine
• 商标名: Halfan
• 别名: 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

登记号

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

理论计算性质

JChem

• Acid pKa: 14.470627
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 4.592538
• LogD (pH = 7.4): 5.4610047
• Log P: 8.056956
• 摩尔折射率: 131.6595 cm^3
• 极化性: 52.36676 Å^3
• 极化表面积: 23.47 Å^2
• 可自由旋转的化学键: 11
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 7.34
• LOG S: -6.66
• 溶解度: 1.11e-04 g/l

分子性质

理化性质

• 溶解度: DMSO; Methanol
• 外观: White Solid
• 熔点: 198-200°C
• 疏水性(logP): 8.9

安全信息

• 保存条件: Refrigerator

详细说明

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.

参考文献

• 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)