[2,8-bis(trifluoromethyl)quinolin-4-yl](piperidin-2-yl)methanol

• ChemBase编号: 242
• 分子式: C17H16F6N2O
• 平均质量: 378.3121592
• 单一同位素质量: 378.11668246
• SMILES: FC(F)(F)c1nc2c(c(C(O)C3NCCCC3)c1)cccc2C(F)(F)F
• Canonical SMILES: OC(c1cc(nc2c1cccc2C(F)(F)F)C(F)(F)F)C1CCCCN1
• InChI: InChI=1S/C17H16F6N2O/c18-16(19,20)11-5-3-4-9-10(15(26)12-6-1-2-7-24-12)8-13(17(21,22)23)25-14(9)11/h3-5,8,12,15,24,26H,1-2,6-7H2
• InChIKey: XEEQGYMUWCZPDN-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: [2,8-bis(trifluoromethyl)quinolin-4-yl](piperidin-2-yl)methanol
• IUPAC传统名: mefloquin
• 商标名: Lariam
• 别名: Mefloquine HCL; Mefloquinone; Mefloquine

登记号

• CAS号: 53230-10-7
• PubChem SID: 160963705; 46505610
• PubChem CID: 4046

理论计算性质

JChem

• Acid pKa: 13.785841
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 0.94418555
• LogD (pH = 7.4): 2.0721047
• Log P: 4.1105947
• 摩尔折射率: 82.5774 cm^3
• 极化性: 31.66879 Å^3
• 极化表面积: 45.15 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.1
• LOG S: -4.0
• 溶解度: 3.80e-02 g/l

分子性质

理化性质

• 溶解度: 5000 mg/L (HCl salt)
• 疏水性(logP): 3.9

详细说明

DrugBank - DB00358

• Drug Groups: approved
• Description: A phospholipid-interacting antimalarial drug (antimalarials). It is very effective against plasmodium falciparum with very few side effects. [PubChem]
• Indication: For the treatment of mild to moderate acute malaria caused by Mefloquineuine-susceptible strains of Plasmodium falciparum (both chloroquine-susceptible and resistant strains) or by Plasmodium vivax. Also for the prophylaxis of Plasmodium falciparum and Plasmodium vivax malaria infections, including prophylaxis of chloroquine-resistant strains of Plasmodium falciparum.
• Pharmacology: Mefloquine is an antimalarial agent which acts as a blood schizonticide. Mefloquine is active against the erythrocytic stages of Plasmodium species. However, the drug has no effect against the exoerythrocytic (hepatic) stages of the parasite. Mefloquine is effective against malaria parasites resistant to chloroquine. Mefloquine is a chiral molecule. According to some research, the (+) enantiomer is more effective in treating malaria, and the (-) enantiomer specifically binds to adenosine receptors in the central nervous system, which may explain some of its psychotropic effects.
• Toxicity: Oral, rat: LD₅₀ = 880 mg/kg. Symptoms of overdose include nausea, vomiting, and weight loss.
• Affected Organisms: Plasmodium
• Biotransformation: Hepatic. Two metabolites have been identified in humans. The main metabolite, 2,8-bis-trifluoromethyl-4-quinoline carboxylic acid, is inactive against Plasmodium falciparum. The second metabolite, an alcohol, is present in minute quantities.
• Absorption: Well absorbed from the gastrointestinal tract. The presence of food significantly enhances the rate and extent of absorption.
• Half Life: 2 to 4 weeks
• Protein Binding: 98%
• Elimination: There is evidence that mefloquine is excreted mainly in the bile and feces. Urinary excretion of unchanged mefloquine and its main metabolite under steady-state condition accounted for about 9% and 4% of the dose, respectively.
• Distribution: * 20 L/kg [healthy adults]
• Clearance: * 30 mL/min
• External Links: Wikipedia; RxList; Drugs.com