{4-[(7-chloroquinolin-4-yl)amino]pentyl}diethylamine

• ChemBase编号: 490
• 分子式: C18H26ClN3
• 平均质量: 319.87214
• 单一同位素质量: 319.18152553
• SMILES: Clc1cc2nccc(NC(CCCN(CC)CC)C)c2cc1
• Canonical SMILES: CCN(CCCC(Nc1ccnc2c1ccc(c2)Cl)C)CC
• InChI: InChI=1S/C18H26ClN3/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21)
• InChIKey: WHTVZRBIWZFKQO-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: {4-[(7-chloroquinolin-4-yl)amino]pentyl}diethylamine
• IUPAC传统名: chloroquine
• 商标名: 3377 RP opalate; Amokin; Aralen; Aralen HCl; Arechin; Arthrochin; Artrichin; Avlochlor; Avloclor; Bemaco; Bemaphate; Bemasulph; Benaquin; Bipiquin; Capquin; Chemochin; Chingamin; Chlorochin; Cidanchin; Cocartrit; Delagil; Dichinalex; Elestol; Gontochin; Heliopar; Imagon; Iroquine; Klorokin; Lapaquin; Malaquin; Malaren; Malarex; Mesylith; Neochin; Nivachine; Nivaquine; Nivaquine B; Pfizerquine; Plaquenil; Quinachlor; Quinagamin; Quinagamine; Quinercyl; Quingamine; Quinilon; Quinoscan; Resochen; Resochin; Resoquina; Resoquine; Reumachlor; Reumaquin; Roquine; Sanoquin; Silbesan; Siragan; Solprina; Sopaquin; Tanakan; Tresochin; Trochin
• 别名: Chloroquine Phosphate; Chloroquina; Chlorochine; Chloroquinium; Chloraquine; Chlorquin; Clorochina; Hydroxychloroquine Sulfate; Chloroquine; N4-(7-Chloro-4-quinolinyl)-N1,N1-diethyl-1,4-pentanediamine Diphosphate Salt; Aralen Diphosphate; Aralen Phosphate; Arechin; Avloclor; Bemaphate; Chingamin; Chingamin Phosphate; SN 7618; Sanoquin; Tanakan; Chloroquine Diphosphate Salt; {4-[(7-chloroquinolin-4-yl)amino]pentyl}diethylamine

登记号

• CAS号: 54-05-7; 50-63-5
• MDL号: MFCD00024009
• PubChem SID: 46506925; 160963953
• PubChem CID: 2719
• CHEBI ID: 3638
• ATC码: P01BA01
• CHEMBL: 76
• Chemspider ID: 2618
• DrugBank ID: DB00608
• KEGG ID: D02366
• 美国药典/FDA物质标识码: 886U3H6UFF
• 维基百科标题: Chloroquine

理论计算性质

JChem

• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): -0.7626644
• LogD (pH = 7.4): 0.87859994
• Log P: 3.933881
• 摩尔折射率: 96.423 cm^3
• 极化性: 38.081703 Å^3
• 极化表面积: 28.16 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 5.28
• LOG S: -4.26
• 溶解度: 1.75e-02 g/l

分子性质

理化性质

• 溶解度: 10.6 mg/L; Dimethyl Sulfoxide (Sparingly); Water
• 外观: White Solid
• 熔点: 200-202°C
• 疏水性(logP): 4.3; 5.06

安全信息

• 保存条件: -20°C Freezer

药理学性质

• 半衰期: 1-2 months
• 代谢: Liver
• 法定药品分级: Rx-only (US)
• 美国（FDA）药品许可证: Chloroquine

产品相关信息

• 纯度: 95%

详细说明

DrugBank - DB00608

• Drug Groups: approved
• Description: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses. [PubChem]
• Indication: For the suppressive treatment and for acute attacks of malaria due to P. vivax, P.malariae, P. ovale, and susceptible strains of P. falciparum, Second-line agent in treatment of Rheumatoid Arthritis
• Pharmacology: Chloroquine is the prototype anti malarial drug, most widely used to treat all types of malaria except for disease caused by chloroquine resistant Plasmodium falciparum. It is highly effective against erythrocytic forms of Plasmodium vivax, Plasmodium ovale and Plasmodium malariae, sensitive strains of Plasmodium falciparum and gametocytes of Plasmodium vivax. Being alkaline, the drug reaches high concentration within the food vacuoles of the parasite and raises its pH. It is found to induce rapid clumping of the pigment. Chloroquine inhibits the parasitic enzyme heme polymerase that converts the toxic heme into non-toxic hemazoin, thereby resulting in the accumulation of toxic heme within the parasite. It may also interfere with the biosynthesis of nucleic acids.
• Affected Organisms: Plasmodium
• Biotransformation: Hepatic (partially)
• Absorption: Completely absorbed from gastrointestinal tract
• Half Life: 1-2 months
• Protein Binding: ~55% of the drug in the plasma is bound to nondiffusible plasma constituents
• Elimination: Excretion of chloroquine is quite slow, but is increased by acidification of the urine.
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - C379965

Standard anti-malarial drug. Substrate for MRP in multidrug resistant cell line and inhibits photoaffinity labelling of MRP by quinoline-based photoactive drug IAAQ.

参考文献

• Luthman, H., et al.: Nucleic Acids Res., 11, 1295 (1983)
• Vezmar, M., et al.: Biochem. Pharmacol., 56, 733 (1983)
• Krajewski, W.A., et al.: J. Biomol. Struct. Dyn., 16, 1097 (1983)