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

• ChemBase ID: 490
• Molecular Formular: C18H26ClN3
• Molecular Mass: 319.87214
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: {4-[(7-chloroquinolin-4-yl)amino]pentyl}diethylamine
• IUPAC Traditional name: chloroquine
• Brand Name: 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
• Synonyms: 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

Database IDs

• CAS Number: 54-05-7; 50-63-5
• MDL Number: MFCD00024009
• PubChem SID: 160963953; 46506925
• PubChem CID: 2719
• CHEBI ID: 3638
• ATC CODE: P01BA01
• CHEMBL: 76
• Chemspider ID: 2618
• DrugBank ID: DB00608
• KEGG ID: D02366
• Unique Ingredient Identifier: 886U3H6UFF
• Wikipedia Title: Chloroquine

CALCULATED PROPERTIES

JChem

• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.7626644
• LogD (pH = 7.4): 0.87859994
• Log P: 3.933881
• Molar Refractivity: 96.423 cm^3
• Polarizability: 38.081703 Å^3
• Polar Surface Area: 28.16 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 5.28
• LOG S: -4.26
• Solubility (Water): 1.75e-02 g/l

PROPERTIES

Physical Property

• Solubility: 10.6 mg/L; Dimethyl Sulfoxide (Sparingly); Water
• Apperance: White Solid
• Melting Point: 200-202°C
• Hydrophobicity(logP): 4.3; 5.06

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Half Life: 1-2 months
• Metabolism: Liver
• Legal Status: Rx-only (US)
• US Licence: Chloroquine

Product Information

• Purity: 95%

DETAILS

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.

REFERENCES

• 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)