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54-05-7 molecular structure
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{4-[(7-chloroquinolin-4-yl)amino]pentyl}diethylamine

ChemBase ID: 490
Molecular Formular: C18H26ClN3
Molecular Mass: 319.87214
Monoisotopic Mass: 319.18152553
SMILES and InChIs

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

Cite this record

CBID:490 http://www.chembase.cn/molecule-490.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
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

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) -0.7626644  LogD (pH = 7.4) 0.87859994 
Log P 3.933881  Molar Refractivity 96.423 cm3
Polarizability 38.081703 Å3 Polar Surface Area 28.16 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 5.28  LOG S -4.26 
Solubility (Water) 1.75e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
10.6 mg/L expand Show data source
Dimethyl Sulfoxide (Sparingly) expand Show data source
Water expand Show data source
Apperance
White Solid expand Show data source
Melting Point
200-202°C expand Show data source
Hydrophobicity(logP)
4.3 expand Show data source
5.06 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Half Life
1-2 months expand Show data source
Metabolism
Liver expand Show data source
Legal Status
Rx-only (US) expand Show data source
US Licence
Chloroquine expand Show data source
Purity
95% expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia TRC TRC
DrugBank - DB00608 external link
Item Information
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 external link
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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