1476-52-4

Usage

Uses

Used in Pharmaceutical Industry:
Desethyl Chloroquine is used as an active pharmaceutical ingredient for the therapy and prevention of malaria. Its role in this application is attributed to its ability to target and disrupt the life cycle of the Plasmodium parasite, which is responsible for causing malaria.
Used in COVID-19 Research:
Desethyl Chloroquine is also used as a research compound in the context of COVID-19. Its potential antiviral properties and immunomodulatory effects have made it a subject of interest for scientists investigating possible treatments for the novel coronavirus. However,

InChI:InChI=1/C16H22ClN3/c1-3-18-9-4-5-12(2)20-15-8-10-19-16-11-13(17)6-7-14(15)16/h6-8,10-12,18H,3-5,9H2,1-2H3,(H,19,20)

Upstream product

• 54-05-7 Chloroquine 
• 86-98-6 4,7-dichloroquinoline 
• 75-04-7 ethylamine 

Downstream Products

• 91828-61-4 rac-N-acetyldesethylchloroquine 
• 91828-61-4 (R)-(-)-N-acetyldesethylchloroquine 
• 91828-61-4 (S)-(+)-N-acetyldesethylchloroquine 
• 126443-94-5 2-(3-{[4-(7-Chloro-quinolin-4-ylamino)-pentyl]-ethyl-amino}-propionylamino)-3-(4-hydroxy-phenyl)-propionic acid methyl ester 

Relevant academic research and scientific papers

A convenient, short synthesis of desethylchloroquine [7-chloro-4-(4'-ethylamino-1'-methylbutylamino)quinoline]

A short, efficient 2-step synthesis of desethylchloroquine is achieved by generating an internal amide ion from the secondary nitrogen in chloroquine, followed by in situ reaction with 2,2,2-trichloroethyl chloroformate giving rapid elimination of ethylene. The carbamate thus produced easily undergoes deprotection to the target compound at room temperature.

Bacterial Biosynthetic P450 Enzyme PikCD50N: A Potential Biocatalyst for the Preparation of Human Drug Metabolites

Human drug metabolites (HDMs) are important chemicals widely used in drug-related studies. However, acquiring these enzyme-derived and regio-/stereo-selectively modified compounds through chemical approaches is complicated. PikC is a biosynthetic P450 enz

Identification of human cytochrome P450s that metabolise anti-parasitic drugs and predictions of in vivo drug hepatic clearance from in vitro data

Objective: Knowledge about the metabolism of anti-parasitic drugs (APDs) will be helpful in ongoing efforts to optimise dosage recommendations in clinical practise. This study was performed to further identify the cytochrome P450 (CYP) enzymes that metabolise major APDs and evaluate the possibility of predicting in vivo drug clearances from in vitro data. Methods: In vitro systems, rat and human liver microsomes (RLM, HLM) and recombinant cytochrome P450 (rCYP), were used to determine the intrinsic clearance (CLint) and identify responsible CYPs and their relative contribution in the metabolism of 15 commonly used APDs. Results and discussion: CLint determined in RLM and HLM showed low (r2=0.50) but significant (Pint values were scaled to predict in vivo hepatic clearance (CLH) using the 'venous equilibrium model'. The number of compounds with in vivo human CL data after intravenous administration was low (n=8), and the range of CL values covered by these compounds was not appropriate for a reasonable quantitative in vitro-in vivo correlation analysis. Using the CLH predicted from the in vitro data, the compounds could be classified into three different categories: high-clearance drugs (> 70% liver blood flow; amodiaquine, praziquantel, albendazole, thiabendazole), low-clearance drugs (int drug categories. The identified CYPs for some of the drugs provide a basis for how these drugs are expected to behave pharmacokinetically and help in predicting drug-drug interactions in vivo.

Photoreactivity of biologically active compounds. X: Photoreactivity of chloroquine in aqueous solution

Photochemical degradation of chloroquine (CQ) as a function of pH was studied in order to obtain information on the photoreactivity of both the dicationic and the monocationic form of CQ. The photodecomposition rate was strongly dependent on the state of ionization of CQ. The main degradation product formed from the monocationic form of CQ was identified as a dimerization product, confirmed by mass-spectrometry (EI, and high resolution MS). Formation of the secondary amine DesCQ was detected for both the dicationic and the monocationic form of CQ. Oxygen is probably not directly involved in the main reaction(s) leading to photolysis of CQ. In the monocationic form CQ is a source of superoxide ions and hydroxyl radicals during irradiation, whereas in the dicationic form, formation of such radicals could not be detected. Under the experimental conditions used, no photodechlorination of CQ could be detected. Reactions performed in the darkness showed that monocationic CQ was susceptible to attack by hydroxyl radicals and superoxide ions. Decomposition of the dicationic form of CQ could not be detected under the same experimental conditions.