Page last updated: 2024-12-07

desethylchloroquine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Desethylchloroquine is a derivative of chloroquine, an antimalarial drug. It has been studied as a potential treatment for COVID-19, as it exhibits antiviral activity against SARS-CoV-2 in vitro. Desethylchloroquine is synthesized through a multi-step process, often starting with chloroquine and modifying it chemically. Research has shown that desethylchloroquine might be effective against other viral infections besides COVID-19. It is studied for its potential to inhibit viral replication and entry into host cells, as well as for its potential to modulate the immune response. The importance of studying desethylchloroquine lies in the search for effective therapies against viral infections. Its unique mechanism of action and potential effectiveness against various viruses, including SARS-CoV-2, make it a promising candidate for further investigation. However, further research is needed to determine its safety and efficacy in humans.'

desethylchloroquine: metabolite of chloroquine [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID95478
CHEMBL ID1236
CHEBI ID166514
SCHEMBL ID12948893
MeSH IDM0050371

Synonyms (39)

Synonym
CHEBI:166514
4-n-(7-chloroquinolin-4-yl)-1-n-ethylpentane-1,4-diamine
n-deethylchloroquine
monoethyl chloroquine
deethylchloroquine
n4-(7-chloro-4-quinolinyl)-n1-ethyl-1,4-pentanediamine
monodesethylchloroquine
1476-52-4
nsc13254
nsc-13254
chloroquine m (des-ethyl)
desethylchloroquine
desethyl chloroquine
CHEMBL1236
FT-0665926
n4-(7-chloroquinolin-4-yl)-n1-ethylpentane-1,4-diamine
nsc 13254
zc9z9xx2pd ,
unii-zc9z9xx2pd
1,4-pentanediamine, n4-(7-chloro-4-quinolinyl)-n1-ethyl-
AKOS015924646
bdbm50408762
SCHEMBL12948893
{4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amine
c16h22cln3
J-008379
wr-29623
7-chloro-4-((4-(ethylamino)-1-methylbutyl)amino)quinoline
hydroxychloroquine sulfate impurity d [ep impurity]
monoethyl chloroquine [usp impurity]
quinoline, 7-chloro-4-((4-(ethylamino)-1-methylbutyl)amino)-
A934099
FT-0665927
HY-135811
C90277
CS-0114230
STARBLD0009562
desethyl chloroquine (with exact weight protocol)
DTXSID201033929

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"5 mg of base per kilogram every 6 hours) produced smoother blood-concentration profiles with lower early peak levels and no adverse cardiovascular or neurologic effects."( Chloroquine treatment of severe malaria in children. Pharmacokinetics, toxicity, and new dosage recommendations.
Berry, C; Brown, J; Churchill, FC; Greenwood, BM; Miller, KD; White, NJ; Williams, SB, 1988
)
0.27

Pharmacokinetics

ExcerptReferenceRelevance
" method and pharmacokinetic parameters were derived from the concentration-time data using a non-linear computer programme."( Comparison of the pharmacokinetics of chloroquine after single intravenous and intramuscular administration in healthy Africans.
Aderounmu, AF; Ekman, L; Lindström, B; Salako, LA; Walker, O, 1986
)
0.27
" Pharmacokinetic parameters calculated using model-independent methods showed good agreement with model-dependent methods."( Pharmacokinetics of chloroquine diphosphate in the dog.
Aderounmu, AF; Fleckenstein, L, 1983
)
0.27
" In the patients, the median range Cmax value was significantly higher (1547 (996-2446) vs 838 (656-1587) ng ml-1), and AUC(0,28d) was greater (281 (250-515) vs 122 (103-182) micrograms ml-1 h)."( The pharmacokinetics of chloroquine in healthy Thai subjects and patients with Plasmodium vivax malaria.
Karbwang, J; Limpaibul, L; Na-Bangchang, K; Tan-Ariya, P; Thanavibul, A, 1994
)
0.29
"Stereoselective pharmacokinetic properties of chloroquine were investigated in humans after a single oral dose of the separate enantiomers."( Stereoselective pharmacokinetic properties of chloroquine and de-ethyl-chloroquine in humans.
Augustijns, P; Verbeke, N, 1993
)
0.29
" Twenty-five women completed the pharmacokinetic study."( Chloroquine pharmacokinetics in pregnant and nonpregnant women with vivax malaria.
Fernandez, C; Greenwood, BM; Lee, SJ; McGready, R; Nosten, F; Paw, MK; Singhasivanon, P; Stepniewska, K; Thwai, KL; Viladpai-nguen, SJ; Villegas, L; White, NJ, 2008
)
0.35
"In order to determine the pharmacokinetic disposition of chloroquine (CQ) and its active metabolite, desethylchloroquine (DECQ), when administered as intermittent presumptive treatment in pregnancy (IPTp) for malaria, 30 Papua New Guinean women in the second or third trimester of pregnancy and 30 age-matched nonpregnant women were administered three daily doses of 450 mg CQ (8."( Pharmacokinetics of chloroquine and monodesethylchloroquine in pregnancy.
Baiwog, F; Davis, TM; Gomorrai, S; Ilett, KF; Karunajeewa, HA; Law, I; Mueller, I; Page-Sharp, M; Rogerson, S; Salman, S; Siba, P, 2010
)
0.84
"Despite extensive use and accumulated evidence of safety, there have been few pharmacokinetic studies from which appropriate chloroquine (CQ) dosing regimens could be developed specifically for pregnant women."( Optimal antimalarial dose regimens for chloroquine in pregnancy based on population pharmacokinetic modelling.
Baiwog, F; Davis, TME; Ilett, KF; Karunajeewa, HA; Kose, K; Mueller, I; Page-Sharp, M; Rogerson, SJ; Salman, S; Siba, PM, 2017
)
0.46

Dosage Studied

ExcerptRelevanceReference
" In six patients, the concentrations were followed during a one day dosage interval."( Chloroquine levels in blood during chronic treatment of patients with rheumatoid arthritis.
Augustijns, P; Geusens, P; Verbeke, N, 1992
)
0.28
" We conclude that simple alterations in dosage and frequency of administration can give parenteral chloroquine an acceptable therapeutic ratio and reinstate it as the treatment of choice for severe malaria in areas where chloroquine resistance is not a major problem."( Chloroquine treatment of severe malaria in children. Pharmacokinetics, toxicity, and new dosage recommendations.
Berry, C; Brown, J; Churchill, FC; Greenwood, BM; Miller, KD; White, NJ; Williams, SB, 1988
)
0.27
" The dosage of chloroquine recommended roughly 40 years ago for regular long-term prophylaxis should therefore not be changed."( Chloroquine and desethylchloroquine concentrations during regular long-term malaria prophylaxis.
Bergqvist, Y; Hellgren, U; Rombo, L, 1987
)
0.62
" The present knowledge of CQ kinetics could provide a basis for revision of current dosage regimens in malaria suppression and rheumatoid disease to ensure efficacious and safe therapy."( The single dose kinetics of chloroquine and its major metabolite desethylchloroquine in healthy subjects.
Bergqvist, Y; Domeij-Nyberg, B; Frisk-Holmberg, M; Termond, E, 1984
)
0.51
" vivax malaria and seven healthy male Thais, after the standard oral dosage regimen of CQ (a total dose of 1500 mg given over 3 days)."( The pharmacokinetics of chloroquine in healthy Thai subjects and patients with Plasmodium vivax malaria.
Karbwang, J; Limpaibul, L; Na-Bangchang, K; Tan-Ariya, P; Thanavibul, A, 1994
)
0.29
" With a daily dosage regimen, the divergent pharmacokinetic behaviour of chloroquine enantiomers generates a calculated R:S ratio of blood concentrations amounting to 1:0."( Stereoselective pharmacokinetic properties of chloroquine and de-ethyl-chloroquine in humans.
Augustijns, P; Verbeke, N, 1993
)
0.29
" Whole blood chloroquine levels on the last day of dosing confirmed normal absorption (range 413-3248, mean 1141, SD 616 ng/mL)."( Survey of resistance to chloroquine by Plasmodium vivax in Indonesia.
Baird, JK; Basri, H; Dewi, RM; Khairani, M; Leksana, B; Masbar, S; Sustriayu Nalim, MF; Tjitra, E; Wignall, FS,
)
0.13
"A dose-response relationship for hydroxychloroquine (HCQ), in terms of the proportion of patients achieving the Paulus 20% criteria for improvement, had previously been observed in patients with rheumatoid arthritis (RA) receiving a 6-week loading regimen of 400, 800, or 1,200 mg HCQ daily."( Hydroxychloroquine concentration-response relationships in patients with rheumatoid arthritis.
Baethge, BA; Botstein, GR; Caldwell, J; Dietz, F; Ettlinger, R; Furst, DE; Gibbs, JP; Golden, HE; Lindsley, H; McLaughlin, GE; Moreland, LW; Munster, T; Roberts, WN; Rooney, TW; Rothschild, B; Sack, M; Sebba, AI; Shen, D; Weisman, M; Welch, KE; Yocum, D, 2002
)
0.31
" In view of toxicological importance of CQ metabolites, it is suggested that caution should be exercised in evaluation of higher dosage regimen of CQ in pregnant women."( Evidence for increased metabolism of chloroquine during the early third trimester of human pregnancy.
Bolaji, OO; Chukwuani, MC; Makinde, ON; Ogunbona, FA; Onyeji, CO, 2004
)
0.32
" We aimed to determine the dosage of chloroquine commonly prescribed, the doses commonly taken, and whether concentration-dependent adverse events occurred in routine practice."( Chloroquine is grossly overdosed and overused but well tolerated in Guinea-bissau.
Bergqvist, Y; Kofoed, PE; Rodrigues, A; Rombo, L; Ursing, J, 2009
)
0.35
"Rheumatoid arthritis (RA) patients who had taken CQ for at least 6 months and stable CQ dosage for at least 2 months were included."( Prevalence and risk factors for chloroquine maculopathy and role of plasma chloroquine and desethylchloroquine concentrations in predicting chloroquine maculopathy.
Arromdee, E; Boonprasert, R; Chandranipapongse, W; Chatsiricharoenkul, S; Chiowchanwisawakit, P; Danwiriyakul, W; Katchamart, W; Koolvisoot, A; Nilganuwong, S; Pongnarin, P; Ruangvaravate, N; Srinonprasert, V, 2013
)
0.61
" To optimize ID PfSPZ dosing so as to achieve 100% infection, 30 adults aged 18-45 years were randomized to one of six groups composed of five volunteers each."( Optimizing Intradermal Administration of Cryopreserved Plasmodium falciparum Sporozoites in Controlled Human Malaria Infection.
Adams, M; Billingsley, PF; Chakravarty, S; Dube, TJ; Edelman, R; Green, M; Hoffman, SL; James, E; Laurens, MB; Li, ML; Lyke, KE; Manoj, A; Plowe, CV; Ruben, A; Sim, BKL; Strauss, K, 2015
)
0.42
"Despite extensive use and accumulated evidence of safety, there have been few pharmacokinetic studies from which appropriate chloroquine (CQ) dosing regimens could be developed specifically for pregnant women."( Optimal antimalarial dose regimens for chloroquine in pregnancy based on population pharmacokinetic modelling.
Baiwog, F; Davis, TME; Ilett, KF; Karunajeewa, HA; Kose, K; Mueller, I; Page-Sharp, M; Rogerson, SJ; Salman, S; Siba, PM, 2017
)
0.46
" In several endemic areas, including the Brazilian Amazon basin, anti-malarial drugs are dispensed in small plastic bags at a dosing regimen based on age."( Doses of chloroquine in the treatment of malaria by Plasmodium vivax in patients between 2 and 14 years of age from the Brazilian Amazon basin.
de Ataide, MA; de Sena, LWP; Dias, RM; Ferreira, MVD; Mello, AGNC; Vieira, JLF, 2019
)
0.51
" The dosage is a critical factor in a clinical trial: too low and the drug will not have an effect, too high and the side effects may counteract any potential benefits."( Concentration-dependent mortality of chloroquine in overdose.
Baud, FJ; Clemessy, JL; Hoglund, RM; Megarbane, B; Tarning, J; Watson, JA; White, NJ, 2020
)
0.56
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
aminoquinolineAny member of the class of quinolines in which the quinoline skeleton is substituted by one or more amino or substituted-amino groups.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Histidine-rich protein PFHRP-IIPlasmodium falciparum (malaria parasite P. falciparum)IC50 (µMol)15.00000.07651.12552.9000AID157853
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (17)

Assay IDTitleYearJournalArticle
AID423727Elimination half life in Paua New Guinean children with uncomplicated malaria2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Pharmacokinetics and efficacy of piperaquine and chloroquine in Melanesian children with uncomplicated malaria.
AID351893Antimalarial activity after 72 hrs against chloroquine-sensitive Plasmodium falciparum D6 infected human erythrocytes by SYBR green assay2007Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11
Design, synthesis, and evaluation of 10-N-substituted acridones as novel chemosensitizers in Plasmodium falciparum.
AID423747Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Pharmacokinetics and efficacy of piperaquine and chloroquine in Melanesian children with uncomplicated malaria.
AID17461Acid dissociation constant evaluated towards Hematin mu-oxo dimer1999Journal of medicinal chemistry, Nov-04, Volume: 42, Issue:22
Structural specificity of chloroquine-hematin binding related to inhibition of hematin polymerization and parasite growth.
AID423728AUC (0 to 42 days) in Paua New Guinean children with uncomplicated malaria2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Pharmacokinetics and efficacy of piperaquine and chloroquine in Melanesian children with uncomplicated malaria.
AID553547Drug level in malaria patient whole blood assessed as desethychloroquine level on day 12009Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1
Chloroquine is grossly overdosed and overused but well tolerated in Guinea-bissau.
AID228277Cellular accumulation ratio (CAR) for chloroquine sensitive HB3 strain of Plasmodium falciparum1997Journal of medicinal chemistry, Feb-14, Volume: 40, Issue:4
Synthesis, antimalarial activity, and molecular modeling of tebuquine analogues.
AID157855Parasite growth in chloroquine-sensitive Plasmodium falciparum K11999Journal of medicinal chemistry, Nov-04, Volume: 42, Issue:22
Structural specificity of chloroquine-hematin binding related to inhibition of hematin polymerization and parasite growth.
AID157856Parasite growth in chloroquine-sensitive Plasmodium falciparum NF541999Journal of medicinal chemistry, Nov-04, Volume: 42, Issue:22
Structural specificity of chloroquine-hematin binding related to inhibition of hematin polymerization and parasite growth.
AID351890Antimalarial activity after 72 hrs against chloroquine-resistant Plasmodium falciparum Dd2 infected human erythrocytes by SYBR green assay2007Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11
Design, synthesis, and evaluation of 10-N-substituted acridones as novel chemosensitizers in Plasmodium falciparum.
AID158707In vitro inhibition of chloroquine-sensitive Plasmodium falciparum HB31997Journal of medicinal chemistry, Feb-14, Volume: 40, Issue:4
Synthesis, antimalarial activity, and molecular modeling of tebuquine analogues.
AID553549Drug level in malaria patient whole blood assessed as desethychloroquine level on day 142009Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1
Chloroquine is grossly overdosed and overused but well tolerated in Guinea-bissau.
AID423729AUC (0 to infinity) in Paua New Guinean children with uncomplicated malaria2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Pharmacokinetics and efficacy of piperaquine and chloroquine in Melanesian children with uncomplicated malaria.
AID496819Antimicrobial activity against Plasmodium falciparum2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID423748Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Pharmacokinetics and efficacy of piperaquine and chloroquine in Melanesian children with uncomplicated malaria.
AID157853Inhibition of hematin polymerization1999Journal of medicinal chemistry, Nov-04, Volume: 42, Issue:22
Structural specificity of chloroquine-hematin binding related to inhibition of hematin polymerization and parasite growth.
AID553548Drug level in malaria patient whole blood assessed as desethychloroquine level on day 42009Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1
Chloroquine is grossly overdosed and overused but well tolerated in Guinea-bissau.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (114)

TimeframeStudies, This Drug (%)All Drugs %
pre-199048 (42.11)18.7374
1990's30 (26.32)18.2507
2000's18 (15.79)29.6817
2010's14 (12.28)24.3611
2020's4 (3.51)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 21.05

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index21.05 (24.57)
Research Supply Index4.95 (2.92)
Research Growth Index4.35 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (21.05)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials14 (11.11%)5.53%
Reviews1 (0.79%)6.00%
Case Studies2 (1.59%)4.05%
Observational0 (0.00%)0.25%
Other109 (86.51%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]