Compounds > gsk 369796
Page last updated: 2024-08-02 15:41:01

gsk 369796

Description

N-tert-butylisoquine: an antimalarial; structure in first source [MeSH]

Cross-References

ID SourceID
PubMed CID10316203
CHEMBL ID147806
MeSH IDM0547646

Synonyms (17)

Synonym
2-(tert-butylamino-methyl)-5-(7-chloro-quinolin-4-ylamino)-phenol
zinc1912685 ,
n-tert-butylisoquine
CHEMBL147806 ,
gsk369796
n-tert-butyl isoquine
gsk-369796
bdbm50134936
ntbisq
gsk 369796
459133-38-1
gtpl10411
2-[(tert-butylamino)methyl]-5-[(7-chloroquinolin-4-yl)amino]phenol
2-((tert-butylamino)methyl)-5-((7-chloro-4-quinolyl)amino)phenol
NSC8QP4B6Z ,
phenol, 5-((7-chloro-4-quinolinyl)amino)-2-(((1,1-dimethylethyl)amino)methyl)-
unii-nsc8qp4b6z

Protein Targets (7)

Inhibition Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
Cytochrome P450 1A2Homo sapiens (human)IC5029.0000AID346854
Cytochrome P450 3A4Homo sapiens (human)IC50100.0000AID346855
Cytochrome P450 2C8Homo sapiens (human)IC5023.0000AID346852
Cytochrome P450 2D6Homo sapiens (human)IC503.0000AID346850
Cytochrome P450 2C9 Homo sapiens (human)IC5090.0000AID346853
Cytochrome P450 2C19Homo sapiens (human)IC5024.0000AID346851
Potassium voltage-gated channel subfamily H member 2Homo sapiens (human)IC507.5000AID346849

Bioassays (34)

Assay IDTitleYearJournalArticle
AID346860Antimalarial activity as reduced parasitaemia against Plasmodium berghei ANKA infected CD1 mice (Mus musculus) after 4 days2009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
ISSN: 1520-4804		Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century.
AID346852Inhibition of human recombinant CYP2C82009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
ISSN: 1520-4804		Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century.
AID346875Clearance in iv and orally dosed mouse blood2009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
ISSN: 1520-4804		Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century.
AID346856Inhibition of human recombinant CYP3A4 using N-N,diethyl-formamide as substrate2009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
ISSN: 1520-4804		Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century.
AID346865Protein binding in mouse2009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
ISSN: 1520-4804		Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century.
AID346858Antimalarial activity against chloroquine-sensitive Plasmodium falciparum HB3 in human erythrocytes after 48 hrs by [3H]hypoxanthine uptake2009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
ISSN: 1520-4804		Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century.
AID346848Elimination half life in orally dosed mouse2009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
ISSN: 1520-4804		Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century.
AID346879Elimination half life in orally dosed monkey2009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
ISSN: 1520-4804		Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century.
AID346859Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 in human erythrocytes after 48 hrs by [3H]hypoxanthine uptake2009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
ISSN: 1520-4804		Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century.
AID346878Oral bioavailability in monkey2009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
ISSN: 1520-4804		Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century.
AID347270Ratio of drug level in blood to plasma in dog2009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
ISSN: 1520-4804		Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century.
AID1558342Cytotoxicity against BHK21 cells after 24 to 48 hrs by CCK8 assay2020Journal of medicinal chemistry, 01-23, Volume: 63, Issue:2
ISSN: 1520-4804		Drugs for the Treatment of Zika Virus Infection.
AID346849Inhibition of human cloned ERG2009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
ISSN: 1520-4804		Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century.
AID346851Inhibition of human recombinant CYP2C192009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
ISSN: 1520-4804		Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century.
AID346845Oral bioavailability in mouse2009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
ISSN: 1520-4804		Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century.
AID346847Clearance in iv and orally dosed rat blood2009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
ISSN: 1520-4804		Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century.
AID152136In vitro antimalarial activity against Plasmodium falciparum HB2003Journal of medicinal chemistry, Nov-06, Volume: 46, Issue:23
ISSN: 0022-2623		Isoquine and related amodiaquine analogues: a new generation of improved 4-aminoquinoline antimalarials.
AID346863Antimalarial activity as ED100 in peripheral blood at day 23 against Plasmodium yoelii 17X infected CD1 mice (Mus musculus)2009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
ISSN: 1520-4804		Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century.
AID346855Inhibition of human recombinant CYP3A4 using phenyl-piperazinyl-methyl-benzyl-resofurin as substrate2009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
ISSN: 1520-4804		Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century.
AID347271Toxicity in monkey assessed as increase in QTc interval2009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
ISSN: 1520-4804		Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century.
AID346850Inhibition of human recombinant CYP2D62009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
ISSN: 1520-4804		Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century.
AID346880Protein binding in human2009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
ISSN: 1520-4804		Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century.
AID346876Oral bioavailability in rat2009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
ISSN: 1520-4804		Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century.
AID346861Antimalarial activity as reduced parasitaemia against Plasmodium yoelii 17X infected CD1 mice (Mus musculus) after 4 days2009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
ISSN: 1520-4804		Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century.
AID346877Oral bioavailability in dog2009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
ISSN: 1520-4804		Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century.
AID346866Clearance in iv and orally dosed monkey blood2009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
ISSN: 1520-4804		Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century.
AID346846Clearance in iv and orally dosed dog blood2009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
ISSN: 1520-4804		Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century.
AID347037Ratio of drug level in blood to plasma in human2009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
ISSN: 1520-4804		Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century.
AID1558341Antiviral activity against Zika virus MR766 infected in African green monkey Vero cells by plaque assay2020Journal of medicinal chemistry, 01-23, Volume: 63, Issue:2
ISSN: 1520-4804		Drugs for the Treatment of Zika Virus Infection.
AID152139In vitro antimalarial activity against chloroquine-resistant Plasmodium falciparum K12003Journal of medicinal chemistry, Nov-06, Volume: 46, Issue:23
ISSN: 0022-2623		Isoquine and related amodiaquine analogues: a new generation of improved 4-aminoquinoline antimalarials.
AID346854Inhibition of human recombinant CYP1A22009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
ISSN: 1520-4804		Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century.
AID346853Inhibition of human recombinant CYP2C92009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
ISSN: 1520-4804		Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century.
AID346864Binding affinity to heme in DMSO assessed as equilibrium constant by UV-visible spectrophotometry2009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
ISSN: 1520-4804		Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century.
AID346857Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 in human erythrocytes after 48 hrs by [3H]hypoxanthine uptake2009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
ISSN: 1520-4804		Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century.

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (50.00)29.6817
2010's2 (33.33)24.3611
2020's1 (16.67)2.80

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (16.67%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (83.33%)84.16%
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
quinacrine
1
acridines;
aromatic ether;
organochlorine compound;
tertiary amino compound		antimalarial;
EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor		202020204.0low000010
pyridine
1
azaarene;
mancude organic heteromonocyclic parent;
monocyclic heteroarene;
pyridines		environmental contaminant;
NMR chemical shift reference compound		2009200915.0low000100
amodiaquine
1
aminoquinoline;
organochlorine compound;
phenols;
secondary amino compound;
tertiary amino compound		anticoronaviral agent;
antimalarial;
drug allergen;
EC 2.1.1.8 (histamine N-methyltransferase) inhibitor;
non-steroidal anti-inflammatory drug;
prodrug		202020204.0low000010
berberine
1
alkaloid antibiotic;
berberine alkaloid;
botanical anti-fungal agent;
organic heteropentacyclic compound		antilipemic drug;
antineoplastic agent;
antioxidant;
EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor;
EC 1.1.1.21 (aldehyde reductase) inhibitor;
EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor;
EC 1.21.3.3 (reticuline oxidase) inhibitor;
EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor;
EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor;
EC 2.7.11.10 (IkappaB kinase) inhibitor;
EC 3.1.1.4 (phospholipase A2) inhibitor;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor;
EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
geroprotector;
hypoglycemic agent;
metabolite;
potassium channel blocker		202020204.0low000010
chloroquine
3
aminoquinoline;
organochlorine compound;
secondary amino compound;
tertiary amino compound		anticoronaviral agent;
antimalarial;
antirheumatic drug;
autophagy inhibitor;
dermatologic drug		2003202013.3low000210
emodin
1
trihydroxyanthraquinoneantineoplastic agent;
laxative;
plant metabolite;
tyrosine kinase inhibitor		202020204.0low000010
mefloquine hydrochloride
1
organofluorine compound;
piperidines;
quinolines;
secondary alcohol		2009200915.0low000100
tubercidin
1
antibiotic antifungal agent;
N-glycosylpyrrolopyrimidine;
ribonucleoside		antimetabolite;
antineoplastic agent;
bacterial metabolite		202020204.0low000010
emetine
1
isoquinoline alkaloid;
pyridoisoquinoline		antiamoebic agent;
anticoronaviral agent;
antiinfective agent;
antimalarial;
antineoplastic agent;
antiprotozoal drug;
antiviral agent;
autophagy inhibitor;
emetic;
expectorant;
plant metabolite;
protein synthesis inhibitor		202020204.0low000010
bromocriptine
1
indole alkaloidantidyskinesia agent;
antiparkinson drug;
dopamine agonist;
hormone antagonist		202020204.0low000010
halofantrine
1
phenanthrenes2009200915.0low000100
ribavirin
1
1-ribosyltriazole;
aromatic amide;
monocarboxylic acid amide;
primary carboxamide		anticoronaviral agent;
antiinfective agent;
antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor		202020204.0low000010
mefloquine
1
[2,8-bis(trifluoromethyl)quinolin-4-yl]-(2-piperidyl)methanolantimalarial202020204.0low000010
epigallocatechin gallate
1
flavans;
gallate ester;
polyphenol		antineoplastic agent;
antioxidant;
apoptosis inducer;
geroprotector;
Hsp90 inhibitor;
neuroprotective agent;
plant metabolite		202020204.0low000010
sinefungin
1
adenosines;
non-proteinogenic alpha-amino acid		antifungal agent;
antimicrobial agent		202020204.0low000010
pinocembrin
1
(2S)-flavan-4-one;
dihydroxyflavanone		antineoplastic agent;
antioxidant;
metabolite;
neuroprotective agent;
vasodilator agent		202020204.0low000010
epicatechin gallate
1
catechin;
gallate ester;
polyphenol		EC 3.2.1.1 (alpha-amylase) inhibitor;
EC 3.2.1.20 (alpha-glucosidase) inhibitor;
metabolite		202020204.0low000010
desethylamodiaquine
1
2009200915.0low000100
methotrexate
1
dicarboxylic acid;
monocarboxylic acid amide;
pteridines		abortifacient;
antimetabolite;
antineoplastic agent;
antirheumatic drug;
dermatologic drug;
DNA synthesis inhibitor;
EC 1.5.1.3 (dihydrofolate reductase) inhibitor;
immunosuppressive agent		202020204.0low000010
vx 497
1
202020204.0low000010
(-)-gallocatechin gallate
1
catechin;
gallate ester;
polyphenol		antineoplastic agent;
EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor;
human xenobiotic metabolite;
plant metabolite		202020204.0low000010
benzoic acid [5-amino-1-(4-methoxyphenyl)sulfonyl-3-pyrazolyl] ester
1
benzoate ester202020204.0medium000010
quinine
1
cinchona alkaloidantimalarial;
muscle relaxant;
non-narcotic analgesic		2009200915.0low000100
luteolin
1
3'-hydroxyflavonoid;
tetrahydroxyflavone		angiogenesis inhibitor;
anti-inflammatory agent;
antineoplastic agent;
apoptosis inducer;
c-Jun N-terminal kinase inhibitor;
EC 2.3.1.85 (fatty acid synthase) inhibitor;
immunomodulator;
nephroprotective agent;
plant metabolite;
radical scavenger;
vascular endothelial growth factor receptor antagonist		202020204.0low000010
rutin
1
disaccharide derivative;
quercetin O-glucoside;
rutinoside;
tetrahydroxyflavone		antioxidant;
metabolite		202020204.0low000010
myricetin
1
7-hydroxyflavonol;
hexahydroxyflavone		antineoplastic agent;
antioxidant;
cyclooxygenase 1 inhibitor;
food component;
geroprotector;
hypoglycemic agent;
plant metabolite		202020204.0low000010
astragalin
1
beta-D-glucoside;
kaempferol O-glucoside;
monosaccharide derivative;
trihydroxyflavone		plant metabolite;
trypanocidal drug		202020204.0low000010
galidesivir
1
202020204.0low000010
amodiaquine hydrochloride
2
2003200918.0low000200
nitd008
1
202020204.0low000010
sofosbuvir
1
isopropyl ester;
L-alanyl ester;
nucleotide conjugate;
organofluorine compound;
phosphoramidate ester		antiviral drug;
hepatitis C protease inhibitor;
prodrug		202020204.0low000010
novobiocin
1
carbamate ester;
ether;
hexoside;
hydroxycoumarin;
monocarboxylic acid amide;
monosaccharide derivative;
phenols		antibacterial agent;
antimicrobial agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
Escherichia coli metabolite;
hepatoprotective agent		202020204.0low000010
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
quinacrine
1
acridines;
aromatic ether;
organochlorine compound;
tertiary amino compound		antimalarial;
EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor		201720177.0low000010
amodiaquine
4
aminoquinoline;
organochlorine compound;
phenols;
secondary amino compound;
tertiary amino compound		anticoronaviral agent;
antimalarial;
drug allergen;
EC 2.1.1.8 (histamine N-methyltransferase) inhibitor;
non-steroidal anti-inflammatory drug;
prodrug		2009201810.8low000220
chloroquine
1
aminoquinoline;
organochlorine compound;
secondary amino compound;
tertiary amino compound		anticoronaviral agent;
antimalarial;
antirheumatic drug;
autophagy inhibitor;
dermatologic drug		2009200915.0low000100
4-aminoquinoline
1
201820186.0low000010
mefloquine
1
201720177.0low000010
heme
1
2009200915.0low000100
ConditionIndicatedStudiesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
Congenital Zika Syndrome0
1
202020204.0medium000010
Infections, Plasmodium0
3
2003200917.0high000300
Malaria1
3
2003200917.0high000300
Parasitemia0
1
201820186.0medium000010
Zika Virus Infection0
1
202020204.0medium000010

Bioavailability (1)

ArticleYear
Synthesis, antimalarial activity, and preclinical pharmacology of a novel series of 4'-fluoro and 4'-chloro analogues of amodiaquine. Identification of a suitable "back-up" compound for N-tert-butyl isoquine.
Journal of medicinal chemistry, , Apr-09, Volume: 52, Issue:7		2009