Compounds > 2-tert-butylprimaquine
Page last updated: 2024-11-12

2-tert-butylprimaquine

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Description

2-tert-butylprimaquine: has anti blood-schizontocidal antimalarial activity; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID9926920
CHEMBL ID330383
SCHEMBL ID5080647
MeSH IDM0461704

Synonyms (5)

Synonym
CHEMBL330383 ,
2-tert-butylprimaquine
bdbm50412261
SCHEMBL5080647
4-n-(2-tert-butyl-6-methoxyquinolin-8-yl)pentane-1,4-diamine

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" Total runtime for the method was 5min, which was suitable to produce high-throughput results for pharmacokinetic evaluation."( Development and validation of a sensitive and selective UHPLC-MS/MS method for quantitation of an investigational anti-malarial compound, 2-tert-butylprimaquine (NP-96) in rat plasma, and its application in a preclinical pharmacokinetic study.
Jain, M; Jain, R; Mayatra, SJ; Prasad, B; Singh, S, 2010)		0.56
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

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)2.90000.07651.12552.9000AID341400
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID341402Binding affinity to heme in HEPES buffer at pH 7.4 upto 60 uM after 30 mins by Jobs plot2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
2-tert-butyl-8-quinolinamines exhibit potent blood schizontocidal antimalarial activity via inhibition of heme crystallization.
AID341400Inhibition of beta-hematin formation after 16 hrs2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
2-tert-butyl-8-quinolinamines exhibit potent blood schizontocidal antimalarial activity via inhibition of heme crystallization.
AID341404Binding affinity to heme in HEPES buffer at pH 7.4 after 30 mins by Hills plot2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
2-tert-butyl-8-quinolinamines exhibit potent blood schizontocidal antimalarial activity via inhibition of heme crystallization.
AID341399Antimalarial activity against chloroquine-sensitive Plasmodium falciparum D6 infected in human erythrocytes after 48 hrs2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
2-tert-butyl-8-quinolinamines exhibit potent blood schizontocidal antimalarial activity via inhibition of heme crystallization.
AID109952Compound was evaluated for the blood-schizonticidal antimalarial activity against Plasmodium berghei (sensitive strain) in mice (Mus musculus) at 100 mg/kg/day x 4 (oral); indicates complete elimination of malaria parasites from the body, and animals surv2004Journal of medicinal chemistry, Jan-15, Volume: 47, Issue:2
Discovery of a bulky 2-tert-butyl group containing primaquine analogue that exhibits potent blood-schizontocidal antimalarial activities and complete elimination of methemoglobin toxicity.
AID496886Antimalarial activity against chloroquine-resistant Plasmodium falciparum2010European journal of medicinal chemistry, Aug, Volume: 45, Issue:8
Quinolines and structurally related heterocycles as antimalarials.
AID549912Inhibition of beta-hematin formation2011Bioorganic & medicinal chemistry, Jan-01, Volume: 19, Issue:1
Synthesis, antiprotozoal, antimicrobial, β-hematin inhibition, cytotoxicity and methemoglobin (MetHb) formation activities of bis(8-aminoquinolines).
AID157693Inhibitory activity I50 against chloroquine-sensitive Plasmodium falciparum2004Journal of medicinal chemistry, Jan-15, Volume: 47, Issue:2
Discovery of a bulky 2-tert-butyl group containing primaquine analogue that exhibits potent blood-schizontocidal antimalarial activities and complete elimination of methemoglobin toxicity.
AID110077Compound was evaluated for the blood-schizonticidal antimalarial activity against Plasmodium berghei (sensitive strain) in mice (Mus musculus) at 50 mg/kg/day x 4 (oral); indicates complete elimination of malaria parasites from the body, and animals survi2004Journal of medicinal chemistry, Jan-15, Volume: 47, Issue:2
Discovery of a bulky 2-tert-butyl group containing primaquine analogue that exhibits potent blood-schizontocidal antimalarial activities and complete elimination of methemoglobin toxicity.
AID341405Toxicity against human erythrocytes assessed as potentiation of heme-induced hemolysis at 10 uM in presence of heme2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
2-tert-butyl-8-quinolinamines exhibit potent blood schizontocidal antimalarial activity via inhibition of heme crystallization.
AID110078Compound was evaluated for the blood-schizonticidal antimalarial activity against Plasmodium yoelii nigeriensis (multidrug-resistant strain) in mice (Mus musculus) at 100 mg/kg/day x 4 (oral); indicates complete elimination of malaria parasites from the b2004Journal of medicinal chemistry, Jan-15, Volume: 47, Issue:2
Discovery of a bulky 2-tert-butyl group containing primaquine analogue that exhibits potent blood-schizontocidal antimalarial activities and complete elimination of methemoglobin toxicity.
AID660298Inhibition of beta-hematin formation2012European journal of medicinal chemistry, Jun, Volume: 52Amino acid, dipeptide and pseudodipeptide conjugates of ring-substituted 8-aminoquinolines: synthesis and evaluation of anti-infective, β-haematin inhibition and cytotoxic activities.
AID1378964Schizontocidal activity against chloroquine-sensitive Plasmodium falciparum after 3 days2017European journal of medicinal chemistry, Oct-20, Volume: 139Quinoline hybrids and their antiplasmodial and antimalarial activities.
AID109951Compound was evaluated for the blood-schizonticidal antimalarial activity against Plasmodium berghei (sensitive strain) in mice (Mus musculus) at 10 mg/kg/day x 4 (oral); indicates that all of the treated animals show negative parasitaemia up to D+7 (surv2004Journal of medicinal chemistry, Jan-15, Volume: 47, Issue:2
Discovery of a bulky 2-tert-butyl group containing primaquine analogue that exhibits potent blood-schizontocidal antimalarial activities and complete elimination of methemoglobin toxicity.
AID110080Compound was evaluated for the blood-schizonticidal antimalarial activity against Plasmodium yoelii nigeriensis (multidrug-resistant strain) in mice (Mus musculus) at 50 mg/kg/day x 4 (oral); indicates that all of the treated animals show negative parasit2004Journal of medicinal chemistry, Jan-15, Volume: 47, Issue:2
Discovery of a bulky 2-tert-butyl group containing primaquine analogue that exhibits potent blood-schizontocidal antimalarial activities and complete elimination of methemoglobin toxicity.
AID341398Toxicity against human erythrocytes assessed as potentiation of heme-induced hemolysis in presence of variable concentration of heme2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
2-tert-butyl-8-quinolinamines exhibit potent blood schizontocidal antimalarial activity via inhibition of heme crystallization.
AID341406Toxicity against human erythrocytes assessed as heme-induced hemolysis up to 30 uM in absence of heme2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
2-tert-butyl-8-quinolinamines exhibit potent blood schizontocidal antimalarial activity via inhibition of heme crystallization.
AID496905Antiplasmodial activity against Plasmodium berghei infected in mice (Mus musculus) assessed as suppression of parasitaemia at 100 mg/kg, po2010European journal of medicinal chemistry, Aug, Volume: 45, Issue:8
Quinolines and structurally related heterocycles as antimalarials.
AID110076Compound was evaluated for the blood-schizonticidal antimalarial activity against Plasmodium berghei (sensitive strain) in mice (Mus musculus) at 25 mg/kg/day x 4 (oral); indicates complete elimination of malaria parasites from the body, and animals survi2004Journal of medicinal chemistry, Jan-15, Volume: 47, Issue:2
Discovery of a bulky 2-tert-butyl group containing primaquine analogue that exhibits potent blood-schizontocidal antimalarial activities and complete elimination of methemoglobin toxicity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (25.00)29.6817
2010's6 (75.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.31

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.31 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.31)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (25.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (75.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
chloroquine
Chloroquine: 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.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.		4.9260aminoquinoline;
organochlorine compound;
secondary amino compound;
tertiary amino compound		anticoronaviral agent;
antimalarial;
antirheumatic drug;
autophagy inhibitor;
dermatologic drug
ciprofloxacin
Ciprofloxacin: A broad-spectrum antimicrobial carboxyfluoroquinoline.. ciprofloxacin : A quinolone that is quinolin-4(1H)-one bearing cyclopropyl, carboxylic acid, fluoro and piperazin-1-yl substituents at positions 1, 3, 6 and 7, respectively.		2.0710aminoquinoline;
cyclopropanes;
fluoroquinolone antibiotic;
N-arylpiperazine;
quinolinemonocarboxylic acid;
quinolone antibiotic;
quinolone;
zwitterion		antibacterial drug;
antiinfective agent;
antimicrobial agent;
DNA synthesis inhibitor;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
environmental contaminant;
topoisomerase IV inhibitor;
xenobiotic
pentamidine
Pentamidine: Antiprotozoal agent effective in trypanosomiasis, leishmaniasis, and some fungal infections; used in treatment of PNEUMOCYSTIS pneumonia in HIV-infected patients. It may cause diabetes mellitus, central nervous system damage, and other toxic effects.. pentamidine : A diether consisting of pentane-1,5-diol in which both hydroxyl hydrogens have been replaced by 4-amidinophenyl groups. A trypanocidal drug that is used for treatment of cutaneous leishmaniasis and Chagas disease.		3.8530aromatic ether;
carboxamidine;
diether		anti-inflammatory agent;
antifungal agent;
calmodulin antagonist;
chemokine receptor 5 antagonist;
EC 2.3.1.48 (histone acetyltransferase) inhibitor;
NMDA receptor antagonist;
S100 calcium-binding protein B inhibitor;
trypanocidal drug;
xenobiotic
primaquine
Primaquine: An aminoquinoline that is given by mouth to produce a radical cure and prevent relapse of vivax and ovale malarias following treatment with a blood schizontocide. It has also been used to prevent transmission of falciparum malaria by those returning to areas where there is a potential for re-introduction of malaria. Adverse effects include anemias and GI disturbances. (From Martindale, The Extra Pharmacopeia, 30th ed, p404). primaquine : An N-substituted diamine that is pentane-1,4-diamine substituted by a 6-methoxyquinolin-8-yl group at the N(4) position. It is a drug used in the treatment of malaria and Pneumocystis pneumonia.		3.360aminoquinoline;
aromatic ether;
N-substituted diamine		antimalarial
acetylcysteine
N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.		7.0610acetylcysteine;
L-cysteine derivative;
N-acetyl-L-amino acid		antidote to paracetamol poisoning;
antiinfective agent;
antioxidant;
antiviral drug;
ferroptosis inhibitor;
geroprotector;
human metabolite;
mucolytic;
radical scavenger;
vulnerary
mefloquine
(-)-(11S,2'R)-erythro-mefloquine : An optically active form of [2,8-bis(trifluoromethyl)quinolin-4-yl]-(2-piperidyl)methanol having (-)-(11S,2'R)-erythro-configuration. An antimalarial agent, used in racemic form, which acts as a blood schizonticide; its mechanism of action is unknown.		3.2510[2,8-bis(trifluoromethyl)quinolin-4-yl]-(2-piperidyl)methanolantimalarial
artemisinin
(+)-artemisinin : A sesquiterpene lactone obtained from sweet wormwood, Artemisia annua, which is used as an antimalarial for the treatment of multi-drug resistant strains of falciparum malaria.		3.2510organic peroxide;
sesquiterpene lactone		antimalarial;
plant metabolite
piperaquine
piperaquine : An aminoquinoline that is 1,3-di(piperazin-1-yl)propane in which the nitrogen at position 4 of each of the piperazine moieties is replaced by a 7-chloroquinolin-4-yl group.		3.1510aminoquinoline;
N-arylpiperazine;
organochlorine compound		antimalarial
levofloxacin
Levofloxacin: The L-isomer of Ofloxacin.. levofloxacin : An optically active form of ofloxacin having (S)-configuration; an inhibitor of bacterial topoisomerase IV and DNA gyrase.		3.25109-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid;
fluoroquinolone antibiotic;
quinolone antibiotic		antibacterial drug;
DNA synthesis inhibitor;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
topoisomerase IV inhibitor
quinine
[no description available]		3.2510cinchona alkaloidantimalarial;
muscle relaxant;
non-narcotic analgesic
amphotericin b
Amphotericin B: Macrolide antifungal antibiotic produced by Streptomyces nodosus obtained from soil of the Orinoco river region of Venezuela.. amphotericin B : A macrolide antibiotic used to treat potentially life-threatening fungal infections.		2.4720antibiotic antifungal drug;
macrolide antibiotic;
polyene antibiotic		antiamoebic agent;
antiprotozoal drug;
bacterial metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Infections, Plasmodium
[description not available]		02.0210
Malaria
A protozoan disease caused in humans by four species of the PLASMODIUM genus: PLASMODIUM FALCIPARUM; PLASMODIUM VIVAX; PLASMODIUM OVALE; and PLASMODIUM MALARIAE; and transmitted by the bite of an infected female mosquito of the genus ANOPHELES. Malaria is endemic in parts of Asia, Africa, Central and South America, Oceania, and certain Caribbean islands. It is characterized by extreme exhaustion associated with paroxysms of high FEVER; SWEATING; shaking CHILLS; and ANEMIA. Malaria in ANIMALS is caused by other species of plasmodia.		02.0210
Extravascular Hemolysis
[description not available]		02.0310
Plasmodium falciparum Malaria
[description not available]		02.0310
Hemolysis
The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.		02.0310
Malaria, Falciparum
Malaria caused by PLASMODIUM FALCIPARUM. This is the severest form of malaria and is associated with the highest levels of parasites in the blood. This disease is characterized by irregularly recurring febrile paroxysms that in extreme cases occur with acute cerebral, renal, or gastrointestinal manifestations.		02.0310
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		02.0510