Compounds > 5-hydroxyprimaquine
Page last updated: 2024-10-15

5-hydroxyprimaquine

Description

5-hydroxyprimaquine: structure given in first source; RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID135516690
CHEMBL ID1211
CHEBI ID190367
SCHEMBL ID5639040
MeSH IDM0158442

Synonyms (15)

Synonym
CHEMBL1211
5-hydroxyprimaquine
57695-07-5
8-(5-aminopentan-2-ylamino)-6-methoxyquinolin-5-ol
CHEBI:190367
5-hpq
5-quinolinol, 8-((4-amino-1-methylbutyl)amino)-6-methoxy-
SCHEMBL5639040
DCIFAKQLYKKQAG-UHFFFAOYSA-N
5-hydroxy-6-methoxy-8-[(4-amino-1-methylbutyl)amino]quinoline
8-[(4-amino-1-methylbutyl)amino]-6-methoxy-5-quinolinol #
8-[(5-amino-2-pentanyl)amino]-6-methoxy-5(1h)-quinolinone
8-((5-aminopentan-2-yl)amino)-6-methoxyquinolin-5-ol
8-[(5-aminopentan-2-yl)amino]-6-methoxyquinolin-5(1h)-one
DTXSID40973289

Toxicity

ExcerptReference
"Primaquine-induced hemolytic anemia is a toxic side effect that is due to premature splenic sequestration of intact erythrocytes."( Primaquine-induced hemolytic anemia: role of membrane lipid peroxidation and cytoskeletal protein alterations in the hemotoxicity of 5-hydroxyprimaquine.
Bowman, ZS; Jollow, DJ; McMillan, DC; Morrow, JD, 2005)
[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]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID91118In vitro decreasing the GSH content in normal in human erythrocytes at 0.05 mM1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Synthesis of certain hydroxy analogues of the antimalarial drug primaquine and their in vitro methemoglobin-producing and glutathione-depleting activity in human erythrocytes.
AID91117In vitro decreasing the GSH content in normal in human erythrocytes at 0.01 mM1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Synthesis of certain hydroxy analogues of the antimalarial drug primaquine and their in vitro methemoglobin-producing and glutathione-depleting activity in human erythrocytes.
AID91125In vitro methemoglobin (metHb) forming activity in normal human erythrocytes at 0.05 mM1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Synthesis of certain hydroxy analogues of the antimalarial drug primaquine and their in vitro methemoglobin-producing and glutathione-depleting activity in human erythrocytes.
AID91124In vitro methemoglobin (metHb) forming activity in Glucose-6-phosphate dehydrogenase- (G6PD-) deficient human erythrocytes at 0.05 mM1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Synthesis of certain hydroxy analogues of the antimalarial drug primaquine and their in vitro methemoglobin-producing and glutathione-depleting activity in human erythrocytes.
AID91126In vitro methemoglobin (metHb) forming activity in normal human erythrocytes.1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Synthesis of certain hydroxy analogues of the antimalarial drug primaquine and their in vitro methemoglobin-producing and glutathione-depleting activity in human erythrocytes.
[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-19902 (25.00)18.7374
1990's3 (37.50)18.2507
2000's2 (25.00)29.6817
2010's0 (0.00)24.3611
2020's1 (12.50)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
5,5-dimethyl-1-pyrroline-1-oxide
5,5-dimethyl-1-pyrroline-1-oxide: do not confuse with DMPO (4',5'-dihydroxy-7-methoxy-4-phenyl-5,2'-oxidocoumarin). 5,5-dimethyl-1-pyrroline N-oxide : A member of the class of 1-pyrroline nitrones (1-pyrroline N-oxides) resulting from the formal N-oxidation of 5,5-dimethyl-1-pyrroline. Used as a spin trap for the study of radicals formed by enzymatic acetaldehyde oxidation.		2.38201-pyrroline nitronesneuroprotective agent;
spin trapping reagent
ethylmaleimide
Ethylmaleimide: A sulfhydryl reagent that is widely used in experimental biochemical studies.		2.0210maleimidesanticoronaviral agent;
EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor;
EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor;
EC 2.7.1.1 (hexokinase) inhibitor
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.		3.580aminoquinoline;
aromatic ether;
N-substituted diamine		antimalarial
edetic acid
Edetic Acid: A chelating agent that sequesters a variety of polyvalent cations such as CALCIUM. It is used in pharmaceutical manufacturing and as a food additive.		1.9710ethylenediamine derivative;
polyamino carboxylic acid;
tetracarboxylic acid		anticoagulant;
antidote;
chelator;
copper chelator;
geroprotector
ditiocarb
Ditiocarb: A chelating agent that has been used to mobilize toxic metals from the tissues of humans and experimental animals. It is the main metabolite of DISULFIRAM.. diethyldithiocarbamic acid : A member of the class of dithiocarbamic acids that is diethylcarbamic acid in which both of the oxygens are replaced by sulfur.		1.9710dithiocarbamic acidschelator;
copper chelator
dithiothreitol
1,4-dimercaptobutane-2,3-diol : A glycol that is butane-2,3-diol in which a hydrogen from each of the methyl groups is replaced by a thiol group.. 1,4-dithiothreitol : The threo-diastereomer of 1,4-dimercaptobutane-2,3-diol.		2.02101,4-dimercaptobutane-2,3-diol;
butanediols;
dithiol;
glycol;
thiol		chelator;
human metabolite;
reducing agent
8-(3-carboxy-1-methylpropylamino)-6-methoxyquinoline
8-(3-carboxy-1-methylpropylamino)-6-methoxyquinoline: primaquine metabolite in rats; structure given in first source		1.9810organonitrogen compound;
organooxygen compound
hydroxyl radical
Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.		1.9710oxygen hydride;
oxygen radical;
reactive oxygen species
5,6-dihydroxy-8-aminoquinoline
5,6-dihydroxy-8-aminoquinoline: metabolite of primaquine		2.3720
ConditionIndicatedRelationship StrengthStudiesTrials
Plasmodium vivax Malaria
[description not available]		02.4110
Malaria, Vivax
Malaria caused by PLASMODIUM VIVAX. This form of malaria is less severe than MALARIA, FALCIPARUM, but there is a higher probability for relapses to occur. Febrile paroxysms often occur every other day.		02.4110
Anemia, Hemolytic, Acquired
[description not available]		02.4220
Extravascular Hemolysis
[description not available]		02.0210
Anemia, Hemolytic
A condition of inadequate circulating red blood cells (ANEMIA) or insufficient HEMOGLOBIN due to premature destruction of red blood cells (ERYTHROCYTES).		02.4220
Hemolysis
The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.		02.0210
Deficiency of Glucose-6-Phosphate Dehydrogenase
[description not available]		01.9710
Glucosephosphate Dehydrogenase Deficiency
A disease-producing enzyme deficiency subject to many variants, some of which cause a deficiency of GLUCOSE-6-PHOSPHATE DEHYDROGENASE activity in erythrocytes, leading to hemolytic anemia.		01.9710