ArticleMalaria journal2019
Formation primaquine-5,6-orthoquinone, the putative active and toxic metabolite of primaquine via direct oxidation in human erythrocytes.
Article in Malaria journal, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed, 26 citations in OpenAlex.
- Bioequivalence of a new coated 15 mg primaquine formulation for malaria elimination.Malaria journal · 2024Trial
- Primaquine-derived 5,6-orthoquinone concentrations in urine associated with CYP2D6 genotype-predicted phenotype and blood methemoglobin levels.Antimicrobial agents and chemotherapy · 2026Article
- Primaquine-5,6-Orthoquinone Is Directly Hemolytic to Older G6PD Deficient RBCs in a Humanized Mouse Model.The Journal of pharmacology and experimental therapeutics · 2024Article
- Harnessing cholesterol uptake of malaria parasites for therapeutic applications.EMBO molecular medicine · 2024Article
- Protein Haptenation and Its Role in Allergy.Chemical research in toxicology · 2024Review
- Quantification of Tafenoquine and 5,6-Orthoquinone Tafenoquine by UHPLC-MS/MS in Blood, Plasma, and Urine, and Application to a Pharmacokinetic Study.Molecules (Basel, Switzerland) · 2022Article
- Measurements of 5,6-Orthoquinone, a Surrogate for the Presumed Active Primaquine Metabolite 5-Hydroxyprimaquine, in the Urine of Cambodian Adults.Antimicrobial agents and chemotherapy · 2022Article
- Comparative pharmacokinetics and tissue distribution of primaquine enantiomers in mice.Malaria journal · 2022Article
- Comparative metabolism and tolerability of racemic primaquine and its enantiomers in human volunteers during 7-day administration.Frontiers in pharmacology · 2022Article
- Anti-Inflammatory Activation of Phellodendri Chinensis Cortex is Mediated by Berberine Erythrocytes Self-Assembly Targeted Delivery System.Drug design, development and therapy · 2022Article
- Primaquine Loaded Solid Lipid Nanoparticles (SLN), Nanostructured Lipid Carriers (NLC), and Nanoemulsion (NE): Effect of Lipid Matrix and Surfactant on Drug Entrapment, in vitro Release, and ex vivo Hemolysis.AAPS PharmSciTech · 2021Article
- Enantioselective Interactions of Anti-Infective 8-Aminoquinoline Therapeutics with Human Monoamine Oxidases A and B.Pharmaceuticals (Basel, Switzerland) · 2021Article
- Nopol-Based Quinoline Derivatives as Antiplasmodial Agents.Molecules (Basel, Switzerland) · 2021Article
- Article
- Tafenoquine: A Step toward Malaria Elimination.Biochemistry · 2020Article
- Hemolytic Dynamics of Weekly Primaquine Antirelapse Therapy Among Cambodians With Acute Plasmodium vivax Malaria With or Without Glucose-6-Phosphate Dehydrogenase Deficiency.The Journal of infectious diseases · 2019Article
- Identification and Characterization of Key Chemical Constituents in ProcessedJournal of analytical methods in chemistry · 2019Article
- NPC1161B, an 8-Aminoquinoline Analog, Is Metabolized in the Mosquito and InhibitsFrontiers in pharmacology · 2019Article
Corrections and comments
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Authors and funding
10 authors at 3 institutions in 1 country.
Funding
Abstract
backgroundThe activity and haemolytic toxicity associated with primaquine has been linked to its reactive metabolites. The reactive metabolites are thought to be primarily formed through the action of cytochrome P
methodsPrimaquine and its enantiomers were incubated separately with human red blood cells and haemoglobin. Post-incubation analysis was performed with UPLC-MS/MS to identify products of biotransformation.
resultsThe major metabolite detected was identified as primaquine-5,6-orthoquinone, reflecting the pathway yielding putative active and haematotoxic metabolites of primaquine, which was formed by oxidative demethylation of 5-hydroxyprimaquine. Incubation of primaquine with haemoglobin in a cell-free system yielded similar results. It appears that the observed biotransformation is due to non-enzymatic processes, perhaps due to reactive oxygen species (ROS) present in erythrocytes or in the haemoglobin incubates.
conclusionThis study presents new evidence that primaquine-5,6-orthoquinone, the metabolite of primaquine reflecting the oxidative biotransformation pathway, is generated in erythrocytes, probably by non-enzymatic means, and may not require transport from the liver or other tissues.
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Registered trials
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