Literature DB >> 25313206

Carboxymefloquine, the major metabolite of the antimalarial drug mefloquine, induces drug-metabolizing enzyme and transporter expression by activation of pregnane X receptor.

Rita Piedade1, Stefanie Traub1, Andreas Bitter1, Andreas K Nüssler2, José P Gil3, Matthias Schwab4, Oliver Burk5.   

Abstract

Malaria patients are frequently coinfected with HIV and mycobacteria causing tuberculosis, which increases the use of coadministered drugs and thereby enhances the risk of pharmacokinetic drug-drug interactions. Activation of the pregnane X receptor (PXR) by xenobiotics, which include many drugs, induces drug metabolism and transport, thereby resulting in possible attenuation or loss of the therapeutic responses to the drugs being coadministered. While several artemisinin-type antimalarial drugs have been shown to activate PXR, data on nonartemisinin-type antimalarials are still missing. Therefore, this study aimed to elucidate the potential of nonartemisinin antimalarial drugs and drug metabolites to activate PXR. We screened 16 clinically used antimalarial drugs and six major drug metabolites for binding to PXR using the two-hybrid PXR ligand binding domain assembly assay; this identified carboxymefloquine, the major and pharmacologically inactive metabolite of the antimalarial drug mefloquine, as a potential PXR ligand. Two-hybrid PXR-coactivator and -corepressor interaction assays and PXR-dependent promoter reporter gene assays confirmed carboxymefloquine to be a novel PXR agonist which specifically activated the human receptor. In the PXR-expressing intestinal LS174T cells and in primary human hepatocytes, carboxymefloquine induced the expression of drug-metabolizing enzymes and transporters on the mRNA and protein levels. The crucial role of PXR for the carboxymefloquine-dependent induction of gene expression was confirmed by small interfering RNA (siRNA)-mediated knockdown of the receptor. Thus, the clinical use of mefloquine may result in pharmacokinetic drug-drug interactions by means of its metabolite carboxymefloquine. Whether these in vitro findings are of in vivo relevance has to be addressed in future clinical drug-drug interaction studies.
Copyright © 2015, American Society for Microbiology. All Rights Reserved.

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Year:  2014        PMID: 25313206      PMCID: PMC4291335          DOI: 10.1128/AAC.04140-14

Source DB:  PubMed          Journal:  Antimicrob Agents Chemother        ISSN: 0066-4804            Impact factor:   5.191


  40 in total

1.  Role of cytochrome P450 3A in the metabolism of mefloquine in human and animal hepatocytes.

Authors:  F Fontaine; G de Sousa; P C Burcham; P Duchêne; R Rahmani
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2.  Dexamethasone enhances constitutive androstane receptor expression in human hepatocytes: consequences on cytochrome P450 gene regulation.

Authors:  J M Pascussi; S Gerbal-Chaloin; J M Fabre; P Maurel; M J Vilarem
Journal:  Mol Pharmacol       Date:  2000-12       Impact factor: 4.436

3.  Effect of rifampin on plasma concentrations of mefloquine in healthy volunteers.

Authors:  W Ridtitid; M Wongnawa; W Mahatthanatrakul; P Chaipol; M Sunbhanich
Journal:  J Pharm Pharmacol       Date:  2000-10       Impact factor: 3.765

Review 4.  Emerging artemisinin resistance in the border areas of Thailand.

Authors:  Kesara Na-Bangchang; Juntra Karbwang
Journal:  Expert Rev Clin Pharmacol       Date:  2013-05       Impact factor: 5.045

5.  Human hepatocytes: isolation, culture, and quality procedures.

Authors:  Daniel Knobeloch; Sabrina Ehnert; Lilianna Schyschka; Peter Büchler; Michael Schoenberg; Jörg Kleeff; Wolfgang E Thasler; Natascha C Nussler; Patricio Godoy; Jan Hengstler; Andreas K Nussler
Journal:  Methods Mol Biol       Date:  2012

6.  Antimalarial artemisinin drugs induce cytochrome P450 and MDR1 expression by activation of xenosensors pregnane X receptor and constitutive androstane receptor.

Authors:  Oliver Burk; Katja A Arnold; Andreas K Nussler; Elke Schaeffeler; Ekaterina Efimova; Bonnie A Avery; Mitchell A Avery; Martin F Fromm; Michel Eichelbaum
Journal:  Mol Pharmacol       Date:  2005-03-10       Impact factor: 4.436

7.  Pharmacokinetic interaction between mefloquine and ritonavir in healthy volunteers.

Authors:  Y Khaliq; K Gallicano; C Tisdale; G Carignan; C Cooper; A McCarthy
Journal:  Br J Clin Pharmacol       Date:  2001-06       Impact factor: 4.335

8.  Ketoconazole increases plasma concentrations of antimalarial mefloquine in healthy human volunteers.

Authors:  W Ridtitid; M Wongnawa; W Mahatthanatrakul; N Raungsri; M Sunbhanich
Journal:  J Clin Pharm Ther       Date:  2005-06       Impact factor: 2.512

9.  Primaquine metabolism by human liver microsomes: effect of other antimalarial drugs.

Authors:  K N Bangchang; J Karbwang; D J Back
Journal:  Biochem Pharmacol       Date:  1992-08-04       Impact factor: 5.858

10.  Artemisinin antimalarials moderately affect cytochrome P450 enzyme activity in healthy subjects.

Authors:  Sara Asimus; Doaa Elsherbiny; Trinh N Hai; Britt Jansson; Nguyen V Huong; Max G Petzold; Ulrika S H Simonsson; Michael Ashton
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Journal:  Bioorg Chem       Date:  2020-11-19       Impact factor: 5.275

2.  Target Hopping from Protein Kinases to PXR: Identification of Small-Molecule Protein Kinase Inhibitors as Selective Modulators of Pregnane X Receptor from TüKIC Library.

Authors:  Enni-Kaisa Mustonen; Tatu Pantsar; Azam Rashidian; Juliander Reiner; Matthias Schwab; Stefan Laufer; Oliver Burk
Journal:  Cells       Date:  2022-04-12       Impact factor: 7.666

3.  Population Pharmacokinetics of Mefloquine Intermittent Preventive Treatment for Malaria in Pregnancy in Gabon.

Authors:  Michael Ramharter; Matthias Schwab; Clara Menendez; Reinhold Kerb; Thorsten Lehr; Ghyslain Mombo-Ngoma; Rella Zoleko Manego; Daisy Akerey-Diop; Arti Basra; Jean-Rodolphe Mackanga; Heike Würbel; Jan-Georg Wojtyniak; Raquel Gonzalez; Ute Hofmann; Mirjam Geditz; Pierre-Blaise Matsiegui; Peter G Kremsner
Journal:  Antimicrob Agents Chemother       Date:  2019-01-29       Impact factor: 5.191

Review 4.  Regulation of PXR Function by Coactivator and Corepressor Proteins: Ligand Binding Is Just the Beginning.

Authors:  Juan Pablo Rigalli; Dirk Theile; Julie Nilles; Johanna Weiss
Journal:  Cells       Date:  2021-11-12       Impact factor: 6.600

Review 5.  A Review of Modifications of Quinoline Antimalarials: Mefloquine and (hydroxy)Chloroquine.

Authors:  Dawid J Kucharski; Michalina K Jaszczak; Przemysław J Boratyński
Journal:  Molecules       Date:  2022-02-02       Impact factor: 4.411

6.  Discrepancy in interactions and conformational dynamics of pregnane X receptor (PXR) bound to an agonist and a novel competitive antagonist.

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Review 7.  The role of pregnane X receptor (PXR) in substance metabolism.

Authors:  Ye Lv; Yi-Yang Luo; Hui-Wen Ren; Cheng-Jie Li; Zhi-Xin Xiang; Zhi-Lin Luan
Journal:  Front Endocrinol (Lausanne)       Date:  2022-08-16       Impact factor: 6.055

8.  Pharmacokinetics of mefloquine and its effect on sulfamethoxazole and trimethoprim steady-state blood levels in intermittent preventive treatment (IPTp) of pregnant HIV-infected women in Kenya.

Authors:  Michael Green; Kephas Otieno; Abraham Katana; Laurence Slutsker; Simon Kariuki; Peter Ouma; Raquel González; Clara Menendez; Feiko ter Kuile; Meghna Desai
Journal:  Malar J       Date:  2016-01-05       Impact factor: 2.979

  8 in total

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