AKR1D1*36 C>T (rs1872930) allelic variant is associated with variability of the CYP2C9 genotype predicted pharmacokinetics of ibuprofen enantiomers – a pilot study in healthy volunteers

1. K. D. Rainsford, Fifty years since the discovery of ibuprofen, Inflammopharmacol.19 (2011) 293–297; https://doi.org/10.1007/s10787-011-0103-710.1007/s10787-011-0103-722120888Search in Google Scholar

2. M. De Martino, A. Chiarugi, A. Boner, G. Montini and L. de’ Angelis, Working towards an appropriate use of ibuprofen in children: An evidence-based appraisal, Drugs77 (2017) 1295–1311; https://doi.org/10.1007/s40265-017-0751-z.10.1007/s40265-017-0751-z552947628597358Search in Google Scholar

3. H. Hao, G. Wang and Sun, Enantioselective pharmacokinetics of ibuprofen and involved mechanisms, Drug Metab. Rev. 37 (2005) 215–234; https://doi.org/10.1081/DMR-20004799910.1081/DMR-200047999Search in Google Scholar

4. K. D. Rainsford, Ibuprofen: pharmacology, efficacy and safety, Inflammopharmacol.17 (2009) 275–342; https://doi.org/10.1007/s10787-009-0016-x10.1007/s10787-009-0016-x19949916Search in Google Scholar

5. G. Ding, Y. Liu, J. Sun, Y. Takeuchi, T. Toda, T. Hayakawa, S. Fukushima, S. Kishimoto, W. Lin and Inotsume, Effect of absorption rate on pharmacokinetics of ibuprofen in relation to chiral inversion in humans, J. Pharm. Pharmacol.59 (2007) 1509–13; https://doi.org/10.1211/jpp.59.11.000710.1211/jpp.59.11.000717976261Search in Google Scholar

6. T. J. Legg, A. L. Laurent, R. Leyva and D. Kellstein, Ibuprofen sodium is absorbed faster than standard Ibuprofen tablets: results of two open-label, randomized, crossover pharmacokinetic studies, Drugs R.D.14 (2014) 283–290; https://doi.org/10.1007/s40268-014-0070-810.1007/s40268-014-0070-8426981825395311Search in Google Scholar

7. F. Jamali and D. R. Brocks, The Pharmacokinetics of Ibuprofen in Humans and Animals, in Ibuprofen (Ed. K. Rainsford), 1^st ed., John Wiley & Sons, New York 2015, pp. 81–131; https://doi.org/10.1002/9781118743614.ch410.1002/9781118743614.ch4Search in Google Scholar

8. S. C. Tan, B. K. Patel, S. H. Jackson, C. G. Swift and A. J. Hutt, Stereoselectivity of ibuprofen metabolism and pharmacokinetics following the administration of the racemate to healthy volunteers, Xenobiotica32 (2002) 683–697; https://doi.org/10.1080/0049825021014299410.1080/0049825021014299412296989Search in Google Scholar

9. J. Kirchheiner, I. Meineke, G. Freytag, C. Meisel, I. Roots and J. Brockmöller, Enantiospecific effects of cytochrome P450 2C9 amino acid variants on ibuprofen pharmacokinetics and on the inhibition of cyclooxygenases 1 and 2, Clin. Pharmacol. Ther.72 (2002) 62–75; https://doi.org/10.1067/mcp.2002.12572610.1067/mcp.2002.12572612152005Search in Google Scholar

10. S. Y. Chang, W. Li, S. C. Traeger, B. Wang, D. Cui, H. Zhang, B. Wen and A. D. Rodrigues, Confirmation that cytochrome P450 2C8 (CYP2C8) plays a minor role in (S)-(+)- and (R)-(−)-ibuprofen hydroxylation in vitro, Drug Metab. Dispos. 36 (2008) 2513–2522; https://doi.org/10.1124/dmd.108.02297010.1124/dmd.108.02297018787056Search in Google Scholar

11. A. D. Rodrigues, Impact of CYP2C9 genotype on pharmacokinetics: Are all cyclooxygenase inhibitors the same? Drug Metab. Dispos.33 (2005) 1567–1575; https://doi.org/10.1124/dmd.105.00645210.1124/dmd.105.006452Search in Google Scholar

12. F. Mazhar, N. Haider, J. Sultana, S. Akram and Y. Ahmed, Prospective study of NSAIDs prescribing in Saudi Arabia: Cardiovascular and gastrointestinal risk in patients with diabetes mellitus, Int. J. Clin. Pharmacol. Ther.56 (2018) 64–71; https://doi.org/10.5414/CP20307110.5414/CP203071Search in Google Scholar

13. O. O. Moninuola, W. Milligan, P. Lochhead and H. Khalili, Systematic review with meta-analysis: association between acetaminophen and nonsteroidal anti-inflammatory drugs (NSAIDs) and risk of Crohn’s disease and ulcerative colitis exacerbation, Aliment. Pharmacol. Ther.47 (2018) 1428–1439; https://doi.org/10.1111/apt.1460610.1111/apt.14606Search in Google Scholar

14. A. Pilotto, D. Seripa, M. Franceschi, C. Scarcelli, D. Colaizzo, E. Grandone, V. Niro, A. Andriulli, G. Leandro, F. Di Mario and B. Dallapiccola, Genetic susceptibility to nonsteroidal anti-inflammatory drug-related gastroduodenal bleeding: role of cytochrome P450 2C9 polymorphisms, Gastroenterology133 (2007) 465–471; https://doi.org/10.1124/dmd.105.00645210.1124/dmd.105.006452Search in Google Scholar

15. G. S. Pazhayattil and A. C. Shirali, Drug-induced impairment of renal function, Int. J. Nephrol. Renovasc. Dis.7 (2014) 457–468, https://doi.org/10.2147/IJNRD.S3974710.2147/IJNRD.S39747Search in Google Scholar

16. G. V. Rollason, C. F. Samer, Y. Daali and J. A. Desmeules, Prediction by pharmacogenetics of safety and efficacy of non-steroidal anti-inflammatory drugs: a review, Curr. Drug Metab.15 (2014) 326–343; https://doi.org/10.2174/138920021566614020221445410.2174/1389200215666140202214454Search in Google Scholar

17. U. Yasar, S. Lundgren, E. Eliasson, A. Bennet, B. Wiman, U. de Faire and A. Rane, Linkage between the CYP2C8 and CYP2C9 genetic polymorphisms, BiochemBiophysResCommun.299 (2002) 25–28; https://doi.org/10.1016/S0006-291X(02)02592-510.1016/S0006-291X(02)02592-5Search in Google Scholar

18. W. C. Speed, S. P. Kang, D. P. Tuck, L. N. Harris and K. K. Kidd, Global variation in CYP2C8-CYP2C9 functional haplotypes, Pharmacogenomics J.9 (2009) 283–290; https://doi.org/10.1038/tpj.2009.1010.1038/tpj.2009.10278240519381162Search in Google Scholar

19. T. S. Tracy, A. S. Chaudhry, B. Prasad, K. E. Thummel, E. G. Schuetz, X. B. Zhong, Y. C. Tien, H. Jeong, X. Pan, L. M. Shireman, J. Tay-Sontheimer and Y. S. Lin, Interindividual variability in cytochrome P450-mediated drug metabolism, Drug Metab. Dispos. 44 (2016) 343–351; https://doi.org/10.1124/dmd.115.06790010.1124/dmd.115.067900476738626681736Search in Google Scholar

20. J. Kirchheiner and J. Brockmöller, Clinical consequences of cytochrome P450 2C9 polymorphisms, Clin. Pharmacol. Ther. 77 (2005) 1–16; https://doi.org/10.1016/j.clpt.2004.08.00910.1016/j.clpt.2004.08.00915637526Search in Google Scholar

21. A. S. Chaudhry, R. K. Thirumaran, K. Yasuda, X. Yang, Y. Fan, S. C. Strom and E. G. Schuetz, Genetic variation in aldo-keto reductase 1D1 (AKR1D1) affects the expression and activity of multiple cytochrome P450s, Drug Metab. Dispos. 41 (2013) 1538–1547; https://doi.org/10.1124/dmd.113.05167210.1124/dmd.113.051672416200523704699Search in Google Scholar

22. T. M. Penning, The aldo-keto reductases (AKRs): Overview, Chem. Biol. Interact.234 (2015) 236–246; https://doi.org/10.1016/j.cbi.2014.09.02410.1016/j.cbi.2014.09.024438879925304492Search in Google Scholar

23. N. Nakov, L. Bogdanovska, J. Acevska, J. Tonic-Ribarska, R. Petkovska A. Dimitrovska, L. Kasabova and D. Svinarov, High-throughput HPLC-MS/MS method for quantification of ibuprofen enantiomers in human plasma: Focus on investigation of metabolite interference, J. Chromatogr. Sci.54 (2016) 1820–1826; https://doi.org/10.1093/chromsci/bmw16610.1093/chromsci/bmw16627733482Search in Google Scholar

24. K. Jakovski, A. Kapedanovska Nestorovska, N. Labacevski and A. J. Dimovski, Characterization of the most common CYP2C9 and CYP2C19 allelic variants in the population of R. Macedonia, Pharmazie68 (2013) 893–898, https://doi.org/10.1691/ph.2013.3579Search in Google Scholar

25. A. Kapedanovska Nestorovska, K. Jakovski, Z. Naumovska, Z. Sterjev, N. Matevska Geskovska, A. J. Dimovski and Lj. Suturkova, Allele frequency and genotype distribution of aldo keto reductase 1D1 (AKR1D1) rs1872930 genetic variant in a Macedonian population, Maced. Pharm. Bull. 64 (2018), in press.10.33320/maced.pharm.bull.2018.64.01.005Search in Google Scholar

26. C. Martínez, E. García-Martín, G. Blanco, F. J. Gamito, J. M. Ladero and J. A. Agúndez, The effect of the cytochrome P450 CYP2C8 polymorphism on the disposition of (R)-ibuprofen enantiomer in healthy subjects, Br. J. Clin. Pharmacol.59 (2005) 62–69; https://doi.org/10.1111/j.1365-2125.2004.02183.x10.1111/j.1365-2125.2004.02183.x188495915606441Search in Google Scholar

27. E. García-Martín, C. Martínez, B. Tabarés, J. Frías and J. A. Agúndez, Interindividual variability in ibuprofen pharmacokinetics is related to interaction of cytochrome P450 2C8 and 2C9 amino acid polymorphisms, Clin. Pharmacol. T her.76 (2004) 119–127; https://doi.org/10.1016/j.clpt.2004.04.00610.1016/j.clpt.2004.04.00615289789Search in Google Scholar

28. D. Ochoa, R. Prieto-Pérez, M. Román, M. Talegón, A. Rivas, G. Galicia, F. Abad-Santos and T. Cabaleiro, Effect of gender and CYP2C9 and CYP2C8 polymorphisms on the pharmacokinetics of ibuprofen enantiomers, Pharmacogenomics16 (2015) 939–948; https://doi.org/10.2217/pgs.15.4010.2217/pgs.15.4026122864Search in Google Scholar

29. R. López-Rodríguez, J. Novalbos, S. Gallego-Sandín, M. Román-Martínez, J. Torrado, J. P. Gisbert and F. Abad-Santos, Influence of CYP2C8 and CYP2C9 polymorphisms on pharmacokinetic and pharmacodynamic parameters of racemic and enantiomeric forms of ibuprofen in healthy volunteers, Pharmacol. Res.58 (2008) 77–84; https://doi.org/10.1016/j.phrs.2008.07.00410.1016/j.phrs.2008.07.00418694831Search in Google Scholar

30. M. Karazniewicz-Lada, M. Luczak and F. Glowka, Pharmacokinetic studies of enantiomers of ibuprofen and its chiral metabolites in humans with different variants of genes coding CYP2C8 and CYP2C9 isoenzymes, Xenobiotica39 (2009) 476–485; https://doi.org/10.1080/0049825090286270510.1080/0049825090286270519480553Search in Google Scholar

31. A. D. Rodrigues and T. H. Rushmore, Cytochrome P450 pharmacogenetics in drug development: in vitro studies and clinical consequences, Curr. Drug Metab.3 (2002) 289–309; https://doi.org/10.2174/138920002333752210.2174/138920002333752212083322Search in Google Scholar

32. D. H. Solomon, M. E. Husni, P. A. Libby, N. D. Yeomans, A. M. Lincoff, T. F. Lϋscher, V. Menon, D. M. Brennan, L. M. Wisniewski, S. E. Nissen and J. S. Borer, The risk of major NSAID toxicity with celecoxib, ibuprofen, or naproxen: A secondary analysis of the PRECISION trial, Am. J. Med.130 (2017) 1415–1422.e4; https://doi.org/10.1016/j.amjmed.2017.06.02810.1016/j.amjmed.2017.06.02828756267Search in Google Scholar

33. N. Moore and J. M. Scheiman, Gastrointestinal safety and tolerability of oral non-aspirin over-the-counter analgesics, Postgrad. Med.130 (2018) 188–199; https://doi.org/10.1016/j.amjmed.2017.06.0210.1080/00325481.2018.1429793Search in Google Scholar