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image of Immobilized Lipases for S-Naproxen Synthesis: Techniques, Materials, and Pharmaceutical Applications - A Review

Abstract

Naproxen is a widely used Non-Steroidal Anti-Inflammatory Drug (NSAID) and is notable for its analgesic, antipyretic and anti-inflammatory properties. It shows its pharmacological effect by inhibiting Cyclooxygenase (COX) enzymes and suppressing prostaglandin synthesis. This mechanism plays an important role in reducing inflammation and controlling pain. The pharmacokinetic properties, bioavailability and side effect profile of naproxen are the determining factors in the selection of synthesis methods. In recent years, factors such as environmental sustainability and stereoselectivity have become increasingly important in the synthesis of -naproxen, and enzymatic synthesis methods have gained prominence. Enzymatic processes offer high stereoselectivity, providing the advantage of producing -naproxen in the preferred enantiomer form. Moreover, the use of biocatalysts reduces energy consumption by making the reaction conditions milder and avoiding the use of toxic reagents for an environmentally friendly production process. The review focuses on the chemical structure, pharmacological effects, biotransformation mechanisms, and enantiomeric properties of naproxen. The review also includes current formulation approaches to address solubility and bioavailability issues of naproxen. This review contributes to the understanding of current strategies to enhance the therapeutic efficacy of naproxen and highlights potential areas for future research.

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2026-02-10
2026-02-23
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References

  1. Ha M.W. Paek S.M. Recent advances in the synthesis of ibuprofen and naproxen. Molecules 2021 26 16 4792 10.3390/molecules26164792 34443379
    [Google Scholar]
  2. Salahshoori I. Mahdavi S. Moradi Z. Otadi M. Zare Kazemabadi F. Nobre M.A.L. Ali Khonakdar H. Baghban A. Wang Q. Mohammadi A.H. Advancements in molecular simulation for understanding pharmaceutical pollutant Adsorption: A State-of-the-Art review. J. Mol. Liq. 2024 410 125513 10.1016/j.molliq.2024.125513
    [Google Scholar]
  3. Han J. Xia J. San H. Zhang H. Jiang Z. Wang H. Liu Y. Sun S. Serdechnova M. Lu X. Blawert C. Zheludkevich M.L. Chen H. In vitro performance of a LDH nano capsules in-situ incorporated PEO coating loaded with naproxen sodium on Mg alloy. Corros. Sci. 2025 244 112625 10.1016/j.corsci.2024.112625
    [Google Scholar]
  4. Kaur K. Bansal N. Singh R. Kaur V. Capalash N. Surfactant-induced AIE-active tin(IV) micelles for sensing naproxen residues in pharmaceutical effluents. J. Mol. Liq. 2024 397 124153 10.1016/j.molliq.2024.124153
    [Google Scholar]
  5. Borodkin G.I. Elanov I.R. Shubin V.G. Mechanochemical fluorination of naproxen and its salts with F–TEDA–BF4. Russ. J. Org. Chem. 2023 59 11 1858 1866 10.1134/S1070428023110039
    [Google Scholar]
  6. Shaheen M.A. Feng S. Anthony M. Tahir M.N. Hassan M. Seo S.Y. Ahmad S. Iqbal M. Saleem M. Lu C. Metal-based scaffolds of schiff bases derived from naproxen: Synthesis, antibacterial activities, and molecular docking studies. Molecules 2019 24 7 1237 10.3390/molecules24071237 30934936
    [Google Scholar]
  7. Mohseni M. Shokrollahi P. Barzin J. Gelatin/O-carboxymethyl chitosan injectable self-healing hydrogels for ibuprofen and naproxen dual release. Int. J. Biol. Macromol. 2024 263 Pt 1 130266 10.1016/j.ijbiomac.2024.130266 38368982
    [Google Scholar]
  8. Shirazian S. Alzhrani R.M. Zare M.H. Design and synthesis of drug hydrogels containing carboxymethylcellulose with honeycomb structure and pH-sensitivity as drug delivery systems for adriamycin, metformin, and naproxen. Int. J. Biol. Macromol. 2024 271 Pt 1 132568 10.1016/j.ijbiomac.2024.132568 38782329
    [Google Scholar]
  9. Song J.S. Sohn Y.T. Crystal forms of naproxen. Arch. Pharm. Res. 2011 34 1 87 90 10.1007/s12272‑011‑0110‑7 21468919
    [Google Scholar]
  10. Kassab A.E. Gedawy E.M. Repurposing of indomethacin and naproxen as anticancer agents: Progress from 2017 to present. RSC Advances 2024 14 54 40031 40057 10.1039/D4RA07581A 39717807
    [Google Scholar]
  11. Löbmann K. Laitinen R. Grohganz H. Gordon K.C. Strachan C. Rades T. Coamorphous drug systems: enhanced physical stability and dissolution rate of indomethacin and naproxen. Mol. Pharm. 2011 8 5 1919 1928 10.1021/mp2002973 21815614
    [Google Scholar]
  12. Tehrani E. Faraji A.R. Shojaei N. Shahinmehr S. Najafi A. Hekmatian Z. Tehrani Z. Bornas B. An overview of the characteristics, toxicity, and treatment methods for the degradation of pharmaceutically active compounds: Naproxen as a case study. J. Environ. Chem. Eng. 2023 11 6 111575 10.1016/j.jece.2023.111575
    [Google Scholar]
  13. Aziziaram Z. Bilal I. Zhong Y. Mahmod A. Roshandel M.R. Protective effects of curcumin against naproxen-induced mitochondrial dysfunction in rat kidney tissue. Cellul., Mol. and Biomed. Rep. 2021 1 1 23 32 10.55705/cmbr.2021.138879.1001
    [Google Scholar]
  14. Tong S. Guan Y.X. Yan J. Zheng B. Zhao L. Enantiomeric separation of (R, S)-naproxen by recycling high speed counter-current chromatography with hydroxypropyl-β-cyclodextrin as chiral selector. J. Chromatogr. A 2011 1218 32 5434 5440 10.1016/j.chroma.2011.06.015 21737088
    [Google Scholar]
  15. Patel R.N. Enzymatic synthesis of chiral intermediates for drug development. Adv. Synth. Catal. 2001 343 6-7 527 546 10.1002/1615‑4169(200108)343:6/7<527::AID‑ADSC527>3.0.CO;2‑I
    [Google Scholar]
  16. Harrison I.T. Lewis B. Nelson P. Rooks W. Roszkowski A. Tomolonis A. Fried J.H. Nonsteroidal antiinflammatory agents. I. 6-Substituted 2-naphthylacetic acids. J. Med. Chem. 1970 13 2 203 205 10.1021/jm00296a008 5418489
    [Google Scholar]
  17. Zhang G. Yin Z.Z. Zuo X. Chen H. Chen G. Gao J. Kong Y. Carboxymethyl potato starch hydrogels encapsulated cyclodextrin metal-organic frameworks for enantioselective loading of S-naproxen and its programmed release. Int. J. Biol. Macromol. 2024 262 Pt 1 130013 10.1016/j.ijbiomac.2024.130013 38340930
    [Google Scholar]
  18. Cao Y. Khan A. Ghorbani F. Mirzaei H. Singla P. Balakheyli H. Soltani A. Aghaei M. Azmoodeh Z. Aarabi M. Tavassoli S. Predicting adsorption behavior and anti-inflammatory activity of naproxen interacting with pure boron nitride and boron phosphide fullerene-like cages. J. Mol. Liq. 2021 339 116678 10.1016/j.molliq.2021.116678
    [Google Scholar]
  19. Salazar J. Hidalgo-Rosa Y. Burboa P.C. Wu Y. Escalona N. Leiva A. Zarate X. Schott E. UiO-66(Zr) as drug delivery system for non-steroidal anti-inflammatory drugs. J. Control. Release 2024 370 392 404 10.1016/j.jconrel.2024.04.035 38663750
    [Google Scholar]
  20. Wibrianto A. Putri F.S.D. Nisa U.K. Mahyahani N. Sugito S.F.A. Wardana A.P. Sakti S.C.W. Chang J.Y. Fahmi M.Z. Strategic assessment of boron-enriched carbon dots/naproxen: diagnostic, toxicity, and in vivo therapeutic evaluation. Mol. Pharm. 2024 21 2 801 812 10.1021/acs.molpharmaceut.3c00919 38217878
    [Google Scholar]
  21. Arfeen M. Srivastava A. Srivastava N. Khan R.A. Almahmoud S.A. Mohammed H.A. Design, classification, and adverse effects of NSAIDs: A review on recent advancements. Bioorg. Med. Chem. 2024 112 117899 10.1016/j.bmc.2024.117899 39217686
    [Google Scholar]
  22. Parolini M. Toxicity of the Non-Steroidal Anti-Inflammatory Drugs (NSAIDs) acetylsalicylic acid, paracetamol, diclofenac, ibuprofen and naproxen towards freshwater invertebrates: A review. Sci. Total Environ. 2020 740 140043 10.1016/j.scitotenv.2020.140043 32559537
    [Google Scholar]
  23. Rodríguez-Cal y Mayor A. Castañeda-Hernández G. Favari L. Martinez-Cruz A. Guízar-Sahagún G. Cruz-Antonio L. Pharmacokinetics and anti-inflammatory effect of naproxen in rats with acute and subacute spinal cord injury. Naunyn Schmiedebergs Arch. Pharmacol. 2020 393 3 395 404 10.1007/s00210‑019‑01745‑9 31641817
    [Google Scholar]
  24. Farque M.O. Islam R.M. Rahman Joni M.F. Akter M. Akter S. Islam M.D. Salim M.D.J.B. Aziz A.A. Kabir E. Uzzaman M. Structural modification of Naproxen; physicochemical, spectral, medicinal, and pharmacological evaluation. Inform. Med. Unlocked 2025 53 101617 10.1016/j.imu.2025.101617
    [Google Scholar]
  25. Angiolillo D.J. Weisman S.M. Clinical pharmacology and cardiovascular safety of naproxen. Am. J. Cardiovasc. Drugs 2017 17 2 97 107 10.1007/s40256‑016‑0200‑5 27826802
    [Google Scholar]
  26. Thomson P. Fragkas N. Kafu L.M. Aithal G.P. Lucena M.I. Terracciano L. Meng X. Pirmohamed M. Brees D. Kullak-Ublick G.A. Odermatt A. Hammond T. Kammüller M. Naisbitt D.J. Patients with naproxen-induced liver injury display T-cell memory responses toward an oxidative (S)- O-desmethyl naproxen metabolite but not the acyl glucuronide. Allergy 2024 79 1 200 214 10.1111/all.15830 37515456
    [Google Scholar]
  27. Küçükgüzel Ş.G. Anticancer and antimicrobial activities of naproxen and naproxen derivatives. Mini Rev. Med. Chem. 2020 20 13 1300 1310 10.2174/1389557520666200505124922.
    [Google Scholar]
  28. Shinu P. Sharma M. Gupta G.L. Mujwar S. Kandeel M. Kumar M. Nair A.B. Goyal M. Singh P. Attimarad M. Venugopala K.N. Nagaraja S. Telsang M. Aldhubiab B.E. Morsy M.A. Computational design, synthesis, and pharmacological evaluation of naproxen-guaiacol chimera for gastro-sparing anti-inflammatory response by selective COX2 inhibition. Molecules 2022 27 20 6905 10.3390/molecules27206905 36296501
    [Google Scholar]
  29. Gouda A.M. Beshr E.A. Almalki F.A. Halawah H.H. Taj B.F. Alnafaei A.F. Alharazi R.S. Kazi W.M. AlMatrafi M.M. Arylpropionic acid-derived NSAIDs: New insights on derivatization, anticancer activity and potential mechanism of action. Bioorg. Chem. 2019 92 103224 10.1016/j.bioorg.2019.103224 31491568
    [Google Scholar]
  30. Nedeljković N. Dobričić V. Bošković J. Vesović M. Bradić J. Anđić M. Kočović A. Jeremić N. Novaković J. Jakovljević V. Vujić Z. Nikolić M. Synthesis and investigation of anti-inflammatory activity of new thiourea derivatives of naproxen. Pharmaceuticals 2023 16 5 666 10.3390/ph16050666 37242450
    [Google Scholar]
  31. Cooper C. Chapurlat R. Al-Daghri N. Herrero-Beaumont G. Bruyère O. Rannou F. Roth R. Uebelhart D. Reginster J.Y. Safety of oral non-selective non-steroidal anti-inflammatory drugs in osteoarthritis: What does the literature say? Drugs Aging 2019 36 S1 Suppl. 1 15 24 10.1007/s40266‑019‑00660‑1 31073921
    [Google Scholar]
  32. Muneer S. Muhammad I.N. Asad Abrar M. Munir I. Kaukab I. Sagheer A. Zafar H. Sultana K. High performance liquid chromatographic determination of naproxen in prepared pharmaceutical dosage form and human plasma and its application to pharmacokinetic study. J. Chromatogr. Sep. Tech. 2017 8 3 1 5 10.4172/2157‑7064.1000369
    [Google Scholar]
  33. Khanra M. Ravichandiran V. Swain S.P. Lipase enzymes for sustainable synthesis of pharmaceuticals and chiral organic building blocks. Adv. Sustain. Syst. 2023 2400495
    [Google Scholar]
  34. Ghanem A. Aboul-Enein M.N. El-Azzouny A. El-Behairy M.F. Lipase-mediated enantioselective kinetic resolution of racemic acidic drugs in non-standard organic solvents: Direct chiral liquid chromatography monitoring and accurate determination of the enantiomeric excesses. J. Chromatogr. A 2010 1217 7 1063 1074 10.1016/j.chroma.2009.10.080 19914624
    [Google Scholar]
  35. Davies N.M. Anderson K.E. Clinical pharmacokinetics of naproxen. Clin. Pharmacokinet. 1997 32 4 268 293 10.2165/00003088‑199732040‑00002 9113437
    [Google Scholar]
  36. Zdun B. Cieśla P. Kutner J. Borowiecki P. Expanding access to optically active non-steroidal anti-inflammatory drugs via lipase-catalyzed kr of racemic acids using trialkyl orthoesters as irreversible alkoxy group donors. Catalysts 2022 12 5 546 10.3390/catal12050546
    [Google Scholar]
  37. Xu Z. Zhang G. Wang R. Zhang G. Chen G. Bian H. Jiang T. Kong Y. Degradable chiral mesoporous silica nanoparticles and carboxymethyl chitosan/cystamine hydrogels for selective loading and controlled release of S-naproxen. Int. J. Biol. Macromol. 2025 288 138706 10.1016/j.ijbiomac.2024.138706 39672415
    [Google Scholar]
  38. Simić S. Zukić E. Schmermund L. Faber K. Winkler C.K. Kroutil W. Shortening synthetic routes to small molecule active pharmaceutical ingredients employing biocatalytic methods. Chem. Rev. 2022 122 1 1052 1126 10.1021/acs.chemrev.1c00574 34846124
    [Google Scholar]
  39. Albayati S.H. Nezhad N.G. Taki A.G. Rahman R.N.Z.R.A. Efficient and easible biocatalysts: Strategies for enzyme improvement. A review. Int. J. Biol. Macromol. 2024 276 Pt 2 133978 10.1016/j.ijbiomac.2024.133978 39038570
    [Google Scholar]
  40. Shuai W. Das R.K. Naghdi M. Brar S.K. Verma M. A review on the important aspects of lipase immobilization on nanomaterials. Biotechnol. Appl. Biochem. 2017 64 4 496 508 10.1002/bab.1515 27277552
    [Google Scholar]
  41. Ozyilmaz E. Ascioglu S. Yilmaz M. Calix[4]arene tetracarboxylic acid-treated lipase immobilized onto metal-organic framework: Biocatalyst for ester hydrolysis and kinetic resolution. Int. J. Biol. Macromol. 2021 175 79 86 10.1016/j.ijbiomac.2021.02.003 33548316
    [Google Scholar]
  42. Zhao P. Tian L. Li X. Ali Z. Zhang B. Zhang H. Zhang Q. Effect of the structure and length of flexible chains on dendrimers grafted Fe3O4@ SiO2/PAMAM magnetic nanocarriers for lipase immobilization. ACS Sustain. Chem.& Eng. 2016 4 12 6382 6390 10.1021/acssuschemeng.6b00967
    [Google Scholar]
  43. Vetrano A. Gabriele F. Germani R. Spreti N. Characterization of lipase from Candida rugosa entrapped in alginate beads to enhance its thermal stability and recyclability. New J. Chem. 2022 46 21 10037 10047 10.1039/D2NJ01160C
    [Google Scholar]
  44. Ascioglu S. Ozyilmaz E. Yildirim A. Sayin S. Yilmaz M. Fabrication of lipase-immobilized proline-conjugated zirconium-based metal-organic framework (UiO-66-NH2) to enhance catalytic activity, stability, and enantioselectivity. Biochem. Eng. J. 2024 204 109242 10.1016/j.bej.2024.109242
    [Google Scholar]
  45. Sampaio C.S. Angelotti J.A.F. Fernandez-Lafuente R. Hirata D.B. Lipase immobilization via cross-linked enzyme aggregates: Problems and prospects – A review. Int. J. Biol. Macromol. 2022 215 434 449 10.1016/j.ijbiomac.2022.06.139 35752332
    [Google Scholar]
  46. Ghanem A. Aboul-Enein H.Y. Lipase-mediated chiral resolution of racemates in organic solvents. Tetrahedron Asymmetry 2004 15 21 3331 3351 10.1016/j.tetasy.2004.09.019
    [Google Scholar]
  47. Sikora A. Siódmiak T. Marszałł M.P. Kinetic resolution of profens by enantioselective esterification catalyzed by Candida antarctica and Candida rugosa lipases. Chirality 2014 26 10 663 669 10.1002/chir.22362 25080075
    [Google Scholar]
  48. Mohammadi M. Gandomkar S. Habibi Z. Yousefi M. One pot three-component reaction for covalent immobilization of enzymes: Application of immobilized lipases for kinetic resolution of rac-ibuprofen. RSC Advances 2016 6 58 52838 52849 10.1039/C6RA11284F
    [Google Scholar]
  49. Mangiagalli M. Ami D. de Divitiis M. Brocca S. Catelani T. Natalello A. Lotti M. Short-chain alcohols inactivate an immobilized industrial lipase through two different mechanisms. Biotechnol. J. 2022 17 6 2100712 10.1002/biot.202100712 35188703
    [Google Scholar]
  50. Lotti M. Pleiss J. Valero F. Ferrer P. Enzymatic production of biodiesel: Strategies to overcome methanol inactivation. Biotechnol. J. 2018 13 5 1700155 10.1002/biot.201700155 29461685
    [Google Scholar]
  51. Ingenbosch K.N. Vieyto-Nuñez J.C. Ruiz-Blanco Y.B. Mayer C. Hoffmann-Jacobsen K. Sanchez-Garcia E. Effect of organic solvents on the structure and activity of a minimal lipase. J. Org. Chem. 2022 87 3 1669 1678 10.1021/acs.joc.1c01136 34706196
    [Google Scholar]
  52. Mateo C. Palomo J.M. Fernandez-Lorente G. Guisan J.M. Fernandez-Lafuente R. Improvement of enzyme activity, stability and selectivity via immobilization techniques. Enzyme Microb. Technol. 2007 40 6 1451 1463 10.1016/j.enzmictec.2007.01.018
    [Google Scholar]
  53. Sheldon R.A. Enzyme immobilization: the quest for optimum performance. Adv. Synth. Catal. 2007 349 8-9 1289 1307 10.1002/adsc.200700082
    [Google Scholar]
  54. Arroyo M. Sinisterra J.V. High enantioselective esterification of 2-arylpropionic acids catalyzed by immobilized lipase from Candida antarctica: A mechanistic approach. J. Org. Chem. 1994 59 16 4410 4417 10.1021/jo00095a014
    [Google Scholar]
  55. Tsai S.W. Tsai C.S. Chang C.S. Lipase-catalyzed synthesis of (S)-naproxen ester prodrug by transesterification in organic solvents. Appl. Biochem. Biotechnol. 1999 80 3 205 220 10.1385/ABAB:80:3:205 10488552
    [Google Scholar]
  56. Xin J-Y. Zhang S. Dong J. Zhang H-D. Xia C-G. Improving the catalytic performance of Candida rugosa lipase on naproxen resolution by methanobactin-mediated gold nanoparticles hybridization. Mater. Express 2021 11 4 557 563
    [Google Scholar]
  57. Dogan V. Sayin S. Uyanik A. Yilmaz M. Functional group effects of new calixarene derivatives on catalytic and enantioselective behavior of lipase. Polycyclic Aromatic Compounds 2019 39 4 318 331 10.1080/10406638.2017.1326949
    [Google Scholar]
  58. Itoh T. Takagi Y. Murakami T. Hiyama Y. Tsukube H. Crown ethers as regulators of enzymatic reactions: Enhanced reaction rate and enantioselectivity in lipase-catalyzed hydrolysis of 2-cyano-1-methylethyl acetate. J. Org. Chem. 1996 61 6 2158 2163 10.1021/jo951598+
    [Google Scholar]
  59. Sayin S. Yilmaz E. Yilmaz M. Improvement of catalytic properties of Candida Rugosa lipase by sol–gel encapsulation in the presence of magnetic calix[4]arene nanoparticles. Org. Biomol. Chem. 2011 9 11 4021 4024 10.1039/c1ob05115f 21509361
    [Google Scholar]
  60. Pereira E.B. De Castro H.F. De Moraes F.F. Zanin G.M. Kinetic studies of lipase from candida rugosa: A comparative study between free and immobilized enzyme onto porous chitosan beads. Appl Biochem Biotechnol. 2001 91-93 1-9 739 752 10.1385/abab:91‑93:1‑9:739.
    [Google Scholar]
  61. Salgın S. Çakal M. Salgın U. Kinetic resolution of racemic naproxen methyl ester by magnetic and non-magnetic cross-linked lipase aggregates. Prep. Biochem. Biotechnol. 2020 50 2 148 155 10.1080/10826068.2019.1679178 31647366
    [Google Scholar]
  62. Giorno L. Damore E. Drioli E. Cassano R. Picci N. Influence of OR ester group length on the catalytic activity and enantioselectivity of free lipase and immobilized in membrane used for the kinetic resolution of naproxen esters. J. Catal. 2007 247 2 194 200 10.1016/j.jcat.2007.01.021
    [Google Scholar]
  63. Xin J. Zhao Y. Zhao G. Zheng Y. Ma X. Xia C. Li S. Enzymatic resolution of ( R, S )-Naproxen in water-saturated ionic liquid. Biocatal. Biotransform. 2005 23 5 353 361 10.1080/10242420500292401
    [Google Scholar]
  64. Yilmaz E. Can K. Sezgin M. Yilmaz M. Immobilization of Candida rugosa lipase on glass beads for enantioselective hydrolysis of racemic Naproxen methyl ester. Bioresour. Technol. 2011 102 2 499 506 10.1016/j.biortech.2010.08.083 20846857
    [Google Scholar]
  65. Yilmaz E. Sezgin M. Yilmaz M. Enantioselective hydrolysis of rasemic naproxen methyl ester with sol–gel encapsulated lipase in the presence of sporopollenin. J. Mol. Catal., B Enzym. 2010 62 2 162 168 10.1016/j.molcatb.2009.10.003
    [Google Scholar]
  66. Sayin S. Akoz E. Yilmaz M. Enhanced catalysis and enantioselective resolution of racemic naproxen methyl ester by lipase encapsulated within iron oxide nanoparticles coated with calix[8]arene valeric acid complexes. Org. Biomol. Chem. 2014 12 34 6634 6642 10.1039/C4OB01048E 25012138
    [Google Scholar]
  67. Akoz E. Akbulut O.Y. Yilmaz M. Calix[n]arene carboxylic acid derivatives as regulators of enzymatic reactions: enhanced enantioselectivity in lipase-catalyzed hydrolysis of (R/S)-naproxen methyl ester. Appl. Biochem. Biotechnol. 2014 172 1 509 523 10.1007/s12010‑013‑0527‑1 24092454
    [Google Scholar]
  68. Uyanik A. Sen N. Yilmaz M. Improvement of catalytic activity of lipase from Candida rugosa via sol–gel encapsulation in the presence of calix(aza)crown. Bioresour. Technol. 2011 102 6 4313 4318 10.1016/j.biortech.2010.12.105 21256747
    [Google Scholar]
  69. Akoz E. Sayin S. Kaplan S. Yilmaz M. Improvement of catalytic activity of lipase in the presence of calix[4]arene valeric acid or hydrazine derivative. Bioprocess Biosyst. Eng. 2015 38 3 595 604 10.1007/s00449‑014‑1299‑x 25326059
    [Google Scholar]
  70. Ozyilmaz E. Sayin S. Preparation of new Calix[4]arene-immobilized biopolymers for enhancing catalytic properties of Candida rugosa lipase by sol-gel encapsulation. Appl. Biochem. Biotechnol. 2013 170 8 1871 1884 10.1007/s12010‑013‑0308‑x 23780340
    [Google Scholar]
  71. Yilmaz E. Sezgin M. Enhancement of the activity and enantioselectivity of lipase by sol-gel encapsulation immobilization onto β-cyclodextrin-based polymer. Appl. Biochem. Biotechnol. 2012 166 8 1927 1940 10.1007/s12010‑012‑9621‑z 22383051
    [Google Scholar]
  72. Sahin O. Erdemir S. Uyanik A. Yilmaz M. Enantioselective hydrolysis of (R/S)-Naproxen methyl ester with sol–gel encapculated lipase in presence of calix[n]arene derivatives. Appl. Catal. A Gen. 2009 369 1-2 36 41 10.1016/j.apcata.2009.08.030
    [Google Scholar]
  73. Yilmaz E. Sezgin M. Yilmaz M. Immobilization of Candida rugosa lipase on magnetic sol–gel composite supports for enzymatic resolution of (R,S)-Naproxen methyl ester. J. Mol. Catal., B Enzym. 2011 69 1-2 35 41 10.1016/j.molcatb.2010.12.007
    [Google Scholar]
  74. Ozyilmaz E. Sayin S. Arslan M. Yilmaz M. Improving catalytic hydrolysis reaction efficiency of sol–gel-encapsulated Candida rugosa lipase with magnetic β-cyclodextrin nanoparticles. Colloids Surf. B Biointerfaces 2014 113 182 189 10.1016/j.colsurfb.2013.08.019 24090713
    [Google Scholar]
  75. Ozyilmaz E. Bayrakci M. Yilmaz M. Improvement of catalytic activity of Candida rugosa lipase in the presence of calix[4]arene bearing iminodicarboxylic/phosphonic acid complexes modified iron oxide nanoparticles. Bioorg. Chem. 2016 65 1 8 10.1016/j.bioorg.2015.12.001 26698535
    [Google Scholar]
  76. Akceylan E. Sahin O. Yilmaz M. Improvement of catalytic activity of lipase in the presence of wide rim substituted calix[4]arene carboxylic acid-grafted magnetic nanoparticles. J. Incl. Phenom. Macrocycl. Chem. 2014 79 1-2 113 123 10.1007/s10847‑013‑0332‑z
    [Google Scholar]
  77. Ozyilmaz E. Ascioglu S. Yilmaz M. Preparation of one-pot immobilized lipase with Fe3O4 nanoparticles into metal-organic framework for enantioselective hydrolysis of (R, S)-naproxen methyl ester. ChemCatChem 2021 13 16 3687 3694 10.1002/cctc.202100481
    [Google Scholar]
  78. Ascioglu S. Ozyilmaz E. Yildirim A. Sayin S. Yilmaz M. Preparation of two new chiral metal-organic frameworks for lipase immobilization and their use as biocatalysis in the enantioselective hydrolysis of racemic naproxen methyl ester. Int. J. Biol. Macromol. 2024 282 Pt 2 136946 10.1016/j.ijbiomac.2024.136946 39490851
    [Google Scholar]
  79. Thakur S. Riyaz B. Patil A. Kaur A. Kapoor B. Mishra V. Novel drug delivery systems for NSAIDs in management of rheumatoid arthritis: An overview. Biomed. Pharmacother. 2018 106 1011 1023 10.1016/j.biopha.2018.07.027 30119166
    [Google Scholar]
  80. Laine L. Approaches to nonsteroidal anti-inflammatory drug use in the high-risk patient. Gastroenterology 2001 120 3 594 606 10.1053/gast.2001.21907 11179238
    [Google Scholar]
  81. Tomić M. Micov A. Pecikoza U. Stepanović-Petrović R. Clinical uses of nonsteroidal anti-inflammatory drugs (NSAIDs) and potential benefits of NSAIDs modified-release preparations, Microsized and nanosized carriers for nonsteroidal anti-inflammatory drugs. Elsevier 2017 1 29
    [Google Scholar]
  82. Aletaha D. Neogi T. Silman A.J. Funovits J. Felson D.T. Bingham C.O. III Birnbaum N.S. Burmester G.R. Bykerk V.P. Cohen M.D. Combe B. Costenbader K.H. Dougados M. Emery P. Ferraccioli G. Hazes J.M.W. Hobbs K. Huizinga T.W.J. Kavanaugh A. Kay J. Kvien T.K. Laing T. Mease P. Ménard H.A. Moreland L.W. Naden R.L. Pincus T. Smolen J.S. Stanislawska-Biernat E. Symmons D. Tak P.P. Upchurch K.S. Vencovský J. Wolfe F. Hawker G. 2010 Rheumatoid arthritis classification criteria: An American College of Rheumatology/European League against Rheumatism collaborative initiative. Arthritis Rheum. 2010 62 9 2569 2581 10.1002/art.27584 20872595
    [Google Scholar]
  83. Chalan P. van den Berg A. Kroesen B.J. Brouwer L. Boots A. Rheumatoid arthritis, immunosenescence and the hallmarks of aging. Curr. Aging Sci. 2015 8 2 131 146 10.2174/1874609808666150727110744 26212057
    [Google Scholar]
  84. Gibofsky A. Overview of epidemiology, pathophysiology, and diagnosis of rheumatoid arthritis. Am. J. Manag. Care 2012 18 13 Suppl. S295 S302 23327517
    [Google Scholar]
  85. Piplani S. Jelic V. Johnson A. Shah U. Kolli S. Kong S. Tanasijevic N. Bejugam V.R. Goguri S.R. Mogga P. Kasire S.P. Chaturvedi S. Jain P. Prevalence, causes and outcomes of acute gastrointestinal bleeding in rheumatoid arthritis: a systematic review and meta-analysis. Mediterr. J. Rheumatol. 2024 35 2 210 219 10.31138/mjr.230324.pca 39211013
    [Google Scholar]
  86. Sadiq M. Ahmad I. Kazmi T. Kazmi U. Hyder N. Comparative study of oral naproxen and aspirin for acute rheumatic fever treatment: Safety and efficacy analysis. Pak. Heart J. 2024 57 2 153 158 10.47144/phj.v57i2.2717
    [Google Scholar]
  87. Okafo S.E. Ordu J.I. Ofagbor G. Agbamu E. Evaluation of physicochemical, in vivo analgesic and antiinflammatory activities of Brachystegia eurycoma gum-based naproxen loaded niosomal gels. Ger. J. Pharm. Biomater. 2023 2 1 26 37 10.5530/gjpb.2023.1.3
    [Google Scholar]
  88. Babasahib S.K. Born R.W. Raghavendra N.M. Trans ethosomal hybrid composites of naproxen-sulfapyridine in hydrogel carrier: Anti-inflammatory response in complete Freund’s adjuvant induced arthritis rats. Artif. Cells Nanomed. Biotechnol. 2022 50 1 59 70 10.1080/21691401.2022.2047712 35261304
    [Google Scholar]
  89. Akhtar M.F. Zubair S. Saleem A. Alsharif K.F. Abdel-Daim M.M. Comparison of individual and combination treatments with naproxen, prednisolone and hydroxychloroquine to treat complete freund’s adjuvant induced arthritis. Inflammopharmacology 2021 29 6 1719 1731 10.1007/s10787‑021‑00875‑y 34550498
    [Google Scholar]
  90. Anjum F. Zakir F. Verma D. Aqil M. Singh M. Jain P. Mirza M.A. Anwer M.K. Iqbal Z. Exploration of nanoethosomal transgel of naproxen sodium for the treatment of arthritis. Curr. Drug Deliv. 2020 17 10 885 897 10.2174/1567201817666200724170203 32713340
    [Google Scholar]
  91. Varagani S. A comparative study on assessment of safety and efficacy of diclofenac, naproxen and etoricoxib in reducing pain in osteoarthritis patients-an observational study. Int. J. Curr. Res. Med. Sci 2024 10 8 31 38
    [Google Scholar]
  92. Sambrook P. Naganathan V. 4 What is the relationship between osteoarthritis and osteoporosis? Baillieres Clin. Rheumatol. 1997 11 4 695 710 10.1016/S0950‑3579(97)80005‑2 9429732
    [Google Scholar]
  93. Hussain S.M. Neilly D.W. Baliga S. Patil S. Meek R.M.D. Knee osteoarthritis: A review of management options. Scott. Med. J. 2016 61 1 7 16 10.1177/0036933015619588 27330013
    [Google Scholar]
  94. Neogi T. Dell’Isola A. Englund M. Turkiewicz A. Frequent use of prescription NSAIDs among people with knee or hip osteoarthritis despite contraindications to or precautions with NSAIDs. Osteoarthritis Cartilage 2024 32 12 1628 1635 10.1016/j.joca.2024.07.010 39068982
    [Google Scholar]
  95. Cioroianu G.O. Florescu A. Simionescu C.E. Sas T.N. Tarniţă D.N. Rogoveanu O.C. The therapeutic benefits of NSAIDs and physical therapy in knee osteoarthritis. Rom. J. Morphol. Embryol. 2024 65 2 217 224 10.47162/RJME.65.2.08 39020536
    [Google Scholar]
  96. Faheem A.N. Ali A. Shamim A. Mohapatra S. Siddiqui A. Iqbal Z. Mirza M.A. Development of a naproxen and gaultheria oil based topical nanoemulsion for the amelioration of osteoarthritis. RSC Pharmaceutics 2024 1 3 498 512 10.1039/D4PM00059E
    [Google Scholar]
  97. Monteiro J.D.B.B. Pinto C.B. Schnitzer T. 288 - pain rating variability as a predictor of treatment response in osteoarthritis clinical trials. Osteoarthritis and cartilage 2024 32 1 209
    [Google Scholar]
  98. Munir M. Khan A. Sayyar T. Mufti M. Siddiqui I. Abbasi S.T. Comparison of naproxen and diacerein in the treatment of knee joint osteoarthritis. J. Rawalpindi Med. Coll. 2023 27 3 10.37939/jrmc.v27i3.2034
    [Google Scholar]
  99. Paglia D.N. Kanjilal D. Kadkoy Y. Moskonas S. Wetterstrand C. Lin A. Galloway J. Tompson J. Culbertson M.D. O’Connor J.P. Naproxen treatment inhibits articular cartilage loss in a rat model of osteoarthritis. J. Orthop. Res. 2021 39 10 2252 2259 10.1002/jor.24937 33274763
    [Google Scholar]
  100. Heidari-Beni M. Moravejolahkami A.R. Gorgian P. Askari G. Tarrahi M.J. Bahreini-Esfahani N. Herbal formulation “turmeric extract, black pepper, and ginger” versus Naproxen for chronic knee osteoarthritis: A randomized, double-blind, controlled clinical trial. Phytother. Res. 2020 34 8 2067 2073 10.1002/ptr.6671 32180294
    [Google Scholar]
  101. Syed Y.Y. Sumatriptan/naproxen sodium: A review in migraine. Drugs 2016 76 1 111 121 10.1007/s40265‑015‑0521‑8 26628293
    [Google Scholar]
  102. Kelman L. The triggers or precipitants of the acute migraine attack. Cephalalgia 2007 27 5 394 402 10.1111/j.1468‑2982.2007.01303.x 17403039
    [Google Scholar]
  103. Ettlin D.A. The international classification of headache disorders, 3rd edition (beta version). Cephalalgia 2013 33 9 629 808 10.1177/0333102413485658 23771276
    [Google Scholar]
  104. Pehlivanlar E. Carradori S. Simsek R. Migraine and its treatment from the medicinal chemistry perspective. ACS Pharmacol. Transl. Sci. 2024 7 4 951 966 10.1021/acsptsci.3c00370 38633587
    [Google Scholar]
  105. Puledda F. Sacco S. Diener H.C. Ashina M. Al-Khazali H.M. Ashina S. Burstein R. Liebler E. Cipriani A. Chu M.K. Cocores A. Dodd-Glover F. Ekizoğlu E. Garcia-Azorin D. Göbel C. Goicochea M.T. Hassan A. Hirata K. Hoffmann J. Jenkins B. Kamm K. Lee M.J. Ling Y.H. Lisicki M. Martinelli D. Monteith T.S. Ornello R. Ozge A. Peres M. Pozo-Rosich P. Romanenko V. Schwedt T.J. Souza M.N.P. Takizawa T. Terwindt G.M. Thuraiaiyah J. Togha M. Vandenbussche N. Wang S.J. Yu S. Tassorelli C. International headache society global practice recommendations for the acute pharmacological treatment of migraine. Cephalalgia 2024 44 8 03331024241252666 10.1177/03331024241252666 39133176
    [Google Scholar]
  106. Ruscheweyh R. Dresler T. Förderreuther S. Gaul C. Gossrau G. Jürgens T.P. Ruschil V. Straube A. Scheidt J. What do patients’ efficacy and tolerability ratings of acute migraine medication tell us? Cross-sectional data from the DMKG Headache Registry. Cephalalgia 2023 43 5 10.1177/03331024231174855 37177799
    [Google Scholar]
  107. Nanaware S. Nayak A. Jain A.P. Development and characterization of nasal In-Situ gel of sumatriptan and naproxen for effctive treatment of migraine using 32 factorial designs. Int. J. Adv. Sci. Res. 2021 12 02 Suppl. 2 273 283
    [Google Scholar]
  108. Joshi S.S. Nemichandra S.C. Harsha S. Prashant A. Paneyala S. Iqbal R. Colaco K.V.C. Assessment of alteration of serum adiponectin levels in migraineurs: An interventional case control study. Ann. Neurosci. 2020 27 3-4 148 152 10.1177/0972753121990141 34556953
    [Google Scholar]
  109. Cady R. O’Carroll P. Dexter K. Freitag F. Shade C.L. SumaRT/Nap vs naproxen sodium in treatment and disease modification of migraine: A pilot study. Headache 2014 54 1 67 79 10.1111/head.12211 24021029
    [Google Scholar]
  110. Weisman S.M. Brunton S. Efficacy and safety of naproxen for acute pain. J. Fam. Pract. 2020 69 7 Suppl Suppl. S33 S38 10.12788/jfp.0064 33104105
    [Google Scholar]
  111. Amaechi O. Huffman M.M. Featherstone K. Pharmacologic therapy for acute pain. Am. Fam. Physician 2021 104 1 63 72 34264611
    [Google Scholar]
  112. Weisman S. Naproxen for post-operative pain. J. Pharm. Pharm. Sci. 2021 24 62 70 10.18433/jpps31629 33600307
    [Google Scholar]
  113. Muhammad N. Khan R. Seraj F. Khan A. Ullah U. Wadood A. Ajmal A. Uzma Ali B. Khan K.M. Ain Nawaz N.U. AlMasoud N. Alomar T.S. Rauf A. In vivo analgesic, anti-inflammatory and molecular docking studies of S-naproxen derivatives. Heliyon 2024 10 2 e24267 10.1016/j.heliyon.2024.e24267 38304837
    [Google Scholar]
  114. Haddadi R. Cheraghi-poor M. Peroxisome proliferator activated receptor-gamma (PPAR-γ) ligand, pioglitazone, increases analgesic and anti-inflammatory effects of naproxen. Naunyn Schmiedebergs Arch. Pharmacol. 2024 397 3 1633 1646 10.1007/s00210‑023‑02715‑y 37698622
    [Google Scholar]
  115. Cigerim L. Kaplan V. Analgesic efficacy of naproxen-codeine, naproxen+dexamethasone, and naproxen on myofascial pain: A randomized double-blind controlled trial. Cranio 2023 41 2 119 125 10.1080/08869634.2020.1824411 32941116
    [Google Scholar]
  116. Khan B.A. Ahmad S. Khan M.K. Hosny K.M. Bukhary D.M. Iqbal H. Murshid S.S. Halwani A.A. Alissa M. Menaa F. Fabrication and characterizations of pharmaceutical emulgel co-loaded with naproxen-eugenol for improved analgesic and anti-inflammatory effects. Gels 2022 8 10 608 10.3390/gels8100608 36286109
    [Google Scholar]
  117. Cooper S.A. Desjardins P.J. Bertoch T. Paredes-Diaz A. Troullos E. Tajaddini A. Centofanti R. An R. Morella D. Analgesic efficacy of naproxen sodium versus hydrocodone/acetaminophen in acute postsurgical dental pain: a randomized, double-blind, placebo-controlled trial. Postgrad. Med. 2022 134 5 463 470 10.1080/00325481.2021.2008180 34878953
    [Google Scholar]
  118. Simmons D.L. Wagner D. Westover K. Nonsteroidal anti-inflammatory drugs, acetaminophen, cyclooxygenase 2, and fever. Clin. Infect. Dis. 2000 31 Suppl. 5 S211 S218 10.1086/317517 11113025
    [Google Scholar]
  119. Aronoff D.M. Neilson E.G. Antipyretics: Mechanisms of action and clinical use in fever suppression. Am. J. Med. 2001 111 4 304 315 10.1016/S0002‑9343(01)00834‑8 11566461
    [Google Scholar]
  120. Josa M. Urizar J. Rapado J. Dios-Viéitez C. Castañeda-Hernández G. Flores-Murrieta F. Renedo M.J. Trocóniz I.F. Pharmacokinetic/pharmacodynamic modeling of antipyretic and anti-inflammatory effects of naproxen in the rat. J. Pharmacol. Exp. Ther. 2001 297 1 198 205 10.1016/S0022‑3565(24)29528‑8 11259545
    [Google Scholar]
  121. Mehmood K.T. Al-Baldawi S. Zúñiga Salazar G. Zúñiga D. Balasubramanian S. Antipyretic use in noncritically ill patients with fever: A review. Cureus 2024 16 1 e51943 10.7759/cureus.51943 38333494
    [Google Scholar]
  122. Çetin İ.İ. Sürücü M. Arı M.E. Kibar A.E. Azak E. Eminoğlu S. Çevik B.Ş. Kocabaş A. Ekici F. Orgun A. The efficacy and safety of naproxen in acute rheumatic fever: The comparative results of 11-year experience with acetylsalicylic acid and naproxen. Turk. J. Pediatr. 2016 58 5 473 479 10.24953/turkjped.2016.05.003 28621087
    [Google Scholar]
  123. Krekels E.H.J. Angesjö M. Sjögren I. Ängeby Möller K. Berge O.G. Visser S.A.G. Pharmacokinetic-pharmacodynamic modeling of the inhibitory effects of naproxen on the time-courses of inflammatory pain, fever, and the ex vivo synthesis of TXB2 and PGE2 in rats. Pharm. Res. 2011 28 7 1561 1576 10.1007/s11095‑011‑0389‑6 21347567
    [Google Scholar]
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  • Article Type:
    Review Article
Keywords: lipase ; biocatalysis ; Cyclooxygenase (Cox) ; S-naproxen ; Analgesic ; inflammation
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