Medicinal Chemistry Research

, Volume 23, Issue 1, pp 503–517 | Cite as

Novel ibuprofen prodrugs with improved pharmacokinetics and non-ulcerogenic potential

  • Valmik D. Dhakane
  • Hemant V. Chavan
  • Vishnu N. Thakare
  • Laxman K. Adsul
  • Sadanand N. Shringare
  • Babasaheb P. Bandgar
Original Research


In the present study, we evaluated the anti-inflammatory activity with pharmacokinetic, ulcerogenic properties of various synthesized prodrugs of ibuprofen in experimental animals. Prodrugs 2, 6, 9, 10, 12, and 14 were found to possess significant anti-inflammatory activity with almost non-ulcerogenic potential than standard drug ibuprofen 1a in both normal and inflammation-induced rats. Metabolic stability of prodrugs 2, 6, 9, 10, 12, and 14 were also studied in rat liver microsomes and oral bioavailability was determined by estimating area under curve (AUC) and plasma concentration of these prodrugs at various time intervals. The experimental findings elicited higher AUC and plasma concentration at 1 and 2 h indicating improved oral bioavailability as compared to parent ibuprofen. These prodrugs are found to have least gastric ulceration with retain anti-inflammatory activity observed in experimental animals. Therefore, present experimental findings demonstrated significant improvement of various pharmacokinetic properties with least ulcerogenic potential of ester prodrugs of ibuprofen an anti-inflammatory agent


Prodrug Ibuprofen Anti-inflammatory activity Non-ulcerogenic Pharmacokinetic properties 



Nonsteroidal anti-inflammatory drug


Tris(hydroxymethyl)aminomethane hydrochloride


Nicotinamide adenine dinucleotide phosphate


High performance liquid chromatography


Gas chromatography


Rat liver microsomes


Rat plasma


Active pharmaceutical ingredient


Ulcer index




Dimethyl acetamide


p-Toluene sulfonic acid


Powder X-ray diffraction


Room temperature


1,1,3,3-Tetramethyl guanidine

18 Crown 6



European pharmacopoeia




Below detection limit


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Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • Valmik D. Dhakane
    • 1
  • Hemant V. Chavan
    • 1
  • Vishnu N. Thakare
    • 2
  • Laxman K. Adsul
    • 1
  • Sadanand N. Shringare
    • 1
  • Babasaheb P. Bandgar
    • 1
  1. 1.Medicinal Chemistry Research Laboratory, School of Chemical SciencesSolapur UniversitySolapurIndia
  2. 2.Department of PharmacologySinhgad Institute of Pharmaceutical SciencesLonavalaIndia

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