Determination of the Lipophilicity of Ibuprofen, Naproxen, Ketoprofen, and Flurbiprofen with Thin-Layer Chromatography

Abstract

The lipophilicity is an important parameter that influences the activity of the drugs in the human body. The reversed phase high performance thin layer chromatography was applied to determine the Log P values of ibuprofen, ketoprofen, naproxen, and flurbiprofen. The stationary phase used in the study was silica-gel coated plates. The mobile phase was the mixture of acetonitrile and water in different proportions. The content of acetonitrile varied in 5% increments from 50% to 80%. The Rm0 values were determined for the compounds with a known Log P and for the analyzed substances (ibuprofen, naproxen, ketoprofen, and flurbiprofen). The Log P values were calculated for the analyzed compounds using the regression curve Rm0 = f(Log P) parameters for the compounds with the known lipophilicity. Flurbiprofen is characterized by the highest Log P value: 3.82. The lowest one is noted for ketoprofen: 2.66. The determined Log P values of tested compounds were similar to the values calculated by the software.

Comparison of the Utility of RP-TLC Technique and Different Computational Methods to Assess the Lipophilicity of Selected Antiparasitic, Antihypertensive, and Anti-inflammatory Drugs

“…The parameters characterizing the lipophilic properties of flurbiprofen and ketoprofen determined by Soczewiński-Wachtmeister’s and Ościk’s methods in this paper have lower values in relation to the values of logP reported by Czyrski [28]. The exception is ketoprofen, whose R MWO(m) value is 3.76, which is higher than the literature values of logP.…”

“…In a work prepared by Czyrski [28], the lipophilicity among other NSAIDs like ketoprofen and flurbiprofen using RP-18F 254 plates and the mobile phase composed of acetonitrile and water was studied. The R m0 values were determined for the compounds with a known logP and for ketoprofen (1.8491) and flurbiprofen (2.5076), respectively.…”

The effect of alcohols as vehicles on the percutaneous absorption and skin retention of ibuprofen modified with l-valine alkyl esters

“…However, it is characterized by low solubility (21 mg dm À3 at 25 C in water) and relative high lipophilicity (log P is in the range of 2.41-4.00 the value depends on the measurement method) which result in its poor permeation through the skin. [14][15][16][17][18][19][20][21] Due to the acidic nature (pK a ¼ 4.4), its solubility is dependent on the pH of the environmentit increases with increasing alkalinity: it can vary from 0.024 mg cm À3 (pH ¼ 2.2) to 14.8 mg dm À3 (pH ¼ 9.2). This is closely related to the increase in the ionization degree, which in turn determines the ability of ibuprofen to penetrate the skin.…”

Synthesis and application of magnetic@layered double hydroxide as an anti-inflammatory drugs nanocarrier

“…The release rate of Ibuprofen was 90% within 24 h, 94% in 48 h, and 96% in 72 h. The values for Diclofenac in 24 h 78%, within 48 h of 81% in 72 h and 82%, respectively, indicating less Diclofenac release in comparison to Ibuprofen per unit of time. This can be due to lower solubility in water [ 34 ], highly lipophilicity [ 35 ] of Diclofenac, small size, and more sterile effect of Diclofenac compared to Ibuprofen [ 36 ] that cannot be easily released between layers. The release gradually arrived the maximum amount of 90% for Ibuprofen and 78% for Diclofenac in the first 6 h. On the other hand, the most absorbed drug in the outer layer of the Fe 3 O 4 @LDH and bonded drug to the substrate by its hydrogen bonds release in the 24 h especially in first 6 h which is useful for quickly developing as a therapeutic dose.…”