Chromatographic Resolution, Chiroptical Characterization and Preliminary Pharmacological Evaluation of the Enantiomers of Butibufen: a Comparison with Ibuprofen

Q3 · MEDICINE

Article

Author: Hoult, J R S ; Benicka, E ; Hutt, A J ; Jackson, B R ; Patel, B K

AbstractEnantiomeric resolution of butibufen has been achieved on a cellulose tris(3,5-dimethylphenylcarbamate) chiral stationary phase with hexane-isopropanol-trifluoroacetic acid, 100: 1.2: 0.02 (v/v/v) as mobile phase at a flow rate of 1.0 mL min−1.Semi-preparative isolation of the enantiomers then chiroptical characterization indicated that the order of elution was (-)-R- before (+)-S-butibufen. When tested for their effects on the cyclooxygenase and 5-lipoxygenase pathways of eicosanoid metabolism in calcium ionophore-activated rat peritoneal leukocytes it was found that (+) -S-butibufen inhibited generation of thromboxane B2 (TXB2) and prostaglandin E2 (PGE2) (cyclooxygenase pathway), with an IC50 of 1.5 μ (approx.), whereas the (-)-R enantiomer was essentially inactive. Neither enantiomer inhibited the 5-lipoxygenase pathway. In this regard, (+)-S-butibufen was approximately five times less potent as a cyclooxygenase inhibitor than (+)-S-ibuprofen.These results show the enantiomeric specificity and pathway selectivity of this novel non-steroidal anti-inflammatory drug.

01 Feb 1997·Bioorganic & Medicinal ChemistryQ3 · MEDICINE

Conversion of cyclooxygenase inhibitors into hydroxythiazole 5-lipoxygenase inhibitors

Q3 · MEDICINE

Article

Author: Jennifer B. Bouska ; Randy L. Bell ; Keren I. Hulkower ; Francis A.J. Kerdesky ; Clint D.W. Brooks

Representative examples of NSAID cyclooxygenase inhibitors such as naproxen, ibufenac, ibuprofen, and butibufen have been transformed into 5-lipoxygenase inhibitors by replacement of the carboxylic acid moiety with a 4-hydroxythiazole group.

01 Jun 1995·Methods and findings in experimental and clinical pharmacology

Influence of butibufen on enzyme activity and lysosomal stabilization ex vivo: a comparative study with hydrocortisone and acetylsalicylic acid.

Article

Author: Alguacil, L F ; Ferrándiz, B ; Alamo, C ; López-Muñoz, F

Here we report the results of a study on the influence of butibufen (50 and 250 mg/kg) on enzyme activity and lysosomal membrane stabilization. The influence of hydrocortisone acetate (25 and 75 mg/kg) and acetylsalicylic acid (ASA) (50 mg/kg) was comparatively studied. We determined beta-glucuronidase and acid phosphatase free and total activity and the ratio between both types of activity (a ratio which indicates lysosomal membrane stability). This determination was carried out using hepatic homogenates from Sprague-Dawley rats. The drugs were administered orally 18 and 3 h before sacrifice. The results show that none of the drugs used in this study modify free or total beta-glucuronidase activity. The ratio between free and total activity of this enzyme was not modified by the drugs when compared to controls. On the contrary, the figures for acid phosphatase were modified by all the drugs employed, showing statistical significance (p < 0.001 for 250 mg/kg butibufen and 75 mg/kg hydrocortisone and p < 0.001 for 50 mg/kg ASA). The ratio of free/total activity was modified only by hydrocortisone (75 mg/kg) (p < 0.001). Thus our results indicated that the antiinflammatory drugs employed in this study can reduce acid phosphatase activity and only hydrocortisone seems to be able to stabilize the lysosomal membrane. Acid phosphatase enzyme inhibition might partially contribute to the antiinflammatory action of these drugs.

100 Deals associated with Butibufen Sodium

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Indication	Country/Location	Organization	Date
Pain	AR	Merck KGaA	31 May 2000
Inflammation	-	-	-
Rheumatoid Arthritis	-	-	-

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