Commercially viable resolution of ibuprofen

Abstract

Ibuprofen belongs to the non-steroidal anti-inflammatory drug (NSAID) family known as profens. Studies demonstrate that (S-ibuprofen is 160 times more potent than (R-ibuprofen in vitro, while the accumulation of (R-ibuprofen can cause serious side effects such as gastrointestinal pain. Candida rugosa lipase was used to enantioselectively esterify racemic ibuprofen with decan-1-ol and butan-1-ol in cyclohexane with an enantiomeric ratio (E) of 130 and 46, respectively, in up to 46% conversion. Separation by bulb-to-bulb distillation of (R)-ibuprofen and unreacted alcohol from the corresponding (S)-alkyl ibuprofen ester was possible for the decyl but not the butyl case. The enantioselective hydrolysis of (S)-alkyl ibuprofen esters with the same biocatalyst in aqueous phosphate buffer was twice as slow for the decyl alcohol versus the butyl example. The combined environmentally friendly enantioselective esterification and hydrolysis of ibuprofen insured the isolation of (S)-ibuprofen with a greater than 99% enantiomeric excess.

Attitude of Dentists Towards the Administration of Analgesics for Management of Post-Endodontic Pain in Hamadan

“…In our study, the most frequently prescribed painkiller for endodontic pain in patients with renal insufficiency was acetaminophen (77.5%) followed by ibuprofen (11.3%), mefenamic acid (6.3%), tramadol (3.8%) and aspirin (1.3%). Considering renal side effects of ibuprofen and aspirin discussed in studies by Chavez-Flores and Lanes, acetaminophen is used for pain relief as the analgesic of choice for patients with renal insufficiency (39,40). In our study, most dentists prescribed acetaminophen for these patients, which is in agreement with previous studies (39,40).…”

“…Considering renal side effects of ibuprofen and aspirin discussed in studies by Chavez-Flores and Lanes, acetaminophen is used for pain relief as the analgesic of choice for patients with renal insufficiency (39,40). In our study, most dentists prescribed acetaminophen for these patients, which is in agreement with previous studies (39,40). When prescribing a combination of two analgesics, most understudy dentists recommended a combination of acetaminophen and ibuprofen.…”

Enzymatic Hydrolytic Resolution of Racemic Ibuprofen Ethyl Ester Using an Ionic Liquid as Cosolvent

“…4 ]-buffer (30:70, v/v) system, the conversion degree and enantiomeric excess of product increased sharply with increasing temperature from 45 to 75˝C, with the optimum reaction temperature being 75˝C (Figure 3). This is slightly higher than that used in solvent-free systems (70˝C) [20].…”

“…However, (S)-ibuprofen is about 160 times more active than (R)-ibuprofen. Moreover, the presence of (R)-ibuprofen can cause serious side effects, such as gastrointestinal tract irritation, and disruption of normal lipid metabolism and membrane function [4,5]. Therefore, much effort has been therefore devoted to the production of pure (S)-ibuprofen.…”

“…For example, the stability of lipases such as CaLB [13][14][15][16] and Pseudomonas cepacia lipase (PcL) [15,17] are catalytically active in imidazolium and pyridinium ILs containing BF 4´, PF 6´a nd Tf 2 N´ [14]. [OmPy][BF 4 ] provide high enantioselectivity to hesperidinase when used as co-solvent in the enzymatic conversion of rutin to isoquercitrin. The reaction time decreased 0.33-fold, and the rutin conversion and isoquercitrin yield increased 1.67-fold and 2.33-fold, respectively, in [OmPy] [BF 4 ] -containing buffer systems.…”