Pharmaceuticals ibuprofen

Buser, H.-R., Poiger, T. and Muller, M. D. (1999). Occurrence and environmental behaviour of the chiral pharmaceutical ibuprofen in surface waters and in waste-water, Environ. Sci. Technol., 33, 2529-2535. 

This study also suggests that molecular size and structure play a role in this interaction. The binding behaviors of dextrin oligomers for four different pharmaceuticals (ibuprofen, ketoprofen, furosemide, and warfarin) were observed under the same experimental conditions. Ibuprofen and ketoprofen, two compounds that are similar in chemical structure and pharmaceutical use, showed obvious differences in interaction patterns (Fig. 13A and B). Ketoprofen, having an extra aromatic ring, required an octa-saccharide (DP = 8) for binding, whereas ibuprofen required a heptasac-... 

Huppert N, Wtirtele M, Hahn HH (1998) Determination of the plasticizer N-butylbenzenesulfonamide and the pharmaceutical Ibuprofen in waste water using solid phase microextraction (SPME). Fresenius J Anal Chem 362, 529-536. 

Considerable advances in asymmetric hydroformylation, a process which, among other things, provides a potential route to enantiomericaHy pure biologically active compounds, have occurred. Of particular interest are preparations of nonsteroidal antiinflammatory (NSAI) pharmaceuticals such as Naproxen (8) and Ibuprofen (9), where the represents a chiral center. 

Lipase-catalyzed kinetic resolutions are often practical for the preparation of optically active pharmaceuticals (61). For example, suprofen [40828-46-4] (45), which is a nonsteroidal antiinflamatory dmg, can be resolved by Candida glindracea]i 2Lse in >95% ee at 49% conversion (61). Moreover, hpase-based processes for the resolution of naproxen [22204-53-1] and ibuprofen [15687-27-1] (61) have also been developed. 

To get around this problem, pharmaceutical companies attempt to devise methods of enantioselective synthesis, which allow them to prepare only a single enantiomer rather than a racemic mixture. Viable methods have already been developed for the preparation of (5)-ibuprofen, which is now being marketed in Europe. We ll look further into enantioselective synthesis in the Chapter 19 Focus On. 

Hydroformylation has been extensively studied since it produces optically active aldehydes which could be important precursors for pharmaceutical and fine chemical compounds. Thus, asymmetric hydroformylation of styrene (Scheme 27) is a model reaction for the synthesis of ibuprofen or naproxen. Phosphorus ligands were used for this reaction with excellent results, espe-... 

Stuer et al. [46] evaluated the presence of the 25 most used pharmaceuticals in the primary health sector in Denmark (e.g., paracetamol, acetyl salicylic acid, diazepam, and ibuprofen). They compared PECs with experimental determinations and they conclude that measured concentrations were in general within a factor of 2-5 of PECs. Carballa et al. [45] also determined PECs for pharmaceuticals (17), musk fragrances (2) and hormones (2) in sewage sludge matrix. For that purpose they used three different approaches (1) extrapolation of the per capita use in Europe to the number of Spanish inhabitants for musk fragrances (2) annual prescription items multiplied by the average daily dose for pharmaceuticals and (3) excretion rates of different groups of population for hormones. They indicated that these PECs fitted with the measured values for half of them (carbamazepine, diazepam, ibuprofen, naproxen, diclofenac, sulfamethoxazole, roxithromycin, erythromycin, and 17a-ethiny I e strad iol). 

Recently, with the development of more advanced and sensitive analytical methods, studies on the fate of pharmaceuticals in WWTP have taken into account the analysis of pharmaceuticals sorbed into sludge (Table 4, and references therein). The antiseptics triclocarban and triclosan and the antibiotic ofloxacin have been reported in sludge at concentrations up to 441, 133, and 58 mg kgdw-1, respectively. Compounds such as the anti-inflammatory ibuprofen, the antiepileptic carbamazepine and the antidepressant fluoxetine have also frequently been reported though at lower levels (11,6 and 3 mg kgdw 1, respectively), whereas the (3-blockers were found at low... 

In order to determine more precisely the fate of pharmaceuticals during sludge treatment, different experiments have been conducted in controlled conditions. In continuous anaerobic reactors treating sludge spiked with pharmaceuticals, Carballa et al. [114] observed removals higher than 80% for naproxen, sulfamethoxazole, and roxithromycin, while 40% and 23% of ibuprofen and iopromide, respectively, were eliminated at both mesophilic (37°C) and thermophilic (55°C) temperatures. For diclofenac and diazepam, elimination of about 60% was observed in mesophilic conditions while in thermophilic conditions, 38% and 73% of these two compounds, respectively, were eliminated. In these experiments, the sludge retention time (15 or 30 days) did not seem to influence pharmaceutical removal... 

During the aerobic thermophilic treatment of sludge, ibuprofen and galaxolide were removed, respectively, 95% and more than 75% of initial concentrations after 20 days of incubation. However, even after 45 days incubation no complete elimination was observed [61]. Observations in composted sludge, which is considered to be an aerobic treatment, showed that several pharmaceuticals, including carbamazepine, diphenhydramine, fluoxetine, and triclosan, were not significantly removed by composting at mesophilic or thermophilic temperatures [148]. 

Along similar lines, the presence of related substances found in pharmaceutical drugs may be estimated by using HPLC method, for examples atenolol, buclizine hydrochloride, ibuprofen, and the like. 

Pharmaceutical grade ibuprofen, pseudoephedrine HCl, chlorpheniramine maleate, nipagen and syrup preparation were kindly supplied by Berko tlag Sanayi A. , Istanbul. 0.03 M H PO and KH PO solutions were prepared with analytical grade chemicals and milliQ water. HPLC grade acetoiutrile was used. 

---