L-Ibuprofen

Conte, U. Giunchedi, P. Maggi, L. Sangalli, M.E. Gazzaniga, A. Colombo, P. Manna, A.L. Ibuprofen delayed release dosage forms a proposal for the preparation of an in vitro/in vivo pulsatile system. Eur. J. Pharm. Biopharm. 1992, 38 (6), 209-212. 

Other asymmetric synthetic processes used for the manufacturing of (S)-(-l-)-naproxen can also be applied to the production of (S)-(-l-)-ibuprofen these include the Rh-phosphite catalyzed hydroformylation [33], hydrocyanation [21], and hydrocarboxylation reactions [20],... 

Sample preparation Condition an Analytichem AASP propylbenzenesulfonic acid (SCX) SPE cartridge with isopropanol at 4 mL/min for 1.5 min and with mobile phase at 4 mL/min for 2 min. 100 p-L Ibuprofen solution in dichloromethane + 100 pL 500 pg/mL... 

B.H. (2006) (S)-(-l-)-Ibuprofen-based hydrogelators an approach toward antiinflammatory drug delivery. Tetrahedron Lett., 47, 7153-7156. 

The same technique was used by Kowalska and coworkers [29] to investigate the oscillatory transenantiomerization of some profens [i.e., S-(-l-)-ibuprofen, 5-(-l-)-naproxen, and S,/ -( )-2-phenylpropionic acid] when stored in 70% ethanol at two different temperatures (6 C and 22°C). In this work, the instability of various optical antipodes was pointed out and attributed to change their steric configurations from the S-form to the i -form, and vice versa. Such phenomenon, which took place by a keto-enol tautomerism, was much more remarkable at low temperatures. 

Bhushan, R. and Parshad, V., Resolution of (-l-)-ibuprofen using L-arginine-impregnated thin-layer chromatography, /. Chromatogr. A, 721, 369-372, 1996. 

It was discovered that 3-iiitro-2-piperidiiio-, 3-iiitro-7-piperidiiio-, and 7-A -diethaiiolamiiio-3-iiitro-l, 8-iiaphthyridiii-2(lH)-oiies and 2-diethanol-amino-7-piperidino-3-nitro-l,8-naphthyridine showed remarkable aetivity to inhibit human platelet aggregation in vitro indueed by araehidonie aeid, eollagen, and ADR Tliis aetivity was eomparable to papaverine, dipyridamole, and ibuprofen (94EJMC735). 

C2H3CIO 75-36-5) see Acebutolol Acetiamine Acetylcholine chloride L-Alanine Benfurodil hemisuccinate . Chlorprothixene Flumetasone Ibuprofen lotalamic acid loxitalamic acid Levodopa Methestrol dipropionate Midecamycin acetate Naproxen Nimesulide Paclitaxel Paramethasone Phensuximide Retinol Rocuronium bromide Rofecoxib Ropinirole Tazarotene Thiopropazate Tiracizine Vecuronium bromide... 

CHN 74-90-8) see L-Alanine Alfentanil Dimethadione Edetic acid Ibuprofen Indanorex Mecamylamine Molsidomine Nadoxolol D-Penicillamine Phensuximide L-Tryptophan Vetrabutine hydrogen peroxide... 

Derrick studied the interaction of L-tryptophan and ibuprofen with human serum albumin (HSA),74 which is an abundant transport blood protein capable of binding efficiently several species.75 They acquired 1H NMR spectra of L-Tryptophan-HSA system for different ligand protein molar ratios, that is 3 1, 5 1, 7 1 and 10 1. The aromatic resonances of L-Tryptophan are difficult to be observed due to the overlap with HSA signals, even at 10 1 molar ratio, so that the spectral subtraction was performed. D values of L-Tryptophan were calculated by integration of the subtracted spectra and were in good agreement with those predicted by computer simulations. In the case of ibuprofen, only for 140 1 molar ratio, the resonances of ibuprofen are clearly visible also in this case, the... 

Ibuprofen LAC from T. versicolor Flask scale 10 mg L-1 Negligible after 24 h, even [3]... 

Kwakman et al. [65] described the synthesis of a new dansyl derivative for carboxylic acids. The label, N- (bromoacetyl)-A -[5-(dimethylamino)naphthalene-l-sulfonyl]-piperazine, reacted with both aliphatic and aromatic carboxylic acids in less than 30 min. Excess reagent was converted to a relatively polar compound and subsequently separated from the derivatives on a silica cartridge. A separation of carboxylic acid enantiomers was performed after labeling with either of three chiral labels and the applicability of the method was demonstrated by determinations of racemic ibuprofen in rat plasma and human urine [66], Other examples of labels used to derivatize carboxylic acids are 3-aminoperylene [67], various coumarin compounds [68], 9-anthracenemethanol [69], 6,7-dimethoxy-l-methyl-2(lH)-quinoxalinone-3-propionylcarboxylic acid hydrazide (quinoxalinone) [70], and a quinolizinocoumarin derivative termed Lumarin 4 [71],... 

When a preparation of ibuprofen was administered to a patient, the volume of distribution was found to be 5 L, and the half-life of elimination was 2 hours. What is the total clearance of ibuprofen ... 

A comparison between carbamoylmethyl and aminoalkyl esters has been reported for a small series of prodrugs of ibuprofen (8.28) [39]. A further interest of this work is the systematic comparison made between the enantiomers of ibuprofen, i. e., the active (+)-(S)-form and the inactive (-)-(/ )-form. As shown in Table 8.4, the ethyl esters were hydrolyzed very slowly in human plasma, with t1/2 values in the order of 100 - 200 h. In contrast, the hydrolysis of the carbamoylmethyl and aminoalkyl esters occurred with t1/2 values in the order of some or several minutes. The carbamoylmethyl esters were hydrolyzed very rapidly with low substrate enantioselectivity, while the 2-(imidazol-l-yl)ethyl esters were hydrolyzed somewhat more slowly and with marked substrate enantioselectivity. 

Ibuprofen (8.28) and naproxen (8.26) were derivatized with the same l-[(ethoxycarbonyl)oxy] ethyl pro-moiety to yield two prodrugs designated as... 

FIG. 12. Permeability of ibuprofen from different formulations via excised human stratum comeum. Redrawn from Stoye, L, Permeabilitdtsverdnderung von humanem Stratum corneum nach Applikation nicht-steroidaler Antirheumatika in verschiedenen kolloidalen Trdgersystemen, Ph.D. Thesis TU Braunschweig, 1997. 

Interestingly, when a water-soluble bisphosphine, a 86/14 mixture of tetra- and trisulfonated l,3-bis(diphenylphosphino)propane was used as ligand, the rate of carbonylation did not change considerably, however, the selectivity to Ibuprofen was only 22 % and the major product was 3-IPPA (78 %). 

Carbonylation of IBPE and other 2-arylethanols with various organosoluble Pd-catalysts was studied in detail with special emphasis on the role of the promoters p-toluenesulfonic acid and LiCl [55], Some of the catalytic species, such as [PdCl(PPh3)2] formed from [Pd(PPh3)4] or from Pd(II) precursors in aqueous methylethylketone (MEK) under reaction conditions (54 bar CO, 105 °C) were identified by P NMR spectroscopy. Ibuprofen was obtained in a fast reaction (TOP = 850 h" ) with 96% yield (3-IPPA 3.9 %), while the carbonylation of l-(6-methoxynaphtyl)ethanol gave 2-(6-methoxynaphtyl)propionic acid (Naproxen) with high selectivity (97.2 %) but with moderate reaction rates (TOP = 215 h" ). 

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