(S)-(+)-Ibuprofen Chemische Eigenschaften,Einsatz,Produktion Methoden
R-Sätze Betriebsanweisung:
R63:Kann das Kind im Mutterleib möglicherweise schädigen.
R22:Gesundheitsschädlich beim Verschlucken.
S-Sätze Betriebsanweisung:
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
Beschreibung
Dexibuprofen, the S-(+)-isomer of the widely used NSAID agent ibuprofen, was
launched in Austria for the treatment of rheumatoid arthritis. While the racemic
compound is commonly used clinically, the antiinflammatory activity is mediated via
the S-isomer by inhibition of prostaglandin synthesis. It has also been
demonstrated that the R-isomer is converted to the Santipode in vivo via a CoA
thioester intermediate. Since CoA plays a pivotal role in intermediary metabolism
and maintenance of the [acyl-CoA], generation of R-ibuprofen-CoA competitively
inhibits many CoA-dependent reactions, which consequently produces
perturbations of hepatocyte Intermediary metabolism and mitocondrial function.
Pure S-ibuprofen usage, therefore, is preferred allowing a reduction in dosage level
and an improved side effect profile.
Chemische Eigenschaften
Colourless, Crystalline Solid
Verwenden
A nonsteroidal anti-inflammatory drug (NSAID); activity resides primarily in the (S)-isomer
Allgemeine Beschreibung
(
S)-(+)-Ibuprofen is the enantiomer associated with the anti-inflammatory action of ibuprofen, which is widely used as a nonsteroidal anti-inflammatory drug in racemic form.
Biologische Aktivität
Non-steroidal anti-inflammatory drug (NSAID) that inhibits cyclooxygenase 1 and cyclooxygenase 2 (IC 50 values are 12 and 80 μ M respectively). Active isomer of ibuprofen.
läuterung methode
Crystallise the (+) and (-) acids from EtOH or aqueous EtOH. The racemate which crystallises from pet ether with m 75-77o is sparingly soluble in H2O and has IR (film) 1705 (C=O), 2300—3700 (OH broad)cm-1. It is used as a non-steroidal anti-inflammatory. [Shiori et al. J Org Chem 43 2936 1978, Kaiser et al. J Pharm Sci 65 269 1976, J Pharm Sci 81 221 1992, Freer Acta Cryst (C) 49 1378 1993 for the (S+)-enantiomer.]
(S)-(+)-Ibuprofen Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
