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(S)-(+)-Ibuprofen

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(S)-(+)-Ibuprofen Basic information
(S)-(+)-Ibuprofen Chemical Properties
  • Melting point:49-53 °C(lit.)
  • alpha 57 º (c=2, EtOH)
  • Boiling point:285.14°C (rough estimate)
  • Density 1.0364 (rough estimate)
  • refractive index 59 ° (C=2, EtOH)
  • Flash point:>230 °F
  • storage temp. Store at RT
  • solubility 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 1.5 mg/mL
  • pka4.41±0.10(Predicted)
  • form solid
  • color white
  • optical activity[α]20/D +59°, c = 2 in ethanol
  • Water Solubility insoluble
  • BRN 3590022
  • Stability:Stable. Incompatible with strong oxidizing agents.
  • InChIKeyHEFNNWSXXWATRW-JTQLQIEISA-N
  • CAS DataBase Reference51146-56-6(CAS DataBase Reference)
Safety Information
  • Hazard Codes Xn
  • Risk Statements 63-22
  • Safety Statements 45-36/37
  • WGK Germany 3
  • HS Code 29163990
MSDS
(S)-(+)-Ibuprofen Usage And Synthesis
  • DescriptionDexibuprofen, 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.
  • Chemical PropertiesColourless, Crystalline Solid
  • OriginatorGebro Broschek (Austria)
  • UsesA nonsteroidal anti-inflammatory drug (NSAID); activity resides primarily in the (S)-isomer
  • Usessedative
  • UsesIbuprofen is a non-steroidal anti-inflammatory drug with diverse biochemical actions, most notably inhibiting COX-1 and COX-2 (IC50s = 2.6 and 1.53, μM, respectively). It is commonly synthesized as a racemic mixture of (S)- and (R)-isomers. (S)-Ibuprofen is an enantiomer that more potently inhibits COX activity, thromboxane formation, and platelet aggregation than the (R)-form. (S)-Ibuprofen also inhibits activation of NF-κB more effectively than (R)-ibuprofen (IC50s = 62 and 122 μM, respectively). However, the enantiomers are equipotent in blocking superoxide formation, β-glucuronidase release, and LTB4 generation by stimulated neutrophils (IC50 values range from 0.14 to 0.58 μM). A majority of (R)-ibuprofen can be inverted to (S)-ibuprofen in humans after oral administration.
  • brand nameSeractil
  • Biological ActivityNon-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.
  • Purification MethodsCrystallise 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.]
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