(R)-Flurbiprofen Axetil
Product Code：F019051
English Name：(R)-Flurbiprofen Axetil
English Alias：(2R)-1-acetoxyethyl 2-(2-fluoro-[1,1'-biphenyl]-4-yl)propanoate
CAS No.：2375240-97-2
Molecular Formula：C₁₉H₁₉FO₄
Molecular Weight：330.35
High Optical Purity：Confirmed by HPLC (ee ≥99.0%), NMR with chiral shift reagents, and X-ray crystallography, suitable for stereoisomer impurity analysis of Flurbiprofen Axetil.
Stability Assurance：Stable for 36 months at -20℃ under light-protected, sealed storage; degradation rate <0.1% in ethanol-water solution within 6 months.
Chiral Impurity Control：Used for UPLC-MS/MS detection of (R)-isomer in Flurbiprofen Axetil API and formulations, controlling optical impurity content to meet ICH Q3A standards (≤0.5%).
Process Optimization Research：Monitors (R)-Flurbiprofen Axetil formed during asymmetric esterification, improving (S)-isomer selectivity by >90% via adjusting chiral catalyst dosage (e.g., Salen-Co complex) and temperature (0-5℃).
Method Validation：Serves as a chiral standard for developing isomer separation methods, verifying UPLC resolution (≥3.5) and LOD (0.005 ng/mL).
Flurbiprofen Axetil, a non-steroidal anti-inflammatory drug (NSAID), is used for postoperative analgesia, with the (S)-isomer as the active component. The (R)-isomer may exhibit lower anti-inflammatory activity and potential toxicity. As a chiral impurity, (R)-Flurbiprofen Axetil may originate from incomplete racemic resolution or side reactions in asymmetric synthesis. With stricter FDA requirements for chiral drug impurity control, studying such stereoisomers is crucial for ensuring drug safety.
Detection Technology：UPLC-MS/MS with Chiralpak IB column (1.7μm) and n-hexane-ethanol (90:10) gradient elution achieves separation within 4 minutes, with LOD of 0.002 ng/mL for trace chiral impurity analysis.
Formation Mechanism：Formed by reaction of flurbiprofen with (R)-1-acetoxyethanol under acidic catalysis (e.g., p-toluenesulfonic acid). Using enzymatic catalysis (e.g., porcine pancreatic lipase) or asymmetric hydrogenation reduces (R)-isomer formation by >85%.
Safety Evaluation：In vitro cytotoxicity shows IC₅₀ of 78.6 μM against THP-1 cells ((S)-Flurbiprofen Axetil IC₅₀=8.2 μM), with low toxicity but requiring ≤0.5% limit. Accelerated stability testing is ongoing to monitor racemization rates under different pH conditions.
This product is intended for laboratory use only!
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