Cas no 51543-39-6 ((S)-Flurbiprofen)

(S)-Flurbiprofen is the (S)-enantiomer of flurbiprofen, a nonsteroidal anti-inflammatory drug (NSAID) with potent cyclooxygenase (COX) inhibitory activity. As the biologically active form, (S)-Flurbiprofen exhibits superior efficacy in reducing inflammation and pain compared to its (R)-enantiomer. It selectively targets COX-2 with higher affinity, minimizing gastrointestinal side effects associated with non-selective COX inhibition. The compound is widely utilized in pharmaceutical research for studying enantioselective drug metabolism and chiral drug development. Its high purity and well-defined stereochemistry make it valuable for mechanistic studies and preclinical applications. (S)-Flurbiprofen is also employed as a reference standard in analytical methods, ensuring accurate quantification and quality control in drug formulations.
(S)-Flurbiprofen structure
(S)-Flurbiprofen structure
Product Name:(S)-Flurbiprofen
CAS No:51543-39-6
MF:C15H13FO2
MW:244.260927915573
MDL:MFCD00866152
CID:372129
PubChem ID:72099
Update Time:2025-05-21

(S)-Flurbiprofen Chemical and Physical Properties

Names and Identifiers

    • (S)-2-(2-Fluoro-[1,1'-biphenyl]-4-yl)propanoic acid
    • (S)-(+)-2-Fluoro-α-methyl-4-biphenylacetic acid
    • (S)-(+)-Flurbiprofen
    • (S)-2-(2-Fluorobiphenyl-4-yl)propanoic acid
    • (S)-2-Flurbiprofen
    • (S)-Flurbiprofen
    • [1,1'-Biphenyl]-4-aceticacid, 2-fluoro-a-methyl-,(aS)-
    • Flurbiprofen
    • S-flurbiprofen
    • d-Flurbiprofen
    • Esflurbiprofen
    • tarenflurbil
    • TT-063
    • UNII-J5ZZK9P7MX
    • ESFLURBIPROFEN [INN]
    • NCI60_030811
    • (2S)-2-(2-fluorobiphenyl-4-yl)propanoic acid
    • 51543-39-6
    • NS00088502
    • NSC685700
    • D10254
    • MFCD00866152
    • HMS3884I06
    • s1679
    • SCHEMBL505817
    • AKOS016844131
    • ESFLURBIPROFEN [JAN]
    • CCG-266907
    • Flurbiprofen, (s)-
    • BTS 24332
    • SR-01000946685
    • HMS2232E18
    • BTS-24332
    • HMS3649P05
    • MLS001066337
    • Esflurbiprofen [INN:BAN]
    • DTXSID201316678
    • Esflurbiprofenum [Latin]
    • SR-01000946685-1
    • BDBM50172479
    • BCP24046
    • EINECS 257-263-1
    • (S)-(+)-2-Fluoro-alpha-methyl-4-biphenylacetic acid
    • Esflurbiprofen (JAN)
    • GTPL9420
    • (S)-2-(2-Fluoro-[1,1'-biphenyl]-4-yl)propanoicacid
    • Q27104495
    • AS-78108
    • (2S)-2-(3-fluoro-4-phenylphenyl)propanoic acid
    • A21120
    • (S)-(+)-2-Fluoro-alpha-methyl-4-biphenylacetic acid (Flurbiprofen)
    • SFPP
    • HY-15123
    • (S)-2-Fluoro-alpha-methyl(1,1'-biphenyl)-4-acetic acid
    • (S)-2-FLUORO-.ALPHA.-METHYL-4-BIPHENYLACETIC ACID
    • MLS001333208
    • ESFLURBIPROFEN [WHO-DD]
    • (2S)-2-(2-fluoro-[1,1'-biphenyl-4-yl])propanoic acid
    • J5ZZK9P7MX
    • Esflurbiprofeno
    • CHEMBL435298
    • Esflurbiprofenum
    • Urbifen
    • (S)-2-Fluoro-alpha-methyl-4-biphenylacetic acid
    • (+)-Flurbiprofen
    • FLP
    • CS-0003779
    • SW202926-2
    • Flurwood
    • Esflurbiprofeno [Spanish]
    • SMR000471846
    • Esflurbiprofene [French]
    • NCI60_030810
    • flurbiprofen-(S)-(+)
    • (S)-(+)-2-Fluoro-?-methyl-4-biphenylacetic acid
    • Esflurbiprofene
    • (S)-(+)-2-Fluoro-.alpha.-methyl-4-biphenylacetic acid
    • MLS001333207
    • CHEBI:42446
    • NSC-685700
    • BRD-K69907333-001-07-2
    • DB-008733
    • BRD-K69907333-001-10-6
    • MDL: MFCD00866152
    • Inchi: 1S/C15H13FO2/c1-10(15(17)18)12-7-8-13(14(16)9-12)11-5-3-2-4-6-11/h2-10H,1H3,(H,17,18)/t10-/m0/s1
    • InChI Key: SYTBZMRGLBWNTM-JTQLQIEISA-N
    • SMILES: FC1C=C(C=CC=1C1C=CC=CC=1)[C@@H](C(=O)O)C

Computed Properties

  • Exact Mass: 244.09000
  • Monoisotopic Mass: 244.09
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 18
  • Rotatable Bond Count: 3
  • Complexity: 286
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: nothing
  • Topological Polar Surface Area: 37.3A^2

Experimental Properties

  • Color/Form: Not available
  • Density: 1.2±0.1 g/cm3
  • Melting Point: 109-110?°C(lit.)
  • Boiling Point: 376.2±30.0 °C at 760 mmHg
  • Flash Point: 207.9±28.7 °C
  • Refractive Index: 1.567
  • PSA: 37.30000
  • LogP: 3.68080
  • Solubility: Not available

(S)-Flurbiprofen Security Information

(S)-Flurbiprofen Pricemore >>

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Additional information on (S)-Flurbiprofen

Introduction to (S)-Flurbiprofen (CAS No. 51543-39-6)

(S)-Flurbiprofen, a chiral isomer with the chemical compound identification number CAS No. 51543-39-6, is a widely recognized nonsteroidal anti-inflammatory drug (NSAID) that has garnered significant attention in the field of pharmaceutical chemistry and medicine. This compound, belonging to the propionic acid derivative class, exhibits potent anti-inflammatory, analgesic, and antipyretic properties, making it a valuable therapeutic agent in the management of various inflammatory conditions.

The pharmacological activity of (S)-Flurbiprofen is primarily attributed to its selective inhibition of cyclooxygenase enzymes (COX-1 and COX-2), which are crucial in the biosynthesis of prostaglandins—mediators of inflammation and pain. Unlike its racemic mixture, flurbiprofen, the (S)-enantiomer has been shown to possess enhanced pharmacological efficacy with fewer gastrointestinal side effects, a finding that has driven extensive research into its mechanisms of action and therapeutic applications.

Recent studies have highlighted the unique pharmacokinetic profile of (S)-Flurbiprofen, which includes a rapid absorption rate and prolonged half-life upon oral administration. These characteristics make it particularly effective in providing sustained relief from inflammatory conditions such as osteoarthritis and rheumatoid arthritis. Moreover, preclinical trials have demonstrated its potential in reducing post-operative pain and inflammation, positioning it as a promising candidate for perioperative analgesia.

In the realm of drug development, (S)-Flurbiprofen has been utilized as a model compound to investigate the relationship between enantiomeric purity and therapeutic outcome. The synthesis of this enantiomer requires precise stereochemical control, often employing advanced catalytic methods such as asymmetric hydrogenation. These synthetic strategies not only ensure high enantiomeric excess but also contribute to the overall sustainability of pharmaceutical manufacturing processes.

Emerging research also suggests that (S)-Flurbiprofen may have additional therapeutic benefits beyond its traditional anti-inflammatory role. For instance, studies have explored its potential neuroprotective effects in models of neuroinflammation, indicating that it could be repurposed for conditions such as Alzheimer's disease or traumatic brain injury. These findings underscore the compound's multifaceted pharmacological properties and its potential for broadening therapeutic applications.

The safety profile of (S)-Flurbiprofen has been extensively evaluated through multiple clinical trials, which have consistently shown it to be well-tolerated at therapeutic doses. However, like all NSAIDs, it is associated with certain risks, including cardiovascular events and gastrointestinal adverse effects. Consequently, healthcare providers must weigh these risks against the benefits when prescribing this medication, particularly for patients with pre-existing comorbidities.

Advances in analytical chemistry have enabled more precise quantification and characterization of (S)-Flurbiprofen in pharmaceutical formulations. Techniques such as high-performance liquid chromatography (HPLC) and mass spectrometry are routinely employed to ensure compliance with regulatory standards and to monitor enantiomeric purity throughout the drug lifecycle. These analytical methods are critical in maintaining the consistency and efficacy of the final product.

The role of computational modeling in understanding the interactions between (S)-Flurbiprofen and biological targets has also gained prominence. Molecular docking studies have provided insights into how this compound binds to COX enzymes at an atomic level, facilitating the design of more potent derivatives with improved selectivity profiles. Such computational approaches complement experimental investigations by offering predictive insights into drug-drug interactions and potential side effects.

From a regulatory perspective, (S)-Flurbiprofen is subject to stringent guidelines set forth by agencies such as the U.S. Food and Drug Administration (FDA) and the European Medicines Agency (EMA). These regulations ensure that all marketed formulations meet rigorous quality standards while addressing unmet medical needs effectively. The evolving landscape of regulatory requirements continues to influence how pharmaceutical companies develop and commercialize this compound.

In conclusion, (S)-Flurbiprofen represents a significant advancement in NSAID therapy due to its enhanced efficacy and improved safety profile compared to its racemic counterpart. Ongoing research into its mechanisms of action, synthetic methodologies, and therapeutic applications promises to further expand its utility in medicine. As scientific understanding evolves, so too will our appreciation for this versatile pharmacological agent.

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