(R)-Ketoprofen

Last updated

(R)-Ketoprofen
R-Ketoprofen.svg
Clinical data
Routes of
administration 		Oral
Legal status
Legal status
  • Investigational
Identifiers
  • (2R)-2-(3-benzoylphenyl)propanoic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C16H14O3
Molar mass 254.285 g·mol−1
3D model (JSmol)
  • C[C@H](C1=CC(=CC=C1)C(=O)C2=CC=CC=C2)C(=O)O
  • InChI=InChI=1S/C16H14O3/c1-11(16(18)19)13-8-5-9-14(10-13)15(17)12-6-3-2-4-7-12/h2-11H,1H3,(H,18,19)/t11-/m1/s1
  • Key:DKYWVDODHFEZIM-LLVKDONJSA-N

(R)-Ketoprofen (also called R(-)-ketoprofen) is the optically pure R-enantiomer of the NSAID ketoprofen. It functions as a cyclooxygenase inhibitor and has been investigated for potential use in conditions including tinnitus and neuropathic pain, although it is not approved for these indications. [1]

Contents

Background and development

This method for treating tinnitus includes administration of substantially optically pure R(-)-ketoprofen. [2]

Mechanism of action

As with other NSAIDs, R-ketoprofen inhibits the cyclooxygenase enzymes, thereby reducing the production of prostaglandins, which mediate inflammation, pain and potentially neurogenic processes. Its proposed application in tinnitus stems from the hypothesis that inflammatory or prostaglandin-mediated mechanisms might contribute to cochlear or auditory pathway dysfunction-associated tinnitus. [3]

Furthermore, the patent includes the statement that R-ketoprofen may be used in "methods of treating or preventing tinnitus or ringing in the ear" including conditions such as acoustic trauma, ototoxicity, cardiovascular diseases causing hearing loss. [4]

Investigational indications

Tinnitus

The patent application discloses R-ketoprofen for the treatment or prevention of tinnitus. [5]

Neuropathic pain

The development overview also mentions "Phase-II for Neuropathic pain in USA (PO)" for R-ketoprofen. As of the last available update 2003, no further progression in trial reporting is publicly documented. [6]

References

  1. ↑ "Methods for the treatment of tinnitus and other disorders using R(−)-ketoprofen". Google Patents. Sepracor, Inc. Retrieved 2025-11-12.
  2. ↑ "Methods for the treatment of tinnitus and other disorders using R(−)-ketoprofen (US6362227B1)". Google Patents. Sepracor, Inc. Retrieved 2025-11-12.
  3. ↑ Bang M, Lee SH, Cho SH, Yu SA, Kim K, Lu HY, et al. (2017). "Herbal Medicine Treatment for Children with Autism Spectrum Disorder: A Systematic Review". Evidence-Based Complementary and Alternative Medicine. 2017: 8614680. doi: 10.3389/fncel.2017.00192 . PMC   5448044 . PMID   28592982.
  4. ↑ "Methods for the treatment of tinnitus and other disorders using R(−)-ketoprofen (US6362227B1)". Google Patents. Sepracor, Inc. Retrieved 2025-11-12.
  5. ↑ "Methods for the treatment of tinnitus and other disorders using R(−)-ketoprofen (US6362227B1)". Google Patents. Sepracor, Inc. Retrieved 2025-11-12.
  6. ↑ "R-ketoprofen – AdisInsight Drug Profile". AdisInsight / Springer Nature. Retrieved 2025-11-12.
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