Article · Wikipedia archive · Last revised Jul 17, 2026

Indoprofen

Indoprofen is a nonsteroidal anti-inflammatory drug (NSAID). It was withdrawn worldwide in the 1980s after postmarketing reports of severe gastrointestinal bleeding.

Last revised
Jul 17, 2026
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≈ 1 min
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Citations
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Wikipedia ↗
Indoprofen
Clinical data
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • Withdrawn
Pharmacokinetic data
BioavailabilityHigh (rapid and complete absorption)
MetabolismGlucuronidation
Elimination half-life2.3 hours
ExcretionRenal
Identifiers
  • 2-[4-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)
    phenyl]propanoic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.046.197
Chemical and physical data
FormulaC17H15NO3
Molar mass281.311 g·mol−1
3D model (JSmol)
  • O=C(O)C(c1ccc(cc1)N3C(=O)c2ccccc2C3)C
  • InChI=1S/C17H15NO3/c1-11(17(20)21)12-6-8-14(9-7-12)18-10-13-4-2-3-5-15(13)16(18)19/h2-9,11H,10H2,1H3,(H,20,21) checkY
  • Key:RJMIEHBSYVWVIN-UHFFFAOYSA-N checkY

Indoprofen is a nonsteroidal anti-inflammatory drug (NSAID). It was withdrawn worldwide in the 1980s after postmarketing reports of severe gastrointestinal bleeding.1

A 2004 study using high-throughput screening found indoprofen to increase production of the survival of motor neuron protein, suggesting it may provide insight into treatments for spinal muscular atrophies.12

Synthesis

The isoindolone ring system forms the nucleus for this profen NSAID.

The nitro group in 2-(4-nitrophenyl)propionic acid (1) is reduced using iron and hydrochloric acid to give 2-(4-aminophenyl)propionic acid (2). Reaction with phthalic anhydride then gives the phthalimide (4). Treatment with zinc in acetic acid yields indoprofen after reduction of one of the amide groups.345

See also

See also

References

References

  1. Frazin N (March 9, 2005). "Pain Reliever May Provide Clues for Treating Spinal Muscular Atrophy". United States National Institute of Neurological Disorders and Stroke. Archived from the original on 2008-07-04. Retrieved 2007-10-06.
  2. Lunn MR, Root DE, Martino AM, Flaherty SP, Kelley BP, Coovert DD, et al. (November 2004). "Indoprofen upregulates the survival motor neuron protein through a cyclooxygenase-independent mechanism". Chemistry & Biology. 11 (11): 1489–93. doi:10.1016/j.chembiol.2004.08.024. PMC 3160629. PMID 15555999.
  3. US patent 4316850, Richard W. J. Carney and George de Stevens, "Tertiary aminoacids", issued 1982-02-23, assigned to Ciba Geigy Corp 
  4. Nannini G, Giraldi PN, Molgora G, Biasoli G, Spinelli F, Logemann W, et al. (August 1973). "New analgesic-anti-inflammatory drugs. 1-Oxo-2-substituted isoindoline derivatives". Arzneimittel-Forschung. 23 (8): 1090–100. doi:10.1002/chin.197344288. PMID 4801034.
  5. "Indoprofen". Pharmaceutical Substances. Thieme. Retrieved 2024-07-11.