Indoprofen Explained

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 It was withdrawn worldwide in the 1980s after postmarketing reports of severe gastrointestinal bleeding.^[1]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.^{[1] [2]}

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.^{[3] [4] [5]}

See also

• Indobufen

Notes and References

1. Web site: Pain Reliever May Provide Clues for Treating Spinal Muscular Atrophy . Frazin . Natalie . vanc . March 9, 2005 . 2007-10-06 . . 2008-07-04 . https://web.archive.org/web/20080704145021/http://www.ninds.nih.gov/news_and_events/news_articles/news_article_SMA_indoprofen.htm . dead .
2. Lunn MR, Root DE, Martino AM, Flaherty SP, Kelley BP, Coovert DD, Burghes AH, Man NT, Morris GE, Zhou J, Androphy EJ, Sumner CJ, Stockwell BR . 6 . Indoprofen upregulates the survival motor neuron protein through a cyclooxygenase-independent mechanism . Chemistry & Biology . 11 . 11 . 1489–93 . November 2004 . 15555999 . 3160629 . 10.1016/j.chembiol.2004.08.024 .
3. US . 4316850 . Richard W. J. Carney and George de Stevens . Tertiary aminoacids . patent . 1982-02-23 . 1972-11-17 . Ciba Geigy Corp.
4. Nannini G, Giraldi PN, Molgora G, Biasoli G, Spinelli F, Logemann W, Dradi E, Zanni G, Buttinoni A, Tommasini R . 6 . New analgesic-anti-inflammatory drugs. 1-Oxo-2-substituted isoindoline derivatives . Arzneimittel-Forschung . 23 . 8 . 1090–100 . August 1973 . 4801034 . 10.1002/chin.197344288 .
5. Web site: Indoprofen . Pharmaceutical Substances . Thieme . 2024-07-11.