# Indoprofen

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Indoprofen
> Markdown URL: https://mediated.wiki/source/Indoprofen.md
> Source: https://en.wikipedia.org/wiki/Indoprofen
> Source revision: 1268657758
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

**Indoprofen** is a [nonsteroidal anti-inflammatory drug](/source/Nonsteroidal_anti-inflammatory_drug) (NSAID). It was withdrawn worldwide in the 1980s after postmarketing reports of severe [gastrointestinal bleeding](/source/Gastrointestinal_bleeding).[1]

A 2004 study using [high-throughput screening](/source/High-throughput_screening) found indoprofen to increase production of the [survival of motor neuron](/source/Survival_of_motor_neuron) protein, suggesting it may provide insight into treatments for [spinal muscular atrophies](/source/Spinal_muscular_atrophy).[1][2]

## Synthesis

The [isoindolone](/source/Isoindolone) ring system forms the nucleus for this [profen](/source/Profen_(drug_class)) 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](/source/Phthalic_anhydride) then gives the [phthalimide](/source/Phthalimide) (4). Treatment with zinc in acetic acid yields indoprofen after [reduction](/source/Reduction_(chemistry)) of one of the [amide](/source/Amide) groups.[3][4][5]

## See also

- [Indobufen](/source/Indobufen)

## References

1. Frazin, Natalie (March 9, 2005). ["Pain Reliever May Provide Clues for Treating Spinal Muscular Atrophy"](https://web.archive.org/web/20080704145021/http://www.ninds.nih.gov/news_and_events/news_articles/news_article_SMA_indoprofen.htm). United States [National Institute of Neurological Disorders and Stroke](/source/National_Institute_of_Neurological_Disorders_and_Stroke). Archived from [the original](http://www.ninds.nih.gov/news_and_events/news_articles/news_article_SMA_indoprofen.htm) on 2008-07-04. Retrieved 2007-10-06.

1. 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 (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](https://doi.org/10.1016/j.chembiol.2004.08.024). [PMC 3160629](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3160629). [PMID 15555999](https://pubmed.ncbi.nlm.nih.gov/15555999)

1. "Tertiary aminoacids". No. 4316850.

1. Nannini G, Giraldi PN, Molgora G, Biasoli G, Spinelli F, Logemann W, Dradi E, Zanni G, Buttinoni A, Tommasini R (August 1973). "New analgesic-anti-inflammatory drugs. 1-Oxo-2-substituted isoindoline derivatives". *Arzneimittel-Forschung*. **23** (8): 1090–100. [doi:10.1002/chin.197344288](https://doi.org/10.1002/chin.197344288). [PMID 4801034](https://pubmed.ncbi.nlm.nih.gov/4801034)

1. ["Indoprofen"](https://pharmaceutical-substances.thieme.com/ps/search-results?query=Indoprofen). *Pharmaceutical Substances*. Thieme. Retrieved 2024-07-11.

---
Adapted from the Wikipedia article [Indoprofen](https://en.wikipedia.org/wiki/Indoprofen) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Indoprofen?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.