{{Short description|Withdrawn NSAID drug}} {{Drugbox | IUPAC_name = 2-[4-(1-oxo-1,3-dihydro-2''H''-isoindol-2-yl)<br />phenyl]propanoic acid | image = Indoprofen.svg | image_class = skin-invert-image
<!--Clinical data--> | tradename = | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_status = Withdrawn | routes_of_administration = Oral
<!--Pharmacokinetic data--> | bioavailability = High (rapid and complete absorption) | protein_bound = | metabolism = Glucuronidation | elimination_half-life = 2.3 hours | excretion = Renal
<!--Identifiers--> | CAS_number_Ref = {{cascite|correct|CAS}} | CAS_number = 31842-01-0 | ATC_prefix = M01 | ATC_suffix = AE10 | PubChem = 3718 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB08951 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 3587 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = CPE46ZU14N | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D04530 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 76162 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 15870
<!--Chemical data--> | C=17 | H=15 | N=1 | O=3 | smiles = O=C(O)C(c1ccc(cc1)N3C(=O)c2ccccc2C3)C | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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) | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = RJMIEHBSYVWVIN-UHFFFAOYSA-N }}
'''Indoprofen''' is a nonsteroidal anti-inflammatory drug (NSAID). It was withdrawn worldwide in the 1980s after postmarketing reports of severe gastrointestinal bleeding.<ref name=NINDS>{{cite web | url = http://www.ninds.nih.gov/news_and_events/news_articles/news_article_SMA_indoprofen.htm | last = Frazin | first = Natalie | name-list-style = vanc | title = Pain Reliever May Provide Clues for Treating Spinal Muscular Atrophy | date = March 9, 2005 | access-date = 2007-10-06 | publisher = United States National Institute of Neurological Disorders and Stroke | archive-date = 2008-07-04 | archive-url = https://web.archive.org/web/20080704145021/http://www.ninds.nih.gov/news_and_events/news_articles/news_article_SMA_indoprofen.htm | url-status = dead }}</ref>
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.<ref name=NINDS/><ref>{{cite journal | vauthors = 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 | display-authors = 6 | title = Indoprofen upregulates the survival motor neuron protein through a cyclooxygenase-independent mechanism | journal = Chemistry & Biology | volume = 11 | issue = 11 | pages = 1489–93 | date = November 2004 | pmid = 15555999 | pmc = 3160629 | doi = 10.1016/j.chembiol.2004.08.024 }}</ref>
==Synthesis== The isoindolone ring system forms the nucleus for this profen NSAID. :class=skin-invert-image|upright=2 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.<ref>{{cite patent |country=US |number=4316850 |inventor=Richard W. J. Carney and George de Stevens |title=Tertiary aminoacids |status=patent |gdate=1982-02-23 |fdate=1972-11-17 |assign1=Ciba Geigy Corp}}</ref><ref>{{cite journal | vauthors = Nannini G, Giraldi PN, Molgora G, Biasoli G, Spinelli F, Logemann W, Dradi E, Zanni G, Buttinoni A, Tommasini R | display-authors = 6 | title = New analgesic-anti-inflammatory drugs. 1-Oxo-2-substituted isoindoline derivatives | journal = Arzneimittel-Forschung | volume = 23 | issue = 8 | pages = 1090–100 | date = August 1973 | pmid = 4801034 | doi = 10.1002/chin.197344288 }}</ref><ref>{{cite web |url=https://pharmaceutical-substances.thieme.com/ps/search-results?query=Indoprofen |title=Indoprofen |work=Pharmaceutical Substances |publisher=Thieme |access-date=2024-07-11}}</ref>
==See also== *Indobufen == References == {{Reflist}}
{{Anti-inflammatory and antirheumatic products}} {{Prostanoidergics}}
Category:Nonsteroidal anti-inflammatory drugs Category:Withdrawn drugs Category:Isoindolines Category:Lactams Category:Propionic acids
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