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Routes of administration | Oral |
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Pharmacokinetic data | |
Bioavailability | High (rapid and complete absorption) |
Metabolism | Glucuronidation |
Elimination half-life | 2.3 hours |
Excretion | Renal |
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ECHA InfoCard | 100.046.197 |
Chemical and physical data | |
Formula | C17H15NO3 |
Molar mass | 281.311 g·mol−1 |
3D model (JSmol) | |
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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 It was withdrawn worldwide in the 1980s after postmarketing reports of severe gastrointestinal bleeding.[1]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]
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]
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pyrazolones / pyrazolidines |
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salicylates |
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acetic acid derivatives and related substances |
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oxicams |
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propionic acid derivatives (profens) |
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n-arylanthranilic acids (fenamates) |
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COX-2 inhibitors (coxibs) |
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other |
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NSAID combinations |
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Key: underline indicates initially developed first-in-class compound of specific group; #WHO-Essential Medicines; †withdrawn drugs; ‡veterinary use. | |
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