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| ECHA InfoCard | 100.049.622 |
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| Formula | C13H17NO2 |
| Molar mass | 219.284 g·mol−1 |
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Alminoprofen is anon-steroidal anti-inflammatory drug.[1][2] the non-proprietary namealminoprofen is derived from the compound's chemical name 2-(4-[{2-methylallyl}amino]phenyl)propanic acid.
Alminoprofen exists as twoenantiomers; thestereocenter is located at thebenzyl group.
Although the pharmacology of non-steroidal anti-inflammatory drugs (non-steroidal anti-inflammatory drug) has been extensively studied, their mechanisms of action at the immunological level are not yet fully understood. Alminoprofen is a newer NSAID with a characteristic anti-inflammatory profile mediated through inhibition ofcyclooxygenases andphospholipase A2 activity.[3]
The effects of alminoprofen were examined in animal studies and compared with those ofibuprofen. At a dose of 30 mg/kg administered intraduodenally, alminoprofen significantly suppressed passiveanaphylactic reaction-induced bronchoconstriction, whereas ibuprofen at the same dose did not. In vitro studies demonstrated that alminoprofen, unlike ibuprofen, inhibitsarachidonate-5-lipoxygenase activity, which initiates the biosynthesis ofleukotrienes. Alminoprofen inhibitedarachidonic acid-induced ear edema in mice and homologous passive cutaneousanaphylaxis in rats at high doses, whereas ibuprofen showed no such effect at comparable doses.[4]
The multistep synthesis of alminoprofen is shown in the following reaction sequence:[5]
The synthesis begins withpara-nitrophenylacetic acid as the starting material. The first step is aMannich reaction withformaldehyde anddimethylamine. The second step is anelimination reaction forming a terminalalkene. In the third step, both the alkene and thenitro group are reduced usingpalladium on carbon as thecatalyst andhydrogen as thereducing agent. The final step is anucleophilic substitution in which thearyl groupamine acts as the nucleophile. The product is aracemate.
{{citation}}: CS1 maint: multiple names: authors list (link){{citation}}: CS1 maint: multiple names: authors list (link){{citation}}: CS1 maint: multiple names: authors list (link){{citation}}: CS1 maint: multiple names: authors list (link)| pyrazolones / pyrazolidines | |
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| acetic acid derivatives and related substances | |
| oxicams | |
| propionic acid derivatives (profens) |
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| n-arylanthranilic acids (fenamates) | |
| COX-2 inhibitors (coxibs) | |
| other | |
| NSAID combinations | |
Key:underline indicates initially developed first-in-class compound of specific group;#WHO-Essential Medicines;†withdrawn drugs;‡veterinary use. | |
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