ChemInform Abstract: Antiinflammatory Agents. Part 4. Syntheses and Biological Evaluation of Potential Prodrugs of 2‐Amino‐3‐benzoylbenzeneacetic Acid and 2‐ Amino‐3‐(4‐chlorobenzoyl)benzeneacetic Acid.

Abstract

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Pharmacology, clinical efficacy and safety of nepafenac ophthalmic suspension

“…converted to 2-amino-3-benzoylbenzeneacetic acid (amfenac) -a NSAID with an arylacetic acid structure exhibiting potent antipyretic and analgesic properties. The anti-inflammatory and analgesic properties of amfenac are mediated through inhibition of COX-1 and COX-2 [14]. The prodrug nepafenac has a low inherent COX-inhibiting activity.…”

“…As a prodrug, nepafenac is the less active form of the drug that is converted to its more active form, amfenac, after a metabolic conversion through intraocular enzymatic hydrolysis [14]. Nepafenac appears to inhibit vitreal protein and PGE 2 synthesis better than other NSAIDs [8,9,12,13,16].…”

“…The prodrug nepafenac has a low inherent COX-inhibiting activity. It is metabolically converted to the active form and then exerts the desired antiinflammatory effect [14]. Nepafenac is the amide analog of amfenac and is designated chemically as 2-amino-3-benzoylbenzeneacetamide with an empirical formula of C 15 H 14 N 2 O 2 .…”

Molecular Design for Enhancement of Ocular Penetration

“…In addition to these NSAIDS adapted from oral drugs, nepafenac, the NSAID used only for eye drops, was recently approved by FDA in 2005. Nepafenac is nonsubstituted amide prodrug of amfenac, 138 which is used as an oral drugs for the treatment of rheumatoid in Japan, and was designed to improve the corneal permeability and tissue distribution profile. 139 Nepafenac showed about 4-to 30-fold higher corneal permeability than conventional NSAIDS such as diclofenac, bromfenac and ketorolac (Tab.…”

Designing Prodrugs and Bioprecursors

“…Amides of ketoprofen-derived arylacetic acids possess a therapeutic index one order of magnitude greater than that of indomethacin [73]. Amides of ketoprofen-derived arylacetic acids possess a therapeutic index one order of magnitude greater than that of indomethacin [73].…”