Tropomyosin receptor kinase A (TrkA) is considered a therapeutic target in pain treatment, and several TrkA inhibitors have been designed and developed as potential analgesics. The subselectivity toward TrkA is closely associated with safety and efficacy and was achieved by developing an allosteric inhibitor to occupy the less conserved non-ATP binding site. Druggable modifications of potent TrkA inhibitors could be challenging due to the unique requirement of functional groups that supply potency but are accompanied by poor druggability. We developed carboxyl acid 5 as a potent (IC₅₀ = 22.4 nM) and subselective TrkA inhibitor (>8000-fold toward TrkB and TrkC). We also converted 5 to corresponding prodrug 39 as a useful tool compound in future analgesic development with promising antinociceptive effects in both hot plate testing and formalin-induced pain models with a suitable ED₅₀ value (7.8 mg/kg).