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Although three peptide\u2010based inhibitors\u2014Ac\u2010YVAD\u2010CMK, Z\u2010YVAD\u2010FMK, and Ac\u2010YVAD\u2010CHO\u2014have long served as prototypical experimental standards, their structural determinants, structure\u2010activity relationships, and developmental liabilities have not been systematically reassessed from a medicinal chemistry perspective. Integrating evidence from 144 studies (2015\u20132025), this review rigorously interrogates these archetypal scaffolds as both pharmacological probes and foundational templates for inhibitor design. We delineate how C\u2010terminal warhead chemistry (chloromethyl ketone, fluoromethyl ketone, and aldehyde) dictates covalency, reversibility, and kinetic selectivity, while N\u2010terminal capping strategies modulate membrane permeability, metabolic stability, and systemic exposure. By correlating chemical architecture with caspase selectivity, off\u2010target engagement, and context\u2010dependent efficacy across inflammatory, infectious, autoimmune, and oncologic models, we define structure\u2010kinetics\u2010pharmacology relationships that govern selectivity, durability, and in vivo predictability. Persistent barriers\u2014including inadequate pharmacokinetic characterization, metabolic fragility, broad caspase cross\u2010reactivity, and limited scaffold diversification\u2014are identified as principal impediments to the clinical translation of all three prototypical inhibitors. By repositioning these legacy peptide inhibitors as foundational chemical templates for translational optimization, this synthesis establishes design principles centered on kinetic selectivity, rational warhead refinement, and context\u2010guided optimization, and outlines strategic pathways for the development of selective, clinically viable Caspase\u20101\u2010targeted therapeutics.<\/jats:p>","DOI":"10.1002\/med.70045","type":"journal-article","created":{"date-parts":[[2026,4,6]],"date-time":"2026-04-06T06:31:08Z","timestamp":1775457068000},"page":"1071-1110","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Comparative Pharmacology of Caspase\u20101 Inhibitors: Ac\u2010YVAD\u2010CMK, Z\u2010YVAD\u2010FMK, and Ac\u2010YVAD\u2010CHO in Multisystem Diseases"],"prefix":"10.1002","volume":"46","author":[{"given":"Yujia","family":"Zheng","sequence":"first","affiliation":[{"name":"Tianjin University of Traditional Chinese Medicine Tianjin P.R. 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