Abstract Pharmaceutical computerized system validation remains documentation-intensive, consuming substantial project effort and impeding Pharma 4.0 adoption. The CSV market grew to $3.92B in 2024 and is projected to reach $14.02B by 2037, highlighting the scale of optimization opportunity. This thesis addressed the tension between regulatory assurance and agility by developing and empirically evaluating a compliance-aware framework that uses Large Language Models to automate Operational Qualification (OQ) test generation from User Requirements Specifications (URS) under GAMP 5 (2nd ed.), 21 CFR Part 11, EU Annex 11, and ALCOA+ constraints. The methodology employed a five-agent, event-driven architecture (GAMP classifier, context provider, research analyst, SME consultant, OQ generator) with confidencegated handoffs, a fail-closed no-fallback policy, and full audit trails; evaluation used 30 synthetic URS spanning GAMP Categories 3–5, K=5 self-consistency, risk-based scoring aligned to ALCOA+, and predefined quantitative metrics. Results demonstrated 96.7% requirements coverage (target ≥95%), 91.3% categorization accuracy, and 7.4 minutes average processing per document. Migration to the open-source DeepSeek model reduced cost by 91% while preserving performance. Security controls achieved 100% semantic preservation with zero unsafe transformations; however, end-to-end completion was 76.7%, below the 90% reliability target, indicating variance and edge-case sensitivity. This research contributes the Compliance-Aware AI Engineering paradigm, establishing regulatory constraints as first-class design parameters, and validates a practical multi-agent architecture for auditable, GxP-aligned OQ generation. In practice, the framework offers a staged implementation path with measurable efficiency gains and clear governance (traceability, authority checks, documentation) suitable for regulated deployment. Future work should focus on variance reduction via reproducible multi-run protocols, expanded adversarial testing, and extension beyond OQ to IQ/PQ and multilingual corpora.