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[PSCI-07] Medicinal Chemistry I: Physicochemical Properties, Stereochemistry, Bioisosterism & Prodrug Design
PSCI-07 • 3. Pharmaceutical ChemistryLearning Objectives
Apply Lipinski's Rule of Five (MW ≤ 500, LogP ≤ 5, HBD ≤ 5, HBA ≤ 10) and Hansch QSAR equations to oral drug design.; Evaluate chiral switching (eutomer vs distomer) across Indian clinical examples ([4.2] Levosalbutamol, [5.4] Esomeprazole, [4.12] Levocetirizine, [3.4] Enalapril).; Analyze carrier-linked and bioprecursor prodrugs ([5.1] Omeprazole, [3.4] Enalapril, [3.40] Clopidogrel, [11.36] Levodopa, [8.52] Isoniazid, [8.73] Acyclovir).
Chapter Overview & Core Explanation
Medicinal chemistry connects a molecule's 3D chemical structure and functional groups directly to its biological activity, solubility, metabolism, and safety.
Key Exam & Clinical Takeaways
- Replacing the carboxylic acid (-COOH) group with an acidic 5-membered tetrazole ring in [3.7] Losartan is a classic non-classical bioisosteric replacement (similar pKa ~4.5, higher lipophilicity).
- [8.73] Acyclovir requires viral thymidine kinase for monophosphorylation, making it virtually non-toxic to uninfected host cells.