Pilocarpine Indication: glaucoma

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Presentation transcript:

Pilocarpine Indication: glaucoma Doses: 0.5 – 4% eye drops; 2-6 times daily Side-effects: intense miosis, cycloplegia PROBLEMS: short duration of action adverse effects low compliance low bioavailability (1%) logP is about 0 weak base Can we make pilocarpine that avoids these problems

Prodrugs covalent modification of parent drug parent drug + pro-moiety pro-moiety cleaves based on enzymatic reaction properties of parent drug can be improved ADME solubility safety

Pilocarpine prodrugs - expected scheme in the eye Bispilocarpic acid diesters Bispilocarpic acid monoesters Pilocarpine Goal is to make eyedrop solution Long duration of action ( 1x daily administration) Reduced peak concentration of pilocarpine  side-effects reduced