Carbachol

• Carbachol (Carbamoylcholine) is a cholinergic agonist that mimics the action of acetylcholine by stimulating both muscarinic and nicotinic receptors.

Chemical Formula:

• C₆H₁₅ClN₂O₂

Mechanism of Action:

• Direct agonist at muscarinic and nicotinic
• Longer duration due to resistance to AChE.

Uses of Carbachol:

• Used topically in glaucoma to reduce intraocular pressure.
• Also used to induce miosis during surgery.

Side Effects of Carbachol:

• Blurred vision
• Lacrimation
• Hypotension
• Diarrhea, nausea

SAR (Structure-Activity Relationship) of Carbachol:

1. Quaternary ammonium group:

   • Essential for binding to muscarinic and nicotinic receptors.
   • The positive charge interacts with the anionic site of the receptor.

2. Ester group replaced with carbamate:

   • Carbamate is more resistant to hydrolysis than an ester → longer duration of action than acetylcholine.

3. Ethylene bridge (2-carbon):

   • Optimal for receptor activity. Alteration decreases potency.

4. Lack of selectivity:

   • Due to similarity with acetylcholine, it activates both muscarinic and nicotinic receptors.

5. Increased enzymatic stability:

   • More stable against acetylcholinesterase hydrolysis.

General Synthesis:

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