Case 1: Anticholinesterase

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1 Harvard-MIT Division of Health Sciences and Technology HST.151: Principles of Pharmocology Instructor: Dr. Carl Rosow, Dr. David Standaert and Prof. Gary Strichartz Case 1: Anticholinesterase February 3, Cholinergic Pharmacology 2. Anticholinesterase inhibitors 3. Therapeutic use 4. Managing toxicity

2 Case: rganophosphate Poisoning A 55 yr old crop duster calls because he has lost control over his chronic twitch, and he is now beginning to have problems with blurry vision and control of his bowels and bladder. He wants to go back to the airfield to finish his crop dusting, but his supervisor makes him call you first.

3 Acetylcholine Synthesized from acetyl-coa and choline by choline acetyltransferase (ChAT) N + Poor absorption and low lipophilicity due to charge on quaternary ammonium Receptor class Muscarinic M 1 Muscarinic M 2 Muscarinic M 3 Muscarinic M 4 Muscarinic M 5 Nicotinic N M Nicotinic N N Multiple systemic effects, esp autonomic pathways and at the neuromuscular junction (NMJ) Post-synaptic ANS ganglia, CNS Heart, smooth muscle Vessels (smooth muscle), exocrine glands CNS CNS NMJ Locations Pre-synaptic ANS ganglia, adrenal medulla, CNS

4 presynaptic acetylcholine (ACh) acetylcholine receptor(achr) H acetate + choline postsynaptic Acetylcholinesterase (AChE) Clears Ach from site of action (also degraded by plasma butyrylcholinesterase) Bound on post-synaptic membrane Rate = 400,000 per min Inhibition of AchE results in build up of Ach at muscarinic and nicotinic synapses! reversible Step 1: Binding Anionic Esterase binding (1) Anionic Esterase Step 2: Formation of covalent intermediate and release choline - H deacylation (3) H 3 C N + H acylation (2) Step 3: Hydrolysis of acyl-enzyme intermediate acetate H 2 Anionic Esterase H N CH choline +

5 Direct-acting agonists Mimics acetylcholine by binding Ach receptor and activating downstream signaling Examples: methacholine, carbachol, bethanechol, pilocarpine Indirect agonists Inhibits AchE from breaking down acetylcholine at synapse Quaternary alcohols + CH2 CH - competes w/ ACh for binding to AChE (step 1) 3 H N edrophonium Examples: edrophonium Carbamate esters - formation of carbamylated enzyme intermediate (step 2) Examples: neostigmine, pryidostigmine + H 3 C CH3 N N neostigmine rganophosphates - formation of phosphorylated enzyme intermediate (step 2) Examples: parathion, malathion are insecticides soman, sarin are nerve agents F P isoflurophate

6 AchE inhibitors: reversible versus irreversible Quaternary alcohols Anionic Esterase reversible binding (1) Anionic Esterase H H 3 C N H - acetate deacylation (3) H 2 Anionic + Esterase H acylation (2) rganophosphates choline Carbamate esters N CH + Anionic Esterase R P R' half-life >100 hrs! Anionic Esterase NH 2 half-life 1-6 hrs

7 Inhibition by organophosphate: "Aging" "aging" Anionic Esterase Anionic Esterase R 1 P H P R 2 R 2 Pralidoxime (2-PAM) NH can regenerate free N+ enzyme if given before aging Anionic Esterase untreatable H

8 Pharmacokinetics of organophosphates Parathion and malathion are biotransformed in the liver to become active (insects perform this process more efficiently) Highly lipid soluble, widely distributed and penetrates CNS When used as insecticides, can be dispersed as aerosols or dusts and absorbed by all possible routes: GI, skin, mucous membranes, lungs Slow hepatic metabolism; urine excretion of hydrolysis products Lipid-soluble drug can remain in systems for weeks to months!

9 Effects of acute /P overdose Muscarinic Ciliary spasm, Miosis Bronchoconstriction Bronchosecretion Diaphoresis Salivation, Lacrimation Bradycardia, Hypotension Incontinence, Diarrhea GI spasms (cramping) Emesis, Nausea Nicotinic Weakness Fasciculation Twitching Flaccid Paralysis (resp.) Severe Cases: also include conduction block, pulmonary edema CNS Confusion Anxiety, Agitation Restlessness, Tremor Ataxia Convulsions Respiratory depression CV collapse Coma DUMBBELLS: Diarrhea (Diaphoresis), Urination, Miosis, Bronchospasm (secretion) Bradycardia, Excite skeletal muscle and CNS (Emesis), Lacrimation, Lethargy, Salivate Mode of death: respiratory failure via flaccid muscular paralysis exacerbated by bronchosecretion and bronchoconstriction Chronic Exposure to Low Doses: blurred vision, incontinence, twitching*** neuropathy associated with axonal demyelination

10 Treatment Lethal Dose Remove contaminated clothing; remove from exposure site Wash skin with soap, bleach (alkaline hydrolysis) Respiratory support ( 2, ventilatory assistance, treat Sz) Atropine anti-muscarinic agent reverses dangerous parasympathetic effects (respiratory) mg IV q15min until respiratory secretions dry (days!) Pralidoxime (2-PAM) - specific for organophosphate poisoning

11 Therapeutic use of AchE inhibitors Myasthenia gravis (edrophonium, pyridostigmine, neostigmine) Photos removed for copyright reasons. Alzheimer's Disease (tacrine and donepezil) Reversal of neuromuscular blockers (neostigmine, physostigmine) Glaucoma (physostigmine, echothiophate)

12 Summary of Key Points Reversible versus irreversible inhibition of AchE causes build up of Ach at synapse Toxicity associated with AchE inhibitors (patient case!) include global nicotinic, muscarinic, & CNS effects (DUMBBELLS) Treatment for Exposure to Irreversible Inhibitors Atropine counteract ACh agonism 2-Pralidoxime prevent aging

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