Local anesthetic agents: Pharmacology

Published on 07/02/2015 by admin

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Last modified 07/02/2015

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Local anesthetic agents: Pharmacology

Terese T. Horlocker, MD

Local anesthetic agents consist of three major chemical moieties (Figure 116-1): a lipophilic aromatic ring, a hydrophilic tertiary amine, and an ester or amide linkage. Changes in the amine or ring chemical structure result in marked alterations in lipid/aqueous solubility, potency, and protein binding. Local anesthetics are classified into two major groups based on the linkage between the lipophilic and hydrophilic components: amino esters and amino amides. Though they exert their effect by the same mechanism, they are metabolized differently (esters in the blood by pseudocholinesterase; amides by normal hepatic pathways) and have different allergic potential (ester greater than amide). The most commonly used local anesthetic agents and their physiochemical properties are described in Table 116-1.

Table 116-1

Physicochemical/Biologic Properties of Local Anesthetic Agents

  Physicochemical Properties Biologic Properties  
Agent pKa* (25° C) Protein Binding (%) pH, Plain Solutions Equieffective Anesthetic Concentration Approximate Anesthetic Duration (min) Site of Metabolism Onset Recommended Maximum Single Dose (mg)
Procaine 9.05 6 5-6.5 2 50 Plasma, liver Fast 500
Chloroprocaine 8.97 ? 2.7-4 2 45 Plasma, liver Fast 800 (1000 with epinephrine)
Tetracaine 8.46 75.6 4.5-6.5 0.25 175 Plasma, liver Fast (spinal anesthesia) 20
Lidocaine 7.91 64 6.5 1 100 Liver Intermediate 300 (500 with epinephrine)
Mepivacaine 7.76 77 4.5 1 100 Liver Intermediate 400 (500 with epinephrine)
Prilocaine 7.9 55       Liver, extrahepatic tissue Intermediate 400 (600 with epinephrine)
Etidocaine 7.7 94 4.5 0.25 200 Liver Fast 400 with epinephrine
Bupivacaine (and levobupivacaine) 8.16 96 4.5-6 0.25 175 Liver Slow 175 (225 with epinephrine)
Ropivacaine 8.2 95 4.5-6 0.5 175 Liver Slow 225 (300 with epinephrine)

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*pH corresponds with 50% ionization.

Epinephrine-containing solutions have a pH that is 1-1.5 units lower than the pH of plain solutions.

When used for a brachial plexus block.

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