The Structure of Bupivacaine and How it Relates to Cardiotoxicity and Lipid Rescue. By: Sean Zajdel SRNA
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1 The Structure of Bupivacaine and How it Relates to Cardiotoxicity and Lipid Rescue By: Sean Zajdel SRNA
2 The basic action of an anesthetic in the body is largely a function of the drug s chemical structure and the resulting interaction with a cellular receptor complex. -John J. Nagelhout PhD, CRNA, FAAN
3 Disclaimer Conflict of Interest: None I have not received any compensation from anyone associated with Intralipid or any other lipid emulsion or pharmaceutical company for this presentation.
4 Objectives Describe the properties of the chemical structure of bupivacaine Explain the potential reasons bupivacaine is associated with increased rates of cardiotoxicity Describe the most current theorized mechanism of lipid rescue and how it relates to the properties of bupivacaines chemical structure
5 Why is this a problem? Medication Amount Cost Bupivacaine 250 mg $2.72 Levo-Bupivacaine 225mg $75.00 Ropivacaine 200 mg $ (MIMS Medeconomics, 2017; Clint Pharmaceuticals, 2017)
6 Toxic Dose Max safe dose = 2.5 mg/kg of bupivacaine 3 mcg/ml is toxic plasma concentation (Nagelhout & Plaus, 2014; Hemmings & Egan, 2012; Evers, Maze & Kharasch, 2011)
7 Bupivacaine Lipophilic Intermediate Amide Bond Hydrophilic Tertiary Amine Amphipathic (Miller, 2015; Hemmings & Egan, 2012)
8 Synonyms are Tough Hydrophilic Lipophobic Lipid insoluble Polar Water soluble WATER LOVING Amphipathic Lipophilic Hydrophobic Water insoluble Non-polar Lipid soluble FAT LOVING Like dissolves/is attracted to Like Lipophilic substances dissolve/are attracted to other lipophilic substances Hydrophilic substances dissolve/are attracted to other hydrophilic substances
9 Degrees of Lipophilicity Almost Completely Lipophilic The more potent, lipophilic local anesthetics such as bupivacaine, tetracaine, and etidocaine are more cardiotoxic than the less lipophilic agents such as procaine, prilocaine, and lidocaine (Hemmings & Egan, 2012 p. 299). Hydrophilic (Barash, Cullen & Stoelting, 2014; Hemmings & Egan, 2012; Evers, Maze & Kharasch, 2011)
10 Bupivacaine (Miller, 2015; Hemmings & Egan, 2012)
11 Phospholipid Bilayer
12
13 (Hall, 2016; Miller, 2015; Barash, Cullen & Stoelting, 2014; Nagelhout & Plaus, 2014; Hemmings & Egan, 2012; Evers, Maze & Kharasch, 2011)
14 Bupivacaine Cellular Cardiotoxic Effects (Miller, 2015; Hemmings & Egan, 2012; Bourne, Wright & Royse, 2010; Heavner, 2002)
15 (Hall, 2016; Hemmings & Egan, 2012; Bourne, Wright & Royse, 2010; Heavner, 2002)
16 Summary of Main Points Before Discussing Lipid Rescue Bupivicaine is the most lipophilic local anesthetic due to the long hydrocarbon chain extending from its amine group. Like dissolves/is attracted to Like
17 What is lipid rescue? (American Society of Regional Anesthesia and Pain Medicine, 2011)
18 (Weinberg et al., 1998)
19 (Burns, 2010)
20 Components of Lipid Emulsion (Intralipid)
21 Lipid Sink Theorized Mechanism of Lipid Rescue The lipid micelle/chylomicron structure is the preferred compartment over other body areas for local anesthetic binding (Bourne, Wright & Royse, 2010) Like dissolves like (Bourne, Wright & Royse, 2010)
22 CACT Theorized Mechanism of Lipid Rescue Carnitine-acylcarnitine transferase (CACT) Mitochondial transport protein that brings fatty acids into mitochondrial matrix to create energy Bupivicaine has been found to block CACT in rats (Bourne, Wright & Royse, 2010)
23 (Giudetti et al., 2016; Bourne, Wright & Royse, 2010).
24 Summary
25 The End Questions? Sean Zajdel SRNA
26 References AMERICAN SOCIETY OF REGIONAL ANESTHESIA AND PAIN MEDICINE, 2011 Barash, P. G., Cullen, B. F., & Stoelting, R. K. (2014). Clinical anesthesia, 7th edn. Bourne, E., Wright, C., & Royse, C. (2010). A review of local anesthetic cardiotoxicity and treatment with lipid emulsion. Local and regional anesthesia, 3, 11. Burns, S. M. (2010). Use of lipid emulsions for treatment of local anesthetic toxicity: a case report. AANA journal, 78(5), 359. Evers, A. S., Maze, M., & Kharasch, E. D. (Eds.). (2011). Anesthetic Pharmacology: Basic Principles and Clinical Practice. Cambridge University Press. Giudetti, A. M., Stanca, E., Siculella, L., Gnoni, G. V., & Damiano, F. (2016). Nutritional and Hormonal Regulation of Citrate and Carnitine/Acylcarnitine Transporters: Two Mitochondrial Carriers Involved in Fatty Acid Metabolism. International journal of molecular sciences, 17(6), 817. Hall, J. E. (2016). Guyton and Hall textbook of medical physiology (13th ed.). Philadelphia, PA:Elsevier. Heavner, J. E. (2002). Cardiac toxicity of local anesthetics in the intact isolated heart model: a review. Regional anesthesia and pain medicine, 27(6), Hemmings, H. C., & Egan, T. D. (2012). Pharmacology and physiology for anesthesia: foundations and clinical application. Elsevier Health Sciences. Ikonnikov, G., & Yelle, D. (2016). Physiology of cardiac conduction and contractility. Retrieved April 19, 2017, from Intralipid, Miller, R. D. (2015). Miller's anesthesia (8th ed., Vol. 1). Philadelphia: Elsevier Saunders. Nagelhout, J. J., & Plaus, K. L. (2014). Nurse anesthesia. Elsevier Health Sciences. Weinberg, G. L., VadeBoncouer, T., Ramaraju, G. A., Garcia-Amaro, M. F., & Cwik, M. J. (1998). Pretreatment or resuscitation with a lipid infusion shifts the dose-response to bupivacaine-induced asystole in rats. The Journal of the American Society of Anesthesiologists, 88(4),
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