67 - Lidocaine for neural blockade  pp. 279-283

Lidocaine for neural blockade

By Mary Hanna Bekhit

Image View Previous Chapter Next Chapter

Lidocaine's chemical name is 2-(diethylamino)-N-(2,6-dimethylphenyl)ethanamide (IUPAC). Its other chemical names include: N-diethylaminoacetyl-2,6,xylidine hydrochloride, 2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide, 2-diethylamino-2′,6′-acetoxylidide, and omega-diethylamino-2′,6′-dimethylacetanilide.Lidocaine is also known as lignocaine (former British Approved Name).

Its proprietary names include Akten, Xylocaine, Xylotox, Leostesin, EMLA, Rucaina, Isicaine, Lidoderm, Cuivasal, Duncaine, Sylestesin, Anestacon, Gravocain, Lidothesin, Xylocitin, and Xylestesin. Lidocaine in its generic form is manufactured by many different pharmaceutical companies worldwide.

Chemical structure/properties (Figure 67.1): lidocaine's aromatic group, a benzene ring, confers its lipophilic properties, and its tertiary amine group possesses hydrophilic properties. The two groups are linked by an amide bond. Lidocaine has a molecular weight of 234 g/mol, melting point of 68°C, and a pKa of 7.9. It is usually prepared as lidocaine hydrochloride, a white, odorless, crystalline powder.

Historical development

Lidocaine is the most widely used and first synthesized amide local anesthetic. Nils Lofgren, a Swedish chemist who later became a professor of organic chemistry at the University of Stockholm, synthesized the chemical in 1943 and named it xylocaine. His coworker Bengt Lundqvist first tested the chemical on himself via injection prior to marketing the drug in 1948.

Bauer LA . Applied Clinical Pharmacokinetics, 2nd ed. New York: McGraw Hill Professional Publishing, 2008, pp. 356–397.
Bernard JM , Macaire P . Dose-range effects of clonidine added to lidocaine for brachial plexus block. Anesthesiology 1997;2:277–284.
Cuvillon P , Nouvellon E , Ripart J , Boyer JC , Dehour L , Mahamat A , L'hermite J , Boisson C , Vialles N , Lefrant JY , de La Coussaye JE . A comparison of the pharmacodynamics and pharmacokinetics of bupivacaine, ropivacaine (with epinephrine) and their equal volume mixtures with lidocaine used for femoral and sciatic nerve blocks: a double-blind randomized study. Anesth Analg 2009;108(2):641–649.
Gawronska-Szklarz B , Zarzycki M , Musial HD , Pudlo A , Loniewski I , Drozdzik M . Lidocaine pharmacokinetics in postmenopausal women on hormone therapy. Menopause 2006;13(5):793–798.
Gissen AJ , Covino BG , Gregus J . Differential sensitivities of mammalian nerve fibers to local anesthetic agents. Anesthesiology 1980; 53:467–474.
Hersh EV . In Fonseca RJ , ed. Oral and Maxillofacial Surgery: Local Anesthetics. Elsevier Health Sciences, 2000, pp. 58–78.
Jaffe RA , Rowe MA . Differential nerve block: direct measurements on individual myelinated and unmyelinated dorsal root axons. Anesthesiology 1996;84:1455–1464.
Mama KR , Steffey EP . In Adams HR , ed. Veterinary Pharmacology and Therapeutics: Local Anesthetics, 8th ed, Blackwell, 2001, pp. 343–359.
Movafegh A , Razazian M , Hajimaohamadi F , Meysamie A . Dexamethasone added to lidocaine prolongs axillary brachial plexus blockade. Anesth Analg 2006;102(1):263–267.
Pratap JN , Shankar RK , Goroszeniuk T . Co-injection of clonidine prolongs the anesthetic effect of lidocaine skin infiltration by a peripheral action. Anesth Analg 2007;104:982–983.
Sakai T , Tomiyasu S , Yamada H , Ono T , Sumikawa K . Quantitative and selective evaluation of differential sensory nerve block after transdermal lidocaine. Anesth Analg 2004;98:248–251.
Tasaki, I . Nervous Transmission. Springfield: CC Thomas, 1953.
Wang JS , Backman JT , Taavitsainen P , Neuvonen PJ , Kivistö KT . Involvement of CYP1A2 and CYP3A4 in lidocaine N-deethylation and 3-hydroxylation in humans. Drug Metab Dispos 2000;28(8):959–695.
Wildsmith JAW , Brown DT , Paul D , Johnson S . Structure-activity relationships in differential nerve block at high and low frequency stimulation. Br J Anaesth 1989;63:444–452.