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Mepivacaine: a Closer Look at Its Properties and Current Utility William G

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Mepivacaine: a Closer Look at Its Properties and Current Utility William G Anesthesia and Pain Control Mepivacaine: a closer look at its properties and current utility William G. Brockmann, DDS, PhD The use of mepivacaine in dentistry has remained strong since its use mepivacaine is based on its vasoconstrictor effect or lack thereof introduction in the 1960s. It has retained its place as a valuable local (depending on the formulation). However, the pharmacokinetics of anesthetic, either as a primary agent or as an alternative to lidocaine mepivacaine are not well understood or assumed to be similar to that or articaine. Mepivacaine is commonly used in medically compromised of other local anesthetics. It is important to understand the unique patients—for whom elevations in blood pressure or heart rate are not pharmacologic characteristics of mepivacaine in order to minimize the advisable—in a formulation with a vasoconstrictor, or in pediatric popu- potential for inadvertent toxicity. lations in a formulation without a vasoconstrictor. Pharmacologically, Received: October 16, 2013 these are the 2 groups most susceptible to side effects and toxicity, Accepted: November 24, 2013 thus mepivacaine is commonly indicated. Most often the decision to urrently used local anesthetics and formulations exclusively with these charac- successful 2,6-xylidine-amide structure, their formulations each have indi- terizations in mind. Whereas the 2 different with emphasis on increasing the dura- Cvidual characteristics that allow them vasoconstrictors used in local anesthetics tion of action. In 1957, af Ekenstam et to claim clinically useful niches to validate bear many similarities to each other with al synthesized (along with many other their continued market presence. While similar clinical limitations, it is worthwhile structures with anesthetic properties) the introduction of articaine—in 1982 to look at mepivacaine by itself. mepivacaine and bupivacaine, both very in Canada and in 2000 in the US—has Rather than being a lidocaine substitute, similar in structure and with longer dura- gained much of the market share in North mepivacaine possesses distinct pharmaco- tions than lidocaine.5 Each preserved the America, lidocaine and mepivacaine have kinetic characteristics of its own that are 2,6-xylidine group on the aromatic ring, remained commonly used agents.1 In important for the clinician to understand. but each had a shortened intermediate Canada, where articaine is the most used This article reviews the unique pharmacol- chain, and replaced the terminal tertiary agent, a survey of general dentists showed ogy of mepivacaine and the potential clini- amine with a less basic methyl-piperidine that from 1993 to 2007, mepivacaine usage cal implications involved with its use. ring. Homologous local anesthetics that declined but remained the third most used share the mepivacaine structure, such agent.2 Mepivacaine’s niche has been con- History and chemistry: as bupivacaine and ropivacaine, are sidered by many dentists to be the “safer” pipecholyl xylidines referred to as pipecholyl xylidines due lidocaine alternative, to be used in elderly In the years immediately after the to the presence of this pipecholyl acid or cardiovascular disease patients, because it development of the xylidine derivative, moiety (Fig. 1). Bupivacaine differs from not only comes without a vasoconstrictor, lidocaine, there followed a series of mepivacaine only by substitution of the but it is available with levonordefrin, which chemical syntheses based upon the same methyl group on the piperidine ring by a is assumed to have less vasopressor potency and 25% of the direct beta effects on the heart.3 It is now known, however, that levonordefrin acts similarly to norepineph- rine, as it elevates not only systolic blood CH3 O O CH3 O pressure, but diastolic and mean arterial CH3 CH3 pressures as well. Used at 5 times the con- N CH3 centration of epinephrine, it possesses rela- NH N NH N NH tively the same or more potential for cardiac H C 3 Lidocaine CH3 stimulation, especially elevations in blood CH3 CH3 4 CH pressure. Mepivacaine is also commonly Mepivacaine Bupivacaine 3 used—in a formulation without levonorde- O CH3 frin—for children, as it is available without NH2 a vasoconstrictor for shorter postoperative HO N duration, whereas articaine and lidocaine H CH3 have longer durations and must have vaso- Pipecolic acid 2,6-Xylidine constrictors for their efficacy. Many general and pediatric practices use mepivacaine Fig. 1. Pipecholyl xylidines compared to lidocaine. 70 November/December 2014 General Dentistry www.agd.org to 27.2 (at pH 6.5).22 In comparison, the Table. Physicochemical properties and relative in vitro conduction blocking relative anesthestic potency of prilocaine potency of the intermediate-acting amide local anesthetics.15 decreases by 66.5%, and mepivacaine decreases by 64.7%. Theoretically, Relative conduction mepivacaine would lose less potency Lipid solubility blocking potency when injected into areas of reduced pH MW base pKa Hydrophobicitya (distribution (in vitro, isolated b and this may be considered an advantage. Anesthetic (g/mol) (36°C) (mol/L) coefficient Q7.4 ) nerve fibers) However, realistically, this is a rare occur- Lidocaine 234 7.8 304 (366) 43 (110) 2.0 rence if a regional block is available. Prilocaine 220 8.0 129 25 1.8 Hypersensitivity and Mepivacaine 246 7.7 90 (130) 21 (42) 1.5 cross reactivity aOctanol/buffer partition coefficients for unprotonated species only: 25°C. Values in parentheses: 36°C. For patients who are known to be allergic b to sulphites, the availability of mepiva- Q7.4 = (total drug/ml octanol)/(total drug/ml buffer) at pH 7.4. Includes ionized and unionized partition coefficients. caine without vasoconstrictor and sodium Margins of error not shown. metabisulphite is a highly valuable clinical asset, since articaine and lidocaine must have vasoconstrictors added for their efficacy. Allergy to mepivacaine itself, as more lipid soluble butyl (C4H9) group. It These methods showed mepivacaine to well as any of the amide local anesthetics was not until the late 1970s, however, that have a correspondingly lower anesthetic is very rare, but does occur.23 Most case bupivacaine was approved for clinical use potency than lidocaine or prilocaine under reports of mepivacaine allergic reactions as a nerve blocker in dentistry.6-8 in vitro conditions.17 However, these mea- prior to the mid-1980s were related to Mepivacaine, being less toxic than surements were derived under controlled the methylparaben used as antimicrobials bupivacaine, was immediately evaluated conditions and do not directly reflect in in the cartridges; these were subsequently for clinical use in various types of regional vivo anesthetic potency. They also do not removed by FDA mandate.24 and dental anesthesia and was identi- correctly reflect the clinical end-points of A large 2009 study that analyzed the fied as having a faster onset and longer mepivacaine use, where success is measured French Pharmacovigilance database over duration than lidocaine without a vaso- by an adequate conduction block, and a 12-year period (1995-2006) found constrictor.9-12 Approved by the FDA in the physiologic variables that affect tissue 16 cases of allergic reactions to amide local 1960, it was subsequently studied in many concentration, diffusion, and ionization anesthetics, of which 11 were immediate dental trials, where it rapidly established are more complex. Animal studies with Type I reactions occurring within 1 hour its dual utility in dentistry when used live nerve blocks have shown the potency with severe symptoms.25 Of the Type 1 in a formulation without a vasoconstric- of mepivacaine to be equivalent or greater, reactions, 6 were due to lidocaine, 2 to tor or in a formulation with 1:20,000 with a faster onset time, and longer dura- mepivacaine, 2 to articaine, and 1 to bupi- levonordefrin (Neo-Cobefrin, Novocol tion of anesthesia than lidocaine and vacaine. Of the other 5 reactions, which Pharmaceutical of Canada, Inc.) which prilocaine.18 Mepivacaine, lidocaine, and were delayed-type skin reactions, 4 were markedly increased its duration.13,14 prilocaine have all been shown in numer- due to lidocaine and 1 to mepivicaine.25 ous clinical studies to have similar inter- Cross-reactivity among the amides, pre- Lipid solubility and potency mediate anesthetic efficacy, regardless of viously thought to be rare, was found in 6 Mepivacaine, lidocaine, and prilocaine differences in their lipid solubility.19-21 cases (38%) and all were between lidocaine are considered to be “intermediate” and mepivacaine. In patients with a true in terms of their lipid solubility and Effectiveness in infected tissues lidocaine or mepivacaine allergy, neither anesthetic potencies (Table).15 The cor- The ionization constant, or pKa, of lidocaine nor mepivacaine should be relation of lipid solubility, and the ability mepivacaine is also the lowest of the inter- used as a substitute due to very possible to penetrate membranes with increased mediate agents (articaine and lidocaine cross-allergenicity.25 affinity for hydrophobic binding sites have the same pKa). At 36°C, the pKa’s A 2006 report in Spain published a are the main determinants of anesthetic of the intermediate-acting agents are all similar case of a patient with confirmed potency.16 The lipid solubility and hydro- close enough to make onset times roughly lidocaine and mepivacaine allergies who phobicity (tendency to be readily soluble equivalent under normal physiologic con- was not allergic to
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