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Bupivacaine 123

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levonordefrin) are absolutely contraindicated (see Chapter10), such as in:

1) Insulin- dependent, poorly controlled diabetes.

2) Patients with sulfite sensitivity or intolerance.

3) Patients with severe, corticoid- controlled asthma

because many are sulfite-

intolerant.

4) Patients with pheochromocytoma, a tumor of the adre-

nal gland cromaffin tissue, which releases excess epinephrine and norepinephrine.

5) Patients who have consumed cocaine in the last 24 hours.

6) Cardiovascular patients simultaneously taking amphet-

amines or psychostimulants.

7) Exceptionally, patients allergic to artificial vasoconstric-

tors such as levonordefrin and the bitartrate or hydrochloride forms of natural vasoconstrictors such as epinephrine and norepinephrine (allergies to the base forms would be incompatible with life because they are natural hormones and neurotransmitters).

Contraindications

This solution is also subject to contraindications, some deriving from its vasoconstrictor, felypressin, and others from the anesthetic.

● Felypressin- specific contraindications (see Chapters 6

and10)

1) It is wholly contraindicated in pregnancy due to the

risk of miscarriage or premature birth because of the effect of its residual oxytoxicity (Anonymous 1970; Oliver 1974; Stepke etal.1994).

2) It is likewise contraindicated for heart attack (angina

or myocardial infarction) patients. Although felypressin may cause the coronary vessels to contract, here the contraindication is not absolute. The maximum absolute dose in such cases is five 1.8- ml cartridges (Oliver1974; Roberts and Sowray1987).

● Prilocaine per se is contraindicated for patients in whom

toxic methemoglobinemia may worsen their condition by further hampering oxygen transport to the tissues (see Chapter9), such as in:

1) Cardiovascular disease including

◼ cardiac insufficiency, coronary insufficiency,

arrhythmias

◼ anemia and red blood cell alterations ◼ insufficient cerebral or peripheral circulation

2) Severe respiratory disease.

3) Children under 1 year and in very old age.

4) Rare cases of congenital methemoglobinemia.

Although in severe (ASA III) illness and congenital methemoglobinemia the solution is absolutely contraindicated, in all the others it may be administered, albeit at lower maximum doses.

Bupivacaine

Like mepivacaine, bupivacaine was synthesized by Bo af Ekenstam etal. from piperidine carboxylic acid (Ekenstam etal.1957). It was initially named LACand subsequently bupivacaine. It was introduced for medical use under the brand name Marcaine (Moore 1984; Dunsky and Moore1984) and approved by the FDA for use in dentistry in 1.8- ml cartridges in 1983 (Dean1983).

This anesthetic is very similar to mepivacaine and like it has two aromatic rings, a benzene ring and a piperidine ring at the amino terminus which, rather than a single carbon atom (methyl, hence mepivacaine), has four (butyl, hence bupivacaine) (Lund et al. 1970; Pricco 1977; Moore1984). The higher the number of terminal carbons the more potent and toxic is the anesthetic: termini with more than five carbons are too toxic and irritating to be used (Aberg etal.1977). The most prominent characteristics of bupivacaine are summarized in Table7.7.

Metabolism

Large proportions of bupivacaine are observed at the injection site 1

hour later (Goehl etal.1973), possibly because of its high lipid solubility. It is metabolized by cytochrome P450, primarily by the 3A4 isoform of the enzyme, although also by isoforms 2C19 and 2D6 (Gantebain et al. 2000). Around 80% is eliminated in the urine, only 5% as free unaltered bupivacaine (Annex 12). Elimination is enhanced by acid urine (Reynolds1971) and 5% is also found in the feces (Goehl etal.1973).

Bupivacaine crosses the placenta, with the umbilical vein containing 40% of the concentration found in the maternal plasma (Covino 1971). Its possible biotransformation pathways are listed in Annex 12.

Remarks

Bupivacaine is a potent, long- lasting local anesthetic, but also more toxic than others (Annex 8) due to its high lipid solubility and high binding rate to plasma proteins. Like all local anesthetics it is toxic to the nervous and cardiovascular systems, although bupivacaine is particularly toxic to the heart, where it induces severe arrhythmia and fibrillation (Reiz and Nath1986; Maxwell etal.1994; Mather and Chang2001) (see Chapter9). As at concentrations of over 1% bupivacaine irritates the tissues (Henn and Brattsand 1966; Ekblom and Widman 1966), it is used at 0.25–0.75%, with the midway value, 0.5%, the most widely used.

It also has a very powerful vasodilatory effect, greater than in lidocaine (Aps and Reynolds1976; Reynolds et al.

1976), and thus must be used with a vasoconstrictor. In light of its high pKa, its onset may be delayed.

43 (Ekenstam1966)

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Table7.7 Bupivacaine

Bupivacaine

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Pharmacological factor Reference

● Name and synonym: bupivacaine, LAC 43

● First synthesized in 1957 by Ekenstam etal. Ekenstam etal. (1957)

● Chemical name: 1- butyl- 2′,6′- pipecoloxylide American Dental Association (1984)

● Formula: C

18H28N2

NH–CO

● Molecular weight: Base 288.43

C4H

Hydrochloride 324.9

● Clearance rate: 0.52 l/min Annex 11

● Volume of distribution: 53 L Annex 11

● Half- life: 150 minutes Annex 11

Physical- chemical property

● pKa value or dissociation constant: 8.1

Annex 6

Denotes slower onset

● Lipid solubility or partition coefficient: n- heptane 27.5

Annex 7

n-octanol 350

Denotes high anesthetic potency and topical anesthesia

● Plasma protein binding: 95%

Annex 9

Denotes long duration of the anesthetic effect

● Vasodilation: ++ (high)

Denotes a need for a vasoconstrictor to be effective

Aps and Reynolds (1976) Reynolds et al. (1976)

Clinical factor Reference/s

● Relative anesthetic potency: 8

● Relative toxicity: 8 Annex 8

● Maximum absolute dose in dentistry: 90 mg (1.3 mg/kg) Dean (1983)

American Dental Association (2003)

● Usable during pregnancy: Yes (FDA category=C)

Table5.11 (Chapter5)

Denotes low risk

● Usable during lactation: Yes

Table5.11 (Chapter5)

Denotes low risk

● Usable with children: Yes, if over 12 years Laskin etal. (1977)

Jensen etal. (1981)

Anesthetic parameter Variable B- 200

Buccal infiltration

Superior lateral incisor

Successful pulpal anesthesia (%) 80 Duration, pulpal anesthesia (minutes) 35 Duration, anesthesia upper lip (minutes) 410

(Annex 21)

Mandibular block

Duration, anesthesia lower lip (minutes) 490

1.8 ml

(Annex 27)

Pharmacological, physical- chemical and clinical properties and anesthetic parameter. Summary: (B- 200) 0.5% bupivacaine with 1:200 000 (5 μg/ml) epinephrine: 80%- 35′/410′- 490′.

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Bupivacaine 125

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FDA authorization in dentistry is for 0.5% bupivacaine in

1.8-

ml cartridges containing 1:200 000 (5 μg/ml) epineph- rine (Dean1983), with the maximum absolute dose set at 90

mg (American Dental Association2003). The main draw-

back to this solution is its low success rate in pulpal anesthesia when infiltrated (anesthetic parameter 80%-

35′/410′- 500′), although its effect in soft tissues is long lasting. One of its advantages is that it retards the onset of initial post-

operative pain after oral surgery (Table7.8). A possible explanation for its scant infiltrative efficacy for pulpal anesthesia may be gleaned from experiments with ropivacaine (another longlasting, high- potency local anesthetic with lipid solubility and plasma protein binding similar to bupivacaine). The former has been observed to bind to and concentrate in the soft tissues and nerves (hence its efficacy in mandibular blocks), but unfortunately to be unable to diffuse well across bone (Kimi et al. 2012), a highly mineralized tissue. That would explain the poor results when cortical and spongy bone must be penetrated to engage with the dental apex and reach the nerve and dental pulp.

The wide gap between the 90 mg maximum authorized

dose for dentistry and the 225

and 175

mg without epinephrine (Lund etal.1975; Moore

mg allowed in medicine with

et al.1977; American Dental Association 1984, 2003) is striking. The medical dose is lower in some European countries: 150

mg with or without epinephrine (Die Arzneimittelkommission der Deutschen Ärzteschaft Informiert1985; Wulf etal.1988). Such a difference, much wider than in other anesthetics, may attest to health authorities’ precautionary approach to the cardiotoxicity associated with bupivacaine.

Pulpal anesthesia is of cardinal importance in dentistry, however, and is a key concern in most solutions. Extensive oral surgery in soft tissue and bone may even entail tooth sectioning. An alternative is to use supplementary (intraligamental or intraosseous anesthetic techniques), although when tissue is surgically sectioned the results

may not be optimal because of leakage from the opened flap (Yamazaki etal.2006).

In light of the foregoing and based on the prudent 90 mg maximum dose, three lines of action are suggested to improve pulpal anesthesia.

1) Raise bupivacaine concentration to 0.75% with 1:200 000

μg/ml) epinephrine. The results with this solution are promising: anesthetic parameter of 95%(Danielsson etal.1985) at the maximum dose of 90 (1.3

mg/kg) for an adult weighing 70 kg or over, which is

equivalent to six and a half 1.8-

ml cartridges.

2) Raise epinephrine concentration in a 0.5% bupivacaine

solution to 1:100

000 (10 μg/ml), the standard in den- tistry (Annex 17). Experimental studies (Ohkado et al. 2000) and clinical trials (Oka et al. 1997) have yielded promising results. Onset time, retarded by the fairly high pKa value (8.1), can be shortened with this concentration (Nespeca1976) and the higher epinephrine content improves hemostasis in surgery, offsetting the intense vasodilatory effect induced by bupivacaine. With this solution, the maximum absolute dose,

mg (1.3 mg/kg) for a >70 kg adult, would translate

90 into 10 1.8-

ml cartridges.

3) Raise both concentrations, bupivacaine to 0.75% and

epinephrine to 1:100 dose would be six and a half 1.8-

000. In that case, the maximum ml cartridges. This

alternative may be the cause for greatest concern because the heart may be sensitized by both bupivacaine and epinephrine.

Indications andContraindications

The sole bupivacaine solution commercially available in dental cartridges is 0.5% anesthetic with 1:200 ml) epinephrine (B-

200). This solution provides for longlasting anesthesia in soft tissue (Table7.8), although its efficacy for pulpal anesthesia with buccal infiltration is

25′/385′

000 (5 μg/

Table7.8 Local anesthetic solutions: duration oflower lip anesthesia after mandibular block andonset offirst pain after surgical

extraction ofmandibular wisdom teeth (data fromAnnex 27)

Local anesthetic solution

0.5% bupivacaine with 1:100 000 epinephrine 490 8 340 5.5 2% lidocaine with 1:100 000 epinephrine 200 3.3 180 3 4% articaine with 1:100 000 epinephrine 260 4.5 190 3.2 4% articaine with 1:200 000 epinephrine 260 4.5 210 3.5 2% mepivacaine with 1:100 000 epinephrine 190 3.2 150 2.5 3% mepivacaine, no vasoconstrictor 190 3.2 150 2.5

Duration, anesthesia lower lip Onset of first pain

(minutes) (hours) (minutes) (hours)

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126

low. It is consequently recommended primarily for mandibular block. Patients must also be advised that anesthesia in the lower lip will last for 6–10

advantage that post-

operative pain will be milder.

hours, with the

The maximum absolute dose of this local anesthesia for

an adult weighing 70

1.8-

ml cartridges.

Indications

kg or more is 90 mg (1.3 mg/kg) or 10

1) Bupivacaine prevents post- operative pain in extensive

oral surgery (often surgical extraction of mandibular wisdom teeth) because it retards the onset of initial painby prolonging anesthetic action in the soft tissue (Nespeca 1976; Laskin et al. 1977). Long-

acting local anesthetics may also reduce the consumption of systemic analgesics such as nonsteroidal anti-

inflammatory agents, acetaminophen, and/or opioids, which all have dosedependent side effects (Chapman and Macleod1985).

2) Bupivacaine prevents post- surgical pain in particularly

painful endodontic therapy, such as in mandibular molars and premolars for the same reason as above (Moore and Dunsky 1983; Dunsky and Moore 1984; Parirokh etal.2012).

3) Bupivacaine is used when long- lasting anesthesia is

needed for the temporary relief of acute pain in soft tissues (not pulpal or osseous) in emergencies (Jensen etal.1981).

4) Bupivacaine is used in chronic orofacial pain (such as

causalgia, trigeminal neuralgia or post-

herpetic neuralgia) to attempt to achieve permanent relief by blocking the Gasserian or the Stellate ganglion, sometimes repeatedly. In such cases it can be used with (Hanowell and Kennedy1979) or without (Adler1975; Hanowell and Kennedy 1979; Khoury et al. 1980) epinephrine.

Contraindications

Contraindications are associated primarily with the long duration of the anesthetic effect in soft tissue and concomitant discomfort in connection with drinking, eating, and speaking and the risk of self-

injury to the tongue, lips, and buccal mucosa. Scantly effective pulpal anesthesia in infiltration, another major drawback, is reason not to use this solution in:

1) Short or medium duration routine procedures (Laskin

etal.1977; Jensen etal.1981).

2) Children under 12 years, due to the high risk of self-

injury to the soft tissues (Laskin et al. 1977; Jensen etal.1981; Moore1984).

3) Patients with special needs (Pricco 1977; Jensen

etal.1981) or psychiatric (Jensen etal.1981) patients, for the above reason.

References

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