CLASSIFICATION OF LOCAL ANESTHETICS

By
PETER Y. BONILLA, B.S.Med.Tech. (RMT).,D.M.D.,M.A.,M.S. Ass. Professor Endodontics-Periodontics Section College of Dentistry Centro Escolar University

LOCAL ANESTHETICS
are

drugs that have little or no irritating effects when injected into the tissues and that will temporarily interrupt conduction when absorbed into the nerve

Local anesthetics
A blockade of all afferent nerve transmission produces anesthesia or a lack of all sensation Blockade of those fibers transmitting pain sensation only results in regional analgesia Interruption of efferent fibers results in motor paralysis and an inhibition of autonomically innervated structures

PROPERTIES OF AN IDEAL LOCAL ANESTHETIC

1. 2.

3.

4.

Its action should be reversible It must be nonirritating to the tissues and produce no secondary local reaction It should have a low degree of systemic toxicity It should have a rapid onset and be of sufficient duration to be advantageous

5. It should have a potency sufficient to give complete anesthesia without the use of harmful concentrated solutions 6. It should have sufficient penetrating properties to be effective as a topical anesthetic 7. It should be relatively free from producing allergic reactions

8. It should be stable in solution and undergo biotransformation readily within the body

9. It should be either sterile or capable of being sterilized by heat without deterioration.

*No local anesthetic in use today fulfills to perfection all these requirements *Systemic toxicity is often considered to be in direct proportion with anesthetic potency

Chemical Groups of LOCAL ANESTHETICS commonly used in dentistry:

I. Ester group A. Benzoic acid esters 1. Cocaine (topical only) naturally occurring 2. Benzocaine (topical only)

Chemical Groups of LOCAL ANESTHETICS commonly used in dentistry:

B. Para-aminobenzoic acid esters 1. Procaine (Novocaine) 2. Tetracaine (Pontocaine) extremely strong local anesthetic for surface anesthesia; no real injection use 3. Propoxycaine (Ravocaine) 4. 2-Chloroprocaine (Nesacaine) (not marketed in an dental cartridge)

Chemical Groups of LOCAL ANESTHETICS

commonly used in dentistry:

II. Nonester group A. Anilide (Nonester type) 1. Bupivacaine (Marcaine, Sensorcaine) 2. Etidocaine (Duranest) 3. Lidocaine (Xylocaine) 4. Mepivacaine (Carbocaine) 5. Prilocaine (Citanest)

Excretion and Absorption of Local Anesthetics

1. Esters: Hydrolyzed by plasma esterase and by products excreted in urine. Note that one by product is PABA (para-amino benzoic acid) 2. Amides: Metabolized in liver by microsomal enzymes and only 10 20% is excreted unchanged

Cocaine
From the leaves of a plant called Erthroxylon coca; 1855 French chemist F. Gaedcke Albert Niemann isolated the alkaloid in its pure formnamed it cocaine 1884, Carl Koller, encouraged by Sigmund Freud, discovered that it is effective surface anesthesia of the cornea

Cocaine
William Steward Halsted in America used the solution to produce anesthesia in the inferior dental nerve; victim of the drugs addictive properties First record of use in Britain, JADA 1886, William Alfred Hunt described use in infiltration 1901, E. Mayer suggested addition of adrenalinepromote vasoconstriction, prolong duration, and intensify depth of anesthesia

Cocaine
Rarely used these days due to problems of misuse Methyl 3-hydroxy-1H-tropan-2carboxylate ester benzoate (chemical name) Unique among local anesthetic agents in that it produces vasoconstriction

Preparation: Topical preparation as a 4 - 10% solution Recommended uses in Dentistry: Should not be considered as a normal part of dental local anesthetic armamentarium due to its obvious disadvantagepotential for abuse Occasionally used topically intranasally during apical surgery on maxillary incisor teeth when the nasal floor is in close proximity

Cocaine

Benzocaine
Most commonly used ester local anesthetic Ethyl-p-aminobenzoate (chemical name)

Dosage Due to its extremely poor solubility in water and poor absorption, toxic reactions to benzocaine are almost unknown

Benzocaine
Preparation: Extremely poor water solubility not suitable for injection; available only in topical preparations Available in number of concentrations up to 20% and in combination with other agents Different flavors have been added to benzocaine gel to make them particularly popular with children

Benzocaine
Recommended uses in Dentistry: Topical application prior to an infiltration means of reducing pain Incorporated into proprietary medications for application to painful intraoral lesions ulcers Sole source of anesthesia for superficial soft tissue manipulation

Procaine
Produced synthetically procaine hydrochloride by two Swedish chemists, Alfred Einhorn & E. Uhlfelder Tested clinically by Henrich Braun and marketed as Novocaine (proprietary name) Archetypal dental local anesthetic prior to the introduction of lignocaine

Procaine
Use has declined for a number of reasons: susceptible persons may become sensitized to this substance; can cause dermatitis, urticaria and even eodema of the glottis Not as potent as cocaine, but it is very much less toxic

Procaine
Preparation: Rarely used as sole anesthetic in Dentistry today No longer available in cartridges in some parts of the world and must be drawn up in ampule Normal presentation is 2% solution, however 1:80,000 adrenaline may be added Not available as a topical agent

Procaine
Recommended uses in Dentistry Only indication for use as a local anesthetic is in patients with proven allergy to the amide group Useful in intravenous sedation relevant to dental practice Recognized regimen to treat arteriospasm when it is administered intra-arterially excellent vasodilatory properties

Procaine
Onset and duration of action Onset of action: 10 minutes (pulpal) Duration of action: plain solution, extremely short-lived pulpal anesthesia of approximately 5 minutes

solution with adrenaline, pulpal anesthesia of 30 minutes

Dosage Maximum dose is 6 mg/kg with ceiling of 400 mg

Tetracaine
Para-butylaminobenzoyl-2dimethylaminoethanol hydrochloride (chemical name) Proprietary name: Pontocaine 10x as potent and 10x as toxic as procaine Chemically it is closely related to procaine but pharmacologically it is closer to cocaine Potent topical agent, does not possess vasoconstricting properties

Tetracaine
Popular for the production of spinal anesthesia No longer available in cartridges for use in dentistry Limited almost exclusively to topical application Rapidly absorbed into systemic circulationtoxic effects, not sprayed on mucous membrane

Tetracaine
Preparation 0.15%, 1% and 2% topical solutions Plain tetracaine hydrochloride Tetracaine hydrochloride with 1:100,000 vasodilator Dosage Maximum of 20 mg (1 ml of 2% solution) be applied at one time

Tetracaine
Duration of action When injected, plain 0.15% solution will produce 30 45 minutes of analgesia Same concentration with 1:100,000 epinephrine will produce 75 120 minutes of analgesia

Tetracaine
Recommended use in Dentistry Although efective when given by injection, it is not used in this manner due to its toxicity. It is available in topical preparations both on its own and in combination with other anesthetic agents such as lignocaine

Propoxycaine (Ravocaine)
2-diethylaminoethyl 4-amino-2propoxybenzoate is its chemical name Equal in potency and toxicity to tetracaine Preparation Not used alone in dentistry, combined with procaine, in a procaine 2%, propoxycaine 0.4% solution with either 1:20,000 levondefrin or 1: 30,000 levarterenol as vasoconstrictor

Propoxycaine
Duration of action Combination of procaine and propoxycaine gives rapid and profound anesthesia with a pulpal analgesia of about 1 1.5 hours and soft tissue duration of 2 3 hours Dosage Suggested maximum dose is 6.6 mgkg (3 mg/lb) Maximum total anesthetic (procaine plus propoxycaine) dosage should not exceed 400 mg

2-Chloroprocaine
Proprietary name: Nesacaine Beta-diethylaminoethyl-2-chloro-4aminobenzoate (chemical name) Differs from other local anesthetic of the ester group in having a chloride atom substituted in the benzene ring 2x as potent but less toxic than procaine hydrolyzed 4x-5x faster than procaine

2-Chloroprocaine
Preparation Not available in dental cartridge, multiple dose vial via disposable 3 to 5 cc syringe with a 25-gauge Leur-Lok needle Available in 1.2% or 3% concentrations, must be used with a vasoconstrictor due to its shortness of duration

2-Chloroprocaine
Onset and duration of action Extremely rapid onset with a satisfactory short-acting anesthetic (low toxicity) thus advantageous in use for children who may inadvertently traumatize the lip, tongue or cheek with longer-acting agents

Lignocaine
Most commonly used dental anesthetic Synthetized in 1943, has been in clinical use since 1948 Proprietary names: Xylocaine, Lignospan, Lignostab, & Lidocaine (North America) Chemical name: 2-diethylamino-2,6acetoxylidide. 2x potency than procaine More profound anesthesia and long duration (spreads more widely through tissues)

Lignocaine
Preparations: Dental cartridges plain 2% solution and a 2% solution with 1:80,000 or 1:100,000 adrenaline Topical 4% and 10% spray, 2% gels, and 5% ointment

Lignocaine
Recommended uses in Dentistry: 2% with 1:80,000 adrenaline--ideal for infiltration, intraosseous, intraligamentary, and regional block anesthesia for majority of patients Contraindicated in those allergic to amides and in individuals where increased adrenaline levels may be hazardous

Lignocaine
Recommended uses in Dentistry: Plain solution is not very effective in obtaining pulpal anesthesia Use for soft tissue procedures is very limitedpoor hemorrhage control Nevertheless, effective topical anesthetic for non-keratinized tissue: reflected mucosa & as a symptomatic treatment for painful mucosal lesions such as ulcers

Lignocaine
Onset and duration of action Short onset of action, pulpal anesthesia obtained in 2-3 minutes ff. infiltration Plain solution is classified as short-acting agent, will provide pulpal anesthesia for 10 minutes; 1-1 hours soft tissue anesthesia Adrenaline containing solution is intermediate in duration providing 45-60 minutes (1-1 hours) of pulpal anesthesia; 3-4 hours soft tissues anesthesia

Prilocaine
Toluidine derivative; related both chemically and pharmacologically to both lignocaine and mepivacaine Proprietary name: Citanest 2-propylamino-o-propionotoluidine (chemical name) As potent as lignocaine but is less toxic Metabolized more rapidly than lignocaine Does not produce topical anesthesia

Prilocaine
Preparations Plain solution is 4% Vasoconstrictor-containing version is 3% with 0.03 IU/ml felypressin (UK) In other parts of the world prilocaine is available with adrenaline Topical anesthetic agent available combination prilocaine & lignocaine EMLA (Eutectic Mixture of Local Anesthetics)

Prilocaine
Recommended use in Dentistry 3% with 0.03 IU felypressin is the alternative to lignocaine with adrenaline when a vasoconstrictorcontaining solution is required Effective when administered as an infiltration or regional block anesthetic Not as effective as lignocaine during intraligamentary techniques 4% plain prilocaine more effective than 2% lignocaine when a vasoconstrictor-free solution must be employed EMLA useful prior to venepuncture in children and during dental sedation; oral application not recommended by manufacturers

Prilocaine
Contraindications Should not be administered to infants, patients with methaemoglobineamia, kidney disease, hypoxia, anemia, liver disease or heart failure, or any other condition in which problems with oxygenation could be critical, such as pregnancy Should not be used in patients who have a history of either sensitivity to an amide-type local anesthetic agent or paraben allergy

Prilocaine
Onset and duration of action Slower onset of action than lignocaine: pulpal anesthesia 4 minutes 4% prilocaine short-acting agent with pulpal anesthesia lasting around 10 minutes 3% with 0.03 IU felypressin provides duration of anesthesia similar to that afforded by lignocaine

Mepivacaine
The least vasodilatory of the amide local anesthetic Proprietary name: Scandonest (UK), Carbocaine Pharmaceutical Manufacturing Co. 1-methyl-2,6-pipecoloxylidide (chemical name) Mepivacaine without adrenaline has a 5year shelf-life, irrespective of the conditions of storage

Mepivacaine
Preparations 3% plain solution 2% solution with 1:80,000 adrenaline Not available in a topical preparation

Mepivacaine
Recommended use in Dentistry: Prime indication is for the use is when vasoconstrictor-free solution must be employed as 3% mepivacaine is more effective than plain lignocaine or prilocaine solutions Solution with adrenaline has identical indications for use as lignocaine with adrenaline although it has a shorter duration of action

Mepivacaine
Onset and duration of action Rapid onset of action: (pulpal) 2 minutes Duration of action: (pulpal) plain solution30 minutes with adrenaline provides anesthesia of similar depth as lignocaine but of slightly shorter duration

Dosages
Anesthetic solution Max. dose (mg/kg) [absolute ceiling (mg)] 4.4 [300] 4.4 [300] 4.4 [300] 6.0 [400] Max. dose Max. dose Max. dose Max. dose of 1.8 ml of 1.8 ml of 2.2 ml of 2.2 ml cartridges cartridges in cartridges cartridges in in an adult a 5-year-old in an adult a 5-year-old of 70 kg child of 20kg of 70 kg child of 20kg 8.3 8.3 5.6 7.4 2.4 2.4 1.6 2.2 6.8 6.8 4.5 6 2 2 1.3 1.8

2% lignocaine 2% mepivacaine 3% mepivacaine 3% prilocaine

4% prilocaine

6.0 [600]

5.5

1.7

4.5

1.4

Bupivacaine
Developed from mepivacaine and is thus chemically related to lignocaine Differs from mepivacaine in that a methyl group in the piperidine ring has been replaced by a butyl group Proprietary name: Marcaine, Sensorcaine 1-butyl-2,6-pipecoloxylidide (chemical name) 4x as potent as lignocaine

Bupivacaine
Preparations: Has recently been available to the dental profession in conventional 1.8 ml cartridges Supplied in 10,30, & 50 ml vials containing 0.25%, 0.375%, 0.5%, 0.75% solutions available with or without 1:200,000 adrenaline

Bupivacaine
Recommended uses in Dentistry Few indications in routine restorative dentistry Main uses are in oral surgeryregional block, long lasting anesthesia Useful for post-operative pain control following procedures such as the surgical removal of impacted third molars Short-term temporary relief of acutely painful conditionstrigeminal neuralgia

Bupivacaine
Onset and duration of action: Onset of action: longer than lignocaine, may take more than 5 minutes pulpal anesthesia Duration of action: longer 1.5 2 hours pulpal anesthesia When used as a regional block, soft tissue anesthesia of 6 8 hours is possible

Bupivacaine
Dosage Total doses in the healthy adult should not exceed 2.0 mg/kg (0.9 mg/lb), not to exceed 225 mg with epinephrine 1:200,000 and 175 mg without vasoconstrictor. These total doses may be repeated up to once every 3 hours not to exceed 400 mg in 24 hours

Etidocaine
Amide derivative that is structurally similar to lidocaine 4x as potent as lidocaine, with a twofold increase in the duration of action, twice as toxic Proprietary name: Duranest 2-ethylpropylethylbutyroxylidide (chemical name)

Etidocaine
Preparations: Dental local anesthetic cartridges as 1.5% solution with 1:200,000 adrenaline Onset and duration of action Onset of action: 2 3 minutes pulpal Duration of action: long-acting anesthetic similar to bupivacaine

Etidocaine
Recommended use in Dentistry: Main indications for use are similar to those mentioned for bupivacaine as a regional block anesthetic When used in infiltration techniques for surgical procedures 1.5% etidocaine with 1:200,000 adrenaline is not as effective as 2% lignocaine with 1:80,000 adrenaline