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Many local anesthetics fall into two general chemical classes, amino esters (top) and amino amides (bottom). A local anesthetic (LA) is a medication that causes absence of all sensation (including pain) in a specific body part without loss of consciousness, [1] providing local anesthesia, as opposed to a general anesthetic, which eliminates all sensation in the entire body and causes ...
Local anesthetics can be either ester- or amide-based. Ester local anesthetics are generally unstable in solution and fast-acting, are rapidly metabolised by cholinesterases in the blood plasma and liver, [4] and more commonly induce allergic reactions. Amide local anesthetics are generally heat-stable, with a long shelf life (around two years).
Structurally, amino esters consist of three molecular components: a lipophilic part (ester); an intermediate aliphatic chain; a hydrophilic part (amine); The chemical linkage between the lipophilic part and the intermediate chain can be of the amide-type or the ester-type, and is the general basis for the current classification of local anesthetics.
ester- benzoic ambucaine [1] diester - aminosalicylic articaine: Astracaine, Septanest, Septocaine, Ultracaine, Zorcaine Amide benzocaine: Anbesol, Orajel Ester - Aminobenzoic Short benzonatate: Tessalon bupivacaine: Marcaine, Sensorcaine, Vivacaine 1957 (Ekenstam) 1963 (Widman and Telivuo) Amide Moderate butacaine: ester- aminobenzoic ...
E.g. of amide LA: lidocaine, prilocaine, articaine, mepivacaine; E.g. of ester LA: benzocaine, procaine; Genuine allergic reactions of an amide LA is very uncommon. An ester LA is more possible to result in an allergic reaction because the compound will be broken down to para-aminobenzoic acid (PABA) which is a trigger for allergic reactions. [30]
Lidocaine, the first amino amide–type local anesthetic (previous were amino esters), was first synthesized under the name 'xylocaine' by Swedish chemist Nils Löfgren in 1943. [59] [60] [61] His colleague Bengt Lundqvist performed the first injection anesthesia experiments on himself. [59] It was first marketed in 1949.
Like lidocaine, bupivacaine is an amino-amide anesthetic; the aromatic head and the hydrocarbon chain are linked by an amide bond rather than an ester as in earlier local anesthetics. As a result, the amino-amide anesthetics are more stable and less likely to cause allergic reactions.
The core −C(=O)−(N) of amides is called the amide group (specifically, carboxamide group). In the usual nomenclature, one adds the term "amide" to the stem of the parent acid's name. For instance, the amide derived from acetic acid is named acetamide (CH 3 CONH 2). IUPAC recommends ethanamide, but this and related formal names are rarely ...