Amino esters

Class of chemical compounds

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Amino esters are a class of local anesthetics. They are named for their ester bond and are unlike amide local anaesthetics.

## Structure

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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.

Amino esters, in reference to anesthetic agents, are rapidly metabolized in the plasma by butyrylcholinesterase to para-aminobenzoic acid derivatives, then excreted in the urine. This suggests their very short half lives. Allergy is more likely to occur with ester-type agents, as opposed to amide-type.

## Examples

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Amino ester-type include:

* Cocaine
* Procaine (Novocain)
* Tetracaine (Pontocaine)
* Benzocaine
* Chloroprocaine

## References

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* University of Texas Med School, Pharmacology Syllabus.
* Katzung. 10th edition. Chapter 26.

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Local anesthetics (primarily sodium channel blockers) (N01B)

Esters by acid|

| Aminobenzoic|

* Benzocaine
* Benzonatate
* Butacaine
* Butamben
* Chloroprocaine
* Dimethocaine
* Lucaine
* Meprylcaine
* Metabutethamine
* Metabutoxycaine
* Nitracaine
* Orthocaine
* Propoxycaine
* Procaine (Novocaine)
* Proxymetacaine
* Risocaine
* Tetracaine

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Benzoic|

* Amylocaine
* Cocaine
* Cyclomethycaine
* α-Eucaine
* β-Eucaine
* Hexylcaine
* Isobucaine
* Piperocaine

ArCO2- (not para-amino or Ph)|

* Amoproxan (3,4,5-Trimethoxybenzoyl)
* 3-(p-Fluorobenzoyloxy)tropane

Amides|

* Articaine
* Bupivacaine#/Levobupivacaine/Ropivacaine
* Butanilicaine
* Carticaine
* Cinchocaine (Dibucaine)
* Etidocaine
* Lidocaine#
* Mepivacaine
* Prilocaine
* Trimecaine

Combinations|

* Anesthetic/vasoconstrictor
* Bupivacaine/meloxicam
* Lidocaine/prilocaine
* TAC
* Iontocaine

* #WHO-EM
* ‡Withdrawn from market
* Clinical trials:
* †Phase III
* §Never to phase III

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