Author: Prof. Dr. med. Peter Altmeyer

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Last updated on: 29.10.2020

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Articaine Hydrochloride; CAS number: 23964-57-0; RS)-4-methyl-3-[2-(propylamino)-propanamido]thiophene-2-carboxylic acid methyl ester rac-4-methyl-3-[2-(propylamino)-propanamido]thiophene-2-carboxylic acid methyl ester (±)-4-methyl-3-[2-(propylamino)-propanamido]thiophene-2-carboxylic acid methyl ester DL-4-methyl-3-[2-(propylamino)-propanamido]thiophene-2-carboxylic acid methyl ester CAS number 23964-58-1

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Articaine (until 1984 carticaine) is a drug from the group of local anaesthetics with the molecular formula C13H20N2O3S, which, like lidocaine, is classified as a local anaesthetic of the acid amide type. Articaine is widely used in dentistry because the substance has good penetration into bone tissue.

Since the intermediate chain of the molecule contains an acid amide bond, it is classified in this group of local anaesthetics. The thiophene ring also carries an ester bond in the side chain. Thus the substance takes a special position within the classification of local anaesthetics. The cleavage of the ester bond by esterases in plasma leads to a metabolite without local anaesthetic effect.

Pharmacodynamics (Effect)
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Like all Na+ blockers, articaine leads to a blockage of the voltage-dependent Na channels. The influx of sodium into the nerve fibre is inhibited, the formation of an action potential is prevented. The onset of action is 2 minutes and the duration of action is 0.5-3 hours. The duration of action is between 20 minutes and 75 minutes. The drug has a good penetration into the bone tissue. It is inactivated by hydrolysis and exposure of a hydrophilic acid group, which allows it to be rapidly eliminated from the body. The plasma half-life is 25 minutes. Articaine has a high plasma protein binding capacity and good general compatibility and is the drug of choice for pregnant women.

Undesirable effects
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In patients with a cholinesterase deficiency, the indication must be strictly defined, since a prolonged and possibly increased effect can be expected.

Possible symptoms are: dizziness, vomiting, headaches, cramps, bradycardia, cardiac arrhythmia, shock, allergic reactions(paragroup allergy!).

Articaine can only be used under special indication in patients with the following underlying diseases:

  • disorders of blood coagulation,
  • severe kidney or liver dysfunction,
  • of known epilepsy.

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Last updated on: 29.10.2020