Articaine

  • (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
  • Carticain
  • 23964-58-1 ( articaine )
  • 23964-57-0 ( articaine hydrochloride)

N01BB08

Local anesthetics

177-178 ° C ( · articaine hydrochloride)

162-167 ° C ( 39 Pa) ( articaine )

980 mg · kg -1 ( LD50, Rat, oral, hydrochloride)

Template: Infobox chemical / molecular formula search available

Articaine (until 1984 Carticain ) is a drug from the group of local anesthetics used mainly dental. Articaine was patented by the former color Höechst 1969 and 1974.

Application

Infiltration and conduction anesthesia ( 0.5-4 % strength, hyperbaric up to 5% )

Type

Articaine is usually classified as a local anesthetic of the amide type, since the intermediate chain containing such an acid amide bond. However, the thiophene ring also carries a side chain with an ester bond, so that articaine has a special position within the classification of local anesthetics. The cleavage of the ester bond by esterases in plasma also leads to a metabolite or local anesthetic effect.

Effect

Articaine change the membrane permeability, so that the sodium influx inhibited the nerve fibers and thus the formation of an action potential is prevented. The onset of action is 2 minutes and the duration of 0.5-3 hours, with the intervention ripe duration between 20 minutes and 75 minutes.

The drug has a good penetration into bone tissue. It is inactivated by hydrolysis and expose a hydrophilic acid group, allowing it to be rapidly eliminated from the body. The plasma half -life is 25 minutes. Articaine has a high plasma protein binding and good general tolerability and is the drug of choice for pregnant women.

Stereoisomerism

Articaine contains a stereocenter, and is therefore chiral. As a local anesthetic, the racemate of [ 1:1 mixture of (R )-isomer and (S)- isomer ] is used.

CAS registry number PubChem Anatomical Therapeutic Chemical Classification System Dangerous Substances Directive (67/548/EEC) Active ingredient
81378
de