Articaine is a dental amide-type local anesthetic. It is the most widely used local anesthetic in a number of European countries and is available in many countries. It is the only local anaesthetic to contain a thiophene ring, meaning it can be described as 'thiophenic'; this conveys lipid solubility.
History
This drug was synthesized by pharmacologist Roman Muschaweck and chemist Robert Rippel. Muschaweck received a "O. Schmiedeberg" medal by the German Society for Experimental and Clinical Pharmacology and Toxicology for his work in 2002. It was brought to the German market in 1976 by Hoechst AG, a life-sciences German company (now Sanofi-Aventis), under the brand name Ultracain. This drug was also referred to as "carticaine" until 1984.
In 1983 it was brought into the North American market, to Canada, under the name Ultracaine for dental use, manufactured in Germany and distributed by Hoechst-Marion-Roussel. This brand is currently manufactured in Germany by Sanofi-Aventis and distributed in North America by Hansamed Limited (since 1999). After Ultracaine's patent protection expired, new generic versions arrived to the Canadian market: (in order of appearance) Septanest (Septodont), Astracaine, (originally by AstraZeneca and now a Dentsply product), Zorcaine (Carestream Health/Kodak) and Orabloc (Pierrel).
It was approved by the FDA in April 2000, and became available in the United States of America two months later under the brand name Septocaine, an anesthetic/vasoconstrictor combination with Epinephrine 1:100,000 (trade name Septodont). Zorcaine became available there a few years later, also. Articadent (Dentsply) became available in the United States in October 2010. The three brands currently available in the United States are all manufactured for these companies by Novocol Pharmaceuticals Inc. (Canada). Ubistesin and Ubistesin Forte (3M ESPE) are also widely used in the United States and Europe. Orabloc (Pierrel) is aseptically manufactured and was approved by the FDA in 2010, became available in Canada in 2011, and in Europe from 2013.
Articaine is currently available for the North American dental market: In Canada: As articaine hydrochloride 4% with epinephrine 1:100,000 (0,01 mg/ml) Ubistesin Forte Ultracaine DSF Septanest SP Astracaine Forte Zorcaine Orabloc (articaine hydrochloride 4% and epinephrine 1:100,000) As articaine hydrochloride 4% with epinephrine 1:200,000 (0,005 mg/ml) Ubistesin Ultracaine DS Septanest N Astracaine Orabloc (articaine hydrochloride 4% and epinephrine 1:200,000) In the USA: As articaine hydrochloride 4% with epinephrine 1:100,000 Septocaine with epinephrine 1:100,000 Zorcaine Articadent with epinephrine 1:100,000 Orabloc (articaine hydrochloride 4% and epinephrine 1:100,000) As articaine hydrochloride 4% with epinephrine 1:200,000 Septocaine with epinephrine 1:200,000 Articadent with epinephrine 1:200,000 Orabloc (articaine hydrochloride 4% and epinephrine 1:200,000)
An epinephrine-free (adrenaline-free) version is available in Europe under the brand name Ultracain D. However, version with epinephrine (adrenaline) is available in Europe under the brand name Supracain 4% with epinephrine concentration of 1:200,000.
Structure and metabolism
The amide structure of articaine is similar to that of other local anesthetics, but its molecular structure differs through the presence of a thiophene ring instead of a benzene ring. Articaine is exceptional because it contains an additional ester group that is metabolized by esterases in blood and tissue. The elimination of articaine is exponential with a half-life of 20 minutes. Since articaine is hydrolized very quickly in the blood, the risk of systemic intoxication seems to be lower than with other anesthetics, especially if repeated injection is performed.
Clinical use
Articaine is used for pain control. Like other local anesthetic drugs, articaine causes a transient and completely reversible state of anesthesia (loss of sensation) during (dental) procedures.
In dentistry, articaine is used mainly for infiltration injections. Articaine, while not proven, has been associated with higher risk of nerve damage when used as a block technique. However, articaine is able to penetrate dense cortical bone — as found in the lower jaw (mandible) — more than most other local anaesthetics.
In people with hypokalemic sensory overstimulation, lidocaine is not very effective, but articaine works well.