Prilocaine

(RS)- N-(2 -methylphenyl ) -2 - ( propylamino) propanamide

• C13H20N2O
• C13H21ClN2O ( Prilocainhydrochlorid )

• 721-50-6 ( prilocaine )
• 1786-81-8 ( Prilocainhydrochlorid )

N01BB04

White to off- white crystalline powder

Local anesthetics

• 220.31 g · mol -1 ( racemate)
• 256.8 g · mol -1 (racemate · hydrochloride)

• 37-38 ° C ( racemate)
• 168-171 ° C ( racemate · hydrochloride)

159-162 ° C ( 133,3 Pa)

7.9 (25 ° C)

Sparingly soluble in water, very slightly soluble in acetone and ethanol 96 %

Hydrochloride

Template: Infobox chemical / molecular formula search available

Prilocaine (trade name: inter alia Xylonest ®) is a local anesthetic of the amide type. It has a relatively rapid onset of action and a duration of action between 3-6 hours.

Application

Prilocaine is mainly applied in anesthesia for infiltration and conduction anesthesia. For surface anesthesia, it also teiweise fix combined with lidocaine.

Adverse effects

In addition to other side effects that may occur during use of local anesthetics, there may be prilocaine to the formation of methemoglobin; therefore it should not be applied or with increased caution in children, in patients with anemia, with deficiency of glucose -6 -phosphate dehydrogenase and in pregnant women.

Stereoisomerism

Prilocaine is chiral and includes a stereogenic center, so there are two enantiomers, the ( R) form and the ( S) form. The commercial preparations containing the drug as a racemate ( 1:1 mixture of enantiomers).

Production

A synthesis of prilocaine, starting from ortho -toluidine and 2- bromopropionyl bromide is described in the literature.

Trade names

Xylonest (D, CH) and generic

Anesderm (A, CH), Emla (D, A, CH), lidocaine / prilocaine Plethora ( EU), Oraqix (D, A, CH)