Prilocaine

Structural formula
	1: 1 mixture of ( R ) -form (top) and ( S ) -form (bottom)
General
Non-proprietary name	Prilocaine
other names	( RS ) - N - (2-methylphenyl) -2- (propylamino) propanamide; (±) - N - (2-methylphenyl) -2- (propylamino) propanamide;
Molecular formula	C 13 H 20 N 2 O; C 13 H 21 ClN 2 O (prilocaine hydrochloride ) ;
Brief description	white to almost white, crystalline powder
External identifiers / databases
EC number	211-957-0
ECHA InfoCard	100.010.871
PubChem	4906
ChemSpider	4737
DrugBank	DB00750
Wikidata	Q413598
Drug information
ATC code	N01 BB04
Drug class	Local anesthetics
properties
Molar mass	220.31 g · mol -1 (racemate) ; 256.8 g · mol -1 (racemate · hydrochloride) ;
Melting point	37-38 ° C (racemate) ; 168–171 ° C (racemate hydrochloride) ;
boiling point	159-162 ° C (133.3 Pa )
pK s value	7.9 (25 ° C)
solubility	slightly soluble in water, very easily soluble in acetone and ethanol 96%
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Hydrochloride;	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Prilocaine is an amide-type local anesthetic . It works quite quickly and its effects last for three to six hours.

application

Prilocaine is mainly used in anesthesia for infiltration and conduction anesthesia. For surface anesthesia, it is sometimes combined with lidocaine .

unwanted effects

In addition to the other side effects that can occur when using local anesthetics, prilocaine can lead to the formation of methemoglobin (the breakdown product o -toluidine has an oxidizing effect on the iron present in hemoglobin ); therefore it should not be used in children, in patients with anemia , in those with glucose-6-phosphate dehydrogenase deficiency and in pregnant women, or with caution. Furthermore, o -toluidine has been classified by ECHA as carcinogenic for humans.

Stereoisomerism

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

Manufacturing

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

Analytics

The reliable qualitative and quantitative determination of prilocaine in blood plasma is possible after appropriate sample preparation by coupling gas chromatography or HPLC with mass spectrometry .

Trade names

Monopreparations

Xylonest (D, CH) and generics

Combination preparations

Anesderm (A, CH), Emla (D, A, CH), Lidocain / Prilocain Plethora (EU), Oraqix (D, A, CH)

Individual evidence

↑ ^a ^b PRILOCAINE CRS data sheet (PDF) at EDQM , accessed on March 10, 2009.

^ ^A ^b ^c The Merck Index : An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006; ISBN 978-0-911910-00-1 .

↑ European Pharmacopoeia, 6th edition, Grundwerk 2008, pp. 3751–3752, ISBN 978-3-7692-3962-1 .

↑ Data sheet Prilocaine hydrochloride from Sigma-Aldrich , accessed on April 22, 2011 ( PDF ).

↑ o-toluidine - List of substances of very high concern for approval. ECHA, accessed on June 15, 2020 .

^ Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dietmar Reichert: Pharmaceutical Substances, 4th edition (2000), 2 volumes published by Thieme-Verlag Stuttgart, ISBN 978-1-58890-031-9 ; online since 2003 with biannual additions and updates.

↑ Kadioglu Y, Atila A: Development and validation of gas chromatography-mass spectroscopy method for determination of prilocaine HCl in human plasma using internal standard methodology , Biomed Chromatogr. 2007 Oct; 21 (10): 1077-1082, PMID 17583875 .

↑ Stockmann S, Spies E, Gehring H, Klose A, Schmeller W, Seyfarth M, Dibbelt L: Evaluation and application of a high performance liquid chromatographic method for prilocaine analysis in human plasma , Clin Lab. 2013; 59 (1-2): 127-132, PMID 23505917 .

[Ph._Eur.-1] PRILOCAINE CRS data sheet (PDF) at EDQM , accessed on March 10, 2009.

[MERCK_Index-2] A ^b ^c The Merck Index : An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006; ISBN 978-0-911910-00-1 .

[EA6-3] European Pharmacopoeia, 6th edition, Grundwerk 2008, pp. 3751–3752, ISBN 978-3-7692-3962-1 .

[Sigma-4] Data sheet Prilocaine hydrochloride from Sigma-Aldrich , accessed on April 22, 2011 ( PDF ).

[5] o-toluidine - List of substances of very high concern for approval. ECHA, accessed on June 15, 2020 .

[A._Kleemann-6] Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dietmar Reichert: Pharmaceutical Substances, 4th edition (2000), 2 volumes published by Thieme-Verlag Stuttgart, ISBN 978-1-58890-031-9 ; online since 2003 with biannual additions and updates.

[7] Kadioglu Y, Atila A: Development and validation of gas chromatography-mass spectroscopy method for determination of prilocaine HCl in human plasma using internal standard methodology , Biomed Chromatogr. 2007 Oct; 21 (10): 1077-1082, PMID 17583875 .

[8] Stockmann S, Spies E, Gehring H, Klose A, Schmeller W, Seyfarth M, Dibbelt L: Evaluation and application of a high performance liquid chromatographic method for prilocaine analysis in human plasma , Clin Lab. 2013; 59 (1-2): 127-132, PMID 23505917 .