Mepivacaine

from Wikipedia, the free encyclopedia
Structural formula
Structural formula of mepivacaine
1: 1 mixture of ( R ) -enantiomer (left) and ( S ) -enantiomer (right)
General
Non-proprietary name Mepivacaine
other names
  • ( RS ) - N - (2,6-Dimethylphenyl) -1-methyl-piperidine-2-carboxamide ( IUPAC )
  • (±) - N - (2,6-Dimethylphenyl) -1-methylpiperidine-2-carboxamide
  • rac - N - (2,6-dimethylphenyl) -1-methylpiperidine-2-carboxamide
Molecular formula C 15 H 22 N 2 O
External identifiers / databases
CAS number
EC number 202-543-0
ECHA InfoCard 100.002.313
PubChem 4062
ChemSpider 3922
DrugBank DB00961
Wikidata Q416760
Drug information
ATC code

N01 BB03

Drug class

Local anesthetic

properties
Molar mass 246.35 g · mol -1
Melting point
  • 150–151 ° C (racemate, free base)
  • 262–264 ° C (racemate, hydrochloride)
pK s value

7.7

solubility

soluble in water (racemate, hydrochloride); Easily soluble in ethanol and methanol

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
06 - Toxic or very toxic

danger

H and P phrases H: 301
P: 301 + 310
Toxicological data

500 mg kg −1 ( LD 50 ,  rat ,  oral , hydrochloride)

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Mepivacaine is a drug for local anesthesia ( local anesthetic ). It was patented by Bofors in 1957 .

application

Mepivacaine is mainly used for infiltration and conduction anesthesia. In the area of ​​conduction anesthesia, it is often used for peripheral nerve blocks. Thanks to its good diffusion in the tissue, it starts to act quickly and lasts between 1.5 and 3 hours.

unwanted effects

As with all local anesthetics , the use of mepivacaine can cause undesirable effects . Depending on the plasma level, these can range from neurological symptoms to cardiac arrhythmias .

Chemical information

Mepivacaine is a local anesthetic of the amide type. Mepivacaine is chiral , the hydrochloride of the racemate [1: 1 mixture of ( R ) form and ( S ) form] is used medicinally .

Analytics

For reliable qualitative and quantitative determination of mepivacaine in various test materials, the coupling of HPLC or gas chromatography with mass spectrometry is suitable after adequate sample preparation . These analytical methods can be used for investigations into pharmacokinetics as well as for toxicological or forensic questions.

Trade names

Monopreparations

Meaverin (D), Mecain (D), Mepinaest (A), Scandicain (D, CH), Scandonest 3% without vasoconstrictor (D, A), various generics (D, CH)

Combination preparations

Estradurine (A, CH), Scandonest 2% with epinephrine (A, CH)

Individual evidence

  1. ↑ a b c d e Entry on mepivacaine. In: Römpp Online . Georg Thieme Verlag, accessed on July 14, 2019.
  2. ↑ a b The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition. 2006, ISBN 0-911910-00-X , p. 1013.
  3. ↑ a b Data sheet Mepivacaine hydrochloride from Sigma-Aldrich , accessed on April 9, 2011 ( PDF ).
  4. ↑ Data sheet MEPIVACAINE HYDROCHLORIDE CRS (PDF) at EDQM , accessed on May 23, 2009.
  5. ↑ Mepivacaine effect: active ingredient mepivacaine ( Memento of the original from June 6, 2016 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. @1@ 2Template: Webachiv / IABot / www.onmeda.de
  6. ^ Gofeminin.de GmbH, Koeln, Germany: Mepivacaine: Contraindications (general, pregnancy / breastfeeding, in children) - Onmeda: Medicine & Health. In: www.onmeda.de. Retrieved June 6, 2016 .
  7. ↑ K. Tonooka, N. Naruki, K. Honma, K. Agei, M. Okutsu, T. Hosono, Y. Kunisue, M. Terada, K. Tomobe, T. Shinozuka: Sensitive liquid chromatography / tandem mass spectrometry method for the simultaneous determination of nine local anesthetic drugs. In: Forensic Sci Int. 265, Mar 4, 2016, pp. 182-185. PMID 26986505
  8. ↑ JD Harkins, W. Karpiesiuk, WE Woods, A. Lehner, GD Mundy, WA Rees, L. Dirikolu, S. Bass, WG Carter, J. Boyles, T. Tobin: Mepivacaine: its pharmacological effects and their relationship to analytical findings in the horse. In: J Vet Pharmacol Ther. 22 (2), Apr 1999, pp. 107-121. PMID 10372595