Mepivacaine

Mepivacaine /mɛˈpɪvəkeɪn/ is a local anesthetic[1] of the amide type. Mepivacaine has a reasonably rapid onset (less rapid than that of procaine) and medium duration of action (longer than that of procaine)[2][3] and is marketed under various trade names including Carbocaine and Polocaine.

Mepivacaine
Clinical data
AHFS/Drugs.comConsumer Drug Information
MedlinePlusa603026
Pregnancy
category
ATC code
Identifiers
  • (RS)-N-(2,6-dimethylphenyl)- 1-methyl-piperidine-2-carboxamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.002.313
Chemical and physical data
FormulaC15H22N2O
Molar mass246.354 g·mol−1
3D model (JSmol)
  • O=C(Nc1c(cccc1C)C)C2N(C)CCCC2
  • InChI=1S/C15H22N2O/c1-11-7-6-8-12(2)14(11)16-15(18)13-9-4-5-10-17(13)3/h6-8,13H,4-5,9-10H2,1-3H3,(H,16,18) Y
  • Key:INWLQCZOYSRPNW-UHFFFAOYSA-N Y
  (verify)

Mepivacaine became available in the United States in the 1960s.

Mepivacaine is used in any infiltration and local anesthesia.

It is supplied as the hydrochloride salt of the racemate,[4] which consists of R(-)-mepivacaine and S(+)-mepivacaine in equal proportions. These two enantiomers have markedly different pharmacokinetic properties.[4]

Mepivacaine was originally synthesized in Sweden at the laboratory of Bofors Nobelkrut in 1956.[5]

References
  1. Porto GG, Vasconcelos BC, Gomes AC, Albert D (January 2007). "Evaluation of lidocaine and mepivacaine for inferior third molar surgery" (PDF). Medicina oral, patología oral y cirugía bucal. 12 (1): E60–4. PMID 17195831.
  2. "Procaine". go.drugbank.com. Retrieved 2023-06-27.
  3. "Mepivacaine". go.drugbank.com. Retrieved 2023-06-27.
  4. Burm AG, Cohen IM, van Kleef JW, Vletter AA, Olieman W, Groen K (January 1997). "Pharmacokinetics of the enantiomers of mepivacaine after intravenous administration of the racemate in volunteers". Anesthesia & Analgesia. 84 (1): 85–9. doi:10.1097/00000539-199701000-00016. PMID 8989005. S2CID 22363370.
  5. Castrén, J.A. (1963). "A clinical evaluation of mepivacaine (Carbocain) in ocular surgery". Acta Ophthalmologica. 41 (3): 262–9. doi:10.1111/j.1755-3768.1963.tb02436.x. PMID 14047466. S2CID 32119846.
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