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) checkY
  • Key:INWLQCZOYSRPNW-UHFFFAOYSA-N checkY
  (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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