Mepivacaine

Local anaesthetic

C, use w/ caution, may cause fetal bradycardia

ATC code

N01BB03 (WHO)

Identifiers

IUPAC name

(RS)-N-(2,6-dimethylphenyl)- 1-methyl-piperidine-2-carboxamide

CAS Number

96-88-8^Y

PubChem CID

4062

IUPHAR/BPS

7224

DrugBank

DB00961^Y

ChemSpider

3922^Y

UNII

B6E06QE59J

KEGG

D08181^Y

ChEBI

CHEBI:6759^Y

ChEMBL

ChEMBL1087^Y

CompTox Dashboard (EPA)

DTXSID9023259

ECHA InfoCard100.002.313

Chemical and physical dataFormulaC₁₅H₂₂N₂OMolar mass246.354 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

O=C(Nc1c(cccc1C)C)C2N(C)CCCC2

InChI

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

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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 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

^ 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.
^ "Procaine". go.drugbank.com. Retrieved 2023-06-27.
^ "Mepivacaine". go.drugbank.com. Retrieved 2023-06-27.
^ ^a ^b 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.
^ 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.

External links

Mepivacaine at RxList

Local anesthetics (primarily sodium channel blockers) (N01B)

Esters by acid

Aminobenzoic	Benzocaine Benzonatate Butacaine Butamben Chloroprocaine Dimethocaine Lucaine Meprylcaine Metabutethamine Metabutoxycaine Nitracaine Orthocaine Propoxycaine Procaine (Novocaine) Proxymetacaine Risocaine Tetracaine
Benzoic	Amylocaine Cocaine Cyclomethycaine α-Eucaine β-Eucaine Hexylcaine Isobucaine Piperocaine
ArCO2- (not para-amino or Ph)	Amoproxan (3,4,5-Trimethoxybenzoyl) 3-(p-Fluorobenzoyloxy)tropane