mepivacaine   Click here for help

GtoPdb Ligand ID: 7224

Synonyms: Carbocaine® | mepivacaine hydrochloride | Polocaine®
Approved drug
mepivacaine is an approved drug (FDA (1960))
Compound class: Synthetic organic
Comment: Mepivacaine is an amide class local anesthetic. It is a racemic mixture of enantiomers. We show the chemical structure without specified stereochemistry to represent the mixture.
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: mepivacaine

2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 35.83
Molecular weight 246.17
XLogP 2.52
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

✖
Canonical SMILES CN1CCCCC1C(=Nc1c(C)cccc1C)O
Isomeric SMILES CN1CCCCC1C(=Nc1c(C)cccc1C)O
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)
InChI Key INWLQCZOYSRPNW-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Mepivacaine is used as a local anaesthetic for dental procedures and for surgery carried out under epidural or spinal block.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The molecular mechanism of action of this drug may be due to inhibition of neuronal sodium channels, which blocks action potentials and subsequent nerve impulses. CHEMBL lists sodium channel alpha subunits as this drug's molecular targets. The genes and proteins for SNC1A-SNC11A are listed in this database in the voltage-gated sodium channels section. See the DrugBank link for further details.