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.
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2D Structure
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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.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. FDA (1960)
IUPAC Name Click here for help
N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboximidic acid
International Nonproprietary Names Click here for help
INN number INN
988 mepivacaine
Synonyms Click here for help
Carbocaine® | mepivacaine hydrochloride | Polocaine®
Database Links Click here for help
CAS Registry No. 96-88-8
ChEMBL Ligand CHEMBL1087
DrugBank Ligand DB00961
DrugCentral Ligand 1700
GtoPdb PubChem SID 178103798
PubChem CID 4062
Search Google for chemical match using the InChIKey INWLQCZOYSRPNW-UHFFFAOYSA-N
Search Google for chemicals with the same backbone INWLQCZOYSRPNW
Search PubMed clinical trials mepivacaine
Search PubMed titles mepivacaine
Search PubMed titles/abstracts mepivacaine
UniChem Compound Search for chemical match using the InChIKey INWLQCZOYSRPNW-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey INWLQCZOYSRPNW-UHFFFAOYSA-N
Wikipedia Mepivacaine

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MedChemExpress
Mepivacaine (links to external site)
Cat. No. HY-B0517