lidocaine   Click here for help

GtoPdb Ligand ID: 2623

Synonyms: Xylocaine®
Approved drug PDB Ligand
lidocaine is an approved drug (FDA (1948))
Compound class: Synthetic organic
Comment: Lidocaine was the first-in-class amino amide-type local anesthetic to be discovered.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: lidocaine

lidocaine is commercially available from our sponsors

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 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.

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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 32.34
Molecular weight 234.17
XLogP 2.1
No. Lipinski's rules broken 0
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.

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Canonical SMILES CCN(CC(=O)Nc1c(C)cccc1C)CC
Isomeric SMILES CCN(CC(=O)Nc1c(C)cccc1C)CC
InChI InChI=1S/C14H22N2O/c1-5-16(6-2)10-13(17)15-14-11(3)8-7-9-12(14)4/h7-9H,5-6,10H2,1-4H3,(H,15,17)
InChI Key NNJVILVZKWQKPM-UHFFFAOYSA-N
References
1. Chevrier P, Vijayaragavan K, Chahine M. (2004)
Differential modulation of Nav1.7 and Nav1.8 peripheral nerve sodium channels by the local anesthetic lidocaine.
Br J Pharmacol, 142 (3): 576-84. [PMID:15148257]
2. Hill RJ, Duff HJ, Sheldon RS. (1989)
Class I antiarrhythmic drug receptor: biochemical evidence for state-dependent interaction with quinidine and lidocaine.
Mol Pharmacol, 36 (1): 150-9. [PMID:2546048]
3. How SW, Cheng AL. (1992)
Present status of cancer treatment in Taiwan.
Gan To Kagaku Ryoho, 19 (8 Suppl): 1136-8. [PMID:1514825]
4. Makielski JC, Limberis J, Fan Z, Kyle JW. (1999)
Intrinsic lidocaine affinity for Na channels expressed in Xenopus oocytes depends on alpha (hH1 vs. rSkM1) and beta 1 subunits.
Cardiovasc Res, 42 (2): 503-9. [PMID:10533585]
5. Nuss HB, Tomaselli GF, Marbán E. (1995)
Cardiac sodium channels (hH1) are intrinsically more sensitive to block by lidocaine than are skeletal muscle (mu 1) channels.
J Gen Physiol, 106 (6): 1193-209. [PMID:8786356]
6. Ragsdale DS, McPhee JC, Scheuer T, Catterall WA. (1996)
Common molecular determinants of local anesthetic, antiarrhythmic, and anticonvulsant block of voltage-gated Na+ channels.
Proc Natl Acad Sci USA, 93 (17): 9270-5. [PMID:8799190]