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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2D Structure
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Physico-chemical Properties
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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
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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)
Selectivity at ion channels
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Nav1.5 Primary target of this compound Hs Channel blocker Pore blocker 4.8 pKd - 5
pKd 4.8 [5]
Voltage: -70.0 – -55.0 mV
Nav1.2 Rn Channel blocker Pore blocker 5.0 pIC50 - 6
pIC50 5.0 [6]
Voltage: -120.0 mV
Nav1.5 Rn Channel blocker Pore blocker 4.2 pIC50 - 2
pIC50 4.2 [2]
Voltage: Physiological
Nav1.8 Rn Channel blocker Pore blocker 4.0 pIC50 - 3
pIC50 4.0 [3]
Voltage: -100.0 mV
Nav1.7 Rn Channel blocker Pore blocker 3.3 pIC50 - 1
pIC50 3.3 [1]
Voltage: -100.0 mV
Nav1.4 Rn Channel blocker Pore blocker 2.7 pIC50 - 4
pIC50 2.7 [4]
Voltage: -130.0 mV