lidocaine   

GtoPdb Ligand ID: 2623

Synonyms: Xylocaine®
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
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
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
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Nav1.5 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