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
No information available.
Summary of Clinical Use
Used in the production of local and regional anaesthesia by injection and is also an active ingredient in a number of over-the-counter formulations for pain relief via topical application. In Europe marketing authorisation was granted in 2013 for Fortacin® a fixed-dose combination of lidocaine and prilocaine, as a treatment for primary premature ejaculation (physiological sexual dysfunction).
Mechanism Of Action and Pharmacodynamic Effects
Lidocaine blocks voltage-gated sodium channels in neuronal cell membranes thereby inhibiting ionic influxes and subsequent signal propagation, leading to a local anaesthetic effect.
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