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)
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]