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
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. U.S.A., 93 (17): 9270-5. [PMID:8799190]