Lidocaine hydrochlorideProduct ingredient for Lidocaine

Name
Lidocaine hydrochloride
Drug Entry
Lidocaine

Ever since its discovery and availability for sale and use in the late 1940s, lidocaine has become an exceptionally commonly used medication 6. In particular, lidocaine's principal mode of action in acting as a local anesthetic that numbs the sensations of tissues means the agent is indicated for facilitating local anesthesia for a large variety of surgical procedures 10,7,8. It ultimately elicits its numbing activity by blocking sodium channels so that the neurons of local tissues that have the medication applied on are transiently incapable of signaling the brain regarding sensations 10,7,8. In doing so, however, it can block or decrease muscle contractile, resulting in effects like vasodilation, hypotension, and irregular heart rate, among others 10,7,8. As a result, lidocaine is also considered a class Ib anti-arrhythmic agent 7,8,12. Nevertheless, lidocaine's local anesthetic action sees its use in many medical situations or circumstances that may benefit from its action, including the treatment of premature ejaculation 5.

Regardless, lidocaine is currently available as a relatively non-expensive generic medication that is written for in millions of prescriptions internationally on a yearly basis. It is even included in the World Health Organization's List of Essential Medicines 9.

Accession Number
DBSALT000900
Structure
Thumb
Synonyms
Lidocaine HCl
UNII
V13007Z41A
CAS Number
6108-05-0
Weight
Average: 288.82
Monoisotopic: 288.1604558
Chemical Formula
C14H25ClN2O2
InChI Key
YECIFGHRMFEPJK-UHFFFAOYSA-N
InChI
InChI=1S/C14H22N2O.ClH.H2O/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);1H;1H2
IUPAC Name
2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide hydrate hydrochloride
SMILES
O.Cl.CCN(CC)CC(=O)NC1=C(C)C=CC=C1C
External Links
PubChem Compound
6314
ChemSpider
21087
ChEBI
60791
ChEMBL
CHEMBL1200409
Wikipedia
Lidocaine
Predicted Properties
PropertyValueSource
Water Solubility0.593 mg/mLALOGPS
logP1.81ALOGPS
logP2.84ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)13.78ChemAxon
pKa (Strongest Basic)7.75ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.34 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity73.93 m3·mol-1ChemAxon
Polarizability27.6 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon