Lidocaine

Lidocaine
Clinical data


Pronunciation	Lidocaine /ˈlaɪdəˌkeɪn/ lignocaine /ˈlɪɡnəˌkeɪn/
Trade names	Xylocaine
AHFS/Drugs.com	Local Monograph Injectable Monograph
Pregnancy category	AU: A US: B (No risk in non-human studies)
Routes of administration	intravenous, subcutaneous, topical, oral
ATC code	C01BB01 (WHO) C05AD01 (WHO) D04AB01 (WHO) N01BB02 (WHO) R02AD02 (WHO) S01HA07 (WHO) S02DA01 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) US: Rx above 5% concentration OTC up to 5% for topical application depending on use (OTC for ≤4% for topical application for skin numbing use or ≤5% for anorectal hemorroidal pain and to prevent premature ejaculation) Above 5% or other routes of administration: RX only.
Pharmacokinetic data
Bioavailability	35% (oral) 3% (topical)
Metabolism	Liver, 90% CYP3A4-mediated
Onset of action	within 1.5 min (IV)
Biological half-life	1.5–2 h
Duration of action	10 to 20 min(IV), 0.5 to 3 h (injection)
Excretion	Kidney
Identifiers
IUPAC name 2-(diethylamino)- N-(2,6-dimethylphenyl)acetamide
Synonyms	N-(2,6-dimethylphenyl)-N²,N²-diethylglycinamide
CAS Number	137-58-6^Y 73-78-9 (hydrochloride)
PubChem (CID)	367
IUPHAR/BPS	2623
DrugBank	DB00281^Y
ChemSpider	3548^Y
UNII	98PI200987^Y
KEGG	D00358^Y
ChEBI	CHEBI:6456^Y
ChEMBL	CHEMBL79^Y
ECHA InfoCard	100.004.821
Chemical and physical data
Formula	C₁₄H₂₂N₂O
Molar mass	234.34 g/mol
3D model (Jmol)	Interactive image
Melting point	68 °C (154 °F)
SMILES O=C(Nc1c(cccc1C)C)CN(CC)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)^Y Key:NNJVILVZKWQKPM-UHFFFAOYSA-N^Y

Local Monograph

OTC up to 5% for topical application depending on use (OTC for ≤4% for topical application for skin numbing use

Lidocaine, also known as xylocaine and lignocaine, is a medication used to numb tissue in a specific area and to treat ventricular tachycardia. It can also be used for nerve blocks. Lidocaine mixed with a small amount of epinephrine is available to allow larger doses for numbing, and to make it last longer. When used as an injectable, it typically begins working within four minutes and lasts for half an hour to three hours. Lidocaine may also be applied directly to the skin for numbing.

Common side effects with intravenous use include sleepiness, muscle twitching, confusion, changes in vision, numbness, tingling, and vomiting. It can cause low blood pressure and an irregular heart rate. There are concerns that injecting it into a joint can cause problems with the cartilage. It appears to be generally safe for use in pregnancy. A lower dose may be required in those with liver problems. It is generally safe to use in those allergic to tetracaine or benzocaine. Lidocaine is an antiarrhythmic medication of the class Ib type. Lidocaine works by blocking sodium channels and thus decreasing the rate of contractions of the heart. When used locally as a numbing agent, local neurons cannot signal the brain.

Lidocaine was discovered in 1946 and went on sale in 1948. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. It is available as a generic medication and is not very expensive. The wholesale cost in the developing world in 2014 was US$0.45 to $1.05 wholesale per 20ml vial of medication.

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