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lidocaine

File:Lidocaine.svg · Wikimedia Commons · See Wikimedia Commons

EntityQ216935· pop 51· linked from 1,092 articles

Also known as Xylocaine®, 2-(Diethylamino)-2',6'-acetoxylidide, 2-(Diethylamino)-N-(2,6-dimethylphenyl)acetamide, alpha-diethylamino-2,6-dimethylacetanilide, xylocaine, lignocaine, Lignocaine

Lidocaine, also known as lignocaine and sold under the brand name Xylocaine among others, is a local anesthetic of the amino amide type. It is also used to treat ventricular tachycardia and ventricular fibrillation. When used for local anaesthesia or in nerve blocks, lidocaine typically begins working within several minutes and lasts for half an hour to three hours. Lidocaine mixtures may also be applied directly to the skin or mucous membranes to numb the area. It is often used mixed with a small amount of adrenaline (epinephrine) to prolong its local effects and to decrease bleeding.

OverviewAI-generated

Lidocaine is a chemical compound with the formula C₁₄H₂₂N₂O. Its IUPAC name is 2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide. The substance has a mass of 234.173 and a weight of 234.34. It carries a charge of 0 and features one hydrogen bond donor and two hydrogen bond acceptors. The calculated xlogp value is 2.3, while the topological polar surface area is 32.3.

The defined daily dose for lidocaine is 3. In scientific literature, the term is associated with 39,291 PubMed entries. Additionally, the subject is referenced by 1,092 other encyclopedia articles.

Synthesized by Vinony from 20 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Key facts

Drug.duration_of_action
10 min to 20 min (IV), 0.5 h to 3 h (local)
Drug.excretion
Kidney
Drug.index2_label
as HCl
Drug.CAS_number
137-58-6
Drug.CAS_number2
73-78-9
Drug.PubChem
3676
Drug.PubChem2
6314
Drug.IUPHAR_ligand
2623
Drug.DrugBank
DB00281
Drug.DrugBank2
DBSALT001508
Drug.ChemSpiderID
3548
Drug.ChemSpiderID2
6075
Drug.UNII
98PI200987
Drug.verifiedrevid
464370713
Drug.Watchedfields
changed
Drug.image
Lidocaine.svg
Drug.image_class
skin-invert-image
Drug.width
200

via Wikipedia infobox

Chemical data

Formula
C14H22N2O
Molecular weight
234.34 g/mol
IUPAC name
2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide
SMILES
CCN(CC)CC(=O)NC1=C(C=CC=C1C)C
InChIKey
NNJVILVZKWQKPM-UHFFFAOYSA-N
XLogP
2.3
Polar surface area
32.3 Ų
H-bond donors
1
H-bond acceptors
2
Formal charge
0

via PubChem

Research

39,291 papers

via PubMed

~20 min read

Encyclopedic overview

27 sections
Contents
  • Medical uses
  • Local numbing agent
  • Heart arrhythmia
  • Epilepsy
  • Other
  • Adverse effects
  • Interactions
  • Contraindications
  • Overdosage
  • Postarthroscopic glenohumeral chondrolysis
  • Pharmacology
  • Mechanism of action
  • Pharmacokinetics
  • Chemistry
  • Synthesis
  • Molecular structure and conformational flexibility
  • Influence of temperature and pressure on conformational preference
  • Veterinary use
  • History
  • Society and culture
  • Dosage forms
  • Names
  • Recreational use
  • Adulterant in cocaine
  • Compendial status
  • References
  • External links

Lidocaine, also known as lignocaine and sold under the brand name Xylocaine among others, is a local anesthetic of the amino amide type. It is also used to treat ventricular tachycardia and ventricular fibrillation. When used for local anaesthesia or in nerve blocks, lidocaine typically begins working within several minutes and lasts for half an hour to three hours. Lidocaine mixtures may also be applied directly to the skin or mucous membranes to numb the area. It is often used mixed with a small amount of adrenaline (epinephrine) to prolong its local effects and to decrease bleeding.

If injected intravenously, it may cause cerebral effects such as 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. This means it works by blocking sodium channels thus decreasing the rate of contractions of the heart. When injected near nerves, the nerves cannot conduct signals to or from the brain.

Excerpted from Wikipedia’s “lidocaine” article, available under the CC BY-SA 4.0 licence.

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