File:Lidocaine.svg · Wikimedia Commons · See Wikimedia Commons
lidocaine
Sign in to saveAlso 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- [Lidocaine].Krankenpflege Journal · 1987
- Lidocaine in the treatment of status epilepticus.Academic emergency medicine : official journal of the Society for Academic Emergency Medicine · 1997
- [Lidocaine hypersensitivity].Fogorvosi szemle · 1973
- The Use and Method of Action of Intravenous Lidocaine and Its Metabolite in Headache Disorders.Headache · 2018
- [Forensic medical assessment of lidocaine and bupivacaine systemic toxicity].Sudebno-meditsinskaia ekspertiza · 2023
via PubMed
~20 min read
Encyclopedic overview
27 sectionsContents
- 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.