Lidocaine

12/7/2015
Lidocaine - Wikipedia, the free encyclopedia
Lidocaine
From Wikipedia, the free encyclopedia
Lidocaine (INN, BAN) /ladken/,

xylocaine, or lignocaine (AAN, former
BAN) /lnken/ is a common local
anesthetic and class-1b antiarrhythmic
drug. Lidocaine is used topically to relieve
itching, burning, and pain from skin
inflammations, injected as a dental
anesthetic, or used as a local anesthetic for
minor surgery.
Lidocaine
It is on the WHO Model List of Essential

Medicines, the most important medications
needed in a basic healthcare system.[1]
Contents
1 Medical uses
1.1 Insensitivity
2 Contraindications
3 Adverse effects
4 Overdosage
5 Interactions
6 Dosage forms
6.1 Adulterant in cocaine
7 Pharmacokinetics
8 Pharmacodynamics
8.1 Anaesthesia
8.2 Antiarrhythmic
9 History
10 Recreational use
11 Compendial status
12 See also
13 References
14 External links
Medical uses
Systematic (IUPAC) name

2-(diethylamino)N-(2,6-dimethylphenyl)acetamide
Clinical data
Trade names
Xylocaine
AHFS/Drugs.com Micromedex Detailed Consumer Information

Pregnancy
category
AU:
Legal status
AU:
Routes of
administration
A
US: B (No risk in non-human studies)
Prescription Only (S4)
US: -only (OTC for 1%)
intravenous, subcutaneous, topical, oral
Pharmacokinetic data
Bioavailability
35% (oral)
3% (topical)
Metabolism
Hepatic, 90% CYP1A2-mediated
Biological halflife
Excretion
1.52 hours
renal
Identifiers
https://en.wikipedia.org/wiki/Lidocaine
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The efficacy profile of lidocaine as a local

anesthetic is characterized by a rapid onset
of action and intermediate duration of
efficacy. Therefore, lidocaine is suitable for
infiltration, block, and surface anesthesia.
Longer-acting substances such as
bupivacaine are sometimes given
preference for subdural and epidural
anesthesias; lidocaine, though, has the
advantage of a rapid onset of action.
Epinephrine (adrenaline) vasoconstricts
arteries, reducing bleeding and also delays
the resorption of lidocaine, almost doubling
the duration of anaesthesia. For surface
anesthesia, several available formulations
can be used for endoscopies, before
intubations, etc. Buffering the pH of
lidocaine makes local freezing less
painful.[2] Lidocaine drops can be used on
the eyes for short ophthalmic procedures.
There is tentative evidence for topical
lidocaine for neuropathic pain.[3]
Intravenous lidocaine also has uses as a
temporary fix for tinnitus. Although not
completely curing the disorder, it has been
shown to reduce the effects by around twothirds.[4][5]
CAS Registry
Number
137-58-6
73-78-9
(https://tools.wmflabs.org/magnustools/cas.php?
language=en&cas=73-78-9&title=)
(hydrochloride)
ATC code
C01BB01 C05AD01 D04AB01 N01BB02

R02AD02 S01HA07 S02DA01
PubChem
CID: 367
IUPHAR/BPS
2623
DrugBank
DB00281
ChemSpider
3548
UNII
98PI200987
KEGG
D00358
ChEBI
CHEBI:6456
ChEMBL
CHEMBL79
Synonyms
N-(2,6-dimethylphenyl)-N2, N2diethylglycinamide
Chemical data
Formula
C14H22N2O
Molecular mass 234.34 g/mol

SMILES
InChI
Lidocaine is also the most important classPhysical data

1b antiarrhythmic drug; it is used
Melting point
68 C (154 F)
intravenously for the treatment of
ventricular arrhythmias (for acute
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myocardial infarction, digoxin poisoning,
cardioversion, or cardiac catheterization) if amiodarone is not available or contraindicated. Lidocaine
should be given for this indication after defibrillation, CPR, and vasopressors have been initiated. A routine
prophylactic administration is no longer recommended for acute cardiac infarction; the overall benefit of
this measure is not convincing.
Inhaled lidocaine can be used as an antitussive (cough suppressor) acting peripherally to reduce the cough
reflex. This application can be implemented as a safety and comfort measure for patients who have to be
intubated, as it reduces the incidence of coughing and any tracheal damage it might cause when emerging
from anesthesia.[6][7][8]
Lidocaine, along with ethanol, ammonia, and acetic acid, has also been proven to be effective in treating
jellyfish stings, both numbing the affected area and preventing further nematocyst discharge.[9][10]
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Insensitivity
Relative insensitivity to lidocaine is genetic. In hypokalemic sensory overstimulation, relative insensitivity to
lidocaine has been described in people who also have attention deficit hyperactivity disorder.[11] In dental
anesthesia, a relative insensitivity to lidocaine can occur for anatomical reasons due to unexpected
positions of nerves. Some people with Ehlers-Danlos syndrome are insensitive to lidocaine.[12]
Contraindications
Absolute contraindications for the use of lidocaine include:
Heart block, second or third degree (without pacemaker)
Severe sinoatrial block (without pacemaker)
Serious adverse drug reaction to lidocaine or amide local anesthetics
Hypersensitivity to corn and corn-related products (corn-derived dextrose is used in the mixed
injections)
Concurrent treatment with quinidine, flecainide, disopyramide, procainamide (class I antiarrhythmic
agents)
Prior use of amiodarone hydrochloride
Adams-Stokes syndrome[13]
Wolff-Parkinson-White syndrome[13]
Lidocaine viscous is not recommended by the FDA to treat tooth pain in children and infants.[14]
Exercise caution in patients with any of these:
Hypotension not due to arrhythmia
Bradycardia
Accelerated idioventricular rhythm
Elderly patients
Pseudocholinesterase deficiency
Intra-articular infusion (this is not an approved indication and can cause chondrolysis)
Porphyria, especially acute intermittent porphyria; lidocaine has been classified as porphyrogenic
because of the hepatic enzymes it induces,[15] although clinical evidence suggests it is not.[16]
Bupivacaine is a safe alternative in this case.
Impaired liver function - people with lowered hepatic function may have an adverse reaction with
repeated administration of lidocaine because the drug is metabolized by the liver. Adverse reactions
may include neurological symptoms (e.g. dizziness, nausea, muscle twitches, vomiting, or
seizures).[17]
Adverse effects
Adverse drug reactions (ADRs) are rare when lidocaine is used as a local anesthetic and is administered
correctly. Most ADRs associated with lidocaine for anesthesia relate to administration technique (resulting
in systemic exposure) or pharmacological effects of anesthesia, and allergic reactions only rarely occur.[18]
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Systemic exposure to excessive quantities of lidocaine mainly result in central nervous system (CNS) and
cardiovascular effects CNS effects usually occur at lower blood plasma concentrations and additional
cardiovascular effects present at higher concentrations, though cardiovascular collapse may also occur
with low concentrations. ADRs by system are:
CNS excitation: nervousness, agitation, anxiety, apprehension, tingling around the mouth
(circumoral paraesthesia), headache, hyperesthesia, tremor, dizziness, pupillary changes, psychosis,
euphoria, hallucinations, and seizures
CNS depression with increasingly heavier exposure: drowsiness, lethargy, slurred speech,
hypoesthesia, confusion, disorientation, loss of consciousness, respiratory depression and apnoea.
Cardiovascular: hypotension, bradycardia, arrhythmias, flushing, venous insufficiency, increased
defibrillator threshold, edema, and/or cardiac arrest some of which may be due to hypoxemia
secondary to respiratory depression.[19]
Respiratory: Bronchospasm, dyspnea, respiratory depression or arrest
Gastrointestinal: metallic taste, nausea, vomiting
Ears: tinnitus
Eyes: local burning, Conjunctival hyperemia, corneal epithelial changes/ulceration, diplopia, visual
changes (opacification)
Skin: itching, depigmentation, rash, urticaria, edema, angioedema, bruising, inflammation of the vein
at the injection site, irritation of the skin when applied topically
Blood: methemoglobinemia
Allergy
ADRs associated with the use of intravenous lidocaine are similar to toxic effects from systemic exposure
above. These are dose-related and more frequent at high infusion rates (3 mg/min). Common ADRs
include: headache, dizziness, drowsiness, confusion, visual disturbances, tinnitus, tremor, and/or
paraesthesia. Infrequent ADRs associated with the use of lidocaine include: hypotension, bradycardia,
arrhythmias, cardiac arrest, muscle twitching, seizures, coma, and/or respiratory depression.[19]
It is generally safe to use lidocaine with vasoconstrictor such as epinephrine including in regions such as the
nose, ears, fingers and toes.[20] While concerns of tissue death if used in these areas have been raised
evidence does not support these concerns.[20]
Overdosage
Overdoses with lidocaine can be a result of excessive administration by topical or parenteral routes,
accidental oral ingestion of topical preparations by children who are more susceptible to overdose,
accidental intravenous (rather than subcutaneous, intrathecal, or paracervical) injection, or prolonged use
of subcutaneous infiltration anesthesia during cosmetic surgical procedures. These occurrences have often
led to severe toxicity or death in both children and adults. Lidocaine and its two major metabolites may be
quantified in blood, plasma, or serum to confirm the diagnosis in potential poisoning victims or to assist in
the forensic investigation in a case of fatal overdose. It is important in the interpretation of analytical
results to recognize that lidocaine is often routinely administered intravenously as an antiarrhythmic agent
in critical cardiac-care situations.[21] Treatment with intravenous lipid emulsions (used for parental
feeding) to reverse the effects of local anaesthetic toxicity is becoming more commonplace.[22]
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Interactions
Any drugs that are also ligands of CYP3A4 and CYP1A2 can potentially increase serum levels and potential
for toxicity or decrease serum levels and the efficacy, depending on whether they induce or inhibit the
enzymes, respectively. Drugs that may increase the chance of methemoglobinemia should also be
considered carefully. Dronedarone and liposomal morphine are both absolutely contraindicated, as they
may increase the serum levels, but hundreds of other drugs require monitoring for interaction.[23]
Dosage forms
Lidocaine, usually in the form of lidocaine hydrochloride, is
available in various forms including:
Injected local anesthetic (sometimes combined with
epinephrine to reduce bleeding)
Dermal patch (sometimes combined with prilocaine)
Intravenous injection
Intravenous infusion
Intraosseous infusion
Nasal instillation/spray (combined with phenylephrine)
Oral gel (often referred to as "viscous lidocaine" or
abbreviated "lidocaine visc" or "lidocaine HCl visc" in
pharmacology; used as teething gel)
Oral liquid
Oral and topical ointments, with and without flavoring,
respectively[24][25]
Topical gel (as with aloe vera gels that include lidocaine)[26]
Topical liquid
Lidocaine hydrochloride 2%
Lidocaine HCl 2% jelly, combined with hypromellose, to
epinephrine 1:80,000 solution for
anesthetize and lubricate the urethra, etc., for inserting a
injection in a cartridge
catheter or instrument
Topical patch (lidocaine 5%), marketed since 1999 in the US
by Endo Pharmaceuticals[27] as "Lidoderm" - and since 2007 in the UK by Grnenthal as
"Versatis".
Topical ointment (lidocaine 5%) as a temporary reliever of discomfort associated anorectal disorders,
such as hemorrhoids, marketed as an over-the-counter product in the US as RectiCare since 2012 by
Ferndale Healthcare, Inc
Topical aerosol spray
Inhaled by nebulizer
As a component of a GI cocktail used in emergency rooms
Ophthalmic solution
Adulterant in cocaine
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Lidocaine is often added to cocaine as a diluent.[28] Cocaine numbs the gums when applied, and since
lidocaine causes stronger numbness,[29] a user gets the impression of high-quality cocaine when in
actuality, the user is receiving a diluted product.[30]
Pharmacokinetics
The onset of action of lidocaine is about 45 to 90 sec and its duration is 10 to 20 min. It is about 95%
metabolized (dealkylated) in the liver mainly by CYP3A4 to the pharmacologically active metabolites
monoethylglycinexylidide (MEGX) and then subsequently to the inactive glycine xylidide. MEGX has a
longer half-life than lidocaine, but also is a less potent sodium channel blocker.[31] The volume of
distribution is 1.1-2.1 l/kg, but congestive heart failure can decrease it. About 60-80% circulates bound to
the protein alpha1 acid glycoprotein. The oral bioavailability is 35% and the topical bioavailability is 3%.
The elimination half-life of lidocaine is biphasic and around 90120
min in most patients. This may be prolonged in patients with hepatic
impairment (average 343 min) or congestive heart failure (average
136 min).[32] Lidocaine is excreted in the urine (90% as metabolites
and 10% as unchanged drug).[33]
Pharmacodynamics
Anaesthesia
Lidocaine alters signal conduction in neurons by blocking the fast
voltage-gated Na+ channels in the neuronal cell membrane
responsible for signal propagation.[34] With sufficient blockage, the
Lidocaine hydrochloride 1% solution
membrane of the postsynaptic neuron will not depolarize and will
for injection
thus fail to transmit an action potential. This creates the anaesthetic
effect by not merely preventing pain signals from propagating to the
brain, but by stopping them before they begin. Careful titration allows for a high degree of selectivity in the
blockage of sensory neurons, whereas higher concentrations also affect other modalities of neuron
signaling.
Antiarrhythmic
The same principle applies for this drug's actions in the heart. Blocking sodium channels in the conduction
system, as well as the muscle cells of the heart, raises the depolarization threshold, making the heart less
likely to initiate or conduct early action potentials that may cause an arrhythmia.[35]
History
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Lidocaine, the first amino amidetype local anesthetic, was first

synthesized under the name 'xylocaine' by Swedish chemist Nils Lfgren in
1943.[36][37][38] His colleague Bengt Lundqvist performed the first
injection anesthesia experiments on himself.[36] It was first marketed in
1949.
Recreational use
Lidocaine is not currently listed by the World Anti-Doping Agency as an
illegal substance.[39] It is used as an adjuvant, adulterant, and diluent to
street drugs such as cocaine and heroin.[40]
Compendial status
Topical lidocaine spray
Japanese Pharmacopoeia 15
United States Pharmacopeia 31[41]
See also
Lidocaine/prilocaine
Dimethocaine (has some DRI activity)
Procaine
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External links
U.S. National Library of Medicine: Drug Information Portal - Lidocaine
(http://druginfo.nlm.nih.gov/drugportal/dpdirect.jsp?name=Lidocaine)
Endo Pharmaceuticals' Lidoderm website (http://www.lidoderm.com/)
Retrieved from "https://en.wikipedia.org/w/index.php?title=Lidocaine&oldid=670535603"
Categories: Acetamides Antiarrhythmic agents Chemical substances for emergency medicine
Local anesthetics Sodium channel blockers World Health Organization essential medicines
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Lidocaine

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12/7/2015

Lidocaine - Wikipedia, the free encyclopedia

Lidocaine (INN, BAN) /ladken/,

It is on the WHO Model List of Essential

Systematic (IUPAC) name

AHFS/Drugs.com Micromedex Detailed Consumer Information

Hepatic, 90% CYP1A2-mediated

Lidocaine - Wikipedia, the free encyclopedia

The efficacy profile of lidocaine as a local

C01BB01 C05AD01 D04AB01 N01BB02

Molecular mass 234.34 g/mol

Lidocaine is also the most important classPhysical data

Lidocaine - Wikipedia, the free encyclopedia

Lidocaine - Wikipedia, the free encyclopedia

Lidocaine - Wikipedia, the free encyclopedia

Lidocaine - Wikipedia, the free encyclopedia

Lidocaine - Wikipedia, the free encyclopedia

Lidocaine, the first amino amidetype local anesthetic, was first

Topical lidocaine spray

Lidocaine - Wikipedia, the free encyclopedia

Lidocaine - Wikipedia, the free encyclopedia

Lidocaine - Wikipedia, the free encyclopedia

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