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Details

Stereochemistry ACHIRAL
Molecular Formula C14H22N2O.C7H8O3S
Molecular Weight 406.539
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LIDOCAINE TOSYLATE

SMILES

CC1=CC=C(C=C1)S(O)(=O)=O.CCN(CC)CC(=O)NC2=C(C)C=CC=C2C

InChI

InChIKey=UNYGCDYHMVDGEG-UHFFFAOYSA-N
InChI=1S/C14H22N2O.C7H8O3S/c1-5-16(6-2)10-13(17)15-14-11(3)8-7-9-12(14)4;1-6-2-4-7(5-3-6)11(8,9)10/h7-9H,5-6,10H2,1-4H3,(H,15,17);2-5H,1H3,(H,8,9,10)

HIDE SMILES / InChI

Molecular Formula C14H22N2O
Molecular Weight 234.3373
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C7H8O3S
Molecular Weight 172.202
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Lidocaine is a local anesthetic and cardiac depressant used to numb tissue in a specific area and for management of cardiac arrhythmias, particularly those of ventricular origins, such as occur with acute myocardial infarction. Lidocaine alters signal conduction in neurons by blocking the fast voltage-gated Na+ channels in the neuronal cell membrane responsible for signal propagation. With sufficient blockage, the membrane of the postsynaptic neuron will not depolarize and will thus fail to transmit an action potential. This creates the anesthetic 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. Lidocaine exerts an antiarrhythmic effect by increasing the electrical stimulation threshold of the ventricle during diastole. In usual therapeutic doses, lidocaine hydrochloride produces no change in myocardial contractility, in systemic arterial pressure, or an absolute refractory period. 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 spinal and epidural anesthesias; lidocaine, though, has the advantage of a rapid onset of action. Lidocaine is also the most important class-1b antiarrhythmic drug; it is used intravenously for the treatment of ventricular arrhythmias (for acute 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 preventative dose is no longer recommended after a myocardial infarction as the overall benefit is not convincing. Inhaled lidocaine can be used as a 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. 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. Systemic exposure to excessive quantities of lidocaine mainly result in a 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.

Originator

Sources: Arkiv foer Kemi, Mineralogi och Geologi (1946), A22, (No. 18), 30 pp.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
XYLOCAINE

Approved Use

INDICATIONS & USAGE Lidocaine Hydrochloride Oral Topical Solution USP, 2% (Viscous) is indicated for the production of topical anesthesia of irritated or inflamed mucous membranes of the mouth and pharynx. It is also useful for reducing gagging during the taking of X-ray pictures and dental impressions.

Launch Date

1951
Primary
VIAFLEX

Approved Use

Indications and Usage Lidocaine hydrochloride administered intravenously is specifically indicated in the acute management of (1) ventricular arrhythmias occurring during cardiac manipulations, such as cardiac surgery and (2) life-threatening arrhythmias which are ventricular in origin, such as occur during acute myocardial infarction.

Launch Date

1984
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
212 ng/mL
84 mg 1 times / day steady-state, topical
dose: 84 mg
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
LIDOCAINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
231 ng/mL
84 mg 2 times / day steady-state, topical
dose: 84 mg
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
LIDOCAINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
4100 ng × h/mL
84 mg 1 times / day steady-state, topical
dose: 84 mg
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
LIDOCAINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
4704 ng × h/mL
84 mg 2 times / day steady-state, topical
dose: 84 mg
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
LIDOCAINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
6.81 h
84 mg 1 times / day steady-state, topical
dose: 84 mg
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
LIDOCAINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
7.94 h
84 mg 2 times / day steady-state, topical
dose: 84 mg
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
LIDOCAINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
2 mg 1 times / day steady, intravenous
Dose: 2 mg, 1 times / day
Route: intravenous
Route: steady
Dose: 2 mg, 1 times / day
Sources:
unhealthy, 17 - 66 years
n = 68
Health Status: unhealthy
Condition: chronic daily headache and chronic cluster headache
Age Group: 17 - 66 years
Sex: M+F
Population Size: 68
Sources:
Other AEs: Nausea and vomiting, Hallucinations...
Other AEs:
Nausea and vomiting (1%)
Hallucinations (8 patients)
Tachycardia (4 patients)
Tremor (3 patients)
Hypotension (2 patients)
Light-headed (1 patient)
Phlebitis (1 patient)
Hypertension (1 patient)
Sources:
800 mg single, intravenous
Overdose
Dose: 800 mg
Route: intravenous
Route: single
Dose: 800 mg
Sources:
unhealthy, 57 years
n = 1
Health Status: unhealthy
Condition: hypertensive, severe precordial pain
Age Group: 57 years
Sex: M
Population Size: 1
Sources:
Disc. AE: Death...
AEs leading to
discontinuation/dose reduction:
Death (grade 5, 1.6%)
Sources:
700 mg 1 times / day steady, transdermal
Recommended
Dose: 700 mg, 1 times / day
Route: transdermal
Route: steady
Dose: 700 mg, 1 times / day
Sources:
unhealthy, adult
n = 404
Health Status: unhealthy
Condition: Neuropathic pain
Age Group: adult
Sex: unknown
Population Size: 404
Sources:
5 % 1 times / day steady, transdermal
Dose: 5 %, 1 times / day
Route: transdermal
Route: steady
Dose: 5 %, 1 times / day
Sources:
unhealthy, adult
n = 300
Health Status: unhealthy
Condition: post-herpetic neuralgia and diabetic polyneuropathy
Age Group: adult
Sex: M+F
Population Size: 300
Sources:
Disc. AE: Headache, Application site irritation...
AEs leading to
discontinuation/dose reduction:
Headache (2 patients)
Application site irritation (2 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Hypertension 1 patient
2 mg 1 times / day steady, intravenous
Dose: 2 mg, 1 times / day
Route: intravenous
Route: steady
Dose: 2 mg, 1 times / day
Sources:
unhealthy, 17 - 66 years
n = 68
Health Status: unhealthy
Condition: chronic daily headache and chronic cluster headache
Age Group: 17 - 66 years
Sex: M+F
Population Size: 68
Sources:
Light-headed 1 patient
2 mg 1 times / day steady, intravenous
Dose: 2 mg, 1 times / day
Route: intravenous
Route: steady
Dose: 2 mg, 1 times / day
Sources:
unhealthy, 17 - 66 years
n = 68
Health Status: unhealthy
Condition: chronic daily headache and chronic cluster headache
Age Group: 17 - 66 years
Sex: M+F
Population Size: 68
Sources:
Phlebitis 1 patient
2 mg 1 times / day steady, intravenous
Dose: 2 mg, 1 times / day
Route: intravenous
Route: steady
Dose: 2 mg, 1 times / day
Sources:
unhealthy, 17 - 66 years
n = 68
Health Status: unhealthy
Condition: chronic daily headache and chronic cluster headache
Age Group: 17 - 66 years
Sex: M+F
Population Size: 68
Sources:
Nausea and vomiting 1%
2 mg 1 times / day steady, intravenous
Dose: 2 mg, 1 times / day
Route: intravenous
Route: steady
Dose: 2 mg, 1 times / day
Sources:
unhealthy, 17 - 66 years
n = 68
Health Status: unhealthy
Condition: chronic daily headache and chronic cluster headache
Age Group: 17 - 66 years
Sex: M+F
Population Size: 68
Sources:
Hypotension 2 patients
2 mg 1 times / day steady, intravenous
Dose: 2 mg, 1 times / day
Route: intravenous
Route: steady
Dose: 2 mg, 1 times / day
Sources:
unhealthy, 17 - 66 years
n = 68
Health Status: unhealthy
Condition: chronic daily headache and chronic cluster headache
Age Group: 17 - 66 years
Sex: M+F
Population Size: 68
Sources:
Tremor 3 patients
2 mg 1 times / day steady, intravenous
Dose: 2 mg, 1 times / day
Route: intravenous
Route: steady
Dose: 2 mg, 1 times / day
Sources:
unhealthy, 17 - 66 years
n = 68
Health Status: unhealthy
Condition: chronic daily headache and chronic cluster headache
Age Group: 17 - 66 years
Sex: M+F
Population Size: 68
Sources:
Tachycardia 4 patients
2 mg 1 times / day steady, intravenous
Dose: 2 mg, 1 times / day
Route: intravenous
Route: steady
Dose: 2 mg, 1 times / day
Sources:
unhealthy, 17 - 66 years
n = 68
Health Status: unhealthy
Condition: chronic daily headache and chronic cluster headache
Age Group: 17 - 66 years
Sex: M+F
Population Size: 68
Sources:
Hallucinations 8 patients
2 mg 1 times / day steady, intravenous
Dose: 2 mg, 1 times / day
Route: intravenous
Route: steady
Dose: 2 mg, 1 times / day
Sources:
unhealthy, 17 - 66 years
n = 68
Health Status: unhealthy
Condition: chronic daily headache and chronic cluster headache
Age Group: 17 - 66 years
Sex: M+F
Population Size: 68
Sources:
Death grade 5, 1.6%
Disc. AE
800 mg single, intravenous
Overdose
Dose: 800 mg
Route: intravenous
Route: single
Dose: 800 mg
Sources:
unhealthy, 57 years
n = 1
Health Status: unhealthy
Condition: hypertensive, severe precordial pain
Age Group: 57 years
Sex: M
Population Size: 1
Sources:
Application site irritation 2 patients
Disc. AE
5 % 1 times / day steady, transdermal
Dose: 5 %, 1 times / day
Route: transdermal
Route: steady
Dose: 5 %, 1 times / day
Sources:
unhealthy, adult
n = 300
Health Status: unhealthy
Condition: post-herpetic neuralgia and diabetic polyneuropathy
Age Group: adult
Sex: M+F
Population Size: 300
Sources:
Headache 2 patients
Disc. AE
5 % 1 times / day steady, transdermal
Dose: 5 %, 1 times / day
Route: transdermal
Route: steady
Dose: 5 %, 1 times / day
Sources:
unhealthy, adult
n = 300
Health Status: unhealthy
Condition: post-herpetic neuralgia and diabetic polyneuropathy
Age Group: adult
Sex: M+F
Population Size: 300
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
yes
yes (co-administration study)
Comment: CYP1A2 is the enzyme principally responsible for the metabolic disposition of lidocaine in subjects with normal liver function.
Page: -
yes
yes (co-administration study)
Comment: Itraconazole and erythromycin had virtually no effect on the pharmacokinetics of intravenous lidocaine, but erythromycin slightly prolonged the elimination half-life (t½) of lidocaine (Study I). When lidocaine was taken orally, both erythromycin and itraconazole increased the peak concentration (Cmax) and the area under the concentration-time curve (AUC) of lidocaine by 40-70% (Study II).
Page: -
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Lidocaine's influence on brain amines in mice.
1976 May-Jun
Transient neurological symptoms after spinal anaesthesia with hyperbaric 5% lidocaine or general anaesthesia.
1999 Apr
Adding low dose meperidine to spinal lidocaine prolongs postoperative analgesia.
1999 Apr
Cauda equina syndrome after spinal anaesthesia with hyperbaric 5% lignocaine: a review of six cases of cauda equina syndrome reported to the Swedish Pharmaceutical Insurance 1993-1997.
1999 Apr
[Premixing of 5% dextrose in Ringer's acetate solution with propofol reduces incidence and severity of pain on propofol injection].
1999 Aug
[Lidocaine induced seizure following topical application of local anesthetics: case report].
1999 May
Potentiation of narcosis after intravenous lidocaine in a patient given spinal opioids.
1999 Sep
Effects of anticonvulsants on local anaesthetic-induced neurotoxicity in rats.
2000 Feb
Low-dose lidocaine reduces secondary hyperalgesia by a central mode of action.
2000 Mar
TASK-3, a new member of the tandem pore K(+) channel family.
2000 Mar 31
The incidence of transient neurological symptoms after spinal anaesthesia with lidocaine compared to prilocaine.
2000 Oct
Pain management for neonatal circumcision.
2001
Giant R-waves in a patient with an acute inferior myocardial infarction.
2001 Apr
The efficacy of topical anaesthesia in flexible nasendoscopy: a double-blind randomised controlled trial.
2001 Feb
Topical anesthesia for phacoemulsification and painless subconjunctival antibiotic injection.
2001 Feb
Influence of patient posture on oxygen saturation during fibre-optic bronchoscopy.
2001 Jan
Comparison of extradural injections of lignocaine and xylazine in azaperone-sedated pigs.
2001 Jan
Cardiac resuscitation after incremental overdosage with lidocaine, bupivacaine, levobupivacaine, and ropivacaine in anesthetized dogs.
2001 Jan
Evaluation of caudal anaesthesia performed in conscious ex-premature infants for inguinal herniotomies.
2001 Jan
Hyperpigmentation following the use of Emla cream.
2001 Jan
Degeneracy and additional alloreactivity of drug-specific human alpha beta(+) T cell clones.
2001 Jul
Evaluation of potentiating effect of a drop of lignocaine on tropicamide-induced mydriasis.
2001 Jun
Differences between nerve terminal impulses of polymodal nociceptors and cold sensory receptors of the guinea-pig cornea.
2001 Jun 1
Split-skin grafting with lidocaine-prilocaine cream: A meta-analysis of efficacy and safety in geriatric versus nongeriatric patients.
2001 Mar
EMLA anaesthetic cream for sharp leg ulcer debridement: a review of the clinical evidence for analgesic efficacy and tolerability.
2001 Mar-Apr
The anesthetic onset and duration of a new lidocaine/prilocaine gel intra-pocket anesthetic (Oraqix) for periodontal scaling/root planing.
2001 May
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/08816s032lbl.pdf
Therapy of ventricular arrhythmias is often initiated with a single IV bolus of 1.0 to 1.5 mg/kg at a rate of 25 to 50 mg/min. of lidocaine hydrochloride injection. Following acute treatment by bolus in patients in whom arrhythmias tend to recur and who are incapable of receiving oral antiarrhythmic agents, intravenous infusion of Lidocaine Hydrochloride and 5% Dextrose Injection, USP is administered continuously at the rate of 1 to 4 mg/min (0.020 to 0.050 mg/kg/min in the average 70 kg adult). The 0.4% solution (4 mg/mL) can be given at a rate of 15 to 60 mL/hr (0.25 to 1 mL/min). The 0.8% solution (8 mg/mL) can be given at a rate of 7.5 to 30 mL/hr (0.12 to 0.5 mL/min). Precise dosage regimen is determined by patient characteristics and response.
Route of Administration: Other
Cells were prepared by dissociation from T175 cell culture flasks using trypsineEDTA (0.05%), cells were kept in serum free media in the cell hotel on board the QPatch HT. These cells were sampled, washed and re-suspended in extracellular recording solution by the QPatch HT immediately before application to well site on the chip. Once in whole-cell configuration, vehicle (0.1% DMSO v/v) was applied to the cells to achieve a stable control recording (4-min total). This was followed by application of test concentrations as a single bolus addition (4-min incubation per test concentration). Lidocaine were prepared in extracellular recording solution from a 10mM(100% DMSO) stock to yield a final 10 mkM(0.1% DMSO) test concentration from which subsequent serial dilutions in extracellular solution were performed (0.3-10 mkM). Voltage protocols for the sodium channels being screened were designed to reflect the high-frequency, pathophysiological state of the channels that may be therapeutic targets (Nav1.3, Nav1.4 and Nav1.7), and the lowfrequency, physiological state of the safety target (Nav1.5). Currents were elicited from NaV1.3, NaV1.4 and NaV1.7 cell lines using a standard two-pulse voltage protocol. From a holding potential of -100 mV, a 20 ms activating step to -20 mV was applied to assess the effect of compounds on resting (closed) state block. The second activating pulse was applied following a 5-s pre-pulse to half inactivation potential (variable depending on the sodium channel studied, -65 to -75 mV) to assess block on the openinactivated state of the channel. This protocol was applied at a sweep interval of 0.067 Hz throughout the duration of the experiment.
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:07:52 GMT 2023
Edited
by admin
on Fri Dec 15 18:07:52 GMT 2023
Record UNII
M0335SFO80
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LIDOCAINE TOSYLATE
Common Name English
ACETAMIDE, 2-(DIETHYLAMINO)-N-(2,6-DIMETHYLPHENYL)-, 4-METHYLBENZENESULFONATE (1:1)
Systematic Name English
Code System Code Type Description
CAS
159309-69-0
Created by admin on Fri Dec 15 18:07:52 GMT 2023 , Edited by admin on Fri Dec 15 18:07:52 GMT 2023
PRIMARY
PUBCHEM
178020
Created by admin on Fri Dec 15 18:07:52 GMT 2023 , Edited by admin on Fri Dec 15 18:07:52 GMT 2023
PRIMARY
EPA CompTox
DTXSID00166630
Created by admin on Fri Dec 15 18:07:52 GMT 2023 , Edited by admin on Fri Dec 15 18:07:52 GMT 2023
PRIMARY
FDA UNII
M0335SFO80
Created by admin on Fri Dec 15 18:07:52 GMT 2023 , Edited by admin on Fri Dec 15 18:07:52 GMT 2023
PRIMARY
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