Lidocaine

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Lidocaine

Lidocaine (INN

International Nonproprietary Name

An International Nonproprietary Name is the official non-proprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization ....
) or lignocaine (former BAN

British Approved Name

A British Approved Name is the official non-proprietary or generic name given to a pharmaceutical substance, as defined in the British Pharmacopoeia....
) is a common local anesthetic

Local anesthetic

A local anesthetic is a medication that causes reversible local anesthesia and a loss of nociception. When it is used on specific nerve pathways , effects such as analgesia and paralysis can be achieved....
and antiarrhythmic

Antiarrhythmic agent

Antiarrhythmic agents are a group of pharmaceuticals that are used to suppress fast rhythms of the heart , such as atrial fibrillation, atrial flutter, ventricular tachycardia, and ventricular fibrillation....
drug. Lidocaine is used topically to relieve itching, burning and pain from skin inflammations, injected as a dental anesthetic, and in minor surgery.

caine, the first amino amide

Amide

In chemistry, an amide is one of three kinds of compounds:* the organic chemistry functional group characterized by a carbonyl group linked to a nitrogen atom , or a compound that contains this functional group ; or...
-type local anesthetic, was first synthesized under the name xylocaine by Swedish chemist Nils Löfgren

Nils Löfgren

Nils L?fgren, born 1913, died 1967, was a Sweden chemist who developed the Anesthesia Lidocaine in 1943. At this time, he had recently finished his licentiate degree, and was teaching organic chemistry at the University of Stockholm....
in 1943. His colleague Bengt Lundqvist made the first injection anesthesia experiments on himself.It was first marketed in 1948.

caine may be prepared in two steps by the reaction of 2,6-xylidine

2,6-Xylidine

2,6-Xylidine is a aromatic amine with the chemical formula 2C6H3NH2. It is an isomer of 2,4-Xylidine and 3,4-Xylidine....
with chloroacetyl chloride

Chloroacetyl chloride

Chloroacetyl chloride is a chlorinated acyl chloride. It is a bifunctional compound, making it a useful building block chemical....
, followed by the reaction with diethylamine

Diethylamine

Diethylamine is a secondary amine with the molecular structure CH3CH2NHCH2CH3. It is a flammable, strongly alkaline liquid....
:

caine is approximately 90% metabolized (de-ethylated) in the liver

Liver

The liver is a vital organ present in vertebrates and some other animals; it has a wide range of functions, a few of which are detoxification, protein synthesis, and production of biochemicals necessary for digestion....
by CYP1A2

CYP1A2

Cytochrome P450 1A2 , a member of the cytochrome P450 mixed-function oxidase system, is involved in the metabolism of xenobiotics in the body....
(and to a minor extent CYP3A4

CYP3A4

Cytochrome P450 3A4 , a member of the cytochrome P450 mixed-function oxidase system, is one of the most important enzymes involved in the metabolism of xenobiotics in the body....
) to the pharmacologically-active metabolites

Metabolomics

Metabolomics is the "systematic study of the unique chemical fingerprints that specific cellular processes leave behind" - specifically, the study of their small-molecule metabolite profiles....
monoethylglycinexylidide and glycinexylidide.

The elimination half-life

Half-life

The half-life of a quantity whose value decreases with time is the interval required for the quantity to decay to half of its initial value. The concept originated in describing how long it takes atoms to undergo radioactive decay but also applies in a wide variety of other situations....
of lidocaine is approximately 1.5–2 hours in most patients.

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Encyclopedia

Lidocaine (INN

International Nonproprietary Name

British Approved Name

A British Approved Name is the official non-proprietary or generic name given to a pharmaceutical substance, as defined in the British Pharmacopoeia....
) is a common local anesthetic

Local anesthetic

Antiarrhythmic agent

History

Lidocaine, the first amino amide

Amide

Nils Löfgren

Preparation

Lidocaine may be prepared in two steps by the reaction of 2,6-xylidine

2,6-Xylidine

2,6-Xylidine is a aromatic amine with the chemical formula 2C6H3NH2. It is an isomer of 2,4-Xylidine and 3,4-Xylidine....
with chloroacetyl chloride

Chloroacetyl chloride

Chloroacetyl chloride is a chlorinated acyl chloride. It is a bifunctional compound, making it a useful building block chemical....
, followed by the reaction with diethylamine

Diethylamine

Diethylamine is a secondary amine with the molecular structure CH3CH2NHCH2CH3. It is a flammable, strongly alkaline liquid....
:

Pharmacokinetics

Lidocaine is approximately 90% metabolized (de-ethylated) in the liver

Liver

CYP1A2

Cytochrome P450 1A2 , a member of the cytochrome P450 mixed-function oxidase system, is involved in the metabolism of xenobiotics in the body....
(and to a minor extent CYP3A4

CYP3A4

Metabolomics

Half-life

Liver failure

Acute liver failure is the appearance of severe complications rapidly after the first signs of liver disease , and indicates that the liver has sustained severe damage ....
(average 343 minutes) or congestive heart failure (average 136 minutes).

Pharmacodynamics

Anesthesia

Lidocaine alters depolarization in neuron

Neuron

Neurons are responsive cell in the nervous system that process and transmit information by electrochemical Signal . They are the core components of the brain, the vertebrate spinal cord, the invertebrate ventral nerve cord, and the peripheral nerves....
s, by blocking the fast voltage gated sodium (Na⁺) channels in the cell membrane. With sufficient blockade, the membrane of the presynaptic neuron will not depolarize and so fail to transmit an action potential

Action potential

An action potential is a self-regenerating wave of electrochemical activity that allows nerve cells to carry a signal over a distance. It is the primary electrical signal generated by nerve cells, and arises from changes in the permeability of the nerve cell's axonal Cell membranes to specific ions....
, leading to its anaesthetic effects. Careful titration allows for a high degree of selectivity in the blockage of sensory neurons, whereas higher concentrations will also affect other modalities of neuron signaling.

Clinical use

Indications

Topical

In medicine, a topical medication is applied to body surface area such as the skin or mucous membranes, for example the vagina, anus, pharynx, eyes and ears....
lidocaine has been shown to relieve postherpetic neuralgia

Postherpetic neuralgia

Postherpetic neuralgia is a neuralgia caused by the varicella zoster virus. Typically, the neuralgia is confined to a dermatomic area of the skin and follows an outbreak of herpes zoster in that same dermatomic area....
in some patients, though there is not enough study evidence to recommend it as a first-line treatment. It also has uses as a temporary fix for tinnitus. Although not completely curing the illness, it has been shown to reduce the effects by around two thirds.

Contraindications

Contraindications for the use of lidocaine include:

Heart block
Heart block

A heart block is a disease in the electrical conduction system of the heart of the heart. This is opposed to coronary artery disease, which is disease of the blood vessels of the heart....
, second or third degree (without pacemaker)
Severe sinoatrial block
Sinoatrial block

A sinoatrial block is a type of heart block which involves an impairment of conduction at the sinoatrial node. An absent P wave on an ECG can indicate sinoatrial block....
(without pacemaker)
Serious adverse drug reaction
Adverse drug reaction

An adverse drug reaction or adverse drug event is an expression that describes the unwanted, negative consequences associated with the use of given medications....
to lidocaine or amide local anaesthetics
Concurrent treatment with quinidine
Quinidine

Quinidine is a pharmaceutical Medication that acts as a class I antiarrhythmic agent in the heart. It is a stereoisomer of quinine, originally derived from the bark of the cinchona tree....
, flecainide
Flecainide

Flecainide acetate is a class Ic antiarrhythmic agent used to prevent and treat cardiac arrhythmias . It is used to treat a variety of cardiac arrhythmias including paroxysmal atrial fibrillation , paroxysmal supraventricular tachycardia , and ventricular tachycardia ....
, disopyramide
Disopyramide

Disopyramide is an antiarrhythmic medication. It is a Antiarrhythmic agent#Class_I_agents used in the treatment of ventricular tachycardias. It has no effect on adrenergic receptor or adrenergic receptors....
, procainamide
Procainamide

Procainamide is a pharmaceutical antiarrhythmic agent used for the medicine Pharmacotherapy of cardiac arrhythmias, classified by the Vaughan Williams classification system as class Ia....
(Class I antiarrhythmic agents)
Prior use of Amiodarone hydrochloride
Hypotension
Hypotension

In physiology and medicine, hypotension refers to an abnormally low blood pressure. This is best understood as a physiologic state, rather than a disease....
not due to Arrhythmia
Bradycardia
Bradycardia

Bradycardia , as applied to adult medicine, is defined as a resting heart rate of under 60 beats per minute, though it is seldom symptomatic until the rate drops below 50 beat/min....
Accelerated idioventricular rhythm
Accelerated idioventricular rhythm

In accelerated idioventricular rhythm, the rate of cardiac contraction is determined by the intrinsic rate of depolarisation of the cardiac cells....

Adverse drug reactions

Adverse drug reaction

An adverse drug reaction or adverse drug event is an expression that describes the unwanted, negative consequences associated with the use of given medications....
s (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, but allergic

Allergy

Allergy is a Disorder of the immune system often also referred to as atopy. Allergic reactions occur to Natural environmental substances known as allergens; these reactions are Acquired disorder, predictable and rapid....
reactions can rarely occur..

Systemic exposure to excessive quantities of lidocaine mainly result in central nervous system

Central nervous system

The central nervous system is the part of the nervous system that functions to coordinate the activity of all parts of the bodies of multicellular organisms....
(CNS) and cardiovascular effects – CNS effects usually occur at lower blood plasma

Blood plasma

Blood plasma is the liquid component of blood, in which the blood cells are suspended. It makes up about 55% of total blood volume. It is composed of mostly water , and contains dissolved proteins, glucose, clotting factors, mineral ions, Hormone and carbon dioxide ....
concentrations and additional cardiovascular effects present at higher concentrations, though cardiovascular collapse may also occur with low concentrations. CNS effects may include CNS excitation (nervousness, tingling around the mouth, tinnitus

Tinnitus

Tinnitus is the perception of sound within the human ear in the absence of corresponding external sound.Tinnitus can be perceived in one or both ears or in the head....
, tremor, dizziness, blurred vision, seizure

Seizure

An epileptic seizure is a transient symptom of abnormal, excessive or synchronous neuronal activity in the brain. It can manifest as an alteration in mental state, tonic or clonic movements, convulsions, and various other psychic symptoms ....
s) followed by depression, and with increasingly heavier exposure: drowsiness, loss of consciousness, respiratory depression and apnoea). Cardiovascular effects include hypotension

Hypotension

In physiology and medicine, hypotension refers to an abnormally low blood pressure. This is best understood as a physiologic state, rather than a disease....
, bradycardia

Bradycardia

Bradycardia , as applied to adult medicine, is defined as a resting heart rate of under 60 beats per minute, though it is seldom symptomatic until the rate drops below 50 beat/min....
, arrhythmias, and/or cardiac arrest

Cardiac arrest

A cardiac arrest, also known as cardiopulmonary arrest or circulatory arrest, is the abrupt cessation of normal circulation of the blood due to failure of the heart to contract effectively during Systole ....
– some of which may be due to hypoxemia

Hypoxia (medical)

Hypoxia is a Pathology condition in which the body as a whole or a region of the body is deprived of adequate oxygen supply. Variations in arterial oxygen concentrations can be part of the normal physiology, for example, during strenuous physical exercise....
secondary to respiratory depression.

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/minute). Common ADRs include: headache, dizziness, drowsiness, confusion, visual disturbances, tinnitus

Tinnitus

Hypotension

In physiology and medicine, hypotension refers to an abnormally low blood pressure. This is best understood as a physiologic state, rather than a disease....
, bradycardia

Bradycardia

Cardiac arrest

Seizure

Coma

In medicine, a coma is a profound state of unconsciousness. A comatose person cannot be awakened, fails to respond normally to pain or light, does not have sleep-wake cycles, and does not take voluntary actions....
, and/or respiratory depression.

Insensitivity to lidocaine

Relative insensitivity to lidocaine runs in families. In hypokalemic sensory overstimulation

Hypokalemic sensory overstimulation

Hypokalemic sensory overstimulation is a form of attention deficit hyperactivity disorder that has several similarities to disorders of ion channels, in particular to the muscle disorder hypokalemic periodic paralysis....
, relative insensitivity to lidocaine has been described in people who also have attention deficit hyperactivity disorder. In dental anesthesia, a relative insensitivity to lidocaine can occur for anatomical reasons due to unexpected positions of nerves.

Dosage forms

Lidocaine, usually in the form of lidocaine hydrochloride, is available in various forms including:

Injected local anesthetic (sometimes combined with epinephrine
Epinephrine

Epinephrine is a hormone and neurotransmitter.Epinephrine increases the "fight or flight" response of the Sympathetic nervous system of the autonomic nervous system....
)
Dermal patch (sometimes combined with prilocaine
Prilocaine

Prilocaine is a local anesthetic of the amino amide type. In its parenteral form , it is often used in dentistry. It is also often combined with lidocaine as a preparation for dermal anesthesia ....
)
Intravenous injection (sometimes combined with epinephrine
Epinephrine

Epinephrine is a hormone and neurotransmitter.Epinephrine increases the "fight or flight" response of the Sympathetic nervous system of the autonomic nervous system....
)
Intravenous infusion
Nasal instillation/spray (combined with phenylephrine
Phenylephrine

Phenylephrine or Neo-Synephrine is an Alpha-1_adrenergic_receptor agonist used primarily as a decongestant, as an agent to dilate the pupil and to increase blood pressure....
)
Oral gel (often referred to as "viscous lidocaine" or abbreviated "lidocaine visc" or "lidocaine hcl visc" in pharmacology; used as teething gel)
Oral liquid
Topical gel (as with Aloe Vera
Aloe vera

Aloe vera, also known as the Medicinal Aloe, is a species of succulent plant that probably originated in northern Africa. The species does not have any naturally occurring populations, although closely related Aloes do occur in northern Africa....
gels that include Lidocaine)
Topical liquid
Topical patch (Lidocaine 5% patch is marketed as "Lidoderm" in the US (since 1999) and "Versatis" in the UK (since 2007 by Grünenthal))
Topical aerosol Spray

Additive in cocaine

Lidocaine is often added to cocaine

Cocaine

Cocaine is a crystalline tropane alkaloid that is obtained from the leaves of the coca plant. The name comes from "coca" in addition to the alkaloid suffix -ine, forming cocaine....
as a diluent

Diluent

A diluent is a Concentration agent.Certain fluids are too viscosity to be pumped easily or too dense to flow from one particular point to the other....
. Cocaine numbs the gums when applied, and since lidocaine causes stronger gingival numbness, users get the impression of high-quality cocaine when in actuality, the user is receiving a diluted product.