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Encyclopedia > Lidocaine
Lidocaine
Systematic (IUPAC) name
2-(diethylamino)-
N-(2,6-dimethylphenyl)acetamide
Identifiers
CAS number 137-58-6
ATC code N01BB02 C01BB01 D04AB01 S02DA01 C05AD01
PubChem 3676
DrugBank APRD00479
Chemical data
Formula C14H22N2O 
Mol. mass 234.34 g/mol
Physical data
Melt. point 68 °C (154 °F)
Pharmacokinetic data
Bioavailability 35% (oral)
3% (topical)
Metabolism Hepatic, 90% CYP1A2-mediated
Half life 1.5–2 hours
Excretion renal
Therapeutic considerations
Pregnancy cat.

A(AU) Image File history File links Lidocaine. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... A section of the Anatomical Therapeutic Chemical Classification System. ... A section of the Anatomical Therapeutic Chemical Classification System. ... A section of the Anatomical Therapeutic Chemical Classification System. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... This article or section does not cite any references or sources. ... For other uses, see Carbon (disambiguation). ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... The liver is an organ present in vertebrates and some other animals. ... This page is a candidate for speedy deletion. ... It has been suggested that Effective half-life be merged into this article or section. ... The kidneys are important excretory organs in vertebrates. ... Kidneys viewed from behind with spine removed The kidneys are bean-shaped excretory organs in vertebrates. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ... For other uses, see Australia (disambiguation). ...

Legal status

Prescription Only (S4)(AU) The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... The Standard for the Uniform Scheduling of Drugs and Poisons, abbreviated SUSDP, is a document used in the regulation of drugs and poisons in Australia. ... For other uses, see Australia (disambiguation). ...

Routes IV, subcutaneous, topical

Lidocaine (INN) (IPA: [ˈlaɪdokeɪn]) or lignocaine (former BAN) (IPA: [ˈlɪgnokeɪn]) is a common local anesthetic and antiarrhythmic drug. Lidocaine is used topically to relieve itching, burning and pain from skin inflammations, injected as a dental anesthetic, and in minor surgery. The most commonly encountered lidocaine preparations are marketed by Abraxis Pharmaceutical Products under the brand names Xylocaine and Xylocard, and as 'Lanacane' topical ointment in the UK, though lidocaine is also found in many other proprietary preparations. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... Intravenous therapy or IV therapy is the giving of liquid substances directly into a vein. ... The subcutis is the layer of tissue directly underlying the cutis. ... In medicine, a topical medication is applied to body surfaces such as the skin or mucous membranes such as the vagina, nasopharynx, or the eye. ... An International Nonproprietary Name (INN) is the official non-proprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization. ... Articles with similar titles include the NATO phonetic alphabet, which has also informally been called the “International Phonetic Alphabet”. For information on how to read IPA transcriptions of English words, see IPA chart for English. ... A British Approved Name (BAN) is the official non-proprietary or generic name given to a pharmaceutical substance, as defined in the British Pharmacopoeia (BP). ... Articles with similar titles include the NATO phonetic alphabet, which has also informally been called the “International Phonetic Alphabet”. For information on how to read IPA transcriptions of English words, see IPA chart for English. ... A local anesthetic is a drug that reversibly inhibits the propagation of signals along nerves. ... Antiarrhythmic agents are a group of pharmaceuticals that are used to suppress fast rhythms of the heart (cardiac arrhythmias), such as atrial fibrillation, atrial flutter, ventricular tachycardia, and ventricular fibrillation. ...

Contents

History

Lidocaine, the first amino amide-type local anesthetic, was developed first by Nils Löfgren and Bengt Lundqvist in 1943 and first marketed in 1948. In chemistry, especially in organic chemistry and biochemistry, an amino group is an ammonia-like functional group. ... Amide functional group Amides possess a conjugated system spread over the O, C and N atoms, consisting of molecular orbitals occupied by delocalized electrons. ... Nils Löfgren was a Swedish scientist who developed the anaesthetic lidocaine (xylocaine) in 1943. ... Year 1943 (MCMXLIII) was a common year starting on Friday (the link will display full 1943 calendar) of the Gregorian calendar. ... Year 1948 (MCMXLVIII) was a leap year starting on Thursday (link will display the 1948 calendar) of the Gregorian calendar. ...


Pharmacokinetics

Lidocaine has a more rapid onset of action and longer duration of action than amino ester-type local anesthetics such as procaine. It is approximately 90% metabolized in the liver by CYP1A2 (and to a minor extent CYP3A4) to the pharmacologically-active metabolites monoethylglycinexylidide and glycinexylidide. In chemistry, especially in organic chemistry and biochemistry, an amino group is an ammonia-like functional group. ... A carboxylic acid ester. ... Procaine is a local anesthetic drug of the amino ester group. ... The liver is an organ present in vertebrates and some other animals. ... This page is a candidate for speedy deletion. ... Cytochrome P450 3A4 (abbreviated CYP3A4) (EC 1. ... 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. ...


The elimination half-life of lidocaine is approximately 1.5–2 hours in most patients. This may be prolonged in patients with hepatic impairment (average 343 minutes) or congestive heart failure (average 136 minutes). (Thomson et al., 1973) Half-Life For a quantity subject to exponential decay, the half-life is the time required for the quantity to fall to half of its initial value. ... Liver failure is the final stage of liver disease. ... Congestive heart failure (CHF), also called congestive cardiac failure (CCF) or just heart failure, is a condition that can result from any structural or functional cardiac disorder that impairs the ability of the heart to fill with or pump a sufficient amount of blood through the body. ...


Pharmacology

Anesthesia

Lidocaine alters depolarization in neurons, 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, leading to its anesthetic 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 signalling. Drawing by Santiago Ramón y Cajal of neurons in the pigeon cerebellum. ... Sodium channels are integral membrane proteins that exist in a cells plasma membrane and regulate the flow of sodium (Na+) ions into it. ... A. A schematic view of an idealized action potential illustrates its various phases as the action potential passes a point on a cell membrane. ...


Clinical use

Indications

Indications for the use of lidocaine include:

Topical lidocaine has been shown to relieve postherpetic neuralgia in some patients, although there is not enough study evidence to recommend it as a first-line treatment. (Khaliq et al., 2007) A cardiac arrhythmia, also called cardiac dysrhythmia, is a disturbance in the regular rhythm of the heartbeat. ... Ventricular fibrillation (V-fib or VF) is a cardiac condition which consists of a lack of coordination of the contraction of the muscle tissue of the large chambers of the heart that eventually leads to the heart stopping altogether. ... Ventricular tachycardia (V-tach or VT) is a fast rhythm that originates in one of the ventricles of the heart. ... In medicine, a topical medication is applied to body surfaces such as the skin or mucous membranes such as the vagina, nasopharynx, or the eye. ... Postherpetic neuralgia (PHN) is a painful condition caused by the varicella zoster virus in a dermatomal distribution (the area governed by a particular sensory nerve) after an attack of herpes zoster (HZ) (commonly known as shingles), usually manifesting after the vesicles have crusted over and begun to heal. ... A first-line treatment or first-line therapy is a medical therapy recommended for the initial treatment of a disease, sign or symptom, usually on the basis of empirical evidence for its efficacy. ...


Contraindications

Contraindications for the use of lidocaine include:

A heart block is a disease in the electrical system of the heart. ... A sinoatrial block is a type of heart block which involves in impairment of conduction at the sinoatrial node. ... An adverse drug reaction (abbreviated ADR) is a term to describe the unwanted, negative consequences sometimes associated with the use of medications. ... Quinidine is a pharmaceutical agent that acts as a class I antiarrhythmic agent in the heart. ... Flecainide acetate is a class Ic antiarrhythmic agent used to prevent and treat tachyarrhythmias (abnormal fast rhythms of the heart). ... Disopyramide (INN, trade names Norpace® and Rythmodan®) is an antiarrhythmic medication. ... Procainamide (trade name Pronestyl®) is a pharmaceutical antiarrhythmic agent used for the medical treatment of cardiac arrhythmias, classified by the Vaughan Williams classification system as class Ia. ... Antiarrhythmic agents are a group of pharmaceuticals that are used to suppress fast rhythms of the heart (cardiac arrhythmias), such as atrial fibrillation, atrial flutter, ventricular tachycardia, and ventricular fibrillation. ... In physiology and medicine, hypotension refers to an abnormally low blood pressure. ... A cardiac arrhythmia, also called cardiac dysrhythmia, is a disturbance in the regular rhythm of the heartbeat. ... 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. ... The rate of cardiac contraction is determined by the intrinsic rate of depolarisation of the cardiac cells. ...

Adverse drug reactions

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, however allergic reactions can rarely occur. An adverse drug reaction (abbreviated ADR) is a term to describe the unwanted, negative consequences sometimes associated with the use of medications. ... An allergy is an abnormal, acquired sensitivity to a given substance, including pollen, drugs, or numerous environmental triggers. ...


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. CNS effects may include CNS excitation (nervousness, tingling around the mouth, tinnitus, tremor, dizziness, blurred vision, seizures) followed by depression (drowsiness, loss of consciousness, respiratory depression and apnea). Cardiovascular effects include hypotension, bradycardia, arrhythmias, and/or cardiac arrest – some of which may be due to hypoxemia secondary to respiratory depression. (Rossi, 2006) A diagram showing the CNS: 1. ... The circulatory system or cardiovascular system is the organ system which circulates blood around the body of most animals. ... Blood plasma is the liquid component of blood, in which the blood cells are suspended. ... Tinnitus (IPA pronunciation: or ,[1] from the Latin word for ringing[2]) is the perception of sound in the human ear in the absence of corresponding external sound(s). ... This article is about epileptic seizures. ... In medicine, hypoventilation exists when ventilation is inadequate to perform gas exchange. ... Apnea (British spelling - apnoea) (Greek απνοια, from α-, privative, πνεειν, to breathe) is a technical term for suspension of external breathing. ... In physiology and medicine, hypotension refers to an abnormally low blood pressure. ... 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. ... A cardiac arrhythmia, also called cardiac dysrhythmia, is a disturbance in the regular rhythm of the heartbeat. ... Hypoxia is a pathological condition in which the body as a whole (generalised hypoxia) or region of the body (tissue hypoxia) is deprived of adequate oxygen supply. ...


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, 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. (Rossi, 2006) Tinnitus (IPA pronunciation: or ,[1] from the Latin word for ringing[2]) is the perception of sound in the human ear in the absence of corresponding external sound(s). ... Paresthesia (paraesthesia in British) is a sensation of tingling, pricking, or numbness of the skin with no apparent physical cause, more generally known as the feeling of pins and needles. ... In physiology and medicine, hypotension refers to an abnormally low blood pressure. ... 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. ... A cardiac arrhythmia, also called cardiac dysrhythmia, is a disturbance in the regular rhythm of the heartbeat. ... This article is about epileptic seizures. ... In medicine, a coma (from the Greek koma, meaning deep sleep) is a profound state of unconsciousness. ...


Dosage forms

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

  • Injected local anesthetic (sometimes combined with epinephrine)
  • Dermal patch (sometimes combined with prilocaine)
  • Intravenous injection (sometimes combined with epinephrine)
  • Intravenous 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
  • Topical gel (as with Aloe Vera 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))

“Adrenaline” redirects here. ... Chemical structure of prilocaine Prilocaine (IPA: ) is a local anesthetic of the amino amide type. ... “Adrenaline” redirects here. ... Phenylephrine or neosynephrine is an α-adrenergic receptor agonist used primarily as a decongestant, as an agent to dilate the pupil and, rarely, to increase blood pressure. ... Binomial name (L.) Burm. ...

Additive in cocaine

Lidocaine is often added to cocaine as a diluent. Cocaine numbs the gums when applied, and since lidocaine causes stronger gingival numbness, customers get the impression of high-quality cocaine when checking the purity this way even if the substance is of poor quality. Usage of lidocaine-diluted cocaine is dangerous due to the potential side effects of lidocaine including causing cardiac arrhythmias. Cocaine is a crystalline tropane alkaloid that is obtained from the leaves of the coca plant. ... Categories: Move to Wiktionary | Stub ... The gingiva, or gums, consist of the tissue surrounding the roots of the teeth and covering the jawbone. ... Cardiac arrhythmia is any of a group of conditions in which the electrical activity of the heart is irregular or is faster or slower than normal. ...


References

  • Khaliq W, Alam S, Puri N (2007). "Topical lidocaine for the treatment of postherpetic neuralgia". Cochrane Database Syst Rev (2): CD004846. DOI:10.1002/14651858.CD004846.pub2. PMID 17443559. 
  • Rossi S, editor. Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006. ISBN 0-9757919-2-3
  • Thomson PD, Melmon KL, Richardson JA, et al (1973). "Lidocaine pharmacokinetics in advanced heart failure, liver disease, and renal failure in humans". Ann. Intern. Med. 78 (4): 499-508. PMID 4694036. 

  Results from FactBites:
 
eMedicine - Toxicity, Lidocaine : Article by Ruben Peralta (2148 words)
Lidocaine is an amide local anesthetic and a less commonly used antiarrhythmic that exerts its effects on nerve axon sodium channels, preventing depolarization.
Lidocaine toxicity occurs with unintended intravascular administration or with administration of an excessive dose.
Lidocaine's main effects are due to decreased conductance of sodium channels, antiarrhythmic effect, sedation, and neural blockade.
MedlinePlus Drug Information: Lidocaine Viscous (548 words)
Lidocaine viscous, a local anesthetic, is used to treat the pain of a sore or irritated mouth and throat often associated with cancer chemotherapy and certain medical procedures.
Lidocaine viscous is not normally used for sore throats due to cold, flu, or infections such as strep throat.
Lidocaine viscous usually is used as needed but not more frequently than every 3 hours, with a maximum of eight doses in 24 hours.
  More results at FactBites »

 
 

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