Grundinformationen
- Standard-SMILES
CCN(CC)CC(=O)Nc1c(C)cccc1C.Cl- InChIKey
IYBQHJMYDGVZRY-UHFFFAOYSA-N- Summenformel
- C14H23ClN2O
- Durchschnittliche Molmasse
- 270,8 g/mol
- Monoisotopische Masse
- 270,14989104
Überblick
Lidocaine Hydrochloride is the hydrochloride salt form of lidocaine, an aminoethylamide and a prototypical member of the amide class anesthetics. Lidocaine interacts with voltage-gated Na+ channels in the nerve cell membrane and blocks the transient increase in permeability of excitable membranes to Na+. This prevents the generation and conduction of nerve impulses and produces a reversible loss of sensation. Lidocaine hydrochloride also exhibits class IB antiarrhythmic effects. The agent decreases the flow of sodium ions into myocardial tissue, especially on the Purkinje network, during phase 0 of the action potential, thereby decreasing depolarization, automaticity and excitability.
Namen und Bezeichner
- Bevorzugter Name
- Lidocaine Hydrochloride
- IUPAC
- 2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide;hydrochloride
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
6108-05-0、73-78-9- PubChem CID
- 6314
- DTXSID
DTXSID4058782- ChEMBL
CHEMBL1200409、CHEMBL541521- UNII
- EC2CNF7XFP
- EC Number
- 200-803-8、612-079-4
Eigenschaften
Berechnete Struktureigenschaften
- Polarare Oberfläche (TPSA)
- 32,3 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 5
- Schwere Atome
- 18
- Formalladung
- 0
- Komplexität
- 228
Experimentelle und physikochemische Eigenschaften
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antiarrhythmics; Local Anesthetics
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Danger
H301 (82.5%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P301+P317, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 183 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
H301 (46.3%): Toxic if swallowed [Danger Acute toxicity, oral]
Gefahrenhinweise
Hazard Classes and Categories
Acute Tox. 3 (46.3%)
Acute Tox. 3 (82.5%)
Toxikologische Informationen
Treatment
The first step in the management of systemic toxic reactions consists of immediate attention to the establishment and maintenance of a patent airway and assisted or controlled ventilation with oxygen and a delivery system capable of permitting immediate positive airway pressure by mask. If convulsions occur, the objective of the treatment is to maintain ventilation and oxygenation and support the circulation. Oxygen must be given and ventilation assisted if necessary (mask and bag or tracheal intubation). Should convulsions not stop spontaneously after 15-20 seconds, an anticonvulsant should be given i.v. to facilitate adequate ventilation and oxygenation. Thiopental sodium 1-3 mg/kg i.v. is the first choice. Alternatively diazepam 0.1 mg/kg bw i.v. may be used, although its action will be slow. Prolonged convulsions may jeopardise the patient's ventilation and oxygenation. If so, injection of a muscle relaxant (e.g. succinylcholine 1 mg/kg bw) will facilitate ventilation, and oxygenation can be controlled. Early endotracheal intubation must be considered in such situations. If cardiovascular depression is evident (hypotension, bradycardia), ephedrine 5-10 mg i.v. should be given and may be repeated, if necessary, after 2-3 minutes. Should circulatory arrest occur, immediate cardiopulmonary resuscitation should be instituted. Continual oxygenation and ventilation and circulatory support as well as treatment of acidosis are of vital importance. (L1712)
Health Effects
Systemic exposure to excessive quantities of lidocaine mainly result in central nervous system (CNS) and cardiovascular effects. CNS effects may include CNS excitation(nervousness, tingling around the mouth) followed by depression. [Wikipedia]
Exposure Routes
Intravenous, Topical, Oral, Buccal, Dental, Intramuscular, or Urethral injection , Infiltration. Information derived from diverse formulations, concentrations and usages reveals that lidocaine is completely absorbed following parenteral administration, its rate of absorption depending, for example, upon various factors such as the site of administration and the presence or absence of a vasoconstrictor agent.
Toxicity Summary
Lidocaine stabilizes the neuronal membrane by inhibiting the ionic fluxes required for the initiation and conduction of impulses thereby effecting local anesthetic action. Lidocaine alters signal conduction in neurons by blocking the fast voltage gated sodium (Na+) channels in the neuronal cell membrane that are 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 anaesthetic effect by not merely preventing pain signals from propagating to the brain but by aborting their birth in the first place.
Chemie und Industrie
Pharmakologische Informationen
FDA Pharmacological Classification
0.5% LIDOCAINE HCL
Local Anesthesia [PE]; Antiarrhythmic [EPC]; Amide Local Anesthetic [EPC]; Amides [CS]
1% LIDOCAINE HCI
Local Anesthesia [PE]; Amide Local Anesthetic [EPC]; Antiarrhythmic [EPC]; Amides [CS]
2% LIDOCAINE HCI
Local Anesthesia [PE]; Antiarrhythmic [EPC]; Amide Local Anesthetic [EPC]; Amides [CS]
MeSH Pharmacological Classification
Drugs that block nerve conduction when applied locally to nerve tissue in appropriate concentrations. They act on any part of the nervous system and on every type of nerve fiber. In contact with a nerve trunk, these anesthetics can cause both sensory and motor paralysis in the innervated area. Their action is completely reversible. (From Gilman AG, et. al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed) Nearly all local anesthetics act by reducing the tendency of voltage-dependent sodium channels to activate.
Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade.
A class of drugs that inhibit the activation of VOLTAGE-GATED SODIUM CHANNELS.
Verwendung und Herstellung
Uses
For production of local or regional anesthesia by infiltration techniques such as percutaneous injection and intravenous regional anesthesia by peripheral nerve block techniques such as brachial plexus and intercostal and by central neural techniques such as lumbar and caudal epidural blocks.
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