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Substance Name: Lidocaine [USP:INN:BAN:JAN]
RN: 137-58-6
UNII: 98PI200987
InChIKey: NNJVILVZKWQKPM-UHFFFAOYSA-N

Note

  • A local anesthetic and cardiac depressant used as an antiarrhythmia agent. Its actions are more intense and its effects more prolonged than those of procaine but its duration of action is shorter than that of bupivacaine or prilocaine.

Molecular Formula

  • C14-H22-N2-O

Molecular Weight

  • 234.3408
 

Classification Codes

  • Anesthetic (Topical)
  • Anesthetics
  • Anesthetics, Local
  • Anti-Arrhythmia Agents
  • Cardiovascular Agents
  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Drug / Therapeutic Agent
  • Human Data
  • Membrane Transport Modulators
  • Mutation Data
  • Peripheral Nervous System Agents
  • Reproductive Effect
  • Sensory System Agents
  • Sodium Channel Blockers
  • Voltage-Gated Sodium Channel Blockers

Names and Synonyms

Name of Substance

  • Lidocaine
  • Lidocaine [USP:INN:BAN:JAN]

MeSH Heading

  • Lidocaine

Synonyms

  • 2',6'-Acetoxylidide, 2-(diethylamino)-
  • 2-(Diethylamino)-2',6'-acetoxylidide
  • 2-(Diethylamino)-N-(2,6-dimethylphenyl)acetamide
  • 4-12-00-02538 (Beilstein Handbook Reference)
  • Acetamide, 2-(diethylamino)-N-(2,6-dimethylphenyl)-
  • alfa-Dietilamino-2,6-dimetilacetanilide
  • alfa-Dietilamino-2,6-dimetilacetanilide [Italian]
  • alpha-Diethylamino-2,6-dimethylacetanilide
  • Alphacaine
  • Anbesol
  • Anestacon
  • BRN 2215784
  • Cappicaine
  • Cito optadren
  • Cuivasil
  • DentiPatch
  • Diethylaminoaceto-2,6-xylidide
  • Duncaine
  • EINECS 205-302-8
  • ELA-Max
  • Esracaine
  • Gravocain
  • HSDB 3350
  • Isicaina
  • Isicaine
  • Jetocaine
  • L-Caine
  • Leostesin
  • Lida-Mantle
  • Lidocaina
  • Lidocaina [INN-Spanish]
  • Lidocaine
  • Lidocaine (VAN)
  • Lidocainum
  • Lidocainum [INN-Latin]
  • Lidoderm
  • Lignocaine
  • Lignocainum
  • Maricaine
  • NSC 40030
  • Remicaine
  • Rucaina
  • Solarcaine
  • Solcain
  • UNII-98PI200987
  • Versatis
  • Xilina
  • Xilocaina
  • Xilocaina [Italian]
  • Xycaine
  • Xylestesin
  • Xylocain
  • Xylocaine
  • Xylocitin
  • Xyloneural (free base)
  • Xylotox
  • Ztilido
  • ZTlido

Systematic Names

  • 2',6'-Acetoxylidide, 2-(diethylamino)-
  • Acetamide, 2-(diethylamino)-N-(2,6-dimethylphenyl)-
  • Lidocaine

Mixture Names

  • EMLA cream
  • Lidaform-HC
  • Lidamantle-HC
  • Neosporin Plus
  • Oraqix
  • Synera

Registry Numbers

CAS Registry Number

  • 137-58-6

FDA UNII

  • 98PI200987

Other Registry Numbers

  • 8059-42-5
  • 8059-66-3
  • 91484-71-8

Related Registry Numbers

  • 6108-05-0 (mono-hydrochloride, mono-hydrate)
  • 73-78-9 (mono-hydrochloride)

System Generated Number

  • 0000137586

Structure Descriptors

InChI

1S/C14H22N2O/c1-5-16(6-2)10-13(17)15-14-11(3)8-7-9-12(14)4/h7-9H,5-6,10H2,1-4H3,(H,15,17)

InChIKey

NNJVILVZKWQKPM-UHFFFAOYSA-N

Smiles

CCN(CC)CC(=O)Nc1c(cccc1C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 21mg/kg (21mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Journal of Toxicology, Clinical Toxicology. Vol. 30, Pg. 413, 1992.
child TDLo oral 300mg/kg/5D-I (300mg/kg)   Pediatric Emergency Care. Vol. 10, Pg. 344, 1994.
child TDLo oral 300mg/kg/5D-I (300mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Pediatric Emergency Care. Vol. 10, Pg. 344, 1994.
guinea pig LD50 subcutaneous 120mg/kg (120mg/kg)   Farmaco, Edizione Scientifica. Vol. 10, Pg. 883, 1955.
guinea pig LDLo intravenous 65mg/kg (65mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 130, Pg. 235, 1961.
human TDLo intravenous 23mg/kg (23mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Archiv fuer Toxikologie. Vol. 28, Pg. 72, 1971.
man TDLo intravenous 1700ug/kg/2M- (1.7mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

CARDIAC: PULSE RATE

BEHAVIORAL: COMA
American Journal of Emergency Medicine. Vol. 4, Pg. 143, 1986.
man TDLo intravenous 8643ug/kg/4H- (8.643mg/kg) BEHAVIORAL: TOXIC PSYCHOSIS Annals of Internal Medicine. Vol. 97, Pg. 149, 1982.
mouse LD50 intraperitoneal 102mg/kg (102mg/kg) PERIPHERAL NERVE AND SENSATION: LOCAL ANESTHETIC

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA
Journal of Medicinal Chemistry. Vol. 24, Pg. 1059, 1981.
mouse LD50 intravenous 20mg/kg (20mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Journal of Pharmacology and Experimental Therapeutics. Vol. 123, Pg. 269, 1958.
mouse LD50 oral 220mg/kg (220mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: REGIDITY
Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 1275, 1966.
mouse LD50 subcutaneous 238mg/kg (238mg/kg)   Journal of Medicinal Chemistry. Vol. 28, Pg. 714, 1985.
rabbit LDLo intravenous 41mg/kg (41mg/kg)   Acta Pharmacologica et Toxicologica. Vol. 31, Pg. 273, 1972.
rat LD50 intraperitoneal 133mg/kg (133mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 243, Pg. 97, 1980.
rat LD50 intravenous 18mg/kg (18mg/kg)   United States Patent Document. Vol. #5264432,
rat LD50 oral 317mg/kg (317mg/kg)   Bollettino Chimico Farmaceutico. Vol. 110, Pg. 330, 1971.
rat LD50 subcutaneous 335mg/kg (335mg/kg)   European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 9, Pg. 188, 1974.
rat LD50 unreported 39400ug/kg (39.4mg/kg)   Farmakologiya i Toksikologiya Vol. 54(3), Pg. 32, 1991.
women TDLo intraspinal 1mL/kg (1mL/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: EUPHORIA
Journal of Clinical Pyschopharmacology. Vol. 10, Pg. 442, 1990.
women TDLo intravenous 16mg/kg (16mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

CARDIAC: CHANGE IN RATE
European Journal of Clinical Pharmacology. Vol. 22, Pg. 129, 1982.
women TDLo oral 39mg/kg (39mg/kg) CARDIAC: CHANGE IN RATE

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
New England Journal of Medicine. Vol. 306, Pg. 381, 1982.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 68.5 deg C   EXP
pKa Dissociation Constant 8.01 (none)   EXP
log P (octanol-water) 2.44 (none)   EXP
Water Solubility 4100 mg/L 30 EXP
Vapor Pressure 1.08E-06 mm Hg 25 EST
Henry's Law Constant 1.31E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.09E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.