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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
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
Classification Codes
- Anesthetic (Topical)
- Anesthetics
- Anesthetics, Local
- Anti-Arrhythmia Agents
- Antiviral (COVID-19)
- 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
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Links to Resources
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Other Resources (Internet Locators)
Search for this InChIKey on the Web
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
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-NSmiles
CCN(CC)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.