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73-78-9, Lidocaine hydrochloride

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Use of Lidocaine hydrochloride
Lidocaine Hcl salt, an amide local anesthetic, has anti-inflammatory properties in vitro and in vivo, possibly due to an attenuation of pro-inflammatory cytokines, intracellular adhesion molecule-1 (ICAM-1), and reduction of neutrophils influx.Target: Lidocaine 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 or as a local anesthetic for minor surgery. Lidocaine, the first amino amide–type local anesthetic, was first synthesized under the name xylocaine by Swedish chemist Nils Lofgren in 1943. His colleague Bengt Lundqvist performed the first injection anesthesia experiments on himself.Lidocaine is approximately 95% metabolized (dealkylated) in the liver by CYP3A4 to the pharmacologically-active metabolites monoethylglycinexylidide (MEGX) and then subsequently to the inactive glycine xylidide. MEGX has a longer half life than lidocaine but also is a less potent sodium channel blocker. The elimination half-life of lidocaine is approximately 90–120 minutes in most patients. This may be prolonged in patients with hepatic impairment (average 343 minutes) or congestive heart failure (average 136 minutes).

Names

Name lidocaine hydrochloride
Synonym More Synonyms

 Lidocaine hydrochloride Biological Activity

Description Lidocaine Hcl salt, an amide local anesthetic, has anti-inflammatory properties in vitro and in vivo, possibly due to an attenuation of pro-inflammatory cytokines, intracellular adhesion molecule-1 (ICAM-1), and reduction of neutrophils influx.Target: Lidocaine 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 or as a local anesthetic for minor surgery. Lidocaine, the first amino amide–type local anesthetic, was first synthesized under the name xylocaine by Swedish chemist Nils Lofgren in 1943. His colleague Bengt Lundqvist performed the first injection anesthesia experiments on himself.Lidocaine is approximately 95% metabolized (dealkylated) in the liver by CYP3A4 to the pharmacologically-active metabolites monoethylglycinexylidide (MEGX) and then subsequently to the inactive glycine xylidide. MEGX has a longer half life than lidocaine but also is a less potent sodium channel blocker. The elimination half-life of lidocaine is approximately 90–120 minutes in most patients. This may be prolonged in patients with hepatic impairment (average 343 minutes) or congestive heart failure (average 136 minutes).
Related Catalog
References [1]. VAN DER Wal S, et al. Lidocaine increases the anti-inflammatory cytokine IL-10 following mechanical ventilation in healthy mice. Acta Anaesthesiol Scand. 2014 Oct 14.[2]. Acevedo-Arcique CM, et al. Lidocaine, dexmedetomidine and their combination reduce isoflurane minimum alveolar concentration in dogs. PLoS One. 2014 Sep 18;9(9):e106620.

 Chemical & Physical Properties

Boiling Point 350.8ºC at 760 mmHg
Melting Point 80-82°C
Molecular Formula C14H23ClN2O
Molecular Weight 270.798
Flash Point 166ºC
Exact Mass 270.149902
PSA 32.34000
LogP 3.45870
Storage condition Refrigerator

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
AN7600000
CHEMICAL NAME :
2′,6′-Acetoxylidide, 2-(diethylamino)-, hydrochloride
CAS REGISTRY NUMBER :
73-78-9
LAST UPDATED :
199712
DATA ITEMS CITED :
27
MOLECULAR FORMULA :
C14-H22-N2-O.Cl-H
MOLECULAR WEIGHT :
270.84
WISWESSER LINE NOTATION :
2N2&1VMR B1 F1 &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent – rabbit
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 137,410,1962
TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration into the eye
SPECIES OBSERVED :
Rodent – rabbit
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 137,410,1962 ** ACUTE TOXICITY DATA **
TYPE OF TEST :
TDLo – Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human – infant
DOSE/DURATION :
1600 ug/kg/9H-I
TOXIC EFFECTS :
Behavioral – convulsions or effect on seizure threshold
REFERENCE :
AEMED3 Annals of Emergency Medicine. (American College of Emergency Physicians, 1125 Executive Circle, Irving, TX 75038) Volume(issue)/page/year: 17,725,1988
TYPE OF TEST :
TDLo – Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human – infant
DOSE/DURATION :
1632 mg/kg/1W-I
TOXIC EFFECTS :
Behavioral – somnolence (general depressed activity) Behavioral – convulsions or effect on seizure threshold
REFERENCE :
CPEDAM Clinical Pediatrics (Philadelphia). (Lippincott/Harper, Journal Fulfillment Dept., 2350 Virginia Ave., Hagerstown, MD 21740) V.1- 1962- Volume(issue)/page/year: 22,190,1983
TYPE OF TEST :
TDLo – Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human – infant
DOSE/DURATION :
10 mg/kg
TOXIC EFFECTS :
Behavioral – convulsions or effect on seizure threshold Behavioral – coma Lungs, Thorax, or Respiration – other changes
REFERENCE :
JTCTDW Journal of Toxicology, Clinical Toxicology. (Marcel Dekker, 270 Madison Ave., New York, NY 10016) V.19- 1982- Volume(issue)/page/year: 28,101,1990
TYPE OF TEST :
TDLo – Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human – child
DOSE/DURATION :
60 mg/kg/1H
TOXIC EFFECTS :
Behavioral – convulsions or effect on seizure threshold Vascular – BP lowering not characterized in autonomic section
REFERENCE :
JTCTDW Journal of Toxicology, Clinical Toxicology. (Marcel Dekker, 270 Madison Ave., New York, NY 10016) V.19- 1982- Volume(issue)/page/year: 24,51,1986
TYPE OF TEST :
TDLo – Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human – man
DOSE/DURATION :
9 mg/kg/4H-C
TOXIC EFFECTS :
Cardiac – cardiomyopathy including infarction
REFERENCE :
DICPBB Drug Intelligence and Clinical Pharmacy. (POB 42435, Cincinnati, OH 45242) V.3- 1969- Volume(issue)/page/year: 19,669,1985
TYPE OF TEST :
TDLo – Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human – man
DOSE/DURATION :
7143 ug/kg
TOXIC EFFECTS :
Cardiac – pulse rate increase, without fall in BP
REFERENCE :
CHETBF Chest. (American College of Chest Physicians, 911 Busse Hwy, Park Ridge, IL 60068) V.57- 1970- Volume(issue)/page/year: 61,682,1972
TYPE OF TEST :
TDLo – Lowest published toxic dose
ROUTE OF EXPOSURE :
Implant
SPECIES OBSERVED :
Human – man
DOSE/DURATION :
5714 ug/kg
TOXIC EFFECTS :
Behavioral – convulsions or effect on seizure threshold
REFERENCE :
CMAJAX Canadian Medical Association Journal. (Canadian Medical Assoc., POB 8650, Ottawa, ON K1G 0G8, Canada) V.1- 1911- Volume(issue)/page/year: 137,219,1987
TYPE OF TEST :
LD50 – Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent – rat
DOSE/DURATION :
122 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 111,224,1954
TYPE OF TEST :
LD50 – Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent – rat
DOSE/DURATION :
570 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
RPOBAR Research Progress in Organic-Biological and Medicinal Chemistry. (New York, NY) V.1-3, 1964-72. Discontinued. Volume(issue)/page/year: 2,299,1970
TYPE OF TEST :
LD50 – Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent – rat
DOSE/DURATION :
21 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
RPOBAR Research Progress in Organic-Biological and Medicinal Chemistry. (New York, NY) V.1-3, 1964-72. Discontinued. Volume(issue)/page/year: 2,299,1970
TYPE OF TEST :
LD50 – Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent – mouse
DOSE/DURATION :
220 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
RPOBAR Research Progress in Organic-Biological and Medicinal Chemistry. (New York, NY) V.1-3, 1964-72. Discontinued. Volume(issue)/page/year: 2,299,1970
TYPE OF TEST :
LD50 – Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent – mouse
DOSE/DURATION :
63 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 274,253,1985
TYPE OF TEST :
LD50 – Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent – mouse
DOSE/DURATION :
163 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 103,353,1960
TYPE OF TEST :
LD50 – Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent – mouse
DOSE/DURATION :
15 mg/kg
TOXIC EFFECTS :
Behavioral – altered sleep time (including change in righting reflex) Lungs, Thorax, or Respiration – respiratory stimulation
REFERENCE :
JPPMAB Journal of Pharmacy and Pharmacology. (Pharmaceutical Soc. of Great Britain, 1 Lambeth High St., London SEI 7JN, UK) V.1- 1949- Volume(issue)/page/year: 14,48T,1962
TYPE OF TEST :
LD50 – Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent – mouse
DOSE/DURATION :
177 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
DDREDK Drug Development Research. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1981- Volume(issue)/page/year: 21,277,1990
TYPE OF TEST :
LDLo – Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal – dog
DOSE/DURATION :
65700 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JNPHAG Journal de Pharmacologie. (SPPIF, B.P.22, F-41353 Vineuil, France) V.1- 1970- Volume(issue)/page/year: 2,240,1971
TYPE OF TEST :
LD50 – Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent – rabbit
DOSE/DURATION :
25600 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,879,1982
TYPE OF TEST :
LD50 – Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intratracheal
SPECIES OBSERVED :
Rodent – rabbit
DOSE/DURATION :
28 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 200,359,1972
TYPE OF TEST :
LD50 – Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent – guinea pig
DOSE/DURATION :
24500 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 113,313,1958
TYPE OF TEST :
LD50 – Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Parenteral
SPECIES OBSERVED :
Amphibian – frog
DOSE/DURATION :
159 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 289,278,1987 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo – Lowest published toxic dose
ROUTE OF EXPOSURE :
Implant
DOSE :
7500 mg/kg
SEX/DURATION :
female 3-17 day(s) after conception
TOXIC EFFECTS :
Reproductive – Maternal Effects – parturition Reproductive – Effects on Embryo or Fetus – fetotoxicity (except death, e.g., stunted fetus) Reproductive – Specific Developmental Abnormalities – musculoskeletal system
REFERENCE :
ANESAV Anesthesiology. (Lippincott/Harper, Journal Fulfillment Dept., 2350 Virginia Ave., Hagerstown, MD 21740) V.1- 1940- Volume(issue)/page/year: 65,626,1986 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS – National Occupational Hazard Survey (1974) NOHS Hazard Code – 83491 No. of Facilities: 397 (estimated) No. of Industries: 3 No. of Occupations: 5 No. of Employees: 13412 (estimated) NOES – National Occupational Exposure Survey (1983) NOES Hazard Code – 83491 No. of Facilities: 1385 (estimated) No. of Industries: 6 No. of Occupations: 17 No. of Employees: 68071 (estimated) No. of Female Employees: 56919 (estimated)

 Safety Information

RIDADR 3249
Packaging Group III
Hazard Class 6.1(b)
HS Code 2924299090

Synonyms

LIDOCAINE HCL
2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide,hydrochloride
2-(Diethylamino)-N-(2,6-dimethylphenyl)acetamidhydrochlorid
Xyloneural
XYLOCAINE HYDROCHLORIDE
N-(2,6-Dimethylphenyl)-N,N-diethylglycinamide hydrochloride (1:1)
MFCD00034865
(Diethylamino)-2′,6′-acetoxylidide Monohydrochloride
2-(diéthylamino)-N-(2,6-diméthylphényl)acétamide chlorhydrate
Xilina hydrochloride
2-(Diethylamino)-N-(2,6-dimethylphenyl)acetamide, hydrochloride (1:1)
N-(2,6-dimethylphenyl)-N,N-diethylglycinamide hydrochloride
Lidocaine hydrochloride
lignocaine hydrochloride
2-(Diethylamino)-N-(2,6-dimethylphenyl)acetamide monohydrochloride
Acetamide, 2-(diethylamino)-N-(2,6-dimethylphenyl)-, hydrochloride (1:1)
Lidocaton
Lidothesin
Laryng-O-jet
N-(2,6-dimethylphenyl)-N2,N2-diethylglycinamide hydrochloride
2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide hydrochloride
EINECS 200-803-8
2′,6′-Acetoxylidide, 2-(diethylamino)-, monohydrochloride (8CI)
Xylocard
2N2&1VMR B1 F1 &&HCl
Lidocaine (hydrochloride)

 

 


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