Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C12H18N2O |
| Molecular Weight | 206.2841 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCNCC(=O)NC1=C(C)C=CC=C1C
InChI
InChIKey=WRMRXPASUROZGT-UHFFFAOYSA-N
InChI=1S/C12H18N2O/c1-4-13-8-11(15)14-12-9(2)6-5-7-10(12)3/h5-7,13H,4,8H2,1-3H3,(H,14,15)
| Molecular Formula | C12H18N2O |
| Molecular Weight | 206.2841 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Norlidocaine (monoethylglycinexylidide, MEGX) is the major metabolite of lidocaine. The lidocaine metabolites formed on the first pass, which include MEGX and GX, have additive central nervous system (CNS) toxicity to lidocaine itself, making oral administration unacceptable. Monoethylglycinexylidide (MEGX) also has local anesthetic activity. It contributes to central nervous system (CNS) toxicity in some patients treated with lidocaine. Lidocaine is eliminated mainly by biotransfomation to monoethylglycinexylidide. MEGX has pharmacologic activity. MEGX has an antiarrhythmic potency of the same order as lidocaine in vitro in a guinea pig atrium model and is about half as potent in vivo in dogs.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effect of 4% topical lidocaine applied to the face on the serum levels of lidocaine and its metabolite, monoethylglycinexylidide. | 2010-12-07 |
|
| Biophysical characterization of recombinant proteins: a key to higher structural genomics success. | 2010-10 |
|
| [Determination of lidocaine and its metabolites in human plasma by liquid chromatography in combination with tandem mass spectrometry]. | 2010-07 |
|
| Lidocaine/monoethylglycinexylidide test, galactose elimination test, and sorbitol elimination test for metabolic assessment of liver cell bioreactors. | 2010-06 |
|
| Is dopexamine superior to dopamine in the treatment of multiple trauma patients--a prospective, double-blind, randomised study. | 2010-05 |
|
| Prognostic value of the monoethylglycinexylidide test in alcoholic cirrhosis. | 2009-10-28 |
|
| Evaluation of quantitative liver function tests in HIV-positive patients under anti-retroviral therapy. | 2009-09-01 |
|
| Cutaneous in vivo metabolism of topical lidocaine formulation in human skin. | 2009 |
|
| Pharmacokinetics of lidocaine and its metabolite in peridural anesthesia administered to pregnant women with gestational diabetes mellitus. | 2008-12 |
|
| Pharmacokinetics of lidocaine following the application of 5% lidocaine patches to cats. | 2008-08 |
|
| Prognostic value of the monoethylglycinexylidide (MEGX)-test prior to liver resection. | 2008-07-11 |
|
| Efficacy of lidocaine for pain control in subcutaneous infiltration during liposuction. | 2008-06-18 |
|
| Reporting a fatality during tumescent liposuction. | 2008-06-10 |
|
| Serum concentrations of lidocaine and its metabolites after prolonged infusion in healthy horses. | 2008-06 |
|
| [Determination of monoethylglycinexylidide concentration in serum using solid phase extraction and capillary gas chromatography-mass spectrometry]. | 2008-05 |
|
| Measuring hepatic functional reserve using MEGX: still a mirage! | 2008-01-30 |
|
| Monoethylglycinexylidide (MEGX) as a liver function test in cirrhosis. | 2007-11-08 |
|
| [Liver function test to predict hepatic failure after liver resection--expensive and without clinical relevance?]. | 2007-08 |
|
| Determination of lidocaine and its two N-desethylated metabolites in dog and horse plasma by high-performance liquid chromatography combined with electrospray ionization tandem mass spectrometry. | 2007-06-01 |
|
| Pharmacokinetics of tilidine and naloxone in patients with severe hepatic impairment. | 2007 |
|
| Differential effect of chronic renal failure on the pharmacokinetics of lidocaine in patients receiving and not receiving hemodialysis. | 2006-12 |
|
| Effect of fluvoxamine and erythromycin on the pharmacokinetics of oral lidocaine. | 2006-08 |
|
| Lidocaine metabolism in isolated perfused liver from streptozotocin-induced diabetic rats. | 2006-08 |
|
| Safety of occluded 4% liposomal lidocaine cream. | 2006-07-27 |
|
| Prognostic value of quantitative liver function tests in viral cirrhosis: a prospective study. | 2006-07 |
|
| [Evaluation of the liver reserve using lidocaine test on experimental liver injuries in rats]. | 2006-06 |
|
| Splanchnic organ injury during coronary surgery with or without cardiopulmonary bypass: a randomized, controlled trial. | 2006-01 |
|
| Assessment of liver function in children with acute lymphoblastic leukemia in remission. | 2006 |
|
| Double-compartment cell culture apparatus: construction and biochemical evaluation for bioartificial liver support. | 2006 |
|
| Effect of ciprofloxin on the pharmacokinetics of intravenous lidocaine. | 2005-10 |
|
| Pharmacokinetics of lidocaine and its active metabolite, monoethylglycinexylidide, after intravenous administration of lidocaine to awake and isoflurane-anesthetized cats. | 2005-07 |
|
| Blockade of spinal nitric oxide synthase on blood pressure variability and hepatic microcirculation. | 2005-06 |
|
| The effect of mild and moderate hepatic impairment on the pharmacokinetics of valdecoxib, a selective COX-2 inhibitor. | 2005-06 |
|
| The effect of erythromycin and fluvoxamine on the pharmacokinetics of intravenous lidocaine. | 2005-05 |
|
| Analysis of lidocaine and its major metabolite, monoethylglycinexylidide, in elk velvet antler by liquid chromatography with UV detection and confirmation by electrospray ionization tandem mass spectrometry. | 2005-04-06 |
|
| Monoethylglycinexylidide and lidocaine determination in porcine microsomal preparations. | 2005-04-01 |
|
| Assessment of the hemodynamic effects of lidocaine administered IV in isoflurane-anesthetized cats. | 2005-04 |
|
| A study of the in vitro interaction between lidocaine and premedications using human liver microsomes. | 2005-04 |
|
| Assessment of hepatic reserve for indication of hepatic resection: how I do it. | 2005 |
|
| Effect of lidocaine on the minimum alveolar concentration of isoflurane in dogs. | 2004-10 |
|
| Pharmacokinetics and transplacental transfer of lidocaine and its metabolite for perineal analgesic assistance to pregnant women. | 2004-10 |
|
| Effect of itraconazole on the pharmacokinetics of inhaled lidocaine. | 2004-09 |
|
| Pharmacokinetics and safety of lidocaine and monoethylglycinexylidide in liposuction: a microdialysis study. | 2004-08 |
|
| Splanchnic oxygen transport, hepatic function and gastrointestinal barrier after normothermic cardiopulmonary bypass. | 2004-07 |
|
| Liquid chromatographic method for the determination of lidocaine and monoethylglycine xylidide in human serum containing various concentrations of bilirubin for the assessment of liver function. | 2004-06-05 |
|
| Clinical review: influence of vasoactive and other therapies on intestinal and hepatic circulations in patients with septic shock. | 2004-06 |
|
| Use of lidocaine metabolism to test liver function during the long-term follow-up of liver transplant recipients. | 2004-06 |
|
| Utility of nonaqueous capillary electrophoresis for the determination of lidocaine and its metabolites in human plasma: a comparison of ultraviolet and mass spectrometric detection. | 2004 |
|
| Development of a protocol for cryopreservation of hepatocytes for use in bioartificial liver systems. | 2004 |
|
| Pharmacokinetics of lidocaine delivered from a transmucosal patch in children. | 2002 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:51:02 GMT 2025
by
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on
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| Record UNII |
D8Q99HC770
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Validated (UNII)
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PARENT -> IMPURITY |
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