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 |
|---|---|---|
| Assessment of hepatic function in cystic fibrosis by lidocaine metabolism. | 2001 Apr |
|
| Long-term follow up of chronic hepatitis C patients after alpha-interferon treatment: a functional study. | 2001 Apr |
|
| The MEGX test: a tool for the real-time assessment of hepatic function. | 2001 Apr |
|
| Impairment of cytochrome P-450-dependent liver activity in cirrhotic patients with Helicobacter pylori infection. | 2001 Dec |
|
| Could local anesthesia while breast-feeding be harmful to infants? | 2001 Feb |
|
| A preliminary evaluation of the discriminative power of the monoethylglycinexylidide formation test after intravenous and oral administration of lidocaine. | 2001 Jun |
|
| The effects of norepinephrine and prostaglandin E1 on pharmacokinetics of lidocaine in isolated perfused rat liver. | 2001 Mar 23 |
|
| Influence of prophylactic use of pentoxifylline on postoperative organ function in elderly cardiac surgery patients. | 2001 May |
|
| Epinephrine does not reduce the plasma concentration of lidocaine during continuous epidural infusion in children. | 2002 Aug-Sep |
|
| Correlation between midazolam and lignocaine pharmacokinetics and MEGX formation in healthy volunteers. | 2002 Feb |
|
| Lidocaine elimination in patients with liver cirrhosis. | 2002 Jul-Aug |
|
| Monitoring of liver metabolic function during interferon-alpha therapy and its relationship to treatment outcome in chronic hepatitis C patients. | 2002 May-Jun |
|
| Pharmacokinetics of lidocaine delivered from a transmucosal patch in children. | 2002 Summer |
|
| Effect of the CYP3A4 inhibitor erythromycin on the pharmacokinetics of lignocaine and its pharmacologically active metabolites in subjects with normal and impaired liver function. | 2003 Jan |
|
| Validity and clinical utility of the aspartate aminotransferase-alanine aminotransferase ratio in assessing disease severity and prognosis in patients with hepatitis C virus-related chronic liver disease. | 2003 Jan 27 |
|
| N-acetylcysteine decreases lactate signal intensities in liver tissue and improves liver function in septic shock patients, as shown by magnetic resonance spectroscopy: extended case report. | 2004 Apr |
|
| Splanchnic oxygen transport, hepatic function and gastrointestinal barrier after normothermic cardiopulmonary bypass. | 2004 Jul |
|
| 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 Jun 5 |
|
| Effect of itraconazole on the pharmacokinetics of inhaled lidocaine. | 2004 Sep |
|
| Development of a protocol for cryopreservation of hepatocytes for use in bioartificial liver systems. | 2004 Spring |
|
| Double-compartment cell culture apparatus: construction and biochemical evaluation for bioartificial liver support. | 2006 |
|
| Effect of fluvoxamine and erythromycin on the pharmacokinetics of oral lidocaine. | 2006 Aug |
|
| Lidocaine metabolism in isolated perfused liver from streptozotocin-induced diabetic rats. | 2006 Aug |
|
| Differential effect of chronic renal failure on the pharmacokinetics of lidocaine in patients receiving and not receiving hemodialysis. | 2006 Dec |
|
| Splanchnic organ injury during coronary surgery with or without cardiopulmonary bypass: a randomized, controlled trial. | 2006 Jan |
|
| Prognostic value of quantitative liver function tests in viral cirrhosis: a prospective study. | 2006 Jul |
|
| Safety of occluded 4% liposomal lidocaine cream. | 2006 Jul-Aug |
|
| [Evaluation of the liver reserve using lidocaine test on experimental liver injuries in rats]. | 2006 Jun |
|
| 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 Jun 1 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 17:43:56 GMT 2023
by
admin
on
Fri Dec 15 17:43:56 GMT 2023
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| Record UNII |
D8Q99HC770
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| Record Status |
Validated (UNII)
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100000127440
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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BINDER->LIGAND |
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| Related Record | Type | Details | ||
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PARENT -> METABOLITE LESS ACTIVE | |||
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PARENT -> METABOLITE ACTIVE |
MAJOR
PLASMA
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PARENT -> IMPURITY |
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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