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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
Structure of NORLIDOCAINE

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)

HIDE SMILES / InChI

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

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Pharmacokinetics of lidocaine delivered from a transmucosal patch in children.
2002 Summer
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
Pharmacokinetics and safety of lidocaine and monoethylglycinexylidide in liposuction: a microdialysis study.
2004 Aug
Splanchnic oxygen transport, hepatic function and gastrointestinal barrier after normothermic cardiopulmonary bypass.
2004 Jul
Clinical review: influence of vasoactive and other therapies on intestinal and hepatic circulations in patients with septic shock.
2004 Jun
Use of lidocaine metabolism to test liver function during the long-term follow-up of liver transplant recipients.
2004 Jun
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 lidocaine on the minimum alveolar concentration of isoflurane in dogs.
2004 Oct
Pharmacokinetics and transplacental transfer of lidocaine and its metabolite for perineal analgesic assistance to pregnant women.
2004 Oct
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
Assessment of hepatic reserve for indication of hepatic resection: how I do it.
2005
Assessment of the hemodynamic effects of lidocaine administered IV in isoflurane-anesthetized cats.
2005 Apr
A study of the in vitro interaction between lidocaine and premedications using human liver microsomes.
2005 Apr
Monoethylglycinexylidide and lidocaine determination in porcine microsomal preparations.
2005 Apr 1
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 Apr 6
Pharmacokinetics of lidocaine and its active metabolite, monoethylglycinexylidide, after intravenous administration of lidocaine to awake and isoflurane-anesthetized cats.
2005 Jul
Blockade of spinal nitric oxide synthase on blood pressure variability and hepatic microcirculation.
2005 Jun
The effect of mild and moderate hepatic impairment on the pharmacokinetics of valdecoxib, a selective COX-2 inhibitor.
2005 Jun
The effect of erythromycin and fluvoxamine on the pharmacokinetics of intravenous lidocaine.
2005 May
Effect of ciprofloxin on the pharmacokinetics of intravenous lidocaine.
2005 Oct
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 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
Pharmacokinetics of tilidine and naloxone in patients with severe hepatic impairment.
2007
[Liver function test to predict hepatic failure after liver resection--expensive and without clinical relevance?].
2007 Aug
Monoethylglycinexylidide (MEGX) as a liver function test in cirrhosis.
2007 Jul-Aug
Prognostic value of the monoethylglycinexylidide test in alcoholic cirrhosis.
2007 Jul-Sep
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
Measuring hepatic functional reserve using MEGX: still a mirage!
2007 Sep-Oct
Pharmacokinetics of lidocaine following the application of 5% lidocaine patches to cats.
2008 Aug
Pharmacokinetics of lidocaine and its metabolite in peridural anesthesia administered to pregnant women with gestational diabetes mellitus.
2008 Dec
Serum concentrations of lidocaine and its metabolites after prolonged infusion in healthy horses.
2008 Jun
Reporting a fatality during tumescent liposuction.
2008 Jun 10
Prognostic value of the monoethylglycinexylidide (MEGX)-test prior to liver resection.
2008 Mar-Apr
[Determination of monoethylglycinexylidide concentration in serum using solid phase extraction and capillary gas chromatography-mass spectrometry].
2008 May
Cutaneous in vivo metabolism of topical lidocaine formulation in human skin.
2009
Efficacy of lidocaine for pain control in subcutaneous infiltration during liposuction.
2009 Mar-Apr
Evaluation of quantitative liver function tests in HIV-positive patients under anti-retroviral therapy.
2009 Sep 1
[Determination of lidocaine and its metabolites in human plasma by liquid chromatography in combination with tandem mass spectrometry].
2010 Jul
Lidocaine/monoethylglycinexylidide test, galactose elimination test, and sorbitol elimination test for metabolic assessment of liver cell bioreactors.
2010 Jun
Is dopexamine superior to dopamine in the treatment of multiple trauma patients--a prospective, double-blind, randomised study.
2010 May
Effect of 4% topical lidocaine applied to the face on the serum levels of lidocaine and its metabolite, monoethylglycinexylidide.
2010 Nov-Dec
Biophysical characterization of recombinant proteins: a key to higher structural genomics success.
2010 Oct
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
XYL was identified by GC/MS as a major metabolite in human liver slices from five individual donors after incubation with either LIDO (100 uM) or its deethylated metabolite, monoethylglycinexylidide (MEGX; 100 uM).
Substance Class Chemical
Created
by admin
on Thu Jul 06 01:01:44 UTC 2023
Edited
by admin
on Thu Jul 06 01:01:44 UTC 2023
Record UNII
D8Q99HC770
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NORLIDOCAINE
Common Name English
MONOETHYLGLYCYLXYLIDIDE
Common Name English
LIDOCAINE HYDROCHLORIDE IMPURITY D [EP IMPURITY]
Common Name English
ACETAMIDE, N-(2,6-DIMETHYLPHENYL)-2-(ETHYLAMINO)-
Systematic Name English
LIDOCAINE IMPURITY D [EP IMPURITY]
Common Name English
N-(2,6-DIMETHYLPHENYL)-2-(ETHYLAMINO)ACETAMIDE
Systematic Name English
MONOETHYLGLYCINEXYLIDIDE
Common Name English
N-(N-ETHYLGLYCYL)-2,6-XYLIDINE
Systematic Name English
2-(ETHYLAMINO)-2',6'-ACETOXYLIDIDE
Common Name English
MEGX
Common Name English
L-86
Code English
N-ETHYLGLYCINEXYLIDIDE
Common Name English
Code System Code Type Description
EVMPD
SUB33486
Created by admin on Thu Jul 06 01:01:44 UTC 2023 , Edited by admin on Thu Jul 06 01:01:44 UTC 2023
PRIMARY
CAS
7728-40-7
Created by admin on Thu Jul 06 01:01:44 UTC 2023 , Edited by admin on Thu Jul 06 01:01:44 UTC 2023
PRIMARY
EPA CompTox
DTXSID60228006
Created by admin on Thu Jul 06 01:01:44 UTC 2023 , Edited by admin on Thu Jul 06 01:01:44 UTC 2023
PRIMARY
MESH
C001173
Created by admin on Thu Jul 06 01:01:44 UTC 2023 , Edited by admin on Thu Jul 06 01:01:44 UTC 2023
PRIMARY
SMS_ID
100000127440
Created by admin on Thu Jul 06 01:01:44 UTC 2023 , Edited by admin on Thu Jul 06 01:01:44 UTC 2023
PRIMARY
CHEBI
55524
Created by admin on Thu Jul 06 01:01:44 UTC 2023 , Edited by admin on Thu Jul 06 01:01:44 UTC 2023
PRIMARY
PUBCHEM
24415
Created by admin on Thu Jul 06 01:01:44 UTC 2023 , Edited by admin on Thu Jul 06 01:01:44 UTC 2023
PRIMARY
FDA UNII
D8Q99HC770
Created by admin on Thu Jul 06 01:01:44 UTC 2023 , Edited by admin on Thu Jul 06 01:01:44 UTC 2023
PRIMARY
CHEBI
222828
Created by admin on Thu Jul 06 01:01:44 UTC 2023 , Edited by admin on Thu Jul 06 01:01:44 UTC 2023
PRIMARY
Related Record Type Details
BINDER->LIGAND
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PARENT -> METABOLITE ACTIVE
MAJOR
PLASMA
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PARENT -> IMPURITY
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
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PARENT -> IMPURITY
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CHROMATOGRAPHIC PURITY (HPLC/UV)
EP