Page last updated: 2024-11-06

glycinexylidide

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

glycinexylidide: dealkylated metabolite of lidocaine; structure; RN given refers to parent cpd with dimethylphenyl moiety in positions 2,6 [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

glycinexylidide : A amino acid amide with 2,6-dimethylaniline and glycine components; an active metabolite of lidocaine, formed by oxidative deethylation. Used as an indicator of hepatic function. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

FloraRankFlora DefinitionFamilyFamily Definition
GlycinegenusA non-essential amino acid. It is found primarily in gelatin and silk fibroin and used therapeutically as a nutrient. It is also a fast inhibitory neurotransmitter.[MeSH]FabaceaeThe large family of plants characterized by pods. Some are edible and some cause LATHYRISM or FAVISM and other forms of poisoning. Other species yield useful materials like gums from ACACIA and various LECTINS like PHYTOHEMAGGLUTININS from PHASEOLUS. Many of them harbor NITROGEN FIXATION bacteria on their roots. Many but not all species of beans belong to this family.[MeSH]

Cross-References

ID SourceID
PubMed CID87833
CHEMBL ID1302
CHEBI ID357241
SCHEMBL ID4107220
MeSH IDM0041427

Synonyms (40)

Synonym
glycinexylidide hcl
glycinexylidide
18865-38-8
gx
CHEMBL1302
AKOS000118700
FT-0669041
2-amino-2',6'-dimethylacetoanilide
n-(2,6-dimethylphenyl)glycinamide
glycylxylidide
2-amino-n-(2,6-dimethyl-phenyl)-acetamide
2-amino-2',6'-acetoxylidide
glycine xylidide
n-(2,6-dimethylphenyl)-2-aminoacetamide
chebi:357241 ,
2-amino-n-(2,6-dimethylphenyl)acetamide
NCGC00246165-01
unii-d2d932w316
d2d932w316 ,
glycinexylidine
S12050
n-glycyl-2,6-xylidine
2-amino-2',6'-dimethylacetanilide
glycyl xylidide
SCHEMBL4107220
2-aminoacetamide, n-(2',6'-dimethylphenyl)-
glycinhexylidide
acetamide, 2-amino-n-(2,6-dimethylphenyl)-
2-amino-n-(2,6-dimethylphenyl)acetamide #
w-49167
astra-6204
.omega.-amino-2,6-dimethylacetanilide
glycinexylidide (2-amino-n-(2,6-dimethylphenyl)acetamide)
FT-0669042
DTXSID40876064
mfcd05267700
EN300-35449
STL186184
Q27225735
G0579

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
"3 ml/min/kg), terminal half-life (148 min), and total volume of distribution (1."( Pharmacokinetics and metabolism of lidocaine in patients with renal failure.
Atkinson, AJ; Collinsworth, KA; Harrison, DC; Perlroth, F; Strong, JM; Winkle, RA, 1975
)
0.25
" 4-compartment model was introduced to analyze pharmacokinetic parameters, and which gave the most reasonable fit with actual results."( [Pharmacokinetics of lidocaine and its metabolites in dog. Comparison between normal and CCl4-induced hepatic lesion].
Yamane, J, 1989
)
0.28
"The pharmacokinetic parameters of lidocaine are pertinent to the determination of both appropriate loading doses and constant infusion rates that achieve a therapeutic plasma concentration while avoiding toxicity."( Pharmacokinetic principles of lidocaine dosing in relation to disease state.
Waller, ES, 1981
)
0.26
"001), and half-life was approximately doubled (4."( Differential effect of chronic renal failure on the pharmacokinetics of lidocaine in patients receiving and not receiving hemodialysis.
Bertoli, M; De Martin, S; Orlando, R; Palatini, P; Pegoraro, P, 2006
)
0.33
" The hypothesis was that the elimination clearance of lidocaine and its metabolites, monoethylglycinexylidide and glycinexylidide, is reduced after a partial hepatectomy, as reflected by observed plasma concentrations that are higher and have a longer half-life than expected based on pharmacokinetic modeling (estimated for normal liver function)."( Lidocaine Intraoperative Infusion Pharmacokinetics during Partial Hepatectomy for Living Liver Donation.
Christians, U; Crouch, CE; Fernandez-Bustamante, A; Hendrickse, A; Henthorn, TK; Kaizer, AM; Schniedewind, B; Wilkey, BJ, 2023
)
1.13
" Pharmacokinetic modeling revealed that the only significant covariate in the model was the fraction of liver remaining after isolation of the donor graft."( Lidocaine Intraoperative Infusion Pharmacokinetics during Partial Hepatectomy for Living Liver Donation.
Christians, U; Crouch, CE; Fernandez-Bustamante, A; Hendrickse, A; Henthorn, TK; Kaizer, AM; Schniedewind, B; Wilkey, BJ, 2023
)
0.91
" Lidocaine and metabolite concentrations were determined by liquid chromatography- mass spectrometry and pharmacokinetic (non-compartmental and compartmental) analysis was performed."( Pharmacokinetics and metabolism of lidocaine HCl 2% with epinephrine in horses following a palmar digital nerve block.
Arthur, RM; Blea, J; Katzman, S; Knych, HK; McKemie, DS, 2023
)
0.91
"Compared to previous reports, the terminal half-life and subsequent detection time observed following administration of lidocaine in combination with epinephrine is prolonged."( Pharmacokinetics and metabolism of lidocaine HCl 2% with epinephrine in horses following a palmar digital nerve block.
Arthur, RM; Blea, J; Katzman, S; Knych, HK; McKemie, DS, 2023
)
0.91

Dosage Studied

ExcerptRelevanceReference
" A computer-aided simulation generated from using the mean kinetic data in a 50-kg woman predicted that plasma lidocaine concentration would reach the postulated toxic range (approximately equal to 6 microgram/ml) after the fourth supplementary dose under a similar dosing scheme as performed in this study."( Plasma concentrations of lidocaine and its principal metabolites during intermittent epidural anesthesia.
Echizen, H; Inoue, R; Ishizaki, T; Kushida, K; Suganuma, T; Tomono, Y, 1985
)
0.27
" Lidoncaine, 5 x 10(-4) M, and MEGX, 2 x 10(-3) M, shifted the dose-response curve of NE to the right, whereas GX, 5 x 10(-4) M, shifted the curve to the left."( Modifications by lidocaine and its N-dealkylated metabolites of the response of the isolated rabbit aorta to transmural electrical stimulation.
Fukuda, S; Takeshita, H; Toda, N, 1980
)
0.26
" Decreased hepatic metabolism after resection raises concerns about safe lidocaine dosing in this patient population."( Lidocaine Intraoperative Infusion Pharmacokinetics during Partial Hepatectomy for Living Liver Donation.
Christians, U; Crouch, CE; Fernandez-Bustamante, A; Hendrickse, A; Henthorn, TK; Kaizer, AM; Schniedewind, B; Wilkey, BJ, 2023
)
0.91
" Clearance of lidocaine is decreased proportionally to the remaining liver mass, which should guide lidocaine infusion administration or dosing adjustments for patients undergoing liver resection surgery."( Lidocaine Intraoperative Infusion Pharmacokinetics during Partial Hepatectomy for Living Liver Donation.
Christians, U; Crouch, CE; Fernandez-Bustamante, A; Hendrickse, A; Henthorn, TK; Kaizer, AM; Schniedewind, B; Wilkey, BJ, 2023
)
0.91
" Clearance of lidocaine is decreased proportionally to the remaining liver mass, which should guide lidocaine infusion administration or dosing adjustments for patients undergoing liver resection surgery."( Lidocaine Intraoperative Infusion Pharmacokinetics during Partial Hepatectomy for Living Liver Donation.
Christians, U; Crouch, CE; Fernandez-Bustamante, A; Hendrickse, A; Henthorn, TK; Kaizer, AM; Schniedewind, B; Wilkey, BJ, 2023
)
0.91
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
drug metabolitenull
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
amino acid amideAn amide of an amino acid formed formally by conversion of the carboxy group to a carboxamido group.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (5)

PathwayProteinsCompounds
Lidocaine (Antiarrhythmic) Action Pathway4922
Lidocaine (Local Anaesthetic) Action Pathway3325
Lidocaine (Local Anaesthetic) Metabolism Pathway416
Lidocaine Pathway, Pharmacokinetics75
Lidocaine metabolism08

Bioassays (17)

Assay IDTitleYearJournalArticle
AID114641Compound was evaluated for ataxia in mice1981Journal of medicinal chemistry, Jul, Volume: 24, Issue:7
New antiarrhythmic agents. 6. Quantitative structure-activity relationships of aminoxylidides.
AID114662Compound was evaluated for protection against tachycardia in mice1981Journal of medicinal chemistry, Jul, Volume: 24, Issue:7
New antiarrhythmic agents. 6. Quantitative structure-activity relationships of aminoxylidides.
AID1130811Toxicity in Swiss albino mouse assessed as convulsion at 100 mg/kg, sc measured up to 20 mins1979Journal of medicinal chemistry, Oct, Volume: 22, Issue:10
New antiarrhythmic agents. 2. Amide alkyl alpha-amino xylidides.
AID1130815Ratio of lidocaine ED50 to compound ED50 for antiarrhythmic activity sc dosed Swiss albino mouse assessed as protection against chloroform-induced ventricular fibrillation1979Journal of medicinal chemistry, Oct, Volume: 22, Issue:10
New antiarrhythmic agents. 2. Amide alkyl alpha-amino xylidides.
AID1130809Antiarrhythmic activity in Swiss albino mouse assessed as protection against chloroform-induced fibrillation at 100 mg/kg, sc treated 20 mins before chloroform challenge1979Journal of medicinal chemistry, Oct, Volume: 22, Issue:10
New antiarrhythmic agents. 2. Amide alkyl alpha-amino xylidides.
AID1130810Toxicity in Swiss albino mouse assessed as ataxia at 100 mg/kg, sc measured up to 20 mins1979Journal of medicinal chemistry, Oct, Volume: 22, Issue:10
New antiarrhythmic agents. 2. Amide alkyl alpha-amino xylidides.
AID23097Compound was evaluated for -Log [fraction ionized x ED50 (protection)]1981Journal of medicinal chemistry, Jul, Volume: 24, Issue:7
New antiarrhythmic agents. 6. Quantitative structure-activity relationships of aminoxylidides.
AID128839Antiarrhythmic activity against arrhythmogenic effects of chloroform in mice after sc administration1981Journal of medicinal chemistry, Jan, Volume: 24, Issue:1
New antiarrhythmic agents. 5. alpha-Aminoaceto-2,6-xylidides with functionalized amide alkyl substituents.
AID25320Dissociation constant (pKa)1981Journal of medicinal chemistry, Jul, Volume: 24, Issue:7
New antiarrhythmic agents. 6. Quantitative structure-activity relationships of aminoxylidides.
AID235615Therapeutic index is defined as the ratio of ED50(ataxia)/ED50(protection)1981Journal of medicinal chemistry, Jan, Volume: 24, Issue:1
New antiarrhythmic agents. 5. alpha-Aminoaceto-2,6-xylidides with functionalized amide alkyl substituents.
AID781327pKa (acid-base dissociation constant) as determined by Morgenthaler ref: ChemMedChem 20072014Pharmaceutical research, Apr, Volume: 31, Issue:4
Comparison of the accuracy of experimental and predicted pKa values of basic and acidic compounds.
AID1130814Antiarrhythmic activity in sc dosed Swiss albino mouse assessed as protection against chloroform-induced ventricular fibrillation1979Journal of medicinal chemistry, Oct, Volume: 22, Issue:10
New antiarrhythmic agents. 2. Amide alkyl alpha-amino xylidides.
AID128299Acute CNS toxicity against arrhythmogenic effects of chloroform in mice after sc administration1981Journal of medicinal chemistry, Jan, Volume: 24, Issue:1
New antiarrhythmic agents. 5. alpha-Aminoaceto-2,6-xylidides with functionalized amide alkyl substituents.
AID1130812Toxicity in Swiss albino mouse assessed as loss of righting reflex at 100 mg/kg, sc measured up to 20 mins1979Journal of medicinal chemistry, Oct, Volume: 22, Issue:10
New antiarrhythmic agents. 2. Amide alkyl alpha-amino xylidides.
AID23494Partition coefficient (logP)1981Journal of medicinal chemistry, Jul, Volume: 24, Issue:7
New antiarrhythmic agents. 6. Quantitative structure-activity relationships of aminoxylidides.
AID1130813Toxicity in Swiss albino mouse assessed as death at 100 mg/kg, sc measured up to 20 mins1979Journal of medicinal chemistry, Oct, Volume: 22, Issue:10
New antiarrhythmic agents. 2. Amide alkyl alpha-amino xylidides.
AID235211Therapeutic index is the ratio of ED50 (ataxia) to ED50 (protection) in mice1981Journal of medicinal chemistry, Jul, Volume: 24, Issue:7
New antiarrhythmic agents. 6. Quantitative structure-activity relationships of aminoxylidides.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (59)

TimeframeStudies, This Drug (%)All Drugs %
pre-199036 (61.02)18.7374
1990's11 (18.64)18.2507
2000's6 (10.17)29.6817
2010's4 (6.78)24.3611
2020's2 (3.39)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 21.83

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index21.83 (24.57)
Research Supply Index4.22 (2.92)
Research Growth Index4.40 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (21.83)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials6 (9.84%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other55 (90.16%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]