Page last updated: 2024-11-06

glycidamide

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

Description

Glycidamide is an epoxide derivative of acrylamide, a compound found in various processed foods and industrial products. It is formed by the reaction of acrylamide with an oxidizing agent. Glycidamide has been identified as a potential human carcinogen, particularly associated with increased risks of endometrial, ovarian, and breast cancers. Its mutagenic potential and ability to form DNA adducts have also been established. Studies on glycidamide focus on its potential health effects, including carcinogenicity and genotoxicity, as well as its formation mechanisms and occurrence in various food products. Understanding the mechanisms of glycidamide formation and its potential risks for human health is crucial for developing strategies to minimize exposure and mitigate the associated health hazards.'

glycidamide: metabolite of acrylamide; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID91550
CHEMBL ID3560005
MeSH IDM0194910

Synonyms (34)

Synonym
brn 1280744
oxiranecarboxamide
ccris 2677
glycidic acid amide
LS-1386 ,
einecs 227-163-2
5694-00-8
oxirane-2-carboxamide
glycidamide
2,3-epoxypropanamide
2-oxiranecarboxamide
AKOS000175961
FT-0669029
hsdb 7804
unii-6g5elx5xyn
5-18-06-00003 (beilstein handbook reference)
6g5elx5xyn ,
FT-0624332
glycamide-
(+/-)-oxiranecarboxamide
glycidamide [hsdb]
FMAZQSYXRGRESX-UHFFFAOYSA-N
AKOS016843442
dtxsid2031374 ,
cas-5694-00-8
dtxcid0011374
NCGC00357136-01
tox21_303874
CHEMBL3560005
glycidamide, analytical standard
Q1532444
hsdb-7804
ls1386
hsdb7804

Research Excerpts

Overview

Glycidamide (GA) is a mutagenic epoxide metabolite of acrylamide (AM), a high production chemical with many industrial uses. Its cytotoxicity is stronger than ACR.

ExcerptReferenceRelevance
"Glycidamide (GA) is an important epoxide metabolite of ACR, and its cytotoxicity is stronger than ACR."( Dynamic assessment of the relationship between oxidative stress and apoptotic pathway in embryonic fibroblast cells exposed to glycidamide: possible protective role of hesperidin.
Aydin, Y; Orta Yilmaz, B, 2023
)
1.84
"Glycidamide (GA) is a mutagenic epoxide metabolite of acrylamide (AM), a high production chemical with many industrial uses. "( Characterization of the adducts formed in the reactions of glycidamide with thymidine and cytidine.
Backman, J; Kronberg, L; Sjöholm, R, 2004
)
2.01
"Glycidamide (GA) is an epoxide metabolite of acrylamide (AA). "( [A study on neurotoxicity of acrylamide and glycidamide].
Deng, H; He, F; Jiao, X, 1997
)
2

Effects

ExcerptReferenceRelevance
"Glycidamide has a close relationship to the toxic mechanism of acrylamide."( Protective effect of allicin against glycidamide-induced toxicity in male and female mice.
Chen, DY; Liu, HY; Wang, ET; Yan, HY; Yuan, Y, 2015
)
1.41
"Glycidamide has a close relationship to the toxic mechanism of acrylamide."( Protective effect of allicin against glycidamide-induced toxicity in male and female mice.
Chen, DY; Liu, HY; Wang, ET; Yan, HY; Yuan, Y, 2015
)
1.41

Treatment

ExcerptReferenceRelevance
"Glycidamide treatment dose-dependently increased the frequency of cII mutations relative to control treatment (P<.001)."( Genotoxicity of acrylamide and glycidamide.
Besaratinia, A; Pfeifer, GP, 2004
)
1.33

Toxicity

ExcerptReferenceRelevance
" The principal toxic effect of acrylamide, both in animals and in humans, is neurotoxicity."( Evaluation of the neurotoxicity of glycidamide, an epoxide metabolite of acrylamide: behavioral, neurochemical and morphological studies.
Bergmark, E; Calleman, CJ; Costa, LG; Deng, H, 1995
)
0.57
" Results showed that toxic effects of AA were greater than those of GA in wheel rotation test, hind limb splay test, and activities of glyceraldehyde-3-phosphate dehydrogenase (GAPDH) in peripheral nerves in rats."( [A study on neurotoxicity of acrylamide and glycidamide].
Deng, H; He, F; Jiao, X, 1997
)
0.56
" The data suggest that CYP2E1 played a major role in metabolizing AA to more toxic GA."( Metabolism of acrylamide to glycidamide and their cytotoxicity in isolated rat hepatocytes: protective effects of GSH precursors.
Kurebayashi, H; Ohno, Y, 2006
)
0.63
" Glycidamide has a close relationship to the toxic mechanism of acrylamide."( Protective effect of allicin against glycidamide-induced toxicity in male and female mice.
Chen, DY; Liu, HY; Wang, ET; Yan, HY; Yuan, Y, 2015
)
1.6

Pharmacokinetics

A pharmacokinetic (PBPK) model has been developed for acrylamide (AMD) and its oxidative metabolite, glycidamide (GLY), in the rat based on available information.

ExcerptReferenceRelevance
" In an effort to improve risk-based decisions for acrylamide (AMD) and its epoxide metabolite, glycidamide (GLY), a physiologically based pharmacokinetic (PBPK) model was developed for describing AMD and GLY kinetics in the rat."( A physiologically based pharmacokinetic model for acrylamide and its metabolite, glycidamide, in the rat.
Andersen, ME; Deskin, R; Gargas, ML; Kirman, CR; Tonner-Navarro, L, 2003
)
0.76
"A pharmacokinetic (PBPK) model has been developed for acrylamide (AMD) and its oxidative metabolite, glycidamide (GLY), in the rat based on available information."( Kinetic and mechanistic data needs for a human phsiologically based pharmacokinetic (PBPK) model for acrylamide: pharmacokinetic model for acrylamide.
Andersen, ME; Olin, SS; Scimeca, J, 2005
)
0.54
"A physiologically based pharmacokinetic model was developed for acrylamide (AA) and three of its metabolites: glycidamide (GA) and the glutathione conjugates of acrylamide (AA-GS) and glycidamide (GA-GS)."( Physiologically based pharmacokinetic/pharmacodynamic model for acrylamide and its metabolites in mice, rats, and humans.
Doerge, DR; Luecke, RH; Young, JF, 2007
)
0.55
" The developed method was successfully applied to a pharmacokinetic study of AA and GA following intravenous and oral administration of AA in rats."( Determination of acrylamide and glycidamide in various biological matrices by liquid chromatography-tandem mass spectrometry and its application to a pharmacokinetic study.
Choi, JH; Jeong, SW; Joo, SH; Kim, KB; Kim, TH; Seo, WS; Shin, BS; Shin, JC; Shin, S; Weon, KY, 2015
)
0.7

Bioavailability

ExcerptReferenceRelevance
" While oral administration was found to attenuate AA bioavailability to 23% from the diet and to 32-52% from aqueous gavage, a first-pass effect or other kinetic change resulted in higher relative internal exposure to GA when compared to the intravenous route."( Toxicokinetics of acrylamide and glycidamide in B6C3F1 mice.
Churchwell, MI; Doerge, DR; McDaniel, LP; Twaddle, NC; Young, JF, 2005
)
0.61
" AA bioavailability after aqueous gavage was 60--98% and from the diet was 32--44%; however, first-pass metabolism or other kinetic change resulted in much higher internal exposures to GA (2- to 7-fold) when compared to the intravenous route."( Toxicokinetics of acrylamide and glycidamide in Fischer 344 rats.
Churchwell, MI; Doerge, DR; McDaniel, LP; Twaddle, NC; Young, JF, 2005
)
0.61
" Our previous toxicokinetic investigations of AA and its important genotoxic metabolite, glycidamide (GA), in rodents showed that AA is highly bioavailable from oral routes of administration, is widely distributed to tissues and that the dietary route, in particular, favors metabolism to GA."( Relationships between biomarkers of exposure and toxicokinetics in Fischer 344 rats and B6C3F1 mice administered single doses of acrylamide and glycidamide and multiple doses of acrylamide.
Churchwell, MI; Doerge, DR; McDaniel, LP; Tareke, E; Twaddle, NC; Young, JF, 2006
)
0.76
" We studied whether the food matrix modulates bioavailability and/or biotransformation and investigated kinetics and biological effectiveness of AA in rats."( Biological effects of acrylamide after daily ingestion of various foods in comparison to water: a study in rats.
Baum, M; Berger, FI; Bertow, D; Eisenbrand, G; Feld, J; Fricker, G; Gerhardt, N; Merz, KH; Richling, E, 2011
)
0.37
" Altogether, no significant differences in bioavailability of AA from water and the different food matrices were observed."( Biological effects of acrylamide after daily ingestion of various foods in comparison to water: a study in rats.
Baum, M; Berger, FI; Bertow, D; Eisenbrand, G; Feld, J; Fricker, G; Gerhardt, N; Merz, KH; Richling, E, 2011
)
0.37

Dosage Studied

Dosing mice and rats with AA (50 mg/kg) led to presence of glycidamide (GA) in serum and tissues.

ExcerptRelevanceReference
" Dosing of AMD via the intravenous, intraperitoneal, or oral route of exposure is incorporated into the model structure."( A physiologically based pharmacokinetic model for acrylamide and its metabolite, glycidamide, in the rat.
Andersen, ME; Deskin, R; Gargas, ML; Kirman, CR; Tonner-Navarro, L, 2003
)
0.55
" In the rat no positive dose-response relationship was obtained, probably due to toxic effects to the bone marrow."( Induction of micronuclei in mouse and rat by glycidamide, genotoxic metabolite of acrylamide.
Golding, B; Granath, F; Grawé, J; Henderson, A; Kotova, N; Paulsson, B; Törnqvist, M, 2003
)
0.58
" Adduct levels were modestly higher in adult mice dosed with GA as opposed to AA; however, treatment of neonatal mice with GA produced 5-7-fold higher whole body DNA adduct levels than with AA, presumably reflective of lower oxidative enzyme activity in newborn mice."( DNA adduct formation from acrylamide via conversion to glycidamide in adult and neonatal mice.
Beland, FA; Churchwell, MI; Doerge, DR; Gamboa da Costa, G; Hamilton, LP; Marques, MM; Von Tungeln, LS, 2003
)
0.57
" Dosing mice and rats with AA (50 mg/kg) led to presence of glycidamide (GA) in serum and tissues."( DNA adducts derived from administration of acrylamide and glycidamide to mice and rats.
Beland, FA; Churchwell, MI; Doerge, DR; Gamboa da Costa, G; McDaniel, LP; Twaddle, NC, 2005
)
0.81
" Furthermore, our results might indicate that the dose-response curve for acrylamide is not linear."( Determination of haemoglobin adducts of acrylamide and glycidamide in smoking and non-smoking persons of the general population.
Angerer, J; Drexler, H; Kütting, B; Letzel, S; Rossbach, B; Schettgen, T, 2004
)
0.57
" Urine samples before dosing and within 46 h after the dose were analysed for d(3)-AAMA and d(3)-GAMA by LC-ESI-MS/MS."( Excretion of mercapturic acids of acrylamide and glycidamide in human urine after single oral administration of deuterium-labelled acrylamide.
Angerer, J; Boettcher, MI; Bolt, HM; Drexler, H, 2006
)
0.59
" The goal was to investigate possible relationships between these circulating biomarkers of exposure and serum toxicokinetic parameters for AA and GA and tissue GA-DNA adducts in rodents from both single and repeated dosing with AA."( Relationships between biomarkers of exposure and toxicokinetics in Fischer 344 rats and B6C3F1 mice administered single doses of acrylamide and glycidamide and multiple doses of acrylamide.
Churchwell, MI; Doerge, DR; McDaniel, LP; Tareke, E; Twaddle, NC; Young, JF, 2006
)
0.53
" A linear dose-response relationship was observed between the GA concentration and the levels of N7-GA-Gua."( Cytogenetic damage induced by acrylamide and glycidamide in mammalian cells: correlation with specific glycidamide-DNA adducts.
Beland, FA; Churchwell, MI; Doerge, DR; Gamboa da Costa, G; Gaspar, JF; Marques, MM; Martins, C; Martins, V; Oliveira, NG; Pingarilho, M; Rueff, J, 2007
)
0.6
" This study evaluated the low-dose MN response in mouse bone marrow and the shape of the dose-response curve."( Investigation of the low-dose response in the in vivo induction of micronuclei and adducts by acrylamide.
Fennell, TR; Friedman, M; Haseman, JK; Recio, L; Snyder, RW; Zeiger, E, 2009
)
0.35
" Based on modes of action (MoA), a nonlinear dose-response approach was applied for neurotoxicity (non-genotoxicity) and carcinogenicity (mixed: genotoxicity and epigenetic MoA)."( Estimation of safe dietary intake levels of acrylamide for humans.
Carson, ML; Gargas, ML; Kirman, CR; Sweeney, LM; Tardiff, RG, 2010
)
0.36
" In all rats, serum AA and GA levels exhibited a dose-response relationship."( Preweaning behaviors, developmental landmarks, and acrylamide and glycidamide levels after pre- and postnatal acrylamide treatment in rats.
Doerge, DR; Ferguson, SA; Garey, J; Paule, MG; Smith, ME; Twaddle, NC,
)
0.37
" We performed a dose-response study with AA in female Sprague-Dawley (SD) rats."( N7-glycidamide-guanine DNA adduct formation by orally ingested acrylamide in rats: a dose-response study encompassing human diet-related exposure levels.
Baum, M; Berger, F; Böhm, N; Eisenbrand, G; Feld, J; Lampen, A; Merz, KH; Reemtsma, T; Richling, E; Scherbl, D; Skipper, PL; Tannenbaum, SR; Watzek, N, 2012
)
1
" Moreover, even at low GA levels, N7-GA-Gua adducts were generated in a linear dose-response manner in MCF10A cells."( Mechanistic insights into the cytotoxicity and genotoxicity induced by glycidamide in human mammary cells.
Bandarra, S; Batinic-Haberle, I; Beland, FA; Castro, M; Churchwell, MI; Fernandes, AS; Gaspar, JF; Gil, OM; Gonçalves, S; Guerreiro, PS; Magro, I; Marques, MM; Miranda, JP; Oliveira, NG; Pingarilho, M; Rueff, J, 2013
)
0.62
"83, respectively); however, no linear dose-response trends were observed."( Acrylamide and Glycidamide Hemoglobin Adducts and Epithelial Ovarian Cancer: A Nested Case-Control Study in Nonsmoking Postmenopausal Women from the EPIC Cohort.
Ardanaz, E; Baglietto, L; Boeing, H; Boutron-Ruault, MC; Bueno-de-Mesquita, HB; Castaño, JM; Chamosa, S; Duell, EJ; Ferrari, P; Fortner, RT; Freisling, H; Gunter, MJ; Idahl, A; Khaw, KT; Klinaki, E; Lujan-Barroso, L; Lundin, E; Mattiello, A; Menéndez, V; Merritt, MA; Obón-Santacana, M; Onland-Moret, NC; Ose, J; Papatesta, EM; Peeters, PH; Riboli, E; Sacerdote, C; Saieva, C; Sánchez-Cantalejo, E; Severi, G; Tagliabue, G; Travis, RC; Trichopoulou, A; Tumino, R; Vesper, HW; Wareham, N; Weiderpass, E, 2016
)
0.79
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Pathways (1)

PathwayProteinsCompounds
Acrylamide biotransformation and exposure biomarkers04

Protein Targets (1)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AR proteinHomo sapiens (human)Potency24.33650.000221.22318,912.5098AID1259381
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (193)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (0.52)18.7374
1990's14 (7.25)18.2507
2000's76 (39.38)29.6817
2010's77 (39.90)24.3611
2020's25 (12.95)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 34.44

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 Index34.44 (24.57)
Research Supply Index5.29 (2.92)
Research Growth Index5.95 (4.65)
Search Engine Demand Index47.56 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (34.44)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews9 (4.57%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other188 (95.43%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]