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galactosamine

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Description

Galactosamine is a hexosamine, a derivative of galactose with an amino group at the C2 position. It is found naturally in glycoproteins and glycosaminoglycans. Galactosamine can be synthesized from galactose by enzymatic reactions involving UDP-galactose and glutamine. Studies on galactosamine focus on its role in various biological processes: It is a precursor for glycosaminoglycans, which are important components of connective tissues. Galactosamine has been studied in relation to liver damage, as it can induce hepatotoxicity through the accumulation of UDP-galactosamine. Its effects on various cell types, including immune cells, are also being investigated. Research into galactosamine aims to understand its role in various disease states and to develop therapeutic strategies involving this molecule.'

2-amino-2-deoxy-D-galactopyranose : The pyranose form of D-galactosamine. [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]

D-galactosamine : The D-stereoisomer of galactosamine. [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]

Cross-References

ID SourceID
PubMed CID24154
CHEMBL ID3304228
CHEBI ID60312
CHEBI ID24156
SCHEMBL ID28731
MeSH IDM0008936

Synonyms (33)

Synonym
galactosamine ,
d-galn
d-galactosamine
C02262
2-amino-2-deoxy-d-galactose
2-amino-2-deoxy-d-galactopyranose
CHEBI:60312 ,
(3r,4r,5r,6r)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol
GALN ,
90-76-6
galactopyranose, 2-amino-2-deoxy-, d-
d-galactopyranose, 2-amino-2-deoxy-
CHEMBL3304228
SCHEMBL28731
d-galactosamine hcl
MSWZFWKMSRAUBD-GASJEMHNSA-N
galnh2
2-deoxy-2-amino-d-galactopyranose
2-deoxy-2-amino-galactose
2-deoxy-2-amino-d-galactopyranoside
2-deoxy-2-amino-galactopyranoside
2-deoxy-2-amino-d-galactose
2-deoxy-2-amino-galactopyranose
2-amino-2-deoxy-d-galactopyranoside
2-amino-2-deoxy-galactopyranoside
2-amino-2-deoxy-galactopyranose
2-amino-2-deoxy-galactose
DTXSID7043871 ,
Q375145
(3r,4r,5r,6r)-3-amino-6-(hydroxymethyl)tetrahydro-2h-pyran-2,4,5-triol
dtxcid5023871
galactosamines
chebi:24156

Research Excerpts

Overview

D-galactosamine is a well-established hepatotoxicant that induces a diffuse type of liver injury closely resembling human viral hepatitis. D-Galactosamines induces diffuse injury of liver tissue followed by the regeneration process.

ExcerptReferenceRelevance
"d-Galactosamine (d-GalN) is a well-known toxin that causes many metabolic and morphological abnormalities resulting in advanced renal failure and liver damage. "( Amphora algae with low-level ionizing radiation exposure ameliorate D-galactosamine-induced inflammatory impairment in rat kidney.
El-Sonbaty, SM; Elbakry, MMM; Moawed, FSM, 2021
)
1.58
"d-galactosamine (d-GalN) is a well-known hepatotoxic agent that causes liver injury. "( M1/M2-macrophage Polarization-based Hepatotoxicity in d-galactosamine-induced Acute Liver Injury in Rats.
Izawa, T; Karim, MR; Kuramochi, M; Kuwamura, M; Pervin, M; Rahman, N; Yamate, J, 2018
)
1.45
"D-galactosamine is a well-established hepatotoxicant that induces a diffuse type of liver injury closely resembling human viral hepatitis. "( Influence of Piper betle on hepatic marker enzymes and tissue antioxidant status in D-galactosamine-induced hepatotoxic rats.
Pugalendi, KV; Pushpavalli, G; Veeramani, C, 2008
)
1.29
"D-galactosamine is a hepatotoxic agent, which induces diffuse injury of liver tissue followed by the regeneration process. "( Hepatotoxic effect of D-galactosamine and protective role of lipid emulsion.
Cervinková, Z; Drahota, Z; Ferencíková, R, 2003
)
1.35
"D-Galactosamine is a well-known inducer of hepatocyte apoptosis."( New apoptosis cascade mediated by lysosomal enzyme and its protection by epigallo-catechin gallate.
Hayashi, Y; Katunuma, N; Le, QT; Murata, E; Ohashi, A, 2004
)
0.88
"D-galactosamine (GalN) is a highly selective hepatotoxin that causes liver damage similar to human viral hepatitis via depletion of uridine nucleotides, which subsequently diminishes synthesis of RNA and proteins. "( The model of D-galactosamine-induced injury of rat hepatocytes in primary culture.
Cervinková, Z; Hézová, R; Kand'ár, R; Kucera, O; Lotková, H; Muzáková, V, 2006
)
1.41
"D-Galactosamine (D-GaIN) is a highly selective hepatotoxin that causes liver injury similar to human viral hepatitis via depletion of uridine nucleotides, which subsequently diminishes synthesis of RNA and proteins. "( Combination of selenium and three naturally occurring antioxidants administration protects D-galactosamine-induced liver injury in rats.
Bolkent, S; Catal, T, 2008
)
1.29
"D-Galactosamine is an amino sugar with unique hepatotoxic properties in animals. "( D-Galactosamine liver injury: absorption of endotoxin and protective effect of small bowel and colon resection in rabbits.
Camara, DS; Caruana, JA; Montes, M; Nolan, JP; Schwartz, KA, 1983
)
1.71
"D-Galactosamine is a known hepatotoxin which induces liver cell necrosis via depletion of UTP and other uridine nucleotides. "( Rat hepatocyte nodules are resistant to the necrogenic effect of D-galactosamine.
Laconi, E; Pani, P; Sarma, DS, 1992
)
1.24
"D-Galactosamine is an hepatocyte-specific inhibitor of RNA synthesis. "( The acute-phase response protects mice from D-galactosamine sensitization to endotoxin and tumor necrosis factor-alpha.
Alcorn, JM; Chojkier, M; Fierer, J, 1992
)
1.26

Effects

Galactosamine (GalN) has been known to induce liver injury by depletion of uracil nucleotides. GalN has been shown in vitro to specifically inhibit sandfly midgut lectin activity.

ExcerptReferenceRelevance
"Galactosamine, which has been shown in vitro to specifically inhibit sandfly midgut lectin activity, was fed to Phlebotomus duboscqi females with blood containing promastigotes of Leishmania major. "( Sandfly midgut lectin: effect of galactosamine on Leishmania major infections.
Kiewegová, A; Svobodová, M; Volf, P, 1998
)
2.02
"Galactosamine (GalN) has been known to induce liver injury by depletion of uracil nucleotides. "( Studies on the age-dependent effects of galactosamine in primary rat hepatocyte cultures.
Abdul-Hussain, SK; Mehendale, HM, 1991
)
1.99

Actions

ExcerptReferenceRelevance
"d-Galactosamine induced an increase in serum amino-transaminases, a reduction in the number of blood leukocytes, an enhancement in neutrophil myeloperoxidase activity, a recruitment of leukocytes toward the liver, an increase in cell death, and an alteration in prothrombin time, activated partial thromboplastin time, and fibrinogen levels."( Yogurt: effect on leukocytes and blood coagulation in an acute liver injury model.
Agüero, G; Alvarez, S; Haro, C; Lazarte, S; Zelaya, H, 2009
)
0.91

Treatment

D-Galactosamine treatment significantly decreased activities of hepatic aminocarboxymuconate-semialdehyde decarboxylase (ACMSDase) resulting in increased QUIN concentrations in serum and tissues. D-galactosamines are a suitable model for the study of the very fast cyclic modulations of the synthesis of the glycan moiety of glycoproteins.

ExcerptReferenceRelevance
"D-Galactosamine treatment of spleen cells had no effect in cytokine induction but rather increased the sensitivity to toxic shock in mice."( MyD88-dependent pro-inflammatory cytokine response contributes to lethal toxicity of staphylococcal enterotoxin B in mice.
Cisney, ED; Fernandez, S; Kissner, TL; Ruthel, G; Saikh, KU; Ulrich, RG, 2011
)
0.93
"D-Galactosamine treatment significantly decreased activities of hepatic aminocarboxymuconate-semialdehyde decarboxylase (ACMSDase) resulting in increased QUIN concentrations in serum and tissues."( Changes in quinolinic acid production and its related enzymes following D-galactosamine and lipopolysaccharide-induced hepatic injury.
Fujii, H; Furuta, N; Maeda, S; Ohashi, H; Saito, K; Seishima, M; Takemura, M; Wada, H, 2004
)
1.11
"In galactosamine/endotoxin-treated animals, which developed liver injury, the increase in both compartments was only 97% and 104%, respectively."( Release of soluble intercellular adhesion molecule 1 into bile and serum in murine endotoxin shock.
Essani, NA; Farhood, A; Fisher, MA; Jaeschke, H; Smith, CW; Vonderfecht, SL, 1996
)
0.81
"Galactosamine-treated animals showed 100% mortality."( An improved model of galactosamine-induced fulminant hepatic failure in the pig.
Kalpana, K; Ong, HS; Prema Raj, J; Soo, KC; Tan, SY, 1999
)
1.34
"D-galactosamine treatment leads to the formation of PAS-positive granules or aggregates in the cytoplasm of mouse liver cells. "( Cytoplasmic aggregates in D-galactosamine induced liver injury.
Antoni, F; Garzó, T; Lapis, K; Mandl, J; Mészáros, K; Schaff, Z; Tompa, A, 1977
)
1.27
"in galactosamine-treated animals."( Blood-brain barrier permeability in galactosamine-induced hepatic encephalopathy. No evidence for increased GABA-transport.
Knudsen, GM; Paulson, OB; Poulsen, HE, 1988
)
1.06
"D-galactosamine-treated rats seem to be a suitable model for the study of the very fast cyclic modulations of the synthesis of the glycan moiety of glycoproteins."( D-galactosamine-induced liver injury: a rat model to study the heterogeneity of the oligosaccharide chains of alpha 1-acid glycoprotein.
Biou, D; Durand, D; Durand, G; Féger, J; Monnet, D, 1985
)
1.55
"Pretreatment of galactosamine/TNF-alpha-injured mice with 800 mg/kg uridine or with 6 mg/kg calmidazolium fully protected the animals, while administration of either verapamil or nifedipine (100 mg/kg, respectively) had no significant effect."( Tumor necrosis factor is a terminal mediator in galactosamine/endotoxin-induced hepatitis in mice.
Tiegs, G; Wendel, A; Wolter, M, 1989
)
0.87

Toxicity

Two strains of mice carry the same mutant lipopolysaccharide gene (Lpsd) which makes them resistant to the toxic effects of endotoxin. CI-1 was also effective in counteracting the toxic effect of beta-galactosamine. All main flavonolignans of silymarin tested dis dis.

ExcerptReferenceRelevance
" Ammonium acetate proved to be less toxic in rats treated with single or repeated doses of galactosamine than in untreated animals."( [Toxicity of ammonium acetate in rats with acute and subacute galactosamine-induced hepatitis (author's transl)].
Gerok, W; Hoppe-Seyler, G; Maier, KP; Senn, HJ, 1979
)
0.72
"0 mg/ml could protect the hepatocytes against the toxic effects of CCl4 and d-GalN."( [Effect of d-catechin on carbon tetrachloride- and d-galactosamine-induced cytotoxicity in primary cultured rat hepatocytes].
Fang, R, 1992
)
0.53
" Rats treated with carrier-antagonist conjugate together with a toxic dose of galactosamine developed significantly less hepatotoxicity than did controls."( Targeted protection of hepatocytes from galactosamine toxicity in vivo.
Keegan-Rogers, V; Wu, GY, 1990
)
0.77
" The decreases in LD50 were 100-fold, 125-fold and 16-fold with galactosamine (GalN), actinomycin D (AcD) and lead acetate (PbAc) respectively and the animals died within 1-2 days."( Effect of hyperreactivity to endotoxin on the toxicity of pertussis vaccine and pertussis toxin in mice.
Furman, BL; Sidey, FM; Wardlaw, AC, 1989
)
0.52
" Exposure of Morris 7777 cells to the targetable antagonist in the presence of a toxic concentration of galactosamine did not protect these cells as evidenced by a steady decline in the number of viable cells in a fashion identical to cells treated with galactosamine alone."( Targeted antagonism of galactosamine toxicity in normal rat hepatocytes in vitro.
Franklin, S; Keegan-Rogers, V; Midford, S; Wu, CH; Wu, GY, 1988
)
0.8
"The toxic properties of human recombinant tumor necrosis factor (TNF) were investigated in mice made hypersensitive to endotoxin by treatment with D-galactosamine."( Lethal toxicity of lipopolysaccharide and tumor necrosis factor in normal and D-galactosamine-treated mice.
Freudenberg, MA; Galanos, C; Lehmann, V, 1987
)
0.7
"Two strains of mice (C57BL/10ScN and C3H/HeJ) that carry the same mutant lipopolysaccharide gene (Lpsd) which makes them resistant to the toxic effects of endotoxin (LPS) are also partially resistant to the hepatotoxic effects of D-galactosamine."( D-Galactosamine hepatotoxicity is associated with endotoxin sensitivity and mediated by lymphoreticular cells in mice.
Chojkier, M; Fierer, J, 1985
)
1.17
"The model of toxic liver injury was used to examine the role of manganese superoxide dismutase (MnSOD) expression in cellular resistance to tumor necrosis factor (TNF)-alpha toxicity."( Induction of MnSOD gene expression in a hepatic model of TNF-alpha toxicity does not result in increased protein.
Compton, A; Czaja, MJ; Oberley, LW; Ridnour, L; Schilsky, ML; Schmiedeberg, P; Xu, Y, 1994
)
0.29
" A similar toxic activity to that exerted by eubacteria is therefore exerted by this non-pathogenic archaeobacterium despite the difference in surface chemistry."( Biological activities of cell envelope fragments of the archaeobacterium Sulfolobus solfataricus: lethal toxicity, local hypersensitivity, pyrogenicity and spleen lymphocyte mitogenicity.
Capasso, C; Galdiero, F; Galdiero, M; Marcatili, A; Morana, A; Scarfogliero, P; Sommese, L, 1993
)
0.29
"In contrast to human carriers of microfilariae, filariae infected rodents generally tolerate an effective microfilaricidal treatment without obvious signs of adverse reactions."( Induction and prevention of shock-like lethal side effects after microfilaricidal treatment in filariae infected rodents.
Zahner, H, 1995
)
0.29
" The results of these studies demonstrated that CS-mediated protection is not selective for a particular species, organ system or toxic chemical."( Cholesteryl hemisuccinate treatment protects rodents from the toxic effects of acetaminophen, adriamycin, carbon tetrachloride, chloroform and galactosamine.
Fariss, MW; Lippman, HR; Mumaw, VR; Ray, SD, 1997
)
0.5
" The mechanism by which toxic liver injury sensitizes hepatocytes to TNF-alpha cytotoxicity is unknown."( Glutathione modulates rat and mouse hepatocyte sensitivity to tumor necrosis factor toxicity.
Czaja, MJ; Jones, BE; Neufeld, DS; Xu, Y, 1998
)
0.3
" CI-1 was also effective in counteracting the toxic effects of beta-galactosamine, as shown by reversed levels of the altered enzymes, glutamic oxaloacetic transaminase (GOT), glutamic pyruvic transminase (GPT) and alkaline phosphatase (ALP) both in isolated hepatic cells as well as in serum."( Hepatoprotective activity of a herbal protein CI-1, purified from Cajanus indicus against beta-galactosamine HCl toxicity in isolated rat hepatocytes.
Bhattacharyya, P; Datta, S; Sinha, S, 1999
)
0.76
" All main flavonolignans of silymarin tested displayed concentration-dependent cytoprotection against the toxic effects of both allyl alcohol and carbon tetrachloride but neither paracetamol nor galactosamine."( Primary cultures of human hepatocytes as a tool in cytotoxicity studies: cell protection against model toxins by flavonolignans obtained from Silybum marianum.
Bachleda, P; Dvorák, Z; Kosina, P; Simánek, V; Ulrichová, J; Walterová, D, 2003
)
0.51
" These novel data highlight the applicability of NMR-based metabonomics in elucidating multicompartmental metabolic consequences of toxicity and toxic salvage."( The mechanism of galactosamine toxicity revisited; a metabonomic study.
Clayton, TA; Coen, M; Holmes, E; Hong, YS; Lindon, JC; Nicholson, JK; Pearce, JT; Reily, MD; Robertson, DG; Rohde, CM, 2007
)
0.68
" This has been exemplified in studies of galactosamine toxicity in the rat where co-administration of glycine ameliorates the toxic response."( Chemical shift calibration of 1H MAS NMR liver tissue spectra exemplified using a study of glycine protection of galactosamine toxicity.
Coen, M; Holmes, E; Hong, YS; Lindon, JC; Nicholson, JK; Reily, MD; Rhode, CM; Robertson, DG, 2009
)
0.83
" Similar (protective) effect had also verapamil, calcium channel blocker, when given in non toxic doses and at the same time schedule as db-cAMP Combination of db-cAMP and verapamil had not synergistic effect in protection from D-GalN+LPS hepatotoxicity; the survival of mice was similar to that seen in protection caused by each agent alone."( The effect of cyclic adenosine monophosphate (cAMP) on acute liver toxicity in mice induced by D-galactosamine and lipopolysaccharide.
Cavar, I; Culo, F; Erceg, D; Kelava, T; Pasalić, M, 2010
)
0.58
" However, mangiferin administration in GAL intoxicated rats or coincubation of hepatocytes with mangiferin significantly altered all these GAL-induced adverse effects."( Mangiferin exerts hepatoprotective activity against D-galactosamine induced acute toxicity and oxidative/nitrosative stress via Nrf2-NFκB pathways.
Das, J; Ghosh, J; Roy, A; Sil, PC, 2012
)
0.63
" The unique observation of galN-pyrazines and altered gut microbial metabolites in fecal profiles of non-responders suggested that gut microfloral metabolism was associated with toxic outcome."( Pharmacometabonomic investigation of dynamic metabolic phenotypes associated with variability in response to galactosamine hepatotoxicity.
Coen, M; Goldfain-Blanc, F; Holmes, E; Lindon, JC; Nicholson, JK; Robertson, DG; Rolland-Valognes, G; Walther, B, 2012
)
0.59
" Moreover, cell lines used in the present study were more sensitive to toxic effects of troglitazone than previously reported."( Development of an optimized cytotoxicity assay system for CYP3A4-mediated metabolic activation via modified piggyBac transposition.
Dai, R; Dai, T; Deng, J; Huang, L; Jia, Y; Jiang, J; Xie, S; Zou, S, 2016
)
0.43
"Fulminant hepatic failure (FHF) is clinical syndrome with very poor prognosis and high mortality there is urgent need for the development of safe and non-toxic hepatoprotective agents for the adequate management of hepatitis."( Hepatoprotective activity of Lepidium sativum seeds against D-galactosamine/lipopolysaccharide induced hepatotoxicity in animal model.
Ahamad, SR; Ahmad, A; Al-Jenoobi, FI; Al-Mohizea, AM; Alkharfy, KM; Ansari, MA; Mohsin, K; Raish, M, 2016
)
0.67
" These results support further development of TLR5 agonists to increase tissue resistance to cytotoxic cytokines, reduce the risk of septic shock and enable safe systemic application of TNF as an anticancer therapy."( TLR5 agonist entolimod reduces the adverse toxicity of TNF while preserving its antitumor effects.
Brackett, CM; Burdelya, LG; Gleiberman, AS; Gudkov, AV; Haderski, GJ; Johnson, CP; Kandar, BM; Natarajan, V; Paszkiewicz, GM; Toshkov, IM, 2020
)
0.56
" They are also not toxic to mammalian cells and can reduce the cytotoxicity induced by Aβ42 and hIAPP aggregates."( Tryptophan-galactosylamine conjugates inhibit and disaggregate amyloid fibrils of Aβ42 and hIAPP peptides while reducing their toxicity.
Escobar Alvarez, D; Frenkel-Pinter, M; Gazit, E; Milordini, G; Paul, A; Segal, D; Zacco, E, 2020
)
0.56

Pharmacokinetics

The pharmacokinetic behavior of glycyrrhizin (GZ) was examined in D-galactosamine-intoxicated (GAL) rats. 10 days after galactosamines injection all pharmacokinetics parameters, as well as those of liver function, returned to basal levels.

ExcerptReferenceRelevance
" In cats with renal failure, 3-desacetylvecuronium pharmacokinetic and pharmacodynamic variables did not differ from those in control cats."( Pharmacokinetics, neuromuscular effects, and biodisposition of 3-desacetylvecuronium (Org 7268) in cats.
Agoston, S; Caldwell, JE; Gruenke, LD; Khuenl-Brady, KS; Miller, RD; Segredo, V; Sharma, ML; Shin, YS, 1991
)
0.28
"kg, a half-life of 16."( The effect of liver dysfunction on colchicine pharmacokinetics in the rat.
Bay, MK; Johnson, RF; Leighton, JA; Maldonado, AL; Schenker, S; Speeg, KV, 1990
)
0.28
" The pharmacokinetic analysis of these data showed that the decreased total plasma clearance of ICG in GAL and CCl4 rats results from both lowered influx across the sinusoidal plasma membrane of hepatocytes and the decreased hepatic plasma flow."( Pharmacokinetics of indocyanine green in rats with experimentally induced hepatic diseases.
Kimura, T; Kurosaki, Y; Nakayama, S; Nakayama, T; Yamao, T, 1993
)
0.29
" 10 days after galactosamine injection all pharmacokinetic parameters, as well as those of liver function, returned to basal levels."( Pharmacokinetics and pharmacodynamics of naproxen in acute experimental hepatitis.
Castañeda-Hernández, G; Favari, L; Hoyo-Vadillo, C, 1993
)
0.64
"The pharmacokinetic behavior of glycyrrhizin (GZ) was examined in D-galactosamine-intoxicated (GAL) rats."( Pharmacokinetics of glycyrrhizin in rats with D-galactosamine-induced hepatic disease.
Kimura, T; Kurosaki, Y; Nakayama, T; Okamoto, M; Wang, Z, 1996
)
0.79
"The pharmacodynamic effect of Macleaya cordata was investigated in this study."( [Experimental studies on pharmacodynamic effect of Macleaya cordata].
Fang, X; Liu, X; Wang, J; Yang, J, 1999
)
0.3
" Here, we systematically evaluated the pharmacodynamic properties of PMX622 in a murine model of endotoxin-induced lethality in galactosamine-sensitized mice."( Pharmacodynamic evaluation of the neutralization of endotoxin by PMX622 in mice.
Cerasoli, F; DeLeo, J; Handley, D; Lake, P; Logdberg, L; Weetall, M, 2004
)
0.53
" However, no significant pharmacokinetic changes were observed in both acute hepatitis rats after oral administration due to comparable intestinal metabolism of LQ."( Pharmacokinetics of liquiritigenin and its two glucuronides, M1 and M2, in rats with acute hepatitis induced by d-galactosamine/lipopolysaccharide or CCl(4).
Baek, SR; Kang, HE; Kim, SG; Kim, YW; Lee, I; Lee, JW; Lee, MG; Sohn, SI, 2010
)
0.57
"The differences in the plasma pharmacokinetic of 21 active compounds between the normal and model groups were compared, and established pharmacokinetics/pharmacodynamics (PK/PD) modeling was to analyze the hepatoprotective effects of PF."( Pharmacokinetic-pharmacodynamic (PK/PD) modeling to study the hepatoprotective effect of Perilla Folium on the acute hepatic injury rats.
Cao, X; Chang, Y; Fan, Y; He, J; Ouyang, H; Wei, S; Zhang, M; Zhu, Y, 2023
)
0.91

Compound-Compound Interactions

Tumor necrosis factor (TNF) in combination with galactosamine (GalN) in mice causes severe apoptosis of hepatocytes, resulting in complete destruction of the liver.

ExcerptReferenceRelevance
"Application of tumor necrosis factor (TNF) in combination with galactosamine (GalN) in mice causes severe apoptosis of hepatocytes, resulting in complete destruction of the liver."( Bilirubin release induced by tumor necrosis factor in combination with galactosamine is toxic to mice.
Libert, C; Van Molle, W, 2003
)
0.79
"Challenges with various TLR ligands (TLRLs)in combination with D-galactosamine (GalN) in rodents may mimic diverse conditions of acute inflammation and organ failure."( Use of TLR9 and TLR7/8 agonists in combination with d-galactosamine in exploring models for distinct severities of systemic inflammation relative to liver injury.
Nishizawa, K; Seki, R, 2020
)
1.04

Bioavailability

ExcerptReferenceRelevance
" In this study we have investigated whether changes in bioavailability and receptor binding could account for the observed differences."( Mechanism of induction of tolerance to tumour necrosis factor (TNF): no involvement of modulators of TNF bioavailability or receptor binding.
Bemelmans, MH; Brouckaert, P; Buurman, WA; Fiers, W; Takahashi, N, 1994
)
0.29
" The bioavailability of GZ, however, was not significantly changed."( Pharmacokinetics of glycyrrhizin in rats with D-galactosamine-induced hepatic disease.
Kimura, T; Kurosaki, Y; Nakayama, T; Okamoto, M; Wang, Z, 1996
)
0.55
" The present study aims to develop a novel silymarin-loaded solid lipid nanoparticle (Sm-loaded SLN) system with enhanced bioavailability and with an ability to provide excellent hepatic protection for poorly water-soluble drugs."( A comparative study on the therapeutic effects of silymarin and silymarin-loaded solid lipid nanoparticles on D-GaIN/TNF-α-induced liver damage in Balb/c mice.
Ayhancı, A; Burukoglu, DD; Cengiz, M; Kutlu, HM, 2015
)
0.42
"The phyto-phospholipid complexation technique is a promising approach to improve the bioavailability and efficacy of flavonoids."( Preparation and evaluation of luteolin-phospholipid complex as an effective drug delivery tool against GalN/LPS induced liver damage.
Khan, J; Saraf, S, 2016
)
0.43
"The objective of this study was to improve the bioavailability and efficacy of luteolin by phospholipid complexation against inflammatory liver damage."( Preparation and evaluation of luteolin-phospholipid complex as an effective drug delivery tool against GalN/LPS induced liver damage.
Khan, J; Saraf, S, 2016
)
0.43
" LPC showed an increase in relative in vivo bioavailability to 535."( Preparation and evaluation of luteolin-phospholipid complex as an effective drug delivery tool against GalN/LPS induced liver damage.
Khan, J; Saraf, S, 2016
)
0.43
"LPC was successfully formulated under optimized conditions and is an efficient drug delivery system for oral administration of luteolin with enhanced bioavailability and hepatoprotective potential."( Preparation and evaluation of luteolin-phospholipid complex as an effective drug delivery tool against GalN/LPS induced liver damage.
Khan, J; Saraf, S, 2016
)
0.43
" The present study takes the advantages of nanocarriers combined with a ligand (galactose) anchoring to orally deliver RES in an attempt to improve its bioavailability and pharmacological activity."( Galactosylated PLGA nanoparticles for the oral delivery of resveratrol: enhanced bioavailability and in vitro anti-inflammatory activity.
Li, S; Lin, H; Siu, FY; Ye, S, 2018
)
0.48
" After oral administration, RES-GNPs significantly enhanced the oral bioavailability of RES, up to 335."( Galactosylated PLGA nanoparticles for the oral delivery of resveratrol: enhanced bioavailability and in vitro anti-inflammatory activity.
Li, S; Lin, H; Siu, FY; Ye, S, 2018
)
0.48
" Nanoparticles can increase the bioavailability and the targeted accumulation of drugs in the liver, so as to significantly improve the therapeutic effect of ALI."( Hepatoprotective Effects of Albumin-Encapsulated Nanoparticles of a Curcumin Derivative COP-22 against Lipopolysaccharide/D-Galactosamine-Induced Acute Liver Injury in Mice.
Dong, S; Jia, M; Li, S; Liu, G; Mu, W; Wang, Q; Yang, J, 2022
)
0.93

Dosage Studied

Study consisted of 5 groups--group 1: control, injected with saline and fed ad libitum. Group 2: acute liver injury, by dosage with 400 mg/kg galactosamine. Group 4: chronic liver disease, using bile duct ligation. Group 5: sham-operated and pair-fed to group 4.

ExcerptRelevanceReference
" In seven experiments it can be shown, that the appearance of the ADB depends upon the time and dosage after GalN treatment."( The appearance and degradation of specific hepatocellular cytoplasmic inclusion bodies in rat liver due to D-galactosamine. I. The relation between the amount of liver glycogen and the appearance of the atypical dense bodies in the liver cell.
Enzan, H; Häberle, B; Lesch, R; Meinhardt, K, 1976
)
0.47
" The statistical evaluation of the results showed an increasing protective effect depending on the increasing dosage of the preparation ES 914."( [Effect of the liver protecting compound ES 914 on D-galactosamine induced experimental hepatitis in the rat].
Chariatte, N; Dittrich, A; Renker, H; Wegmann, A, 1979
)
0.51
" In rats with hepatic encephalopathy (HE) owing to fulminant hepatic failure (FHF) induced by a high dosage of GalN, the latencies of VEPs were delayed."( Changes in free radicals, trace elements, and neurophysiological function in rats with liver damage induced by D-galactosamine.
Chen, RD; Hu, HL, 1992
)
0.49
" The efficiency of the system was assessed by the survival rate of rats treated with either lethal dosage of 7% CCl4 [30 ml/kg body weight (b."( Bioartificial liver using hepatocytes on biosilon microcarriers: treatment of chemically induced acute hepatic failure in rats.
Bocharov, A; Bochkova, N; Shnyra, A; Spirov, V, 1991
)
0.28
" Hence, repeated dosing with the compound induced a transient resistance (greater than or equal to 1 week) to lethal challenges with endotoxin."( SDZ MRL 953, a novel immunostimulatory monosaccharidic lipid A analog with an improved therapeutic window in experimental sepsis.
Aschauer, H; Hildebrandt, J; Lam, C; Liehl, E; Macher, I; Schütze, E; Stütz, P, 1991
)
0.28
" In a similar dosing protocol, SK&F 86002 also protected mice in a second endotoxin shock model in which mice sensitized with Proprionibacterium acnes received LPS 10 days later."( Protective effect of SK&F 86002, a novel dual inhibitor of arachidonic acid metabolism, in murine models of endotoxin shock: inhibition of tumor necrosis factor as a possible mechanism of action.
Badger, AM; Hanna, N; Olivera, D; Talmadge, JE, 1989
)
0.28
" The results are discussed in the light of behavioural findings in which intraperitoneally applied D-galactosamine at this dosage improves the retention performance of an acquired behaviour in the rat."( Effects of intraperitoneally applied D-galactosamine on uridine and cytidine plasma content and brain activity of uridine kinase in the rat.
Matthies, H; Popov, N; Staak, S, 1989
)
0.76
" A stimulation of sulphate incorporation obeying a linear dose-response curve, was demonstrated in somatomedin-incubated fibroblast and glia cell cultures."( A novel assay for the biosynthesis of sulphated polysaccharide and its application to studies on the effects of somatomedin on cultured cells.
Uthne, K; Wasteson, A; Westermark, B, 1973
)
0.25
"The administration of (+)-Cyanidanol-3 [+)-catechin) to the rat using a subchronic dosing regime based on that currently used in the therapy of acute viral hepatitis in man, largely prevented the changes in the disposition of a single dose of [14C]imipramine hydrochloride induced by the hepatotoxin, D-(+)-galactosamine hydrochloride in rats."( The prevention by (+)-Cyanidanol-3 of hepatitis-induced changes in the disposition of imipramine in the rat.
Griffiths, LA; Hackett, AM; Shaw, IC, 1984
)
0.44
" In the control and E-0712-treated rats dosed with D-galactosamine or carbon tetrachloride, SGPT values were positively correlated with PT at 24 hr."( Protective effect of 4-(3,7,11,15-tetramethyl-6,10,14-hexadecatrienoyl)morpholine on liver injury induced by hepatotoxins in rats.
Fujiwara, K; Hayashi, S; Ogata, I; Ohta, Y; Oka, H; Oka, Y; Sato, Y; Takatsuki, K,
)
0.38
" Glutamic or aspartic acids, however, were not protective under a similar dosage regimen."( Modulation of galactosamine-induced liver injury by some amino acids or Triton WR1339.
Castro, JA; de Fenos, OM; de Ferreyra, EC, 1983
)
0.63
" In a dose-response experiment with lipopolysaccharide alone, we found no correlation between serum levels of TNF and survival rate of mice."( Evaluation of the significance of elevated levels of systemic and localized tumor necrosis factor in different animal models of inflammation.
Brackeen, MF; Connolly, KM; Menius, JA; Sekut, L, 1994
)
0.29
"The hepatoprotective action of orally dosed putrescine was investigated using rat models of liver injury."( Protective action of putrescine against rat liver injury.
Fujiwara, K; Matsui, A; Nagoshi, S; Ohta, Y, 1994
)
0.29
" This nuclear imaging method will enable optimisation of the dosing schedule by identification of doses of HPMA copolymer-dox-gal that display receptor saturation (and hence diminished targeting efficiency)."( Gamma scintigraphy of a 123I-labelled N-(2-hydroxypropyl)methacrylamide copolymer-doxorubicin conjugate containing galactosamine following intravenous administration to nude mice bearing hepatic human colon carcinoma.
Duncan, R; Perkins, AC; Pimm, MV; Strohalm, J; Ulbrich, K, 1996
)
0.5
" In vivo, V-PYRRO/NO increased liver cGMP levels while minimally affecting systemic hemodynamics, protecting rats dosed with TNF alpha plus galactosamine from apoptosis and hepatotoxicity."( Targeting nitric oxide (NO) delivery in vivo. Design of a liver-selective NO donor prodrug that blocks tumor necrosis factor-alpha-induced apoptosis and toxicity in the liver.
Billiar, TR; Keefer, LK; Kim, YM; Saavedra, JE; Watkins, SC; Williams, DL, 1997
)
0.5
" TNF-alpha-null (TNF-KO) and wild-type (WT) mice were dosed ip with saline, LPS (0."( Tumor necrosis factor-alpha-null mice are not resistant to cadmium chloride-induced hepatotoxicity.
Harstad, EB; Klaassen, CD, 2002
)
0.31
" To induce liver damage, galactosamine (800 mg/kg) was injected intraperitoneally 30 minutes after dosing with vehicle or D-003."( Lack of protective effect of D-003, a mixture of high-molecular-weight primary acids from sugar cane wax, on liver damage induced by galactosamine in rats.
Mas, R; Mendoza, N; Mendoza, S; Noa, M, 2005
)
0.84
" However, in the rats dosed with galactosamine hydrochloride, which showed highly variable amounts of liver damage at ca."( Hepatotoxin-induced hypertyrosinemia and its toxicological significance.
Charuel, C; Clayton, TA; Everett, JR; Hanton, G; Le Net, JL; Lindon, JC; Nicholson, JK; Provost, JP, 2007
)
0.62
"60 rats were divided into control group, model group, and low, middle, high dosage group, Bifendate group randomly."( [Protective effect of Isodon lophanthoides on acute hepatic injury induced by D-galactosamine in rats].
Hou, SZ; Lai, XP; Li, G; Nagao, Y; Ye, MR; Zhu, CC, 2008
)
0.57
" Modification of oral dosage regimen of LQ may not be necessary in patients with acute hepatitis; but human studies are required."( Pharmacokinetics of liquiritigenin and its two glucuronides, M1 and M2, in rats with acute hepatitis induced by d-galactosamine/lipopolysaccharide or CCl(4).
Baek, SR; Kang, HE; Kim, SG; Kim, YW; Lee, I; Lee, JW; Lee, MG; Sohn, SI, 2010
)
0.57
" To rule out inadvertent intestinal, solid organ, or subcutaneous injection as at least a partial cause for the variability, we performed midline incisions and dosed 10 rats via a flexible catheter, with a toxic dose of galactosamine."( Brief communication: intraperitoneal galactosamine misdosing as a possible interpretation for responder/nonresponder phenotypes.
Arrington-Brown, L; Bertram, R; Brown, HR; Gates, L; Jordan, H; Mellon-Kusibab, K; Miller, RT; Tillman, T, 2014
)
0.86
" The ability to translate these observations in humans offers the potential to improve therapeutic index, reduce cost of therapy and support a monthly dosing schedule for therapeutic suppression of gene expression in the liver using ASOs."( Targeted delivery of antisense oligonucleotides to hepatocytes using triantennary N-acetyl galactosamine improves potency 10-fold in mice.
Aghajan, M; Booten, SL; Carty, R; Chappell, A; Crosby, J; Gaus, H; Graham, MJ; Guo, S; Lima, WF; Low, A; Monia, BP; Murray, HF; Murray, SF; Prakash, TP; Riney, S; Schmidt, K; Seth, PP; Swayze, EE; Yu, J; Zhao, C, 2014
)
0.62
" In an effort to understand whether NVP is metabolized differently in a transiently inflamed liver and whether a heightened immune response alters NVP-induced hepatic responses, female brown Norway rats were dosed with either vehicle or NVP alone (75 mg/kg/day for 15 days) or galactosamine alone (single intraperitoneal [ip] injection on day 7 to mimic viral hepatitis) or a combination of NVP (75/100/150 mg/kg/day for 15 days) and galactosamine (single 750 mg/kg ip on day 7)."( Drug-induced Liver Fibrosis: Testing Nevirapine in a Viral-like Liver Setting Using Histopathology, MALDI IMS, and Gene Expression.
Arrington-Brown, L; Bailey, D; Brown, HR; Cariello, NF; Castellino, S; Elangbam, CS; Fowler, S; Gates, LD; Groseclose, MR; Krull, DL; Mellon-Kusibab, K; Miller, RT; Shah, V; Tillman, T; Yoon, LW, 2016
)
0.61
" However, no efficacious dosing regimen was identified."( Phase IIa, randomised, double-blind study of GSK3389404 in patients with chronic hepatitis B on stable nucleos(t)ide therapy.
Baptiste-Brown, S; Campbell, FM; Chayama, K; Cremer, J; Davies, M; Duan, Z; Elston, R; Han, K; Heo, J; Hou, J; Imamura, M; Jia, J; Karino, Y; Kumada, H; Kumar, R; Kurosaki, M; Kweon, YO; Labio, ME; Lao-Tan, JY; Lim, SG; Paff, M; Park, SJ; Suzuki, F; Suzuki, Y; Tanaka, Y; Tao, Y; Theodore, D; Xie, Q; Xie, W; Yim, HJ; Yoon, JH; Yuen, MF, 2022
)
0.72
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
toxinPoisonous substance produced by a biological organism such as a microbe, animal or plant.
[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 (2)

ClassDescription
D-galactosamineThe D-stereoisomer of galactosamine.
primary amino compoundA compound formally derived from ammonia by replacing one hydrogen atom by an organyl 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 (1)

PathwayProteinsCompounds
galactosamine degradation811

Bioassays (1)

Assay IDTitleYearJournalArticle
AID1761891Hepatoprotective activity against APAP-induced toxicity in human HepG2 cells assessed as cell survival rate at 10 uM after 48 hrs by MTT assay (Rvb = 23 %)2021Journal of natural products, 03-26, Volume: 84, Issue:3
Hepatoprotective Glucosyloxybenzyl 2-Hydroxy-2-isobutylsuccinates from
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (3,407)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901543 (45.29)18.7374
1990's546 (16.03)18.2507
2000's546 (16.03)29.6817
2010's613 (17.99)24.3611
2020's159 (4.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 63.41

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 very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index63.41 (24.57)
Research Supply Index8.17 (2.92)
Research Growth Index4.47 (4.65)
Search Engine Demand Index111.57 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (63.41)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials7 (0.20%)5.53%
Reviews62 (1.75%)6.00%
Case Studies6 (0.17%)4.05%
Observational1 (0.03%)0.25%
Other3,466 (97.85%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]