Page last updated: 2024-12-07

glycidyl nitrate

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

Description

glycidyl nitrate: a nitric oxide donor; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

peptidoglycan : A peptidoglycosaminoglycan formed by alternating residues of beta-(1->4)-linked N-acetylglucosamine and N-acetylmuramic acid {2-amino-3-O-[(S)-1-carboxyethyl]-2-deoxy-D-glucose} residues. Attached to the carboxy group of the muramic acid is a peptide chain of three to five amino acids. [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 CID93035
SCHEMBL ID169655
MeSH IDM000596133

Synonyms (23)

Synonym
nsc-137875
6659-62-7
oxiranemethanol, nitrate
nsc137875
brn 0383635
1-propanol, 2,3-epoxy-, nitrate
2,3-epoxypropyl nitrate
glycidyl nitrate
nsc 137875
einecs 229-698-7
peptidoglycan
oxiran-2-ylmethyl nitrate
AKOS006274225
5-17-03-00048 (beilstein handbook reference)
27814-48-8
SCHEMBL169655
ADZAAKGRMMGJKM-UHFFFAOYSA-N
glyn
glycidyl nitrate;2,3-epoxypropyl nitrate
DTXSID20950492
(oxiran-2-yl)methyl nitrate
2-oxiranemethanol, 2-nitrate, homopolymer
AKOS040751940

Research Excerpts

Overview

Glycidyl nitrate (GLYN) is a NO generating small molecule. It has ability to release NO on bioactivation in SCC VII tumor cells.

ExcerptReferenceRelevance
"Glycidyl nitrate (GLYN) is a NO generating small molecule, and has ability to release NO on bioactivation in SCC VII tumor cells."( Novel nitric oxide generating compound glycidyl nitrate enhances the therapeutic efficacy of chemotherapy and radiotherapy.
Bednarski, M; Knox, SJ; Ning, S; Oronsky, B; Scicinski, J, 2014
)
1.39

Toxicity

ExcerptReferenceRelevance
" Teichoic acid was inactive, exhibiting toxic effects at 400 microgram/ml level."( Stimulation of reticuloendothelial system and toxicity to macrophages of Staphylococcus aureus cell wall, peptidoglycan, and teichoic acid.
Dziarski, R, 1977
)
0.26
" SDS-PAGE of the toxic fraction showed a single band with a Mr of about 150,000, and after dithiothreitol treatment, two bands with Mr of 100,000 and 50,000."( Detection of neutral sugars in purified type G botulinum progenitor toxin and the effects of some glycolytic enzymes on its molecular dissociation and oral toxicity.
Miyata, T; Nukina, M; Sakaguchi, G; Sakaguchi, S, 1991
)
0.28
" The data obtained in these tests indicate that the immunomodulators (IM) under study are capable of changing (increasing or decreasing, depending on the dose) the toxic properties of APP."( [The effect of bacterial and synthetic peptidoglycans on the toxicity of a cell-free pertussis preparation].
Bazhanova, IG; Britsina, MV; Ozeretskovskaia, MN; Shepeleva, IB; Zakharova, NS, 1990
)
0.28
" The toxic effects of nitric oxide are consistent with spectroscopic evidence of the formation of iron-dinitrosyl-dithiolate complexes in TCT-treated cells."( Epithelial autotoxicity of nitric oxide: role in the respiratory cytopathology of pertussis.
Corbett, JA; Goldman, WE; Heiss, LN; Lancaster, JR, 1994
)
0.29
" While lipopolysaccharide-like material exerted negligible toxic effects on the epithelial cells, peptidoglycan was highly toxic."( Cytotoxic effect of peptidoglycan from Treponema denticola.
Grenier, D; Uitto, VJ, 1993
)
0.29
"The type VI secretion system (T6SS) is considered as one of the key competition strategies by injecting toxic effectors for intestinal pathogens to acquire optimal colonization in host gut, a microenviroment with high-density polymicrobial community where bacteria compete for niches and resources."( Diverse toxic effectors are harbored by vgrG islands for interbacterial antagonism in type VI secretion system.
Lu, C; Ma, J; Pan, Z; Sun, M; Yao, H, 2018
)
0.48
" Totally, 47 adverse events (AEs) presented, and 14 drug-related AEs were reported in 7 patients, including 8 grade 1 events (57."( A phase I study of the safety and activity of K-001 in patients with advanced pancreatic ductal adenocarcinoma.
Biskup, E; Chen, D; Cui, J; Han, T; Hu, J; Jiao, F; Liu, J; Liu, M; Mao, T; Pan, Y; Wang, L; Wang, Y; Yang, H; Zhang, H, 2021
)
0.62

Pharmacokinetics

ExcerptReferenceRelevance
" The pharmacokinetic analysis of oral rifampicin was performed using a one-compartment open model with absorption."( The effects of peptidoglycan, a pyrogenic constituent of gram-positive microorganisms, on the pharmacokinetics of rifampicin.
Lavický, J; Rasková, H; Rotta, J; Urbanová, Z; Vanĕcek, J, 1988
)
0.27
" However, its short plasma half-life (20."( A stable phage lysin (Cpl-1) dimer with increased antipneumococcal activity and decreased plasma clearance.
Fischetti, VA; Moreillon, P; Resch, G, 2011
)
0.37

Compound-Compound Interactions

ExcerptReferenceRelevance
"Twenty strains each of methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE) were tested in vitro by standardized methods against nisin alone and combined with bacitracin, ramoplanin and chloramphenicol."( Nisin, alone and combined with peptidoglycan-modulating antibiotics: activity against methicillin-resistant Staphylococcus aureus and vancomycin-resistant enterococci.
Brumfitt, W; Hamilton-Miller, JM; Salton, MR, 2002
)
0.31
" We found marked synergistic IL-8 secretion induced by MDP or DAP-containing DMP in combination with synthetic TLR agonists in THP-1 cells."( Muramyldipeptide and diaminopimelic acid-containing desmuramylpeptides in combination with chemically synthesized Toll-like receptor agonists synergistically induced production of interleukin-8 in a NOD2- and NOD1-dependent manner, respectively, in human
Fujimoto, Y; Fukase, K; Kusumoto, S; Shibata, K; Sugawara, S; Takada, H; Uehara, A; Yang, S, 2005
)
0.33
" However, when LCs were stimulated with PEG in combination with MDP, the strength of Th2 immune responses was synergistically augmented by MDP."( Peptidoglycan in combination with muramyldipeptide synergistically induces an interleukin-10-dependent T helper 2-dominant immune response.
Ikeda, R; Matsui, K, 2014
)
0.4
" Here, we immunized mice with detoxified LPS in combination with immunogenic proteins and looked into the result of bacterial challenge."( Potent T-cell mediated immune response against Legionella pneumophila in mice following vaccination with detoxified lipopolysaccharide non-covalently combined with recombinant flagellin A and peptidoglycan-associated lipoprotein.
Khoramabadi, N; Mehdi Abdol, M; Mohabati Mobarez, A; Papian, S; Talebi Bezmin Abadi, A, 2020
)
0.56
"Our results suggest that combination of polysaccharide antigen derived from Legionella LPS may confer raised cell-mediated responses against the pathogen when combined with Th-1 stimulating protein antigens."( Potent T-cell mediated immune response against Legionella pneumophila in mice following vaccination with detoxified lipopolysaccharide non-covalently combined with recombinant flagellin A and peptidoglycan-associated lipoprotein.
Khoramabadi, N; Mehdi Abdol, M; Mohabati Mobarez, A; Papian, S; Talebi Bezmin Abadi, A, 2020
)
0.56

Bioavailability

ExcerptReferenceRelevance
" Elevated temperature alone was not responsible for observed pharmacokinetic changes leading to the increase of bioavailability of oral rifampicin since another pyrogenic substance (endotoxin) had an opposite effect on pharmacokinetics of previously tested drugs."( The effects of peptidoglycan, a pyrogenic constituent of gram-positive microorganisms, on the pharmacokinetics of rifampicin.
Lavický, J; Rasková, H; Rotta, J; Urbanová, Z; Vanĕcek, J, 1988
)
0.27
" Peptidoglycan pretreatment increased the bioavailability of TMP."( Changes of pharmacokinetics of trimethoprim after pretreatment with streptococcal peptidoglycan.
Celeda, L; Cerný, J; Kubícek, A; Kvĕtina, J; Lavický, J; Raśková, H; Rotta, J,
)
0.13

Dosage Studied

ExcerptRelevanceReference
" CM also activated complement but did not give a clear dose-response relationship in the concentrations used."( Activation of complement by cell surface components of Staphylococcus aureus.
Kim, Y; Michael, AF; Peterson, PK; Quie, PG; Wilkinson, BJ, 1978
)
0.26
"Comparative efficacy of the use of injection and oral dosage forms of rifampicin in the subtherapeutic doses in combination with peptidoglycan , an immunomodulator of microbial origin, was studied in respect to experimental anthracic infection with application of multifactorial analysis."( [Comparative multifactorial analysis of combined administration of injection and peroral forms of an antibiotic with a microbial immunomodulator in experimental anthrax].
Bodunkova, LE; Buravtseva, NP; Fomina, IP; Ivanitskaia, LP; Kogotkova, OI; Nikitin, AV, 1991
)
0.28
" Purified teichoic acid from DIC and non-DIC isolates failed to aggregate platelets in vitro, or in vivo in guinea pigs but inhibited the peptidoglycan-induced aggregation in a dose-response manner."( Disseminated intravascular coagulation associated with Staphylococcus aureus septicemia is mediated by peptidoglycan-induced platelet aggregation.
Kessler, CM; Nussbaum, E; Tuazon, CU, 1991
)
0.28
" The antineoplastic effects of PGM depend strictly on the dosage and treatment schedule used."( Antitumor and antimetastatic activity of the immunoadjuvant peptidoglycan monomer PGM in mice bearing MCa mammary carcinoma.
Hrsak, I; Sava, G; Tomasic, J, 1984
)
0.27
" These impaired responses to peptidoglycan were not due to (1) aberrant kinetic response; (2) shift in the dose-response pattern; (3) decreased cell survival in culture or (4) the inability of peptidoglycan to activate RA cells."( Analysis of in vitro polyclonal B cell differentiation responses to bacterial peptidoglycan and pokeweed mitogen in rheumatoid arthritis.
Carafa, C; Dziarski, R; Levinson, AI; Pardo, I, 1984
)
0.27
" Changes in the weight of organs were not significant and there was no dose-response relationship."( Response of the lymphoid organs of the mouse to the peptidoglycan of a gram-positive bacterium (Streptococcus pyogenes).
Caravano, R; Mauss, H; Oberti, J; Roux, J,
)
0.13
" Optimal sonication of PG did not yield activities equal to those of PCW in dose-response and kinetic studies, which may imply that TA plays some role in complement consumption."( Factors affecting complement activation by Staphylococcus aureus cell walls, their components, and mutants altered in teichoic acid.
Kim, Y; Peterson, PK; Wilkinson, BJ, 1981
)
0.26
" melitensis) on its own also conferred good immunity but the dose-response curve was less regular."( Antagonism between two immunogens extracted from Brucella (cell wall peptidoglycan and lipopolysaccharide fractions) and inactivity of the brucellin allergen in immunization of the mouse.
Bosseray, N; Plommet, M,
)
0.13
" Although lactyl tetrapeptides are the most toxic of the TCT fragments, producing dose-response curves identical to TCT, the smallest analogues of TCT which are active in our assay are of the form X-gamma-(D)-Glu-meso-A2pm, where X may be an amino acid or a blocking group."( Tracheal cytotoxin structural requirements for respiratory epithelial damage in pertussis.
Goldman, WE; Luker, KE; Marshall, GR; Tyler, AN, 1995
)
0.29
" However, dose-response experiments revealed that at least 3,000 ng of sPG per ml was necessary for induction, whereas the optimal LPS concentration was 1 ng/ml."( Soluble peptidoglycan-induced monokine production can be blocked by anti-CD14 monoclonal antibodies and by lipid A partial structures.
Bazil, V; Brade, H; Dziarski, R; Flad, HD; Kusumoto, S; Rietschel, ET; Ulmer, AJ; Weidemann, B, 1994
)
0.29
" To rule out any differences in end-organ sensitivity to glucocorticoids between the two strains, we evaluated dose-response relations of whole body, thymus, spleen, and adrenal weights after 1 week daily administration of graded doses of dexamethasone."( Glucocorticoid and/or glucocorticoid antagonist effects in inflammatory disease-susceptible Lewis rats and inflammatory disease-resistant Fischer rats.
Chrousos, GP; Crofford, L; Karalis, K; Wilder, RL, 1995
)
0.29
" However, the dosage of SEPS capable of inducing HDC and ODC was much higher (100 to 1,000 times) than that of LPS."( Stimulation of the synthesis of histamine and putrescine in mice by a peptidoglycan of gram-positive bacteria.
Abe, M; Ando, T; Endo, Y; Kumagai, K, 1994
)
0.29
" PG stimulated phagocytosis of neutrophils in a dose-dependent manner, whereas dosage exceeding the optimum concentration (500 microgram) inhibited phagocytosis."( Phagocytosis of splenetic neutrophils of mice enhanced by orally administered peptidoglycan from Bifidobacterium thermophilum.
Namioka, S; Samegai, Y; Sasaki, T, 1996
)
0.29
" At high dosage the effect of linenscin OC2 was bacteriolytic on Listeria innocua."( Antibacterial and hemolytic activities of linenscin OC2, a hydrophobic substance produced by Brevibacterium linens OC2.
Boucabeille, C; Henckes, G; Mengin-Lecreulx, D; Simonet, JM; van Heijenoort, J, 1997
)
0.3
" Gliotoxin (2 mg/kg/day) was dosed from day 14 after the initial intramural colonic injection of peptidoglycan-polysaccharide until day 21."( Gliotoxin, an inhibitor of nuclear factor-kappa B, attenuates peptidoglycan-polysaccharide-induced colitis in rats.
Fitzpatrick, LR; Le, T; Wang, J, 2002
)
0.31
" We calculated dose-response curves for peptidoglycan-induced interleukin 6 elaboration in peripheral blood mononuclear cells (PBMCs) from healthy donors and for sterile peritonitis in rats."( Aseptic peritonitis due to peptidoglycan contamination of pharmacopoeia standard dialysis solution.
Costigan, A; Denjoy, N; Giertych, J; Goud, N; Martis, L; Mendoza, O; Mongoven, J; Owen, WF; Patel, M; Perrier, MA; Taminne, M; Verger, C,
)
0.13
" The adjuvant activity of di, tetrasaccharide peptides and stearoyl containing derivatives has at least two peaks in dose-response curves and the greater of them correlates with respective dose-response data for NF-kB stimulation through NOD2."( Evidence for correlation between the intensities of adjuvant effects and NOD2 activation by monomeric, dimeric and lipophylic derivatives of N-acetylglucosaminyl-N-acetylmuramyl peptides.
Andronova, T; Ivanov, V; Makarov, E; Meshcheryakova, E; Philpott, D, 2007
)
0.34
" Thus, a combination of loose regulation of the vanA operon by the two-component system and a gene dosage effect accounts for the partial glycopeptide dependence of VRSA-7."( VanA-type Staphylococcus aureus strain VRSA-7 is partially dependent on vancomycin for growth.
Courvalin, P; Meziane-Cherif, D; Moubareck, C; Périchon, B, 2009
)
0.35
" When dosed in ratios typical for wounds, a slight synergistic effect was measured for peptidoglycan hydrolysis (i."( Novel peptidoglycan-based diagnostic devices for detection of wound infection.
Binder, B; Gewessler, U; Guebitz, GM; Hasmann, A; Hulla, E; Kanzler, G; Schintler, M; Schneider, KP; Wehrschuetz-Sigl, E, 2011
)
0.37
" pylori if once-a-day dosing is required."( Pyridodiazepine amines are selective therapeutic agents for helicobacter pylori by suppressing growth through inhibition of glutamate racemase but are predicted to require continuous elevated levels in plasma to achieve clinical efficacy.
Cederberg, C; de Jonge, BL; Kutschke, A; Newman, JV; Rooney, MT; Yang, W, 2015
)
0.42
" We demonstrate that LP are the most potent non-LPS pro-inflammatory toxins of the bacterial cell walls, signalling via Toll-like receptor-2, not only in vitro, but also when inoculated into mice: A synthetic LP caused sepsis-related pathological symptoms in a dose-response manner."( Lipoproteins/peptides are sepsis-inducing toxins from bacteria that can be neutralized by synthetic anti-endotoxin peptides.
Alexander, C; Bárcena-Varela, S; Brandenburg, K; Correa, W; Ferrer-Espada, R; Fukuoka, S; Gisch, N; Goldmann, T; Gutsmann, T; Heinbockel, L; Heine, H; Martinez de Tejada, G; Sánchez-Gómez, S; Schürholz, T; Wiesmüller, KH, 2015
)
0.42
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7,597)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901695 (22.31)18.7374
1990's789 (10.39)18.2507
2000's1545 (20.34)29.6817
2010's2736 (36.01)24.3611
2020's832 (10.95)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 22.44

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 Index22.44 (24.57)
Research Supply Index8.96 (2.92)
Research Growth Index4.78 (4.65)
Search Engine Demand Index22.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (22.44)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials8 (0.10%)5.53%
Reviews721 (9.30%)6.00%
Case Studies4 (0.05%)4.05%
Observational0 (0.00%)0.25%
Other7,016 (90.54%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]