Page last updated: 2024-12-05

duodote

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

Description

duodote: consists of atropine and pralidoxime chloride; for treating those exposed to organophosphorus-containing nerve agents [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID4884
CHEMBL ID1420
MeSH IDM0507694

Synonyms (24)

Synonym
DIVK1C_000770
KBIO1_000770
SPECTRUM_001144
KBIOGR_000665
KBIO2_006760
KBIO2_004192
KBIO3_002615
KBIO2_001624
KBIOSS_001624
PRESTWICK1_000943
PRESTWICK0_000943
NINDS_000770
SPECTRUM3_001498
SPECTRUM4_000323
SPBIO_000822
SPBIO_003065
SPECTRUM2_000921
atnaa
CHEMBL1420
duodote
gtpl4652
n-methyl-pyridinium-2-aldoxime
[(1-methyl-1,2-dihydropyridin-2-ylidene)methyl](oxo)azanium
n-[(1-methylpyridin-1-ium-2-yl)methylidene]hydroxylamine
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
cholinergic drugAny drug used for its actions on cholinergic systems. Included here are agonists and antagonists, drugs that affect the life cycle of acetylcholine, and drugs that affect the survival of cholinergic neurons.
cholinesterase reactivatorA drug used to reverse the inactivation of cholinesterase caused by organophosphates or sulfonates.
antidote to organophosphate poisoningA role borne by a molecule that acts to counteract or neutralise the deleterious effects of organophosphates or acetylcholinesterase inhibitors (nerve agents).
antidote to sarin poisoningA role borne by a molecule that acts to counteract or neutralise the nerve agent sarin.
[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
pyridinium ion
[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]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Bile salt export pumpHomo sapiens (human)IC50 (µMol)1,000.00000.11007.190310.0000AID1449628
AcetylcholinesteraseHomo sapiens (human)IC50 (µMol)664.00000.00000.933210.0000AID1826689; AID31018; AID551378; AID552421
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AcetylcholinesteraseHomo sapiens (human)Kd140.00000.00801.77505.3000AID1519202
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (36)

Processvia Protein(s)Taxonomy
fatty acid metabolic processBile salt export pumpHomo sapiens (human)
bile acid biosynthetic processBile salt export pumpHomo sapiens (human)
xenobiotic metabolic processBile salt export pumpHomo sapiens (human)
xenobiotic transmembrane transportBile salt export pumpHomo sapiens (human)
response to oxidative stressBile salt export pumpHomo sapiens (human)
bile acid metabolic processBile salt export pumpHomo sapiens (human)
response to organic cyclic compoundBile salt export pumpHomo sapiens (human)
bile acid and bile salt transportBile salt export pumpHomo sapiens (human)
canalicular bile acid transportBile salt export pumpHomo sapiens (human)
protein ubiquitinationBile salt export pumpHomo sapiens (human)
regulation of fatty acid beta-oxidationBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transportBile salt export pumpHomo sapiens (human)
bile acid signaling pathwayBile salt export pumpHomo sapiens (human)
cholesterol homeostasisBile salt export pumpHomo sapiens (human)
response to estrogenBile salt export pumpHomo sapiens (human)
response to ethanolBile salt export pumpHomo sapiens (human)
xenobiotic export from cellBile salt export pumpHomo sapiens (human)
lipid homeostasisBile salt export pumpHomo sapiens (human)
phospholipid homeostasisBile salt export pumpHomo sapiens (human)
positive regulation of bile acid secretionBile salt export pumpHomo sapiens (human)
regulation of bile acid metabolic processBile salt export pumpHomo sapiens (human)
transmembrane transportBile salt export pumpHomo sapiens (human)
acetylcholine catabolic process in synaptic cleftAcetylcholinesteraseHomo sapiens (human)
regulation of receptor recyclingAcetylcholinesteraseHomo sapiens (human)
osteoblast developmentAcetylcholinesteraseHomo sapiens (human)
acetylcholine catabolic processAcetylcholinesteraseHomo sapiens (human)
cell adhesionAcetylcholinesteraseHomo sapiens (human)
nervous system developmentAcetylcholinesteraseHomo sapiens (human)
synapse assemblyAcetylcholinesteraseHomo sapiens (human)
receptor internalizationAcetylcholinesteraseHomo sapiens (human)
negative regulation of synaptic transmission, cholinergicAcetylcholinesteraseHomo sapiens (human)
amyloid precursor protein metabolic processAcetylcholinesteraseHomo sapiens (human)
positive regulation of protein secretionAcetylcholinesteraseHomo sapiens (human)
retina development in camera-type eyeAcetylcholinesteraseHomo sapiens (human)
acetylcholine receptor signaling pathwayAcetylcholinesteraseHomo sapiens (human)
positive regulation of cold-induced thermogenesisAcetylcholinesteraseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (17)

Processvia Protein(s)Taxonomy
protein bindingBile salt export pumpHomo sapiens (human)
ATP bindingBile salt export pumpHomo sapiens (human)
ABC-type xenobiotic transporter activityBile salt export pumpHomo sapiens (human)
bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
canalicular bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transporter activityBile salt export pumpHomo sapiens (human)
ABC-type bile acid transporter activityBile salt export pumpHomo sapiens (human)
ATP hydrolysis activityBile salt export pumpHomo sapiens (human)
amyloid-beta bindingAcetylcholinesteraseHomo sapiens (human)
acetylcholinesterase activityAcetylcholinesteraseHomo sapiens (human)
cholinesterase activityAcetylcholinesteraseHomo sapiens (human)
protein bindingAcetylcholinesteraseHomo sapiens (human)
collagen bindingAcetylcholinesteraseHomo sapiens (human)
hydrolase activityAcetylcholinesteraseHomo sapiens (human)
serine hydrolase activityAcetylcholinesteraseHomo sapiens (human)
acetylcholine bindingAcetylcholinesteraseHomo sapiens (human)
protein homodimerization activityAcetylcholinesteraseHomo sapiens (human)
laminin bindingAcetylcholinesteraseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (22)

Processvia Protein(s)Taxonomy
basolateral plasma membraneBile salt export pumpHomo sapiens (human)
Golgi membraneBile salt export pumpHomo sapiens (human)
endosomeBile salt export pumpHomo sapiens (human)
plasma membraneBile salt export pumpHomo sapiens (human)
cell surfaceBile salt export pumpHomo sapiens (human)
apical plasma membraneBile salt export pumpHomo sapiens (human)
intercellular canaliculusBile salt export pumpHomo sapiens (human)
intracellular canaliculusBile salt export pumpHomo sapiens (human)
recycling endosomeBile salt export pumpHomo sapiens (human)
recycling endosome membraneBile salt export pumpHomo sapiens (human)
extracellular exosomeBile salt export pumpHomo sapiens (human)
membraneBile salt export pumpHomo sapiens (human)
extracellular regionAcetylcholinesteraseHomo sapiens (human)
basement membraneAcetylcholinesteraseHomo sapiens (human)
extracellular spaceAcetylcholinesteraseHomo sapiens (human)
nucleusAcetylcholinesteraseHomo sapiens (human)
Golgi apparatusAcetylcholinesteraseHomo sapiens (human)
plasma membraneAcetylcholinesteraseHomo sapiens (human)
cell surfaceAcetylcholinesteraseHomo sapiens (human)
membraneAcetylcholinesteraseHomo sapiens (human)
neuromuscular junctionAcetylcholinesteraseHomo sapiens (human)
synaptic cleftAcetylcholinesteraseHomo sapiens (human)
synapseAcetylcholinesteraseHomo sapiens (human)
perinuclear region of cytoplasmAcetylcholinesteraseHomo sapiens (human)
side of membraneAcetylcholinesteraseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (94)

Assay IDTitleYearJournalArticle
AID1826694Reactivation of NIMP-inhibited recombinant His-TEV-tagged human AChE expressed in CHO-K1 cells assessed as reactivation constant, KD by measuring thiophenol levels by UV-vis absorption spectroscopy2022Journal of medicinal chemistry, 03-24, Volume: 65, Issue:6
A New Class of Bi- and Trifunctional Sugar Oximes as Antidotes against Organophosphorus Poisoning.
AID1519215Neuroprotection against POX-induced memory impairment in Wistar rat assessed as increase in escape latency at 10 mg/kg, ip administered 15 mins before POX poisoning measured after 2 days during 2 to 4 days of testing by morris water maze hidden platform t2020European journal of medicinal chemistry, Jan-01, Volume: 1856-Methyluracil derivatives as peripheral site ligand-hydroxamic acid conjugates: Reactivation for paraoxon-inhibited acetylcholinesterase.
AID1410756Resurrection of isopropyl phosphate-aged electric eel AChE assessed as realkylated enzyme level at 100 mM in presence of trypsin by LC-MS/MS based bottom-up proteomics analysis (Rvb = 0%)2018Journal of medicinal chemistry, 08-23, Volume: 61, Issue:16
Demonstration of In Vitro Resurrection of Aged Acetylcholinesterase after Exposure to Organophosphorus Chemical Nerve Agents.
AID1826697Reactivation of NEDPA-inhibited recombinant His-TEV-tagged human AChE expressed in CHO-K1 cells assessed as reactivation constant, KD by measuring thiophenol levels by UV-vis absorption spectroscopy2022Journal of medicinal chemistry, 03-24, Volume: 65, Issue:6
A New Class of Bi- and Trifunctional Sugar Oximes as Antidotes against Organophosphorus Poisoning.
AID625286Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for hepatitis2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID31018Reversible inhibition of Human AchE1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Nonquaternary cholinesterase reactivators. 4. Dialkylaminoalkyl thioesters of alpha-keto thiohydroximic acids as reactivators of ethyl methylphosphonyl- and 1,2,2-trimethylpropyl methylphosphonyl-acetylcholinesterase in vitro.
AID1826692Reactivation of NEMP-inhibited recombinant His-TEV-tagged human AChE expressed in CHO-K1 cells assessed as reactivation constant, Kr2 by measuring thiophenol levels by UV-vis absorption spectroscopy2022Journal of medicinal chemistry, 03-24, Volume: 65, Issue:6
A New Class of Bi- and Trifunctional Sugar Oximes as Antidotes against Organophosphorus Poisoning.
AID650715Reactivation of Sp-GBC-inhibited recombinant AChE using acetylthiocholine as substrate at 100 uM after 60 mins by Ellman's method2011Journal of medicinal chemistry, May-12, Volume: 54, Issue:9
Amidine-oximes: reactivators for organophosphate exposure.
AID1519217Neuroprotection against POX-induced memory impairment in Wistar rat assessed as decrease in quadrant percentage time at 10 mg/kg, ip administered 15 mins before POX poisoning measured after 2 days and on day 5 of training session by morris water maze spat2020European journal of medicinal chemistry, Jan-01, Volume: 1856-Methyluracil derivatives as peripheral site ligand-hydroxamic acid conjugates: Reactivation for paraoxon-inhibited acetylcholinesterase.
AID31639Reactivation of para-nitrophenyl methylphosphate (EPMP)-phosphonylated human erythrocyte AChE at pH 7.61986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Nonquaternary cholinesterase reactivators. 4. Dialkylaminoalkyl thioesters of alpha-keto thiohydroximic acids as reactivators of ethyl methylphosphonyl- and 1,2,2-trimethylpropyl methylphosphonyl-acetylcholinesterase in vitro.
AID1826700Reactivation of PARAOXON-inhibited recombinant His-TEV-tagged human AChE expressed in CHO-K1 cells assessed as reactivation constant, KD by measuring thiophenol levels by UV-vis absorption spectroscopy2022Journal of medicinal chemistry, 03-24, Volume: 65, Issue:6
A New Class of Bi- and Trifunctional Sugar Oximes as Antidotes against Organophosphorus Poisoning.
AID1519221Drug uptake in iv dosed Wistar rat brain measured every 1 hr for 3 hrs by microdialysis technique based HPLC/UV detection method2020European journal of medicinal chemistry, Jan-01, Volume: 1856-Methyluracil derivatives as peripheral site ligand-hydroxamic acid conjugates: Reactivation for paraoxon-inhibited acetylcholinesterase.
AID1826691Reactivation of NEMP-inhibited recombinant His-TEV-tagged human AChE expressed in CHO-K1 cells assessed as reactivation constant, KD by measuring thiophenol levels by UV-vis absorption spectroscopy2022Journal of medicinal chemistry, 03-24, Volume: 65, Issue:6
A New Class of Bi- and Trifunctional Sugar Oximes as Antidotes against Organophosphorus Poisoning.
AID625291Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for liver function tests abnormal2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID650713Reactivation of Sp-GF-SMe-inhibited recombinant AChE using acetylthiocholine as substrate assessed at 100 uM after 60 mins by Ellman's method2011Journal of medicinal chemistry, May-12, Volume: 54, Issue:9
Amidine-oximes: reactivators for organophosphate exposure.
AID1519201Reactivation of POX-inhibited human recombinant AChE assessed as reactivation rate constant using ATC as substrate incubated for 60 mins followed by substrate addition by Ellman's method based spectrophotometry2020European journal of medicinal chemistry, Jan-01, Volume: 1856-Methyluracil derivatives as peripheral site ligand-hydroxamic acid conjugates: Reactivation for paraoxon-inhibited acetylcholinesterase.
AID625281Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for cholelithiasis2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID1195820Drug uptake in guinea pigs assessed as increase in auto-fluorescence intensity in hippocampus after 24 hrs by FITC-hematoxylin and eosin staining2015European journal of medicinal chemistry, Jan-27, Volume: 90Discovery of non-oxime reactivators using an in silico pharmacophore model of reactivators for DFP-inhibited acetylcholinesterase.
AID551385Inhibition of human recombinant BChE at 100 mM to 1 nM2011Bioorganic & medicinal chemistry letters, Jan-01, Volume: 21, Issue:1
Preparation, in vitro screening and molecular modelling of symmetrical 4-tert-butylpyridinium cholinesterase inhibitors--analogues of SAD-128.
AID1195815In vivo reactivation of diisopropylfluorophosphate-inhibited guinea pig AChE assessed as enzyme activity in diaphragm treated with 0.026 mg/kg, ip pyridostigmine bromide after 20 mins 8 mg/kg DFP followed by 2 mg/kg atropine methyl bromide treated before 2015European journal of medicinal chemistry, Jan-27, Volume: 90Discovery of non-oxime reactivators using an in silico pharmacophore model of reactivators for DFP-inhibited acetylcholinesterase.
AID552415Reactivation of POX-mediated inactive human recombinant AChE at 100 uM after 15 mins by Ellman's method2011Bioorganic & medicinal chemistry, Jan-15, Volume: 19, Issue:2
Mono-oxime bisquaternary acetylcholinesterase reactivators with prop-1,3-diyl linkage-Preparation, in vitro screening and molecular docking.
AID1195813Toxicity in po dosed guinea pig after 24 hrs2015European journal of medicinal chemistry, Jan-27, Volume: 90Discovery of non-oxime reactivators using an in silico pharmacophore model of reactivators for DFP-inhibited acetylcholinesterase.
AID1195811Reactivation of diisopropylfluorophosphate-inhibited electric eel AChE using acetylcholine as substrate assessed as change in optical density per minute for 60 mins by UV-VIS spectrophotometry2015European journal of medicinal chemistry, Jan-27, Volume: 90Discovery of non-oxime reactivators using an in silico pharmacophore model of reactivators for DFP-inhibited acetylcholinesterase.
AID1410741Resurrection of isopropyl phosphate-aged electric eel AChE assessed as enzyme reactivation by measuring residual activity at 4 mM using acetylthiocholine as substrate at pH 8 after 4 days by Ellman's assay relative to control2018Journal of medicinal chemistry, 08-23, Volume: 61, Issue:16
Demonstration of In Vitro Resurrection of Aged Acetylcholinesterase after Exposure to Organophosphorus Chemical Nerve Agents.
AID650714Reactivation of ETP-inhibited recombinant AChE using acetylthiocholine as substrate assessed at 100 uM after 60 mins by Ellman's method2011Journal of medicinal chemistry, May-12, Volume: 54, Issue:9
Amidine-oximes: reactivators for organophosphate exposure.
AID650705Dissociation constant, pKa of the compound2011Journal of medicinal chemistry, May-12, Volume: 54, Issue:9
Amidine-oximes: reactivators for organophosphate exposure.
AID1826699Reactivation of PARAOXON-inhibited recombinant His-TEV-tagged human AChE expressed in CHO-K1 cells assessed as reactivation constant, Kr by measuring thiophenol levels by UV-vis absorption spectroscopy2022Journal of medicinal chemistry, 03-24, Volume: 65, Issue:6
A New Class of Bi- and Trifunctional Sugar Oximes as Antidotes against Organophosphorus Poisoning.
AID625292Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) combined score2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID1826695Reactivation of NIMP-inhibited recombinant His-TEV-tagged human AChE expressed in CHO-K1 cells assessed as reactivation constant, Kr2 by measuring thiophenol levels by UV-vis absorption spectroscopy2022Journal of medicinal chemistry, 03-24, Volume: 65, Issue:6
A New Class of Bi- and Trifunctional Sugar Oximes as Antidotes against Organophosphorus Poisoning.
AID1410748Resurrection of methylphosphonate-aged electric eel AChE assessed as aged enzyme level at 100 mM in presence of trypsin by LC-MS/MS based bottom-up proteomics analysis (Rvb = 100%)2018Journal of medicinal chemistry, 08-23, Volume: 61, Issue:16
Demonstration of In Vitro Resurrection of Aged Acetylcholinesterase after Exposure to Organophosphorus Chemical Nerve Agents.
AID1195816In vivo reactivation of diisopropylfluorophosphate-inhibited guinea pig AChE assessed as enzyme activity in brain treated with 0.026 mg/kg, ip pyridostigmine bromide after 20 mins 8 mg/kg DFP followed by 2 mg/kg atropine methyl bromide treated before 13 t2015European journal of medicinal chemistry, Jan-27, Volume: 90Discovery of non-oxime reactivators using an in silico pharmacophore model of reactivators for DFP-inhibited acetylcholinesterase.
AID625287Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for hepatomegaly2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID1519222In vivo reactivation of POX-inhibited AChE in rat brain at 10 mg/kg, iv administered at 1 hr post POX poisoning and measured after 1 hr using acetylthiocholine iodide substrate in presence of BChE inhibitor iso-OMPA by Ellman's method2020European journal of medicinal chemistry, Jan-01, Volume: 1856-Methyluracil derivatives as peripheral site ligand-hydroxamic acid conjugates: Reactivation for paraoxon-inhibited acetylcholinesterase.
AID1826701Reactivation of PARAOXON-inhibited recombinant His-TEV-tagged human AChE expressed in CHO-K1 cells assessed as reactivation constant, Kr2 by measuring thiophenol levels by UV-vis absorption spectroscopy2022Journal of medicinal chemistry, 03-24, Volume: 65, Issue:6
A New Class of Bi- and Trifunctional Sugar Oximes as Antidotes against Organophosphorus Poisoning.
AID1519216Neuroprotection against POX-induced memory impairment in Wistar rat assessed as decrease in number of platform area crossing at 10 mg/kg, ip administered 15 mins before POX poisoning measured after 2 days and on day 5 of training session by morris water m2020European journal of medicinal chemistry, Jan-01, Volume: 1856-Methyluracil derivatives as peripheral site ligand-hydroxamic acid conjugates: Reactivation for paraoxon-inhibited acetylcholinesterase.
AID552414Reactivation of GA-mediated inactive human recombinant AChE at 10 uM after 15 mins by Ellman's method2011Bioorganic & medicinal chemistry, Jan-15, Volume: 19, Issue:2
Mono-oxime bisquaternary acetylcholinesterase reactivators with prop-1,3-diyl linkage-Preparation, in vitro screening and molecular docking.
AID625285Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for hepatic necrosis2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID1195818Efficacy against diisopropylfluorophosphate-induced neuropathology in guinea pigs assessed as seizure strength treated with 0.026 mg/kg, ip pyridostigmine bromide after 20 mins 8 mg/kg DFP followed by 2 mg/kg atropine methyl bromide treated before 13 to 12015European journal of medicinal chemistry, Jan-27, Volume: 90Discovery of non-oxime reactivators using an in silico pharmacophore model of reactivators for DFP-inhibited acetylcholinesterase.
AID650702Binding affinity to AChE in rat brain homogenate2011Journal of medicinal chemistry, May-12, Volume: 54, Issue:9
Amidine-oximes: reactivators for organophosphate exposure.
AID551378Inhibition of human recombinant AChE2011Bioorganic & medicinal chemistry letters, Jan-01, Volume: 21, Issue:1
Preparation, in vitro screening and molecular modelling of symmetrical 4-tert-butylpyridinium cholinesterase inhibitors--analogues of SAD-128.
AID650732Neuroprotective activity against rac-GDC-induced AChE inhibition in Swiss Webster mouse assessed as survival at 6.25 mg/kg, ip administered 30 mins prior to rac-GDC-induction measured after 24 hrs2011Journal of medicinal chemistry, May-12, Volume: 54, Issue:9
Amidine-oximes: reactivators for organophosphate exposure.
AID552419Reactivation of DEP-mediated inactive human recombinant AChE at 100 uM after 15 mins by Ellman's method2011Bioorganic & medicinal chemistry, Jan-15, Volume: 19, Issue:2
Mono-oxime bisquaternary acetylcholinesterase reactivators with prop-1,3-diyl linkage-Preparation, in vitro screening and molecular docking.
AID1519202Reactivation of POX-inhibited human recombinant AChE assessed as dissociation rate constant using ATC as substrate incubated for 60 mins followed by substrate addition by Ellman's method based spectrophotometry2020European journal of medicinal chemistry, Jan-01, Volume: 1856-Methyluracil derivatives as peripheral site ligand-hydroxamic acid conjugates: Reactivation for paraoxon-inhibited acetylcholinesterase.
AID650729Neuroprotective activity against rac-GDC-induced AChE inhibition in Swiss Webster mouse assessed as survival at 25 mg/kg, ip administered 30 mins prior to rac-GDC-induction measured after 24 hrs2011Journal of medicinal chemistry, May-12, Volume: 54, Issue:9
Amidine-oximes: reactivators for organophosphate exposure.
AID301889Reactivation of paraoxon inhibited housefly brain AChE2007Bioorganic & medicinal chemistry, Dec-15, Volume: 15, Issue:24
New oxime reactivators connected with CH2O(CH2)nOCH2 linker and their reactivation potency for organophosphorus agents-inhibited acetylcholinesterase.
AID1826702Protective index of reactivation of PARAOXON-inhibited AChE in Swiss mouse at 100 umol/kg, ip treated for 1 min after paraoxon exposure by Dixon's up-and-down method relative to paraoxon alone2022Journal of medicinal chemistry, 03-24, Volume: 65, Issue:6
A New Class of Bi- and Trifunctional Sugar Oximes as Antidotes against Organophosphorus Poisoning.
AID496765Modulation of neurological behavior in zebrafish assessed as prolongation of high intensity light-induced motor response at 10 to 100 uM by photomotor response assay2010Nature chemical biology, Mar, Volume: 6, Issue:3
Rapid behavior-based identification of neuroactive small molecules in the zebrafish.
AID1410746Resurrection of isopropyl phosphate-aged electric eel AChE assessed as aged enzyme level at 100 mM in presence of trypsin by LC-MS/MS based bottom-up proteomics analysis (Rvb = 100%)2018Journal of medicinal chemistry, 08-23, Volume: 61, Issue:16
Demonstration of In Vitro Resurrection of Aged Acetylcholinesterase after Exposure to Organophosphorus Chemical Nerve Agents.
AID31651Reactivation of para-nitrophenyl methylyphosphate (EPMP)-phosphonylated human erythrocyte AChE1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Nonquaternary cholinesterase reactivators. 4. Dialkylaminoalkyl thioesters of alpha-keto thiohydroximic acids as reactivators of ethyl methylphosphonyl- and 1,2,2-trimethylpropyl methylphosphonyl-acetylcholinesterase in vitro.
AID1449628Inhibition of human BSEP expressed in baculovirus transfected fall armyworm Sf21 cell membranes vesicles assessed as reduction in ATP-dependent [3H]-taurocholate transport into vesicles incubated for 5 mins by Topcount based rapid filtration method2012Drug metabolism and disposition: the biological fate of chemicals, Dec, Volume: 40, Issue:12
Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.
AID552420Reactivation of DEP-mediated inactive human recombinant AChE at 10 uM after 15 mins by Ellman's method2011Bioorganic & medicinal chemistry, Jan-15, Volume: 19, Issue:2
Mono-oxime bisquaternary acetylcholinesterase reactivators with prop-1,3-diyl linkage-Preparation, in vitro screening and molecular docking.
AID1519203Reactivation of POX-inhibited human recombinant AChE assessed as bimolecular rate constant using ATC as substrate incubated for 60 mins followed by substrate addition by Ellman's method based spectrophotometry2020European journal of medicinal chemistry, Jan-01, Volume: 1856-Methyluracil derivatives as peripheral site ligand-hydroxamic acid conjugates: Reactivation for paraoxon-inhibited acetylcholinesterase.
AID1826693Reactivation of NIMP-inhibited recombinant His-TEV-tagged human AChE expressed in CHO-K1 cells assessed as reactivation constant, Kr by measuring thiophenol levels by UV-vis absorption spectroscopy2022Journal of medicinal chemistry, 03-24, Volume: 65, Issue:6
A New Class of Bi- and Trifunctional Sugar Oximes as Antidotes against Organophosphorus Poisoning.
AID625279Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for bilirubinemia2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID625283Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for elevated liver function tests2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID1474167Liver toxicity in human assessed as induction of drug-induced liver injury by measuring verified drug-induced liver injury concern status2016Drug discovery today, Apr, Volume: 21, Issue:4
DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans.
AID271559Reactivation of VX-inhibited AChE in rat brain homogenate at 1000 uM2006Bioorganic & medicinal chemistry letters, Sep-15, Volume: 16, Issue:18
Bis-pyridiumaldoxime reactivators connected with CH2O(CH2)n OCH2 linkers between pyridinium rings and their reactivity against VX.
AID650712Reactivation of Sp-GAC-inhibited recombinant AChE using acetylthiocholine as substrate at 100 uM after 60 mins by Ellman's method2011Journal of medicinal chemistry, May-12, Volume: 54, Issue:9
Amidine-oximes: reactivators for organophosphate exposure.
AID301887Reactivation of diisopropyl fluorophosphate inhibited housefly brain AChE2007Bioorganic & medicinal chemistry, Dec-15, Volume: 15, Issue:24
New oxime reactivators connected with CH2O(CH2)nOCH2 linker and their reactivation potency for organophosphorus agents-inhibited acetylcholinesterase.
AID1826690Reactivation of NEMP-inhibited recombinant His-TEV-tagged human AChE expressed in CHO-K1 cells assessed as reactivation constant, Kr by measuring thiophenol levels by UV-vis absorption spectroscopy2022Journal of medicinal chemistry, 03-24, Volume: 65, Issue:6
A New Class of Bi- and Trifunctional Sugar Oximes as Antidotes against Organophosphorus Poisoning.
AID1826696Reactivation of NEDPA-inhibited recombinant His-TEV-tagged human AChE expressed in CHO-K1 cells assessed as reactivation constant, Kr by measuring thiophenol levels by UV-vis absorption spectroscopy2022Journal of medicinal chemistry, 03-24, Volume: 65, Issue:6
A New Class of Bi- and Trifunctional Sugar Oximes as Antidotes against Organophosphorus Poisoning.
AID1826708Permeability coefficient of compound in human BLEC monolayers assessed as radiolabeled 14C-D-glucose levels at 50 uM incubated for 1 hr by mass spectroscopy followed by scintillation counting method2022Journal of medicinal chemistry, 03-24, Volume: 65, Issue:6
A New Class of Bi- and Trifunctional Sugar Oximes as Antidotes against Organophosphorus Poisoning.
AID1410757Resurrection of methylphosphonate-aged electric eel AChE assessed as realkylated enzyme level at 100 mM in presence of trypsin by LC-MS/MS based bottom-up proteomics analysis (Rvb = 0%)2018Journal of medicinal chemistry, 08-23, Volume: 61, Issue:16
Demonstration of In Vitro Resurrection of Aged Acetylcholinesterase after Exposure to Organophosphorus Chemical Nerve Agents.
AID31635Maximum reactivation for GD-inhibited human erythrocyte (RBC) AChE by oximes1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Nonquaternary cholinesterase reactivators. 4. Dialkylaminoalkyl thioesters of alpha-keto thiohydroximic acids as reactivators of ethyl methylphosphonyl- and 1,2,2-trimethylpropyl methylphosphonyl-acetylcholinesterase in vitro.
AID25804Bimolecular rate constant (kn) for reaction of the anionic (oximate) with 7.5 x 10 e-4 M acetylthiocholine (AcSCh) in 0.1 M phosphate buffer1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Nonquaternary cholinesterase reactivators. 4. Dialkylaminoalkyl thioesters of alpha-keto thiohydroximic acids as reactivators of ethyl methylphosphonyl- and 1,2,2-trimethylpropyl methylphosphonyl-acetylcholinesterase in vitro.
AID625282Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for cirrhosis2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID271560Reactivation of VX-inhibited AChE in rat brain homogenate at 10 uM2006Bioorganic & medicinal chemistry letters, Sep-15, Volume: 16, Issue:18
Bis-pyridiumaldoxime reactivators connected with CH2O(CH2)n OCH2 linkers between pyridinium rings and their reactivity against VX.
AID301888Reactivation of diisopropyl fluorophosphate inhibited bovine RBC AChE2007Bioorganic & medicinal chemistry, Dec-15, Volume: 15, Issue:24
New oxime reactivators connected with CH2O(CH2)nOCH2 linker and their reactivation potency for organophosphorus agents-inhibited acetylcholinesterase.
AID552421Inhibition of human recombinant AChE by modified Ellman's method2011Bioorganic & medicinal chemistry, Jan-15, Volume: 19, Issue:2
Mono-oxime bisquaternary acetylcholinesterase reactivators with prop-1,3-diyl linkage-Preparation, in vitro screening and molecular docking.
AID552418Reactivation of MePOX-mediated inactive human recombinant AChE at 10 uM after 15 mins by Ellman's method2011Bioorganic & medicinal chemistry, Jan-15, Volume: 19, Issue:2
Mono-oxime bisquaternary acetylcholinesterase reactivators with prop-1,3-diyl linkage-Preparation, in vitro screening and molecular docking.
AID552413Reactivation of GA-mediated inactive human recombinant AChE at 100 uM after 15 mins by Ellman's method2011Bioorganic & medicinal chemistry, Jan-15, Volume: 19, Issue:2
Mono-oxime bisquaternary acetylcholinesterase reactivators with prop-1,3-diyl linkage-Preparation, in vitro screening and molecular docking.
AID1195814In vivo reactivation of diisopropylfluorophosphate-inhibited guinea pig AChE assessed as enzyme activity in blood treated with 0.026 mg/kg, ip pyridostigmine bromide after 20 mins 8 mg/kg DFP followed by 2 mg/kg atropine methyl bromide treated before 13 t2015European journal of medicinal chemistry, Jan-27, Volume: 90Discovery of non-oxime reactivators using an in silico pharmacophore model of reactivators for DFP-inhibited acetylcholinesterase.
AID625288Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for jaundice2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID1410759Reactivation of EMP-inhibited electric eel AChE assessed as enzyme reactivation by measuring residual activity at 0.04 mM at pH 8 after 1 hr using acetylthiocholine as substrate by Ellman's assay relative to control2018Journal of medicinal chemistry, 08-23, Volume: 61, Issue:16
Demonstration of In Vitro Resurrection of Aged Acetylcholinesterase after Exposure to Organophosphorus Chemical Nerve Agents.
AID625289Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for liver disease2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID23685Partition coefficient (LogD7.6)1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Nonquaternary cholinesterase reactivators. 4. Dialkylaminoalkyl thioesters of alpha-keto thiohydroximic acids as reactivators of ethyl methylphosphonyl- and 1,2,2-trimethylpropyl methylphosphonyl-acetylcholinesterase in vitro.
AID625280Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for cholecystitis2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID552416Reactivation of POX-mediated inactive human recombinant AChE at 10 uM after 15 mins by Ellman's method2011Bioorganic & medicinal chemistry, Jan-15, Volume: 19, Issue:2
Mono-oxime bisquaternary acetylcholinesterase reactivators with prop-1,3-diyl linkage-Preparation, in vitro screening and molecular docking.
AID1826698Reactivation of NEDPA-inhibited recombinant His-TEV-tagged human AChE expressed in CHO-K1 cells assessed as reactivation constant, Kr2 by measuring thiophenol levels by UV-vis absorption spectroscopy2022Journal of medicinal chemistry, 03-24, Volume: 65, Issue:6
A New Class of Bi- and Trifunctional Sugar Oximes as Antidotes against Organophosphorus Poisoning.
AID552417Reactivation of MePOX-mediated inactive human recombinant AChE at 100 uM after 15 mins by Ellman's method2011Bioorganic & medicinal chemistry, Jan-15, Volume: 19, Issue:2
Mono-oxime bisquaternary acetylcholinesterase reactivators with prop-1,3-diyl linkage-Preparation, in vitro screening and molecular docking.
AID1519219Neuroprotection against POX-induced memory impairment in Wistar rat assessed as decrease in total distance to platform at 10 mg/kg, ip administered 15 mins before POX poisoning and measured after 2 days during 2 to 4 days of testing by morris water maze h2020European journal of medicinal chemistry, Jan-01, Volume: 1856-Methyluracil derivatives as peripheral site ligand-hydroxamic acid conjugates: Reactivation for paraoxon-inhibited acetylcholinesterase.
AID625290Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for liver fatty2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID650703Reactivation of sarin-inhibited AChE in rat brain homogenate assessed as reactivation constant incubated for 10 mins post sarin treatment2011Journal of medicinal chemistry, May-12, Volume: 54, Issue:9
Amidine-oximes: reactivators for organophosphate exposure.
AID646762Reactivation of Sp-GBC-inhibited human AChE after 60 mins by Ellman method2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Nonquaternary reactivators for organophosphate-inhibited cholinesterases.
AID301890Reactivation of paraoxon inhibited bovine RBC AChE2007Bioorganic & medicinal chemistry, Dec-15, Volume: 15, Issue:24
New oxime reactivators connected with CH2O(CH2)nOCH2 linker and their reactivation potency for organophosphorus agents-inhibited acetylcholinesterase.
AID1519211Neuroprotection against POX-induced neuronal death in Wistar rat assessed as reduction in brain dentate gyrus damage at 10 mg/kg, ip administered 15 mins before POX poisoning and observed after 2 days by fluoro-jade-B staining based confocal laser scannin2020European journal of medicinal chemistry, Jan-01, Volume: 1856-Methyluracil derivatives as peripheral site ligand-hydroxamic acid conjugates: Reactivation for paraoxon-inhibited acetylcholinesterase.
AID1826689Inhibition of recombinant His-TEV-tagged human AChE expressed in CHO-K1 cells using acetylthiocholine iodide as substrate measured for 6 mins by Ellman's method2022Journal of medicinal chemistry, 03-24, Volume: 65, Issue:6
A New Class of Bi- and Trifunctional Sugar Oximes as Antidotes against Organophosphorus Poisoning.
AID625284Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for hepatic failure2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID1410745Resurrection of isopropyl phosphate-aged electric eel AChE assessed as native enzyme level at 100 mM in presence of trypsin by LC-MS/MS based bottom-up proteomics analysis (Rvb = 0%)2018Journal of medicinal chemistry, 08-23, Volume: 61, Issue:16
Demonstration of In Vitro Resurrection of Aged Acetylcholinesterase after Exposure to Organophosphorus Chemical Nerve Agents.
AID1519190Protection against POX-induced mortality in Wistar rat assessed as increase in survival at 10 mg/kg, ip administered 15 mins before POX poisoning2020European journal of medicinal chemistry, Jan-01, Volume: 1856-Methyluracil derivatives as peripheral site ligand-hydroxamic acid conjugates: Reactivation for paraoxon-inhibited acetylcholinesterase.
AID1474166Liver toxicity in human assessed as induction of drug-induced liver injury by measuring severity class index2016Drug discovery today, Apr, Volume: 21, Issue:4
DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans.
AID1195817In vivo reactivation of diisopropylfluorophosphate-inhibited guinea pig AChE assessed as post DFP survival duration of animal treated with 0.026 mg/kg, ip pyridostigmine bromide after 20 mins 8 mg/kg DFP followed by 2 mg/kg atropine methyl bromide treated2015European journal of medicinal chemistry, Jan-27, Volume: 90Discovery of non-oxime reactivators using an in silico pharmacophore model of reactivators for DFP-inhibited acetylcholinesterase.
AID1410747Resurrection of methylphosphonate-aged electric eel AChE assessed as native enzyme level at 100 mM in presence of trypsin by LC-MS/MS based bottom-up proteomics analysis (Rvb = 0%)2018Journal of medicinal chemistry, 08-23, Volume: 61, Issue:16
Demonstration of In Vitro Resurrection of Aged Acetylcholinesterase after Exposure to Organophosphorus Chemical Nerve Agents.
AID25346Dissociation constant (pKa) (for oxime acid)1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Nonquaternary cholinesterase reactivators. 4. Dialkylaminoalkyl thioesters of alpha-keto thiohydroximic acids as reactivators of ethyl methylphosphonyl- and 1,2,2-trimethylpropyl methylphosphonyl-acetylcholinesterase in vitro.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (15)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (6.67)18.7374
1990's0 (0.00)18.2507
2000's2 (13.33)29.6817
2010's10 (66.67)24.3611
2020's2 (13.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 51.58

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 Index51.58 (24.57)
Research Supply Index2.83 (2.92)
Research Growth Index4.88 (4.65)
Search Engine Demand Index77.24 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (51.58)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (6.25%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other15 (93.75%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]