Page last updated: 2024-12-05
methylparaoxon
Description
Research Excerpts
Clinical Trials
Roles
Classes
Pathways
Study Profile
Bioassays
Related Drugs
Related Conditions
Protein Interactions
Research Growth
Market Indicators
Cross-References
| ID Source | ID |
|---|---|
| PubMed CID | 13708 |
| CHEMBL ID | 26115 |
| CHEBI ID | 165199 |
| SCHEMBL ID | 901276 |
| MeSH ID | M0052363 |
Synonyms (47)
| Synonym |
|---|
| unii-ue1a2xl95h |
| ue1a2xl95h , |
| o,o-dimetyl-o-p-nitrofenylfosfat |
| dimethyl-p-nitrofenylester kyseliny fosforecne |
| phosphoric acid, dimethyl p-nitrophenyl ester |
| phosphoric acid, dimethyl 4-nitrophenyl ester |
| dimethyl-4-nitrophenyl phosphate |
| brn 1884904 |
| bay 11678 |
| methyl paraoxon |
| paraoxon-methyl |
| methylparaoxon |
| methyl-e-600 |
| desmethylnitrophos |
| dimethyl paraoxon |
| o,o-dimetyl-o-p-nitrofenylfosfat [czech] |
| dimethyl-p-nitrofenylester kyseliny fosforecne [czech] |
| dimethyl-p-nitrophenyl phosphate |
| phosphoric acid, dimethyl-4-nitrophenyl ester |
| NCGC00163905-01 |
| 950-35-6 |
| dimethyl p-nitrophenyl phosphate |
| dimethyl 4-nitrophenyl phosphate |
| phosphoric acid dimethyl ester 4-nitro-phenyl ester |
| CHEMBL26115 |
| dimethyl (4-nitrophenyl) phosphate |
| CHEBI:165199 |
| phosphoric acid dimethyl (4-nitrophenyl) ester |
| cas-950-35-6 |
| dtxsid5037571 , |
| dtxcid3017571 |
| tox21_302009 |
| NCGC00255563-01 |
| dimethyl p-nitrophenylphosphate |
| AKOS015902913 |
| SCHEMBL901276 |
| phosphoric acid, dimethyl-p-nitrophenyl ester |
| dimethyl-p-nitrophenylphosphate |
| BAFQDKPJKOLXFZ-UHFFFAOYSA-N |
| methyl-e 600 |
| paraoxon methyl |
| paraoxon-methyl, pestanal(r), analytical standard |
| bdbm50487989 |
| paraoxon-methyl, analytical standard |
| o,o-dimethyl-o-p-nitrophenylphosphoric acid |
| phosphoric acid dimethyl 4-nitrophenyl ester |
| Q27291041 |
Research Excerpts
Toxicity
| Excerpt | Reference | Relevance |
|---|---|---|
| "Mouse livers perfused in situ with the pesticide methyl parathion (O,O-dimethyl O-P-nitrophenyl phosphorothioate) resulted in the appearance of the toxic metabolite, methyl paraoxon (O,O-dimethyl-O-P-nitrophenyl phosphate), in the effluent perfusate." | ( The role of the liver in mediating the acute toxicity of the pesticide methyl parathion in the mouse. Sultatos, LG, ) | 0.13 |
| "Comparison of published LD50 or LC50 levels for a variety of insecticides in several vertebrate species indicate that a wide range of toxicity levels exist, and these cannot be easily predicted within either a chemical group or within a species." | ( Biochemical mechanisms contributing to species differences in insecticidal toxicity. Carr, RL; Chambers, JE, 1995) | 0.29 |
Pharmacokinetics
| Excerpt | Reference | Relevance |
|---|---|---|
| " Pharmacokinetic studies showed that methyl parathion disappeared monoexponentially from plasma and tissues." | ( Placental transfer and pharmacokinetics of a single dermal dose of [14C]methyl parathion in rats. Abdel-Rahman, AA; Abou-Donia, MB; Abu-Qare, AW; Kishk, AM, 2000) | 0.31 |
Bioavailability
| Excerpt | Reference | Relevance |
|---|---|---|
| " After oral administration, peak plasma concentrations were obtained within 3-16 min, and the bioavailability varied from 5 to 71%." | ( Toxicokinetics of methyl paraoxon in the dog. Belpaire, F; De Reu, L; De Schryver, E; Willems, J, 1987) | 0.27 |
Dosage Studied
| Excerpt | Relevance | Reference |
|---|---|---|
| " Oral LD1 values were estimated by dose-response studies (CPF = 80 mg/kg; MPS = 4 mg/kg, in peanut oil, 1 ml/kg)." | ( Interactive toxicity of the organophosphorus insecticides chlorpyrifos and methyl parathion in adult rats. Karanth, S; Liu, J; Olivier, K; Pope, C, 2004) | 0.32 |
| " The dose-response relationships showed different curve characteristics with a linear increase of enzyme inhibition compared with a sigmoidal curve for the overt effects." | ( Comparison of cholin- and carboxylesterase enzyme inhibition and visible effects in the zebra fish embryo bioassay under short-term paraoxon-methyl exposure. Altenburger, R; Küster, E, ) | 0.13 |
| " Additionally, these data raise questions regarding the adequacy of estimating risk of low levels of insecticide exposure from direct extrapolation of insecticide dose-response curves since the capacity of individual oxon molecules at low oxon levels could be greater than individual oxon molecules in vivo associated with the dose-response curve." | ( Concentration-dependent interactions of the organophosphates chlorpyrifos oxon and methyl paraoxon with human recombinant acetylcholinesterase. Kaushik, R; Rosenfeld, CA; Sultatos, LG, 2007) | 0.34 |
| " AChE inhibitors were given intraperitoneally in equitoxic dosage (25% of LD₀₁) 30 min before OPC exposure." | ( Acetylcholinesterase inhibitors as pretreatment before acute exposure to organophosphates: assessment using methyl-paraoxon. Hasan, MY; Kuča, K; Lorke, DE; Nurulain, SM; Petroianu, GA; Shafiullah, M, 2012) | 0.38 |
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
Drug Classes (1)
| Class | Description |
|---|---|
| C-nitro compound | A nitro compound having the nitro group (-NO2) attached to a carbon atom. |
| [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 (20)
Potency Measurements
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| acetylcholinesterase | Homo sapiens (human) | Potency | 8.1222 | 0.0025 | 41.7960 | 15,848.9004 | AID1347395; AID1347397; AID1347398; AID1347399 |
| hypoxia-inducible factor 1 alpha subunit | Homo sapiens (human) | Potency | 24.5412 | 3.1890 | 29.8841 | 59.4836 | AID1224846 |
| AR protein | Homo sapiens (human) | Potency | 37.9099 | 0.0002 | 21.2231 | 8,912.5098 | AID1259243; AID1259247; AID743035; AID743042; AID743054; AID743063 |
| nuclear receptor subfamily 1, group I, member 3 | Homo sapiens (human) | Potency | 28.9240 | 0.0010 | 22.6508 | 76.6163 | AID1224893 |
| progesterone receptor | Homo sapiens (human) | Potency | 24.3365 | 0.0004 | 17.9460 | 75.1148 | AID1346795 |
| glucocorticoid receptor [Homo sapiens] | Homo sapiens (human) | Potency | 39.8107 | 0.0002 | 14.3764 | 60.0339 | AID588533 |
| retinoid X nuclear receptor alpha | Homo sapiens (human) | Potency | 15.8226 | 0.0008 | 17.5051 | 59.3239 | AID588544; AID588546 |
| estrogen-related nuclear receptor alpha | Homo sapiens (human) | Potency | 24.7232 | 0.0015 | 30.6073 | 15,848.9004 | AID1224841; AID1224842; AID1224848; AID1224849; AID1259401; AID1259403 |
| farnesoid X nuclear receptor | Homo sapiens (human) | Potency | 21.8724 | 0.3758 | 27.4851 | 61.6524 | AID743217 |
| estrogen nuclear receptor alpha | Homo sapiens (human) | Potency | 50.4169 | 0.0002 | 29.3054 | 16,493.5996 | AID743069; AID743078 |
| peroxisome proliferator activated receptor gamma | Homo sapiens (human) | Potency | 23.7304 | 0.0010 | 19.4141 | 70.9645 | AID588536; AID588537; AID743094; AID743191 |
| vitamin D (1,25- dihydroxyvitamin D3) receptor | Homo sapiens (human) | Potency | 20.3407 | 0.0237 | 23.2282 | 63.5986 | AID588541; AID743223 |
| cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_a | Homo sapiens (human) | Potency | 34.3762 | 0.0017 | 23.8393 | 78.1014 | AID743083 |
| activating transcription factor 6 | Homo sapiens (human) | Potency | 23.2068 | 0.1434 | 27.6121 | 59.8106 | AID1159516; AID1159519 |
| nuclear factor of kappa light polypeptide gene enhancer in B-cells 1 (p105), isoform CRA_a | Homo sapiens (human) | Potency | 54.9410 | 19.7391 | 45.9784 | 64.9432 | AID1159509 |
| thyroid hormone receptor beta isoform a | Homo sapiens (human) | Potency | 0.1259 | 0.0100 | 39.5371 | 1,122.0200 | AID588547 |
| heat shock protein beta-1 | Homo sapiens (human) | Potency | 24.5412 | 0.0420 | 27.3789 | 61.6448 | AID743210 |
| nuclear factor erythroid 2-related factor 2 isoform 1 | Homo sapiens (human) | Potency | 34.3762 | 0.0006 | 27.2152 | 1,122.0200 | AID743202 |
| Cellular tumor antigen p53 | Homo sapiens (human) | Potency | 55.6246 | 0.0023 | 19.5956 | 74.0614 | AID651631; AID651743 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
Other Measurements
| Protein | Taxonomy | Measurement | Average | Min (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 (124)
Molecular Functions (34)
Ceullar Components (19)
Bioassays (11)
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID227956 | Ratio of kinetic constant Kcat to Km from initial velocity assay against OPAA from Alteromonas sp. JD6.5 | 2000 | Bioorganic & medicinal chemistry letters, Jun-05, Volume: 10, Issue:11 | Substrate and stereochemical specificity of the organophosphorus acid anhydrolase from Alteromonas sp. JD6.5 toward p-nitrophenyl phosphotriesters. |
| AID150556 | Kinetic constant Kcat from initial velocity assay against Organophosphorus acid anhydrolase from Alteromonas sp. JD6.5 | 2000 | Bioorganic & medicinal chemistry letters, Jun-05, Volume: 10, Issue:11 | Substrate and stereochemical specificity of the organophosphorus acid anhydrolase from Alteromonas sp. JD6.5 toward p-nitrophenyl phosphotriesters. |
| AID150557 | Kinetic constant Km from initial velocity assay against Organophosphorus acid anhydrolase from Alteromonas sp. JD6.5 | 2000 | Bioorganic & medicinal chemistry letters, Jun-05, Volume: 10, Issue:11 | Substrate and stereochemical specificity of the organophosphorus acid anhydrolase from Alteromonas sp. JD6.5 toward p-nitrophenyl phosphotriesters. |
| AID1101164 | Resistance index, ratio of bimolecular rate constant Ki for AChE in rganophosphate-resistant clone of Schizaphis graminum OR1 to bimolecular rate constant Ki for AChE in organophosphate-susceptible clone of Schizaphis graminum OSS | 2000 | Journal of agricultural and food chemistry, Oct, Volume: 48, Issue:10 | Comparative toxicity of selected organophosphate insecticides against resistant and susceptible clones of the greenbug, Schizaphis graminum (Homoptera: aphididae). |
| AID1101167 | Inhibition of AChE in organophosphate-susceptible clone of Schizaphis graminum OSS adult or last-instar nymphs homogenates assessed as bimolecular rate constant pre-incubated with compound for 2 min at 25 degC before addition of ATC and DTNB solution | 2000 | Journal of agricultural and food chemistry, Oct, Volume: 48, Issue:10 | Comparative toxicity of selected organophosphate insecticides against resistant and susceptible clones of the greenbug, Schizaphis graminum (Homoptera: aphididae). |
| AID1101165 | Inhibition of AChE in organophosphate-resistant clone of Schizaphis graminum OR2 adult or last-instar nymphs homogenates assessed as bimolecular rate constant pre-incubated with compound for 2 min at 25 degC before addition of ATC and DTNB solution | 2000 | Journal of agricultural and food chemistry, Oct, Volume: 48, Issue:10 | Comparative toxicity of selected organophosphate insecticides against resistant and susceptible clones of the greenbug, Schizaphis graminum (Homoptera: aphididae). |
| AID23272 | Partition coefficient (logP) | 1984 | Journal of medicinal chemistry, May, Volume: 27, Issue:5 | Phosphorus analogues of gamma-aminobutyric acid, a new class of anticonvulsants. |
| AID231138 | Ratio of kinetic constant K1 to K2 from progress curves against OPAA from Alteromonas sp. JD6.5; No data | 2000 | Bioorganic & medicinal chemistry letters, Jun-05, Volume: 10, Issue:11 | Substrate and stereochemical specificity of the organophosphorus acid anhydrolase from Alteromonas sp. JD6.5 toward p-nitrophenyl phosphotriesters. |
| AID1101163 | Resistance index, ratio of bimolecular rate constant Ki for AChE in rganophosphate-resistant clone of Schizaphis graminum OR2 to bimolecular rate constant Ki for AChE in organophosphate-susceptible clone of Schizaphis graminum OSS | 2000 | Journal of agricultural and food chemistry, Oct, Volume: 48, Issue:10 | Comparative toxicity of selected organophosphate insecticides against resistant and susceptible clones of the greenbug, Schizaphis graminum (Homoptera: aphididae). |
| AID231140 | Ratio of kinetic constant Kcat to Km Sp and Kcat to Km Rp from initial velocity assay against OPAA from Alteromonas sp. JD6.5; No data | 2000 | Bioorganic & medicinal chemistry letters, Jun-05, Volume: 10, Issue:11 | Substrate and stereochemical specificity of the organophosphorus acid anhydrolase from Alteromonas sp. JD6.5 toward p-nitrophenyl phosphotriesters. |
| AID1101166 | Inhibition of AChE in organophosphate-resistant clone of Schizaphis graminum OR1 adult or last-instar nymphs homogenates assessed as bimolecular rate constant pre-incubated with compound for 2 min at 25 degC before addition of ATC and DTNB solution | 2000 | Journal of agricultural and food chemistry, Oct, Volume: 48, Issue:10 | Comparative toxicity of selected organophosphate insecticides against resistant and susceptible clones of the greenbug, Schizaphis graminum (Homoptera: aphididae). |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
Research
Studies (61)
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 8 (13.11) | 18.7374 |
| 1990's | 6 (9.84) | 18.2507 |
| 2000's | 26 (42.62) | 29.6817 |
| 2010's | 15 (24.59) | 24.3611 |
| 2020's | 6 (9.84) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
Market Indicators
Research Demand Index: 10.54
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 weak demand-to-supply ratio for research on this compound.
| This Compound (10.54) All Compounds (24.57) |
Study Types
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 68 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||