Page last updated: 2024-11-12
tolfenpyrad
Description
Research Excerpts
Clinical Trials
Roles
Classes
Pathways
Study Profile
Bioassays
Related Drugs
Related Conditions
Protein Interactions
Research Growth
Market Indicators
Description
tolfenpyrad: insecticide; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
tolfenpyrad : An aromatic amide obtained by formal condensation of the carboxy group of 4-chloro-3-ethyl-1-methylpyrazole-5-carboxylic acid with the amino group of 1-[4-(4-methylphenoxy)phenyl]methylamine. [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 Source | ID |
|---|---|
| PubMed CID | 10110536 |
| CHEMBL ID | 2229099 |
| CHEBI ID | 38628 |
| SCHEMBL ID | 26416 |
| MeSH ID | M0555778 |
Synonyms (41)
| Synonym |
|---|
| 129558-76-5 |
| 4-chloro-3-ethyl-1-methyl-n-(4-(p-tolyloxy)benzyl)pyrazole-5-carboxamide |
| 4-chloro-3-ethyl-1-methyl-n-[4-(4-methylphenoxy)benzyl]-1h-pyrazole-5-carboxamide |
| CHEBI:38628 , |
| tolfenpyrad |
| 4-chloro-5-ethyl-2-methyl-n-[[4-(4-methylphenoxy)phenyl]methyl]pyrazole-3-carboxamide |
| C18491 |
| unii-oha74571qt |
| omi 88 |
| 4-chloro-3-ethyl-1-methyl-n-((4-(4-methylphenoxy)phenyl)methyl)-1h-pyrazole-5-carboxamide |
| oha74571qt , |
| tolfenpyrad [iso] |
| FT-0675271 |
| 4-chloro-3-ethyl-1-methyl-n-(4-(p-tolyloxy)benzyl)-1h-pyrazole-5-carboxamide |
| 4-chloro-3-ethyl-1-methyl-n-(4-(p-tolyloxy)benzyl)-1h-pyrazole-5-carboxamide;4-chloro-3-ethyl-1-methyl-n-[4-(p-tolyloxy)benzyl]pyrazole-5-carboxamide;4-chloro-3-ethyl-1-methyl-n-[[4-(4-methylphenoxy)phenyl]methyl]-1h-pyrazole-5-carboxamide;tolfenpyrad |
| SC10169 |
| AKOS015911384 |
| CHEMBL2229099 |
| CS-3302 |
| HY-17516 |
| SCHEMBL26416 |
| T3774 |
| DTXSID6057952 |
| n-[4-(4-methylphenoxy)benzyl]-4-chloro-3-ethyl-1-methyl-5-pyrazolecarboxamide |
| J-005692 |
| tolfenpyrad, pestanal(r), analytical standard |
| tolfenpyrad 10 microg/ml in acetonitrile |
| mfcd08273850 |
| NCGC00390682-01 |
| mmv688934 |
| 4-chloro-3-ethyl-1-methyl-n-(4-(p-tolyloxy)-benzyl)-1h-pyrazole-5-carboxamide |
| BCP24108 |
| 4-chloro-3-ethyl-1-methyl-n-[4-(p-tolyloxy)benzyl]pyrazole-5-carboxamide |
| tolfenpyrad 1000 microg/ml in acetone |
| AS-17574 |
| Q19310096 |
| 1ST20420 |
| 1h-pyrazole-5-carboxamide, 4-chloro-3-ethyl-1-methyl-n-[[4-(4-methylphenoxy)phenyl]methyl]- |
| sr-05000022482 |
| SR-05000022482-1 |
| 1h-pyrazole-5-carboxamide, 4-chloro-3-ethyl-1-methyl-n-[[4-(4-ethylphenoxy)phenyl]methyl]- |
Research Excerpts
Overview
Tolfenpyrad (TFP) is a novel pyrazole heterocyclic insecticide. It is an alternative to highly water-soluble and ecotoxic insecticides that is widely used in China.
Bioavailability
| Excerpt | Reference | Relevance |
|---|---|---|
| "The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs." | ( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019) | 0.51 |
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
Roles (4)
| Role | Description |
|---|---|
| mitochondrial NADH:ubiquinone reductase inhibitor | null |
| agrochemical | An agrochemical is a substance that is used in agriculture or horticulture. |
| EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor | An EC 1.3.5.* (oxidoreductase acting on CH-CH of donor with a quinone or related compound as acceptor) inhibitor that interferes with the action of succinate dehydrogenase (quinone), EC 1.3.5.1. |
| antifungal agent | An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce. |
| [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 (4)
| Class | Description |
|---|---|
| pyrazole insecticide | |
| aromatic amide | An amide in which the amide linkage is bonded directly to an aromatic system. |
| aromatic ether | Any ether in which the oxygen is attached to at least one aryl substituent. |
| organochlorine compound | An organochlorine compound is a compound containing at least one carbon-chlorine bond. |
| [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 (7)
Potency Measurements
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| cytochrome P450 family 3 subfamily A polypeptide 4 | Homo sapiens (human) | Potency | 8.4866 | 0.0123 | 7.9835 | 43.2770 | AID1645841 |
| G | Vesicular stomatitis virus | Potency | 5.3547 | 0.0123 | 8.9648 | 39.8107 | AID1645842 |
| cytochrome P450 2D6 | Homo sapiens (human) | Potency | 15.0916 | 0.0010 | 8.3798 | 61.1304 | AID1645840 |
| Interferon beta | Homo sapiens (human) | Potency | 5.3547 | 0.0033 | 9.1582 | 39.8107 | AID1645842 |
| HLA class I histocompatibility antigen, B alpha chain | Homo sapiens (human) | Potency | 5.3547 | 0.0123 | 8.9648 | 39.8107 | AID1645842 |
| Inositol hexakisphosphate kinase 1 | Homo sapiens (human) | Potency | 5.3547 | 0.0123 | 8.9648 | 39.8107 | AID1645842 |
| cytochrome P450 2C9, partial | Homo sapiens (human) | Potency | 5.3547 | 0.0123 | 8.9648 | 39.8107 | AID1645842 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
Biological Processes (45)
Molecular Functions (18)
Ceullar Components (22)
Bioassays (20)
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1082794 | Stomach toxicity against third-instars Helicoverpa armigera assessed as larvicidal activity at 11 mg/kg at 25 +/- 1 degC after 3 days | 2012 | Journal of agricultural and food chemistry, Feb-15, Volume: 60, Issue:6 | Design, synthesis, and insecticidal activity of novel pyrazole derivatives containing α-hydroxymethyl-N-benzyl carboxamide, α-chloromethyl-N-benzyl carboxamide, and 4,5-dihydrooxazole moieties. |
| AID1082791 | Stomach toxicity against third-instars Helicoverpa armigera assessed as larvicidal activity at 110 mg/kg at 25 +/- 1 degC after 3 days | 2012 | Journal of agricultural and food chemistry, Feb-15, Volume: 60, Issue:6 | Design, synthesis, and insecticidal activity of novel pyrazole derivatives containing α-hydroxymethyl-N-benzyl carboxamide, α-chloromethyl-N-benzyl carboxamide, and 4,5-dihydrooxazole moieties. |
| AID1743961 | Selectivity index, ratio of IC50 for toxicity in rat FAO cells assessed as reduction in cellular respiration to IC50 for inhibition of Haemonchus contortus by L4 development assay | 2021 | Journal of medicinal chemistry, 01-14, Volume: 64, Issue:1 | 1-Methyl-1 |
| AID1743959 | Toxicity in orally dosed Swiss mouse assessed as induction of observable clinical effects measured 2 to 4 days after dosing | 2021 | Journal of medicinal chemistry, 01-14, Volume: 64, Issue:1 | 1-Methyl-1 |
| AID1743960 | Toxicity in human MCF-10A cells | 2021 | Journal of medicinal chemistry, 01-14, Volume: 64, Issue:1 | 1-Methyl-1 |
| AID1082798 | Stomach toxicity against third-instars Helicoverpa armigera assessed as larvicidal activity at 25 +/- 1 degC after 3 days | 2012 | Journal of agricultural and food chemistry, Feb-15, Volume: 60, Issue:6 | Design, synthesis, and insecticidal activity of novel pyrazole derivatives containing α-hydroxymethyl-N-benzyl carboxamide, α-chloromethyl-N-benzyl carboxamide, and 4,5-dihydrooxazole moieties. |
| AID1743958 | Inhibition of Haemonchus contortus by L4 development assay | 2021 | Journal of medicinal chemistry, 01-14, Volume: 64, Issue:1 | 1-Methyl-1 |
| AID1743967 | Toxicity in Swiss mouse assessed as induction of reversible motor depression at 5 mg/kg, po measured at first 15 mins post dosing | 2021 | Journal of medicinal chemistry, 01-14, Volume: 64, Issue:1 | 1-Methyl-1 |
| AID1082796 | Stomach toxicity against Plutella xylostella (diamondback moth) assessed as larvicidal activity at 600 mg/kg by leaf dip method | 2012 | Journal of agricultural and food chemistry, Feb-15, Volume: 60, Issue:6 | Design, synthesis, and insecticidal activity of novel pyrazole derivatives containing α-hydroxymethyl-N-benzyl carboxamide, α-chloromethyl-N-benzyl carboxamide, and 4,5-dihydrooxazole moieties. |
| AID1743964 | Toxicity in rat FAO cells assessed as reduction in cell proliferation incubated for 48 hrs by crystal violet staining based assay | 2021 | Journal of medicinal chemistry, 01-14, Volume: 64, Issue:1 | 1-Methyl-1 |
| AID1743966 | Toxicity in rat FAO cells assessed as reduction in cellular respiration incubated over 1 hrs by extracellular flux analyzer based assay | 2021 | Journal of medicinal chemistry, 01-14, Volume: 64, Issue:1 | 1-Methyl-1 |
| AID1082797 | Stomach toxicity against Plutella xylostella (diamondback moth) assessed as larvicidal activity at 200 mg/kg by leaf dip method | 2012 | Journal of agricultural and food chemistry, Feb-15, Volume: 60, Issue:6 | Design, synthesis, and insecticidal activity of novel pyrazole derivatives containing α-hydroxymethyl-N-benzyl carboxamide, α-chloromethyl-N-benzyl carboxamide, and 4,5-dihydrooxazole moieties. |
| AID1082793 | Stomach toxicity against third-instars Helicoverpa armigera assessed as larvicidal activity at 22 mg/kg at 25 +/- 1 degC after 3 days | 2012 | Journal of agricultural and food chemistry, Feb-15, Volume: 60, Issue:6 | Design, synthesis, and insecticidal activity of novel pyrazole derivatives containing α-hydroxymethyl-N-benzyl carboxamide, α-chloromethyl-N-benzyl carboxamide, and 4,5-dihydrooxazole moieties. |
| AID1082795 | Stomach toxicity against third-instars Helicoverpa armigera assessed as larvicidal activity at 5.5 mg/kg at 25 +/- 1 degC after 3 days | 2012 | Journal of agricultural and food chemistry, Feb-15, Volume: 60, Issue:6 | Design, synthesis, and insecticidal activity of novel pyrazole derivatives containing α-hydroxymethyl-N-benzyl carboxamide, α-chloromethyl-N-benzyl carboxamide, and 4,5-dihydrooxazole moieties. |
| AID1082792 | Stomach toxicity against third-instars Helicoverpa armigera assessed as larvicidal activity at 55 mg/kg at 25 +/- 1 degC after 3 days | 2012 | Journal of agricultural and food chemistry, Feb-15, Volume: 60, Issue:6 | Design, synthesis, and insecticidal activity of novel pyrazole derivatives containing α-hydroxymethyl-N-benzyl carboxamide, α-chloromethyl-N-benzyl carboxamide, and 4,5-dihydrooxazole moieties. |
| AID1347160 | Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors | 2020 | Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49 | Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors. |
| AID1296008 | Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening | 2020 | SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1 | Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening. |
| AID1346987 | P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
| AID1346986 | P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
| AID1347159 | Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay | 2020 | Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49 | Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
Research
Studies (24)
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 0 (0.00) | 29.6817 |
| 2010's | 10 (41.67) | 24.3611 |
| 2020's | 14 (58.33) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
Market Indicators
Research Demand Index: 43.92
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 strong demand-to-supply ratio for research on this compound.
| This Compound (43.92) All Compounds (24.57) |
Study Types
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 1 (4.17%) | 6.00% |
| Case Studies | 3 (12.50%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 20 (83.33%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||