Cyphenothrin is a synthetic pyrethroid insecticide that is widely used to control a variety of pests in agriculture, public health, and household settings. It is a chiral molecule, and the trans-isomer is significantly more active than the cis-isomer. Cyphenothrin is synthesized through a multi-step process involving the coupling of a phenoxymethyl group to an alpha-cyano-3-phenoxybenzyl alcohol. The compound acts as an insecticide by interfering with the nervous system of insects. It binds to voltage-gated sodium channels, preventing the flow of sodium ions and ultimately leading to paralysis and death. Cyphenothrin is highly effective against a broad range of pests, including moths, beetles, flies, and mosquitoes. Its importance lies in its ability to control agricultural pests and vectors of diseases, contributing to increased crop yields and reduced disease transmission. However, cyphenothrin can also be toxic to aquatic organisms, especially fish, and its use has been associated with environmental pollution. Therefore, it is crucial to use cyphenothrin responsibly and in accordance with recommended guidelines to minimize potential risks. Research on cyphenothrin focuses on areas such as its mode of action, environmental fate and effects, resistance development, and potential for human health hazards.'
cyphenothrin: RN given refers to unlabeled cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 38283 |
| CHEMBL ID | 3182113 |
| CHEBI ID | 31450 |
| SCHEMBL ID | 26783 |
| MeSH ID | M0145366 |
| Synonym |
|---|
| s-2703 , |
| cyphenothrin [iso] |
| cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, cyano(3-phenoxyphenyl)methyl ester |
| einecs 254-484-5 |
| sp 2703 |
| s 2703 forte |
| s 2703 |
| gokilaht |
| alpha-cyano-3-phenoxybenzyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate |
| NCGC00181753-01 |
| cyphenothrin |
| 39515-40-7 |
| d.d-t-cyphenothrin (jan) |
| D01511 |
| d.d-t-cyphenothrin |
| CHEBI:31450 , |
| cyano(3-phenoxyphenyl)methyl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate |
| [cyano-(3-phenoxyphenyl)methyl] 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate |
| cyano(3-phenoxyphenyl)methyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate |
| FJDPATXIBIBRIM-UHFFFAOYSA-N |
| dtxcid2012536 |
| dtxsid4032536 , |
| tox21_301919 |
| NCGC00255243-01 |
| cas-39515-40-7 |
| 2,2-dimethyl-3-(2-methylprop-1-enyl)-1-cyclopropanecarboxylic acid [cyano-(3-phenoxyphenyl)methyl] ester |
| A824594 |
| smr001564097 |
| MLS004712077 |
| [cyano-(3-phenoxyphenyl)methyl] 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate |
| hsdb 8429 |
| ccris 9268 |
| s0iu5y1r32 , |
| unii-s0iu5y1r32 |
| FT-0639550 |
| SCHEMBL26783 |
| cyano-3-phenoxybenzyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate |
| cyphenothrin [mi] |
| 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropane carboxylic acid cyano(3-phenoxyphenyl)methyl ester |
| chifenothrine |
| .alpha.-cyano-3-phenoxybenzyl chrysanthemate |
| cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)-, cyano(3-phenoxyphenyl)methyl ester |
| d.d-t-cyphenothrin [jan] |
| s-2703 forte |
| .alpha.-cyano-m-phenoxybenzyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate |
| CHEMBL3182113 |
| AKOS027340221 |
| cyphenothrin, pestanal(r), analytical standard |
| Q5200219 |
| mfcd01960864 |
| AS-15556 |
| cyano(3-phenoxyphenyl)methyl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate |
| Excerpt | Reference | Relevance |
|---|---|---|
| "To address concerns around age-related sensitivity to pyrethroids, a life-stage physiologically based pharmacokinetic (PBPK) model, supported by in vitro to in vivo extrapolation (IVIVE) was developed." | ( Development and Application of a Life-Stage Physiologically Based Pharmacokinetic (PBPK) Model to the Assessment of Internal Dose of Pyrethroids in Humans. Clewell, HJ; Creek, MR; Efremenko, AY; Hinderliter, P; Hines, RN; Lake, BG; Mallick, P; Moreau, M; Osimitz, TG; Pendse, SN; Song, G; Yoon, M, 2020) | 0.56 |
| Excerpt | Relevance | Reference |
|---|---|---|
| " Environmental Protection Agency (EPA) current standard operating procedures (SOP) for pet products (assuming 5% dermal absorption), although the maximum absorbed dosage of one child on one day was equivalent to the default value derived from the SOPs." | ( Cyphenothrin Flea and Tick Squeeze-On for Dogs: Evaluation of Potential Health Risks Based on the Results of Observational Biological Monitoring. Carlson, D; Driver, JH; Holden, LR; Nouvel, L; Ross, JH; Selim, S; Sharp, JK, 2015) | 1.86 |
| Role | Description |
|---|---|
| pyrethroid ester insecticide | null |
| agrochemical | An agrochemical is a substance that is used in agriculture or horticulture. |
| [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] | |
| Class | Description |
|---|---|
| cyclopropanecarboxylate ester | A carboxylic ester resulting from the formal condensation of the hydroxy group of an alcohol or phenol with the carboxy group of cyclopropanecarboxylic acid or its substituted derivatives. |
| [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 | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| AR protein | Homo sapiens (human) | Potency | 58.1965 | 0.0002 | 21.2231 | 8,912.5098 | AID743063 |
| nuclear receptor subfamily 1, group I, member 3 | Homo sapiens (human) | Potency | 61.1306 | 0.0010 | 22.6508 | 76.6163 | AID1224839 |
| progesterone receptor | Homo sapiens (human) | Potency | 43.2771 | 0.0004 | 17.9460 | 75.1148 | AID1346795 |
| pregnane X nuclear receptor | Homo sapiens (human) | Potency | 17.2289 | 0.0054 | 28.0263 | 1,258.9301 | AID1346982 |
| thyroid stimulating hormone receptor | Homo sapiens (human) | Potency | 61.1306 | 0.0016 | 28.0151 | 77.1139 | AID1224843 |
| 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 2 | Rattus norvegicus (Norway rat) | Potency | 68.5896 | 0.0003 | 23.4451 | 159.6830 | AID743065; AID743067 |
| Cellular tumor antigen p53 | Homo sapiens (human) | Potency | 30.6379 | 0.0023 | 19.5956 | 74.0614 | AID651631 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 1 (5.56) | 18.7374 |
| 1990's | 2 (11.11) | 18.2507 |
| 2000's | 7 (38.89) | 29.6817 |
| 2010's | 6 (33.33) | 24.3611 |
| 2020's | 2 (11.11) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
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.
| This Compound (31.89) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 1 (5.56%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 1 (5.56%) | 0.25% |
| Other | 16 (88.89%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||