Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C7H14N4O3 |
| Molecular Weight | 202.2111 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CNC(NCC1CCOC1)=N[N+]([O-])=O
InChI
InChIKey=YKBZOVFACRVRJN-UHFFFAOYSA-N
InChI=1S/C7H14N4O3/c1-8-7(10-11(12)13)9-4-6-2-3-14-5-6/h6H,2-5H2,1H3,(H2,8,9,10)
| Molecular Formula | C7H14N4O3 |
| Molecular Weight | 202.2111 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 1 |
| Optical Activity | ( + / - ) |
DescriptionCurator's Comment: Description was created based on several sources, including
https://www.mitsuichemicals.com/dinotefuran.htm
Curator's Comment: Description was created based on several sources, including
https://www.mitsuichemicals.com/dinotefuran.htm
Dinotefuran is a new furanicotinyl insecticide which represents the third generation of neonicotinoid group. Dinotefuran, which was developed by Mitsui Chemicals, Inc., was registered in Japan April 24, 2002 and the registration has been submitted to the Environment Protection Agency (EPA) in the USA. Dinotefuran was granted Organophosphorus Alternative and Reduced Risk Status by the EPA. Dinotefuran exhibits a insecticidal activity against Hemiptera, Lepidoptera, Coleoptera, Diptera, Dictyoptera and Thysanoptera. Furthermore, it has very low phytotoxicity so that it can be utilized for many kinds of crops. Dinotefuran is water-soluble and has excellent systemic and translaminar action in many plants. This property enables dinotefuran to be applied using various methods and various formulations. The binding assay using insect nAChRs and the electrophysiological study showed that dinotefuran acted on nAChRs as an agonist. However, in the binding study, the affinity of dinotefuran against the binding site of other neonicotinoids was very low, suggesting that this compound acts on a different site than other neonicotinoids.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: H6BDY5 (H6BDY5_PERAM) |
5.02 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | Vectra 3D Approved UseAVAILABLE FROM LICENSED VETERINARIANS ONLY
- 6-way protection, repels and kills fleas, ticks, mosquitoes, lice, biting and sand flies, and mites (excluding mange mites)
- Repels and kills Brown Dog ticks, American Dog ticks, Deer ticks, and Gulf Coast ticks and Lone Star ticks for one month
- Begins reducing flea feeding in 5 minutes; starts to kill fleas within 2 hours
- Kills all stages of the flea life cycle
- Repels and kills ticks that may cause Lyme disease, Rocky Mountain spotted fever, babesiosis, ehrlichiosis, bartonellosis, hepatozoonosis and anaplasmosis
- Kills biting flies that may transmit fly strike
- Convenient topical treatment that allows application down to skin
- Continues to kill and repel fleas and ticks after shampooing
Vectra 3D spreads over the dog’s body to provide full body protection against fleas, ticks and mosquitoes. |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
40.8 OTHER |
50 mg/kg single, oral dose: 50 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
DINOTEFURAN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
566 OTHER |
1000 mg/kg single, oral dose: 1000 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
DINOTEFURAN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
471 OTHER |
1000 mg/kg single, oral dose: 1000 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
DINOTEFURAN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
45.6 OTHER |
50 mg/kg single, oral dose: 50 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
DINOTEFURAN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
83.3 OTHER |
50 mg/kg single, oral dose: 50 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
DINOTEFURAN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
2660 OTHER |
1000 mg/kg single, oral dose: 1000 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
DINOTEFURAN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
2360 OTHER |
1000 mg/kg single, oral dose: 1000 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
DINOTEFURAN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
110 OTHER |
50 mg/kg single, oral dose: 50 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
DINOTEFURAN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3.64 h |
50 mg/kg single, oral dose: 50 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
DINOTEFURAN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
13.8 h |
1000 mg/kg single, oral dose: 1000 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
DINOTEFURAN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
15.2 h |
1000 mg/kg single, oral dose: 1000 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
DINOTEFURAN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
7.86 h |
50 mg/kg single, oral dose: 50 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
DINOTEFURAN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Cyclopropylamines from N,N-dialkylcarboxamides and Grignard reagents in the presence of titanium tetraisopropoxide or methyltitanium triisopropoxide. | 2010-12-10 |
|
| Neonicotinoid insecticides disrupt predation on the eggs of turf-infesting scarab beetles. | 2010-12 |
|
| Optimizing a basal bark spray of dinotefuran to manage armored scales (Hemiptera: Diaspididae) in Christmas tree plantations. | 2010-10 |
|
| Insect nicotinic acetylcholine receptor agonists as flea adulticides in small animals. | 2010-08 |
|
| Ecotoxicity of neonicotinoid insecticides to bees. | 2010 |
|
| Neonicotinoid insecticides: historical evolution and resistance mechanisms. | 2010 |
|
| Comparative acute toxicity of neonicotinoid and pyrethroid insecticides to non-target crayfish (Procambarus clarkii) associated with rice-crayfish crop rotations. | 2009-11 |
|
| Effect of pesticides on adult rove beetle Atheta coriaria (Coleoptera: Staphylinidae) survival in growing medium. | 2009-10 |
|
| Efficacy of a topical ectoparasiticide containing dinotefuran, pyriproxyfen, and permethrin against Amblyomma americanum (Lone Star tick) and Amblyomma maculatum (Gulf Coast tick) on dogs. | 2009-09-11 |
|
| Comparative in vivo adulticidal activity of a topical dinotefuran versus an imidacloprid-based formulation against cat fleas (Ctenocephalides felis) on cats. | 2009-09-11 |
|
| Control of bagworms (Lepidoptera: Psychidae) using contact and soil-applied systemic insecticides. | 2009-06 |
|
| Systemic insecticides for control of black vine weevil (Coleoptera: Curculionidae) in container- and field-grown nursery crops. | 2009-06 |
|
| Surface-applied insecticide treatments for quarantine control of Japanese beetle, Popillia japonica Newman (Coleoptera: Scarabaeidae), larvae in field-grown nursery plants. | 2009-04 |
|
| Sublethal effects of four insecticides on the reproduction and wing formation of brown planthopper, Nilaparvata lugens. | 2009-02 |
|
| Efficacy of systemic insecticides on the gall wasp Quadrastichus erythrinae in wiliwili trees (Erythrina spp.). | 2009-02 |
|
| Susceptibility to neonicotinoids and risk of resistance development in the brown planthopper, Nilaparvata lugens (Stål) (Homoptera: Delphacidae). | 2008-12 |
|
| Applied aspects of neonicotinoid uses in crop protection. | 2008-11 |
|
| Application timing and efficacy of alternatives for the insecticidal control of Tipula paludosa Meigen (Diptera: Tipulidae), a new invasive pest of turf in the northeastern United States. | 2008-10 |
|
| Toxicity of systemic neonicotinoid insecticides to avocado thrips in nursery avocado trees. | 2007-09 |
|
| Current status of the greenhouse whitefly, Trialeurodes vaporariorum, susceptibility to neonicotinoid and conventional insecticides on strawberries in southern California. | 2007-08 |
|
| Agonist actions of neonicotinoids on nicotinic acetylcholine receptors expressed by cockroach neurons. | 2007-07 |
|
| [Residual activity in vitro of treated dog's hair coat with dinotefuran on larvae and adults of Ctenocephalides felis felis (Bouché, 1835) (Siphonaptera: Pulicidae)]. | 2007-01-29 |
|
| Unique and common metabolites of thiamethoxam, clothianidin, and dinotefuran in mice. | 2006-11 |
|
| A nicotinic acetylcholine receptor mutation (Y151S) causes reduced agonist potency to a range of neonicotinoid insecticides. | 2006-11 |
|
| Effect of insecticides on mealybug destroyer (Coleoptera: Coccinellidae) and parasitoid Leptomastix dactylopii (Hymenoptera: Encyrtidae), natural enemies of citrus mealybug (Homoptera: Pseudococcidae). | 2006-10 |
|
| Automated flow fluorescent immunoassay for part per trillion detection of the neonicotinoid insecticide thiamethoxam. | 2006-06-30 |
|
| Insect nicotinic acetylcholine receptors: neonicotinoid binding site specificity is usually but not always conserved with varied substituents and species. | 2006-05-03 |
|
| Evaluation of insecticides for protecting Southwestern ponderosa pines from attack by engraver beetles (Coleoptera: Curculionidae: Scolytinae). | 2006-04 |
|
| Identification of a high-affinity binding site for dinotefuran in the nerve cord of the American cockroach. | 2006-04 |
|
| Neo-nicotinoid metabolic activation and inactivation established with coupled nicotinic receptor-CYP3A4 and -aldehyde oxidase systems. | 2006-02-20 |
|
| Efficacy of systemic insecticides for protection of loblolly pine against southern pine engraver beetles (Coleoptera: Curculionidae: Scolytinae) and wood borers (Coleoptera: Cerambycidae). | 2006-02 |
|
| Effect of Bacillus thuringiensis subsp. israelensis and neonicotinoid insecticides on the fungus gnat Bradysia sp nr. coprophila (Lintner) (Diptera: Sciaridae). | 2006-02 |
|
| Substrate specificity of rabbit aldehyde oxidase for nitroguanidine and nitromethylene neonicotinoid insecticides. | 2006-01 |
|
| Toxicity of four systemic neonicotinoids to adults of Anoplophora glabripennis (Coleoptera: Cerambycidae). | 2005-12 |
|
| Assessment of cross-resistance potential to neonicotinoid insecticides in Bemisia tabaci (Hemiptera: Aleyrodidae). | 2005-12 |
|
| Neonicotinoid nitroguanidine insecticide metabolites: synthesis and nicotinic receptor potency of guanidines, aminoguanidines, and their derivatives. | 2005-09 |
|
| Neonicotinoid insecticide toxicology: mechanisms of selective action. | 2005 |
|
| Dinotefuran: a potential neonicotinoid insecticide against resistant mosquitoes. | 2004-07 |
|
| Insecticidal activity and nicotinic acetylcholine receptor binding of dinotefuran and its analogues in the housefly, Musca domestica. | 2003-10 |
|
| The discovery of dinotefuran: a novel neonicotinoid. | 2003-09 |
|
| Structural effects of dinotefuran and analogues in insecticidal and neural activities. | 2002-07 |
|
| Interaction of dinotefuran and its analogues with nicotinic acetylcholine receptors of cockroach nerve cords. | 2002-02 |
Sample Use Guides
A novel spot-on formulation combining permethrin, pyriproxifen and dinotefuran (Vectra 3D™ spot-on solution for dogs) was evaluated in adult Beagle dogs in a study to determine adulticidal efficacy, egg laying inhibition and viability of Ctenocephalides felis felis eggs (development and emergence of fleas from the collected eggs). Prior to treatment sixteen dogs were checked for their ability to keep fleas 24 hours after infestation and were allocated to treatment groups: 8 dogs served as untreated controls, and 8 dogs were treated once with the tested formulation. The spot on was administered respecting the laboratory recommendations at a dosage of 65-126 mg/kg of permethrin; 8.9-17.4 mg/kg of dinotefuran and 0.8-1.5mg/kg of pyriproxyfen.
Route of Administration:
Topical
The present study demonstrated the effects of dinotefuran (active ingredient of the acaricide Protetor Pet®) on the ovary and midgut cells of semi engorged R. sanguineus females exposed to different concentrations of this chemical. For this, 120 semi-engorged females were divided into four treatment groups with 30 individuals each: group I or control (distilled water), group II (5000ppm), groups III (6250ppm) and group IV (8334ppm of dinotefuran).
| Substance Class |
Chemical
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| Record UNII |
1W509710WF
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EMA VETERINARY ASSESSMENT REPORTS |
VECTRA 3D [AUTHORIZED]
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EPA PESTICIDE CODE |
44312
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EMA VETERINARY ASSESSMENT REPORTS |
VECTRA FELIS [ AUTHORIZED]
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SUB122664
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DINOTEFURAN
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