Structure via PubChem · Public domain (PubChem)
فیپرونیل
Sign in to saveFipronil is a broad-spectrum insecticide that belongs to the phenylpyrazole insecticide class. Fipronil disrupts the insect central nervous system by blocking the ligand-gated ion channel of the GABAA receptor (IRAC group 2B) and glutamate-gated chloride (GluCl) channels. This causes hyperexcitation of contaminated insects' nerves and muscles. Fipronil's specificity towards insects is believed to be due to its greater binding affinity for the GABAA receptors of insects than to those of mammals, and for its action on GluCl channels, which do not exist in mammals. , there does not appear to be s
Chemical data
- Formula
- C12H4Cl2F6N4OS
- Molecular weight
- 437.1 g/mol
- IUPAC name
- 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfinyl)pyrazole-3-carbonitrile
- SMILES
- C1=C(C=C(C(=C1Cl)N2C(=C(C(=N2)C#N)S(=O)C(F)(F)F)N)Cl)C(F)(F)F
- InChIKey
- ZOCSXAVNDGMNBV-UHFFFAOYSA-N
- XLogP
- 4.5
- Polar surface area
- 104 Ų
- H-bond donors
- 1
- H-bond acceptors
- 11
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
2,207 papers- Biodegradation of fipronil: current state of mechanisms of biodegradation and future perspectives.Applied microbiology and biotechnology · 2021
- Recent advances on the influence of fipronil on insect behavior.Current opinion in insect science · 2024
- Insights into the toxicity and biodegradation of fipronil in contaminated environment.Microbiological research · 2023
- Fipronil prevents transmission of Lyme disease spirochetes.Parasitology · 2024
- Fipronil: environmental fate, ecotoxicology, and human health concerns.Reviews of environmental contamination and toxicology · 2003
via PubMed
Wikidata facts
- Subclass of
- alkaloid
- Mass
- 435.939
- Has use
- insecticide
Show 4 more facts
- chemical formula
- C₁₂H₄Cl₂F₆N₄OS
- canonical SMILES
- C1=C(C=C(C(=C1Cl)N2C(=C(C(=N2)C#N)S(=O)C(F)(F)F)N)Cl)C(F)(F)F
- Commons category
- Fipronil
- subject has role
- antiparasitic
Sources (6)
via Wikidata · CC0