Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C12H4Cl2F6N4OS |
| Molecular Weight | 437.148 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=C([S+]([O-])C(F)(F)F)C(=NN1C2=C(Cl)C=C(C=C2Cl)C(F)(F)F)C#N
InChI
InChIKey=ZOCSXAVNDGMNBV-UHFFFAOYSA-N
InChI=1S/C12H4Cl2F6N4OS/c13-5-1-4(11(15,16)17)2-6(14)8(5)24-10(22)9(7(3-21)23-24)26(25)12(18,19)20/h1-2H,22H2
| Molecular Formula | C12H4Cl2F6N4OS |
| Molecular Weight | 437.148 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including:
http://www.pan-uk.org/pestnews/Actives/fipronil.htm
http://npic.orst.edu/factsheets/archive/fiptech.html
http://fluoridealert.org/wp-content/pesticides/fipronil--page.htm
Curator's Comment: description was created based on several sources, including:
http://www.pan-uk.org/pestnews/Actives/fipronil.htm
http://npic.orst.edu/factsheets/archive/fiptech.html
http://fluoridealert.org/wp-content/pesticides/fipronil--page.htm
Fipronil is a member of the phenyl pyrazole class of pesticides, which are principally chemicals with a herbicidal effect. Fipronil, however, acts as an insecticide with contact and stomach action. Fipronil is an extremely active molecule and is a potent disruptor of the insect central nervous system via the (-aminobutyric acid (GABA) regulated chloride channel. Fipronil is classed as a WHO Class II moderately hazardous pesticide. Cutaneous skin reactions appear to be the most common adverse drug experiences reported for fipronil in dogs and cats.Animals exposed to large doses of fipronil via accidental oral absorption are expected to display seizures, and neurological and hepatic function should be monitored. There appear to be no reported interactions between fipronil and approved companion animal drugs and ectoparasiticides.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: Insect GABAA-gated chloride channels |
4.0 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | Frontline Approved UseFipronil provides convenient and effective flea control for dogs and puppies. |
|||
| Curative | Frontline Approved UseFipronil provides convenient and effective tick control for dogs and puppies. |
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| Curative | Frontline Approved UseFipronil provides convenient and effective chewing lice control for dogs and puppies. |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Fipronil is a potent open channel blocker of glutamate-activated chloride channels in cockroach neurons. | 2004-07 |
|
| GABA receptor antagonists and insecticides: common structural features of 4-alkyl-1-phenylpyrazoles and 4-alkyl-1-phenyltrioxabicyclooctanes. | 2004-06-15 |
|
| Effective treatment and control of biting lice, Felicola subrostratus (Nitzsch in Burmeister, 1838), on cats using fipronil formulations. | 2004-05-07 |
|
| Off-label treatment for otoacariosis. | 2004-05-01 |
|
| Insecticide resistance and cross-resistance in Alabama and Florida strains of Culex quinquefasciatus [correction]. | 2004-05 |
|
| Fipronil modulation of GABAA receptor single-channel currents. | 2004-05 |
|
| In vitro metabolism of fipronil by human and rat cytochrome P450 and its interactions with testosterone and diazepam. | 2004-04-15 |
|
| Determination of poultry feed-through insecticide activity in an in vivo anticoccidial assay. | 2004-04 |
|
| Impacts of residual insecticide barriers on perimeter-invading ants, with particular reference to the odorous house ant, Tapinoma sessile. | 2004-04 |
|
| Current trends in the treatment of Sarcoptes, Cheyletiella and Otodectes mite infestations in dogs and cats. | 2004-04 |
|
| An enzyme-linked immunosorbent assay for lipovitellin quantification in copepods: a screening tool for endocrine toxicity. | 2004-02 |
|
| Phenylpyrazole insecticide fipronil induces male infertility in the estuarine meiobenthic crustacean Amphiascus tenuiremis. | 2004-01-15 |
|
| Reproductive adverse effects of fipronil in Wistar rats. | 2004-01-15 |
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| Fipronil effects on estuarine copepod (Amphiascus tenuiremis) development, fertility, and reproduction: a rapid life-cycle assay in 96-well microplate format. | 2004-01 |
|
| The fate of fipronil in modular estuarine mesocosms. | 2004-01 |
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| Insecticidal activity of the enantiomers of fipronil. | 2003-12 |
|
| Fipronil modulation of glutamate-induced chloride currents in cockroach thoracic ganglion neurons. | 2003-12 |
|
| Chloride channels as tools for developing selective insecticides. | 2003-12 |
|
| Phenylpyrazole insecticide photochemistry, metabolism, and GABAergic action: ethiprole compared with fipronil. | 2003-11-19 |
|
| Synthesis of a tritium-labeled, fipronil-based, highly potent, photoaffinity probe for the GABA receptor. | 2003-10-17 |
|
| Origin and extent of resistance to fipronil in the German cockroach, Blattella germanica (L.) (Dictyoptera: Blattellidae). | 2003-10 |
|
| Effects of fipronil and chlorpyrifos on endocrine-related endpoints in female grass shrimp (Palaemonetes pugio). | 2003-09 |
|
| Differential actions of fipronil and dieldrin insecticides on GABA-gated chloride channels in cockroach neurons. | 2003-09 |
|
| Comparison of the activity of selamectin, fipronil, and imidacloprid against flea larvae (Ctenocephalides felis felis) in vitro. | 2003-08-29 |
|
| Improvement of German cockroach (Dictyoptera: Blattellidae) population control by fragmented distribution of gel baits. | 2003-08 |
|
| Evaluation of K9 Advantix vs. Frontline Plus topical treatments to repel brown dog ticks (Rhipicephalus sanguineus) on dogs. | 2003-07 |
|
| Toxicity and pathogenicity of Metarhizium anisopliae var. acridum (Deuteromycotina, Hyphomycetes) and fipronil to the fringe-toed lizard Acanthodactylus dumerili (Squamata: Lacertidae). | 2003-07 |
|
| Effects of boric acid, fipronil, hydramethylnon, and diflubenzuron baits on colonies of ghost ants (Hymenoptera: Formicidae). | 2003-06 |
|
| Determining the foraging range and origin of resurgence after treatment of Argentine ant (Hymenoptera: Formicidae) in urban areas. | 2003-06 |
|
| Operational note effects of fipronil and lambda-cyhalothrin against larval Anopheles quadrimaculatus and nontarget aquatic mosquito predators in Arkansas small rice plots. | 2003-06 |
|
| RdlDv, a novel GABA-gated chloride channel gene from the American dog tick Dermacentor variabilis. | 2003-06 |
|
| The pharmacology of spontaneously open alpha 1 beta 3 epsilon GABA A receptor-ionophores. | 2003-06 |
|
| Toxicity, repellency, and horizontal transmission of fipronil in the formosan subterranean termite (Isoptera: Rhinotermitidae). | 2003-04 |
|
| Effects of exposure duration on transfer of nonrepellent termiticides among workers of Coptotermes formosanus Shiraki (Isoptera: Rhinotermitidae). | 2003-04 |
|
| Horizontal and trophic transfer of diflubenzuron and fipronil among grasshoppers (Melanoplus sanguinipes) and between grasshoppers and darkling beetles (Tenebrionidae). | 2003-04 |
|
| Impact of fipronil on crustacean aquatic organisms in a paddy field-fishpond ecosystem. | 2003-04 |
|
| Comparative speed of kill between nitenpyram, fipronil, imidacloprid, selamectin and cythioate against adult Ctenocephalides felis (Bouché) on cats and dogs. | 2003-03-10 |
|
| Genetically engineered corn rootworm resistance: potential for reduction of human health effects from pesticides. | 2003-03 |
|
| Toxicity of the insecticides fipronil and endosulfan to selected life stages of the grass shrimp (Palaemonetes pugio). | 2003-03 |
|
| Assay of fipronil efficacy to prevent canine monocytic ehrlichiosis in endemic areas. | 2003-02-28 |
|
| Fipronil metabolism and dissipation in a simplified aquatic ecosystem. | 2003-02-26 |
|
| Evaluation of fipronil spot-on in the treatment of flea allergic dermatitis in dogs. | 2003-02 |
|
| ICON rice seed treatment toxicity to crayfish (Procambarus clarkii) in experimental rice paddies. | 2003-01 |
|
| A case of accidental ingestion of ant bait containing fipronil. | 2003 |
|
| Fipronil: environmental fate, ecotoxicology, and human health concerns. | 2003 |
|
| Simple method for the determination of trace levels of pesticides in honeybees using matrix solid-phase dispersion and gas chromatography. | 2002-12-27 |
|
| Preference of food particle size among several urban ant species. | 2002-12 |
|
| [An experimental tool essential for the evaluation of insecticides: the testing huts]. | 2002-11 |
|
| Efficacy of Fipronil and Propoxur in the control of German cockroaches (Dictyoptera: Blatellidae). | 2002-03 |
|
| Cabbage root fly control using non-organophosphorus insecticides. | 2001 |
Sample Use Guides
Dogs, small 2 to 10 kg = ≤22 lbs. bw: 1 pipette with 0.67 mL (equivalent to 32.5 - 6.5 mg/kg fipronil)
Dogs, medium 10 to 20 kg ≈23 to 44 lbs. bw: 1 pipette with 1.34 mL (equivalent to 13.0 - 6.5 mg/kg fipronil)
Dogs, large 20 to 40 kg ≈45 to 88 lbs. bw: 1 pipette with 2.68 mL (equivalent to 13.0 - 6.5 mg/kg fipronil)
Dogs, very large >40 kg =>88 lbs. bw: 1 pipette with 4.02 mL (equivalent to ≤9.7 mg/kg fipronil)
Cats ≥1 kg =≥2.2 lbs. bw: 1 pipette with 0.5 mL (equivalent to ≤48.5 mg/kg fipronil)
Route of Administration:
Topical
| Substance Class |
Chemical
Created
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admin
on
Edited
Mon Mar 31 18:04:09 GMT 2025
by
admin
on
Mon Mar 31 18:04:09 GMT 2025
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| Record UNII |
QGH063955F
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| Record Status |
Validated (UNII)
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WHO-VATC |
QP53AX65
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WHO-VATC |
QP53AX15
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EMA VETERINARY ASSESSMENT REPORTS |
BROADLINE (AUTHORIZED)
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NCI_THESAURUS |
C737
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EPA PESTICIDE CODE |
129121
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EMA VETERINARY ASSESSMENT REPORTS |
CERTIFECT (WITHDRAWN)
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CHEMBL101326
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fipronil
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m5386
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1433761
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ACTIVE MOIETY |
