| Name | GABA receptor (protein family or complex) |
|---|---|
| Synonyms | GABA receptor; GABA receptors; GABA(A) receptor; GABA(A) receptors; Gamma aminobutyric acid receptor; Gamma aminobutyric acid receptors |
| Name | fipronil |
|---|---|
| CAS |
| PubMed | Abstract | RScore(About this table) | |
|---|---|---|---|
| 19572480 | Varro P, Gyori J, Vilagi I: In vitro effects of fipronil on neuronal excitability in mammalian and molluscan nervous systems. Ann Agric Environ Med. 2009 Jun;16(1):71-7. These experiments confirmed that fipronil toxicity is mediated by GABA receptors in the nervous system of invertebrates as well as vertebrates. |
82(1,1,1,2) | Details |
| 12370061 | Narahashi T: Nerve membrane ion channels as the target site of insecticides. Mini Rev Med Chem. 2002 Aug;2(4):419-32. Dieldrin, lindane and fipronil block GABA receptors. |
82(1,1,1,2) | Details |
| 15154517 | Ikeda T, Nagata K, Kono Y, Yeh JZ, Narahashi T: Fipronil modulation of GABAA receptor single-channel currents. Pest Manag Sci. 2004 May;60(5):487-92. Although fipronil is known to inhibit GABA receptors, the detailed mechanism of action remains to be seen. |
81(1,1,1,1) | Details |
| 18651916 | Hirata K, Ishida C, Eguchi Y, Sakai K, Ozoe F, Ozoe Y, Matsuda K: Role of a serine residue (S278) in the pore-facing region of the housefly -gated chloride channel in determining sensitivity to noncompetitive antagonists. Insect Mol Biol. 2008 Aug;17(4):341-50. Gamma-hexachlorocyclohexane (gamma-HCH), fipronil and picrotoxinin are noncompetitive antagonists (NCAs) of -gated channels (GluCls), yet their potencies are weaker than those on gamma-aminobutyric acid receptors (GABARs). |
81(1,1,1,1) | Details |
| 15214624 | Chodorowski Z, Anand JS: Accidental dermal and inhalation exposure with fipronil--a case report. J Toxicol Clin Toxicol. 2004;42(2):189-90. BACKGROUND: Fipronil which has initiated the new generation of insecticides and possesses greater affinity at GABA receptors in insects than humans is supposed to be safer than the old generation of insecticides. |
81(1,1,1,1) | Details |
| 10952672 | Grolleau F, Sattelle DB: Single channel analysis of the blocking actions of BIDN and fipronil on a Drosophila melanogaster GABA receptor (RDL) stably expressed in a Drosophila cell line. Br J Pharmacol. 2000 Aug;130(8):1833-42. |
38(0,1,2,3) | Details |
| 14535785 | Sammelson RE, Casida JE: Synthesis of a tritium-labeled, fipronil-based, highly potent, photoaffinity probe for the GABA receptor. J Org Chem. 2003 Oct 17;68(21):8075-9. |
37(0,1,2,2) | Details |
| 17675213 | Ju XL, Hao YL, Pei JF, Ozoe Y: Investigation of structural requirements for inhibitory activity at the rat and housefly picrotoxinin binding sites in ionotropic GABA receptors using DISCOtech and CoMFA. Chemosphere. 2007 Oct;69(6):864-71. Epub 2007 Aug 1. These compounds consist of three diverse types of noncompetitive GABA receptor antagonists, i.e., trioxabicyclooctanes and their derivatives, picrodendrins and related terpenoids, and fipronil and its analogs. |
35(0,1,1,5) | Details |
| 11677140 | Sirisoma NS, Ratra GS, Tomizawa M, Casida JE: Fipronil-based photoaffinity probe for Drosophila and human beta 3 GABA receptors. Bioorg Med Chem Lett. 2001 Nov 19;11(22):2979-81. Modification of the major insecticide fipronil (1) by replacing three pyrazole substituents for both cyano and amino and trifluoromethyldiazirinyl for trifluoromethylsulfinyl) gives a candidate photoaffinity probe (3) of high potency (IC (50) 2-28 nM) in blocking the chloride channel of Drosophila and human beta 3 GABA receptors. |
37(0,1,2,2) | Details |
| 14611171 | Caboni P, Sammelson RE, Casida JE: Phenylpyrazole insecticide photochemistry, metabolism, and GABAergic action: ethiprole compared with fipronil. J Agric Food Chem. 2003 Nov 19;51(24):7055-61. High biological activity is observed for the sulfide, sulfoxide, sulfone, and desulfinyl derivatives in both the ethiprole and the fipronil series in GABA receptor assays (human recombinant beta3 homomer and house fly head membranes) with [(3) H] EBOB and in topical toxicity to house flies with and without the P450-inhibiting synergist piperonyl butoxide. |
32(0,1,1,2) | Details |
| 17615118 | Narahashi T, Zhao X, Ikeda T, Nagata K, Yeh JZ: Differential actions of insecticides on target sites: basis for selective toxicity. Hum Exp Toxicol. 2007 Apr;26(4):361-6. Fipronil, a phenylpyrazole, is known to act on the gamma-aminobutyric acid receptor to block the chloride channel. |
32(0,1,1,2) | Details |
| 15135087 | Tang J, Amin Usmani K, Hodgson E, Rose RL: In vitro metabolism of fipronil by human and rat cytochrome P450 and its interactions with and diazepam. Chem Biol Interact. 2004 Apr 15;147(3):319-29. Fipronil (5-amino-1-[2,6-dichloro-4-(trifluoromethyl) phenyl]-4-[(trifluoromethyl) su lfinyl]-1H-pyrazole-3-carbonitrile) is a highly active, broad spectrum insecticide from the phenyl pyrazole family, which targets the gamma-amino (GABA) receptor. |
31(0,1,1,1) | Details |
| 16172884 | Raymond-Delpech V, Matsuda K, Sattelle BM, Rauh JJ, Sattelle DB: Ion channels: molecular targets of neuroactive insecticides. Invert Neurosci. 2005 Nov;5(3-4):119-33. Epub 2005 Oct 24. The examples discussed include, channels (pyrethroids, p,p'-dichlorodiphenyl-trichloroethane (DDT), dihydropyrazoles and oxadiazines); nicotinic acetylcholine receptors (cartap, spinosad, imidacloprid and related nitromethylenes/nitroguanidines); (GABA) receptors (cyclodienes, gamma-BHC and fipronil) and receptors (avermectins). |
31(0,1,1,1) | Details |
| 16336717 | Garcia del Pino F, Jove M: Compatibility of entomopathogenic nematodes with fipronil. . J Helminthol. 2005 Dec;79(4):333-7. The survival and infectivity of infective juveniles (IJs) of three species of entomopathogenic nematodes, Steinernema carpocapsae Weiser, S. arenarium (Artyukhovsky) (Rhabditida: Steinernematidae) and Heterorhabditis bacteriophora Poinar (Rhabditida: Heterorhabditidae), were determined after exposure to different concentrations (250, 500, 1000 and 2000 ppm) of fipronil, an insecticide acting on the GABA receptors to block the chloride channel. |
31(0,1,1,1) | Details |
| 14768875 | Chandler GT, Cary TL, Volz DC, Walse SS, Ferry JL, Klosterhaus SL: Fipronil effects on estuarine copepod (Amphiascus tenuiremis) development, fertility, and reproduction: a rapid life-cycle assay in 96-well microplate format. Environ Toxicol Chem. 2004 Jan;23(1):117-24. Fipronil is a novel gamma-aminobutyric acid receptor-specific phenylpyrazole insecticide commonly used near estuarine environments for rice production, turf-grass management, and residential insect control. |
31(0,1,1,1) | Details |
| 10212398 | Wolff MA, Wingate VP: Characterization and comparative pharmacological studies of a functional (GABA) receptor cloned from the tobacco budworm, Heliothis virescens (Noctuidae:Lepidoptera). Invert Neurosci. 1998 Mar;3(4):305-15. The comparative actions of fipronil, picrotoxinin and dieldrin were examined on oocytes expressing the H. virescens wild-type (HVRDL-Ser 285), the site-directed mutant (HVRDL- 285), the Drosophila melanogaster Rdl wild-type (DMRDL- 302) and the Rdl dieldrin resistant (DMRDL-Ser 302) homo-oligomeric GABA receptors. |
9(0,0,1,4) | Details |
| 15748149 | Le Goff G, Hamon A, Berge JB, Amichot M: Resistance to fipronil in Drosophila simulans: influence of two point mutations in the RDL GABA receptor subunit. J Neurochem. 2005 Mar;92(6):1295-305. |
8(0,0,1,3) | Details |
| 18093001 | Narusuye K, Nakao T, Abe R, Nagatomi Y, Hirase K, Ozoe Y: Molecular cloning of a GABA receptor subunit from Laodelphax striatella (Fallen) and patch clamp analysis of the homo-oligomeric receptors expressed in a Drosophila cell line. Insect Mol Biol. 2007 Dec;16(6):723-33. Antagonists such as fipronil (100 nM), 4'-ethynyl-4-n-propylbicycloorthobenzoate (EBOB) (100 nM), dieldrin (100 nM) and SR95531 (gabazine) (1 microM) suppressed -induced currents. |
6(0,0,0,6) | Details |
| 19851797 | El Hassani AK, Dupuis JP, Gauthier M, Armengaud C: Glutamatergic and GABAergic effects of fipronil on olfactory learning and memory in the honeybee. Invert Neurosci. 2009 Nov;9(2):91-100. Epub 2009 Oct 23. We interpret these results as reflecting the involvement of both GluCl and GABA receptors in the impairment of olfactory memory induced by fipronil. |
6(0,0,1,1) | Details |
| 16044331 | Barbara GS, Zube C, Rybak J, Gauthier M, Grunewald B: and induce ionic currents in cultured antennal lobe neurons of the honeybee, Apis mellifera. J Comp Physiol A Neuroethol Sens Neural Behav Physiol. 2005 Sep;191(9):823-36. Epub 2005 Sep 13. Our data indicate the existence of an ionotropic GABA receptor which is permeable to ions and sensitive to picrotoxin (PTX) and the insecticide fipronil. |
6(0,0,1,1) | Details |
| 16027231 | Buckingham SD, Biggin PC, Sattelle BM, Brown LA, Sattelle DB: Insect GABA receptors: splicing, editing, and targeting by antiparasitics and insecticides. Mol Pharmacol. 2005 Oct;68(4):942-51. Epub 2005 Jul 18. RDL is the target of the commercially important insecticide fipronil. |
5(0,0,0,5) | Details |
| 19906878 | Dupuis JP, Bazelot M, Barbara GS, Paute S, Gauthier M, Raymond-Delpech V: Homomeric RDL and heteromeric RDL/LCCH3 GABA receptors in the honeybee antennal lobes: two candidates for inhibitory transmission in olfactory processing. J Neurophysiol. 2010 Jan;103(1):458-68. Epub 2009 Nov 11. The resulting receptors were activated by insect GABA-receptor agonists muscimol and CACA and blocked by antagonists fipronil, dieldrin, and picrotoxin, but not bicuculline, displaying a typical RDL-like pharmacology. |
4(0,0,0,4) | Details |
| 7533909 | Millar NS, Buckingham SD, Sattelle DB: Stable expression of a functional homo-oligomeric Drosophila GABA receptor in a Drosophila cell line. Proc Biol Sci. 1994 Dec 22;258(1353):307-14. We have observed a reversible block of the receptor by the convulsant antagonists, picrotoxinin and EBOB, and by the insecticide fipronil. |
4(0,0,0,4) | Details |
| 11489356 | Ratra GS, Casida JE: GABA receptor subunit composition relative to insecticide potency and selectivity. Toxicol Lett. 2001 Jul 6;122(3):215-22. First, from published data, alpha-endosulfan, lindane and fipronil compete for the [(3) H] EBOB binding site with affinities of 0.3--7 nM in both human recombinant homooligomeric beta 3 receptors and housefly head membranes. |
3(0,0,0,3) | Details |
| 7885191 | Cole LM, Roush RT, Casida JE: Drosophila -gated chloride channel: modified [3H] EBOB binding site associated with --> Ser or Gly mutants of Rdl subunit. Life Sci. 1995;56(10):757-65. This specific binding of [3H] EBOB is strongly inhibited by: a large number and variety of insecticidal channel blockers at 20 nM (lindane, alpha-endosulfan, dieldrin, 12-ketoendrin, fipronil, and a representative bicycloorthobenzoate and dithiane) or 200 nM (picrotoxinin); the insecticidal channel activators avermectin and moxidectin at 20 nM; muscimol at 30 microM and GABA at 300 microM. Cyclodiene resistance in D. melanogaster has been attributed to a mutation resulting in an Ala302--> Ser replacement in the Rdl GABA receptor subunit and in D. simulans to an homologous --> Ser or Gly replacement. |
1(0,0,0,1) | Details |
| 12770091 | Le Corronc H, Alix P, Hue B: Differential sensitivity of two insect -gated channels to dieldrin, fipronil and picrotoxinin. J Insect Physiol. 2002 Apr;48(4):419-431. In the central nervous system of both vertebrates and invertebrates inhibitory neurotransmission is mainly achieved through activation of (GABA) receptors. |
3(0,0,0,3) | Details |
| 18520997 | Es-Salah Z, Lapied B, Le Goff G, Hamon A: RNA editing regulates insect gamma-aminobutyric acid receptor function and insecticide sensitivity. Neuroreport. 2008 Jun 11;19(9):939-43. After replacement of 122 with a both agonist and fipronil potencies were shifted to the right in either fipronil-sensitive receptors or mutated resistant receptors (A301G/T350M). |
3(0,0,0,3) | Details |
| 18446586 | Law RJ, Lightstone FC: Gaba receptor insecticide non-competitive antagonists may bind at allosteric modulator sites. Int J Neurosci. 2008 May;118(5):705-34. Results from several studies have shown that a series of chemically distinct insecticide compounds (picrotoxin, BIDN, TBPS, fipronil, lindane, EBOB, and alpha-endosulfan) affect A receptor function. |
2(0,0,0,2) | Details |
| 7898754 | Buckingham SD, Hosie AM, Roush RL, Sattelle DB: Actions of agonists and convulsant antagonists on a Drosophila melanogaster GABA receptor (Rdl) homo-oligomer expressed in Xenopus oocytes. Neurosci Lett. 1994 Nov 7;181(1-2):137-40. Response of the expressed Drosophila Rdl receptor to was reduced by t-butylbicyclophosphorothionate (TBPS), 4-n-propyl-4'-ethynylbicycloorthobenzoate (EBOB), picrotoxinin and the novel insecticide, fipronil (all at 1.0 x 10 (-5) M). |
2(0,0,0,2) | Details |
| 17206404 | Ci S, Ren T, Su Z: Modeling the interaction of fipronil-related non-competitive antagonists with the beta3-receptor. J Mol Model. 2007 Mar;13(3):457-64. Epub 2007 Jan 6. A three-dimensional model of the beta3-homopentamer of the (GABA) receptor/ ionophore complex was developed by homology modeling using the cyro-electron microscopy structure of nicotinic as a template. |
1(0,0,0,1) | Details |
| 15641641 | Mohamed F, Senarathna L, Percy A, Abeyewardene M, Eaglesham G, Cheng R, Azher S, Hittarage A, Dissanayake W, Sheriff MH, Davies W, Buckley NA, Eddleston M: Acute human self-poisoning with the N-phenylpyrazole insecticide fipronil--a GABAA-gated chloride channel blocker. J Toxicol Clin Toxicol. 2004;42(7):955-63. A high affinity for insect compared to mammalian GABA receptors results in lower animal toxicity than other insecticides blocking this channel. |
1(0,0,0,1) | Details |
| 11181924 | Ikeda T, Zhao X, Nagata K, Kono Y, Shono T, Yeh JZ, Narahashi T: Fipronil modulation of (A) receptors in rat dorsal root ganglion neurons. J Pharmacol Exp Ther. 2001 Mar;296(3):914-21. The (GABA) receptor is an important site of action of a variety of chemicals, including barbiturates, benzodiazepines, picrotoxin, bicuculline, general anesthetics, and certain insecticides. |
1(0,0,0,1) | Details |
| 15578595 | Bass C, Schroeder I, Turberg A, Field LM, Williamson MS: Identification of the Rdl mutation in laboratory and field strains of the cat flea, Ctenocephalides felis (Siphonaptera: Pulicidae). Pest Manag Sci. 2004 Dec;60(12):1157-62. In many insect species, resistance to cyclodiene insecticides is caused by amino acid substitutions at a single residue (A302) within the M2 transmembrane region of the (GABA) receptor sub-unit termed Rdl (resistance to dieldrin). These mutations (A302S and A302G) have also been shown to confer varying levels of cross-resistance to fipronil, a phenylpyrazole insecticide with a similar mode of action to cyclodienes. |
1(0,0,0,1) | Details |
| 16813330 | Li A, Yang Y, Wu S, Li C, Wu Y: Investigation of resistance mechanisms to fipronil in diamondback moth (Lepidoptera: Plutellidae). J Econ Entomol. 2006 Jun;99(3):914-9. The genomic DNA fragments flanking the second membrane-spanning region of Rdl (GABA) receptor gene from P. xylostella, PxRdl, were cloned and sequenced. |
1(0,0,0,1) | Details |
| 19944072 | Ozoe Y, Asahi M, Ozoe F, Nakahira K, Mita T: The antiparasitic isoxazoline A1443 is a potent blocker of insect ligand-gated channels. Biochem Biophys Res Commun. 2010 Jan 1;391(1):744-9. Epub 2009 Nov 26. A structurally unique isoxazoline class compound, A1443, exhibits antiparasitic activity against cat fleas and dog ticks comparable to that of the commercial ectoparasiticide fipronil. This isoxazoline compound inhibits specific binding of the (GABA) receptor channel blocker [(3) H] 4'-ethynyl-4-n-propylbicycloorthobenzoate (EBOB) to housefly-head membranes, with an IC (50) value of 455pM. |
1(0,0,0,1) | Details |
| 20200125 | Janssen D, Derst C, Rigo JM, Van Kerkhove E: Cys-loop ligand-gated channels in Dorsal Unpaired Median neurons of Locusta migratoria. J Neurophysiol. 2010 Mar 3. GluCls were sensitive to ibotenate and blocked by picrotoxin and fipronil. The expression of Rdl-like subunit-containing GABA receptors was demonstrated at the molecular level using RT-PCR. |
1(0,0,0,1) | Details |
| 14637375 | Ikeda T, Zhao X, Kono Y, Yeh JZ, Narahashi T: Fipronil modulation of -induced currents in cockroach thoracic ganglion neurons. Neurotoxicology. 2003 Dec;24(6):807-15. |
0(0,0,0,0) | Details |
| 16102801 | El Hassani AK, Dacher M, Gauthier M, Armengaud C: Effects of sublethal doses of fipronil on the behavior of the honeybee (Apis mellifera). Pharmacol Biochem Behav. 2005 Sep;82(1):30-9. Epub 2005 Aug 15. |
0(0,0,0,0) | Details |
| 15701711 | Zhao X, Yeh JZ, Salgado VL, Narahashi T: Sulfone metabolite of fipronil blocks - and -activated channels in mammalian and insect neurons. J Pharmacol Exp Ther. 2005 Jul;314(1):363-73. Epub 2005 Feb 8. Fipronil sulfone, a major metabolite of fipronil in both insects and mammals, binds strongly to GABA receptors and is thought to play a significant role in poisoning by fipronil. |
243(3,3,3,3) | Details |
| 12766256 | Zhao X, Salgado VL, Yeh JZ, Narahashi T: Differential actions of fipronil and dieldrin insecticides on -gated channels in cockroach neurons. J Pharmacol Exp Ther. 2003 Sep;306(3):914-24. Epub 2003 May 23. Fipronil and dieldrin are known to inhibit GABA receptors in both mammals and insects. |
201(2,3,4,6) | Details |
| 7582519 | Hosie AM, Baylis HA, Buckingham SD, Sattelle DB: Actions of the insecticide fipronil, on dieldrin-sensitive and- resistant GABA receptors of Drosophila melanogaster. Br J Pharmacol. 1995 Jul;115(6):909-12. As the mutation A302--> S reduces the potency of both fipronil and picrotoxinin, homooligomeric RDL receptors should facilitate detailed studies of the molecular basis of convulsant/insecticide antagonist actions on GABA receptors. |
118(1,2,3,3) | Details |
| 19238461 | Cheng J, Ju XL, Chen XY, Liu GY: Homology modeling of human alpha 1 beta 2 gamma 2 and house fly beta 3 GABA receptor channels and Surflex-docking of fipronil. J Mol Model. 2009 Sep;15(9):1145-53. Epub 2009 Feb 24. To further explore the mechanism of selective binding of the representative gamma-aminobutyric acid receptors (GABARs) noncompetitive antagonist (NCA) fipronil to insect over mammalian GABARs, three-dimensional models of human alpha 1 beta 2 gamma 2 and house fly beta 3 GABAR were generated by homology modeling, using the cryo-electron microscopy structure of the nicotinic acetylcholine receptor (nAChR) of Torpedo marmorata as a template. |
118(1,2,3,3) | Details |
| 16611622 | Stehr CM, Linbo TL, Incardona JP, Scholz NL: The developmental neurotoxicity of fipronil: notochord degeneration and locomotor defects in zebrafish embryos and larvae. Toxicol Sci. 2006 Jul;92(1):270-8. Epub 2006 Apr 12. Fipronil is a phenylpyrazole insecticide designed to selectively inhibit insect (GABA) receptors. |
112(1,2,2,2) | Details |
| 9860498 | Hainzl D, Cole LM, Casida JE: Mechanisms for selective toxicity of fipronil insecticide and its sulfone metabolite and desulfinyl photoproduct. Chem Res Toxicol. 1998 Dec;11(12):1529-35. Fipronil, an N-phenylpyrazole with a trifluoromethylsulfinyl substituent, initiated the second generation of insecticides acting at the (GABA) receptor to block the chloride channel. |
93(0,3,3,3) | Details |
| 15158803 | Sammelson RE, Caboni P, Durkin KA, Casida JE: GABA receptor antagonists and insecticides: common structural features of 4-alkyl-1-phenylpyrazoles and 4-alkyl-1-phenyltrioxabicyclooctanes. Bioorg Med Chem. 2004 Jun 15;12(12):3345-55. Structure-activity studies described here reveal that fipronil retains its very high binding potency at the human beta3 and house fly (GABA) receptors and toxicity to house flies on replacing the pyrazole trifluoromethylsulfinyl moiety with tert-butyl or isopropyl and the phenyl trifluoromethyl substituent with ethynyl, trifluoromethoxy, bromo or chloro. |
83(1,1,1,3) | Details |
| 16537435 | Chen L, Durkin KA, Casida JE: Structural model for gamma-aminobutyric acid receptor noncompetitive antagonist binding: widely diverse structures fit the same site. Proc Natl Acad Sci U S A. 2006 Mar 28;103(13):5185-90. Epub 2006 Mar 10. Several major insecticides, including alpha-endosulfan, lindane, and fipronil, and the botanical picrotoxinin are noncompetitive antagonists (NCAs) for the GABA receptor. |
83(1,1,1,3) | Details |