Page last updated: 2024-12-10

fipronil sulfone

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

fipronil sulfone: insecticide fipronil and its metabolite fipronil sulphone inhibit the rat alpha1beta2gamma2L GABA(A) receptor [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

fipronil-sulfone : A member of the class of pyrazoles that is 1H-pyrazole that is substituted at positions 1, 3, 4, and 5 by 2,6-dichloro-4-(trifluoromethyl)phenyl, cyano, (trifluoromethyl)sulfonyl, and amino groups, respectively. It is a metabolite of the agrochemical fipronil. [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]

Cross-References

ID SourceID
PubMed CID3078139
CHEBI ID83487
SCHEMBL ID922220
MeSH IDM0528550

Synonyms (30)

Synonym
unii-ke7t0t1pq7
ke7t0t1pq7 ,
fipronil sulphone
120068-36-2
fipronil sulfone
m & b 46136
1h-pyrazole-3-carbonitrile, 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfonyl)-
1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethanesulfonyl-5-aminopyrazole
5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfonyl)pyrazole-3-carbonitrile
FT-0668543
mb 46136
5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfonylpyrazole
5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulphonylpyrazole
5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfonyl-1 h-pyrazole-3-carbonitrile
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfonyl)-1h-pyrazol-3-carbonitrile
5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfonylpyrazole
5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethanesulphonylpyrazole
1h-pyrazole-3-carbonitrile, 5-amino-1-(2,6-dichloro-
5-amino-1-(2,6-dichloro-4-trifluormethylphenyl)-3-cyano-4-trifluoromethylsulfonylpyrazole
fipronil-sulfone
CHEBI:83487
5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfonyl]-1h-pyrazole-3-carbonitrile
SCHEMBL922220
DTXSID6074750
fipronil sulfone, pestanal(r), analytical standard
fipronil-sulfone 100 microg/ml in acetonitrile
fipronil-sulfone 10 microg/ml in acetonitrile
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfonyl)-1h-pyrazole-3-carbonitrile
Q27156870
AKOS040744763

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Fipronil sulfone was more toxic than fipronil."( Fipronil sulfone induced higher cytotoxicity than fipronil in SH-SY5Y cells: Protection by antioxidants.
Anadón, A; Ares, I; Castellano, V; Martínez, M; Martínez, MA; Martínez-Larrañaga, MR; Ramos, E; Romero, A, 2016
)
2.79

Pharmacokinetics

ExcerptReferenceRelevance
" The amount of fipronil distributed to the fetus was greater than that of fipronil sulfone in the short term, but by contrast, pharmacokinetic data showed that the latter stayed longer in the body."( Preclinical Transplacental Transfer and Pharmacokinetics of Fipronil in Rats.
Chang, YN; Tsai, TH, 2020
)
0.79

Bioavailability

ExcerptReferenceRelevance
" After fipronil administration in male rats, the oral bioavailability decreased, whereas the biotransformation increased as the dose increased, revealing an enhancement of first-pass effect and a fast metabolism in vivo."( Preclinical Transplacental Transfer and Pharmacokinetics of Fipronil in Rats.
Chang, YN; Tsai, TH, 2020
)
0.56

Dosage Studied

ExcerptRelevanceReference
" The method was applied to monitor plasma concentrations following a commonly used dosage regimen for the toxicological evaluation of fipronil in rats."( Quantification of fipronil and its metabolite fipronil sulfone in rat plasma over a wide range of concentrations by LC/UV/MS.
Lacroix, MZ; Puel, S; Toutain, PL; Viguié, C, 2010
)
0.62
") was given to rats, the proportion of dose eliminated in urine and feces 72 h after dosing was ca 4% for each route."( Disposition of fipronil in rats.
Cravedi, JP; Debrauwer, L; Delous, G; Viguié, C; Zalko, D, 2013
)
0.39
" To understand more about the potential risks for human exposure associated with fipronil, urine and serum from dosed Long Evans adult rats (5 and 10mg/kg bw) were analyzed to identify metabolites as potential biomarkers for use in human biomonitoring studies."( Identification of fipronil metabolites by time-of-flight mass spectrometry for application in a human exposure study.
Andersen, EM; Dagnino, S; Freeborn, DL; Garantziotis, S; Herr, DW; Lindstrom, AB; McMahen, RL; McMillan, L; Moser, VC; Strynar, MJ, 2015
)
0.42
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
marine xenobiotic metaboliteAny metabolite produced by metabolism of a xenobiotic compound in marine macro- and microorganisms.
[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]

Drug Classes (5)

ClassDescription
pyrazoles
dichlorobenzeneAny member of the class of chlorobenzenes carrying two chloro groups at unspecified positions.
nitrileA compound having the structure RC#N; thus a C-substituted derivative of hydrocyanic acid, HC#N. In systematic nomenclature, the suffix nitrile denotes the triply bound #N atom, not the carbon atom attached to it.
(trifluoromethyl)benzenesAn organofluorine compound that is (trifluoromethyl)benzene and derivatives arising from substitution of one or more of the phenyl hydrogens.
sulfoneAn organosulfur compound having the structure RS(=O)2R (R =/= H).
[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]

Research

Studies (37)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (2.70)29.6817
2010's29 (78.38)24.3611
2020's7 (18.92)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 31.72

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.

MetricThis Compound (vs All)
Research Demand Index31.72 (24.57)
Research Supply Index3.66 (2.92)
Research Growth Index5.71 (4.65)
Search Engine Demand Index39.34 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (31.72)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other38 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]