Fipronil

Details

• Internal ID: 1a7bd925-c90e-4a6c-8d4d-a8cd9787a151
• Taxonomy: Organoheterocyclic compounds > Azoles > Pyrazoles > Phenylpyrazoles
• IUPAC Name: 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfinyl)pyrazole-3-carbonitrile
• InChI: 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
• InChI Key: ZOCSXAVNDGMNBV-UHFFFAOYSA-N
• Popularity: 3,166 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₄Cl₂F₆N₄OS
• Molecular Weight: 437.10 g/mol
• Exact Mass: 435.9387063 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 4.28
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 120068-37-3
• Termidor
• Fipronil [ISO]
• RM 1601
• MB 46030
• (+/-)-Fipronil
• HSDB 7051
• NSC-758960
• UNII-QGH063955F
• FRONTLINE
• 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1h-pyrazole-3-carbonitrile
• DTXSID4034609
• CHEBI:83394
• Fipronil (ema epar: veterinary)
• QGH063955F
• M & B 46030
• 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfinyl)pyrazole-3-carbonitrile
• 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile
• RM-1601
• MB-46030
• CHEMBL101326
• DTXCID2014609
• EC 424-610-5
• BROADLINE COMPONENT FIPRONIL
• Fipronil (JAN)
• 5-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinylpyrazole
• FIPRONIL COMPONENT OF BROADLINE
• NSC 758960
• (RS)-5-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-(trifluoromethylsulfinyl)pyrazole-3-carbonitrile
• NCGC00094574-06
• FIPRONIL [JAN]
• C12H4Cl2F6N4OS
• FIPRONIL (MART.)
• FIPRONIL [MART.]
• Fluocyanobenpyrazole
• 1H-Pyrazole-3-carbonitrile, 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-
• 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethane)sulfinyl-1H-pyrazole-3-carbonitrile
• 1H-Pyrazole-3-carbonitrile, 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-
• 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-trifluoromethanesulfinyl-1H-pyrazole-3-carbonitrile
• CAS-120068-37-3
• rac-fipronil
• Fipronil [INN:BAN]
• FIPRONIL [HSDB]
• 5-Amino-1-
• FIPRONIL [MI]
• UPCMLD-DP011
• Fluocyanobenpyrazole;Termidor
• CBiol_001754
• SCHEMBL15088
• BSPBio_001315
• BSPBio_002266
• KBioGR_000035
• KBioSS_000035
• 5-amino-1-(2,6-dichloro-alpha,alpha,alpha-trifluoro-p-tolyl)-4-trifluoromethylsulfinylpyrazole-3-carbonitile
• MLS004712079
• SPECTRUM1505354
• CHEBI:5063
• UPCMLD-DP011:001
• UPCMLD-DP011:002
• BCBcMAP01_000152
• KBio2_000035
• KBio2_002603
• KBio2_005171
• KBio3_000069
• KBio3_000070
• Bio1_000040
• Bio1_000529
• Bio1_001018
• Bio2_000035
• Bio2_000515
• HMS1361B17
• HMS1791B17
• HMS1922F08
• HMS1989B17
• HMS2093D09
• HMS3402B17
• Pharmakon1600-01505354
• 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(S)-trifluoromethylsulfinyl]pyrazole-3-carbonitrile
• BCP14931
• HY-B0822
• Tox21_111300
• Tox21_301114
• AC-427
• BDBM50106148
• CM-102
• MFCD00867812
• NSC758960
• s5366
• Fipronil 1000 microg/mL in Acetone
• AKOS015960931
• Fluocyanobenpyrazole, Taurus, Termidor
• Tox21_111300_1
• CCG-213975
• Fipronil 10 microg/mL in Acetonitrile
• KS-5066
• Fipronil 100 microg/mL in Acetonitrile
• IDI1_033785
• NCGC00094574-01
• NCGC00094574-02
• NCGC00094574-03
• NCGC00094574-05
• NCGC00094574-07
• NCGC00094574-08
• NCGC00094574-09
• NCGC00094574-10
• NCGC00094574-11
• NCGC00094574-12
• NCGC00094574-13
• NCGC00094574-15
• NCGC00255014-01
• SMR000777967
• SY066868
• SBI-0206839.P001
• M&B 46030
• CS-0012838
• F0822
• Fipronil, PESTANAL(R), analytical standard
• FT-0631097
• D01042
• AB00643326_02
• EN300-6490177
• A934386
• Q415933
• SR-05000002006
• Q-201115
• SR-05000002006-1
• BRD-A50675702-001-03-0
• BRD-A50675702-001-04-8
• Fipronil, certified reference material, TraceCERT(R)
• Z2417820389
• 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfinylpyrazole
• 5-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulphinylpyrazole
• 5-Amino-3-cyano-1-(2,6-dichloro-4-trifluoro-methylphenyl)-4-trifluoromethylsulfinylpyrazole
• 5-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinyl-pyrazole
• 5-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinylpyrazol e
• 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulphinylpyrazole
• (+-)-5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carbonitrile
• (RS)-5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfinyl)pyrazole-3-carbonitrile
• 5-amino-1 -(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinyl-1 H-pyrazole-3-carbonitrile
• 5-AMINO-1-(2,6-DICHLORO-.ALPHA.,.ALPHA.,.ALPHA.-TRIFLUORO-P-TOLYL)-4-((TRIFLUOROMETHYL)SULFINYL)PYRAZOLE-3-CARBONITRILE
• 5-amino-1-(2,6-dichloro-4-(trifluoromethyl) phenyl)-4-((trifluoromethyl) sulfinyl)-1H-pyrazol-3-carbonitrile
• 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfinyl)-1H-pyrazole-3-carbonitrile
• 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulphinyl pyrazole
• 5-AMINO-1-(2,6-DICHLORO-alpha,alpha,alpha-TRIFLUORO-P-TOLYL)-4-((TRIFLUOROMETHYL)SULFINYL)PYRAZOLE-3-CARBONITRILE
• 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-3-cyano-4-(trifluoromethyl)sulfinylpyrazole
• 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethyl)sulfinylpyrazole-3-carbonitrile
• 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl) -4-trifluoromethylsulphinylpyrazole
• rac-5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carbonitrile

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9944	99.44%
Caco-2	+	0.5592	55.92%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	+	0.7429	74.29%
Subcellular localzation	Mitochondria	0.4222	42.22%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9192	91.92%
OATP1B3 inhibitior	+	0.9398	93.98%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.8651	86.51%
P-glycoprotein inhibitior	-	0.7082	70.82%
P-glycoprotein substrate	-	0.7574	75.74%
CYP3A4 substrate	+	0.5492	54.92%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8866	88.66%
CYP3A4 inhibition	-	0.7904	79.04%
CYP2C9 inhibition	+	0.5990	59.90%
CYP2C19 inhibition	+	0.5105	51.05%
CYP2D6 inhibition	-	0.9290	92.90%
CYP1A2 inhibition	+	0.6036	60.36%
CYP2C8 inhibition	+	0.6001	60.01%
CYP inhibitory promiscuity	-	0.7380	73.80%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6419	64.19%
Carcinogenicity (trinary)	Non-required	0.5384	53.84%
Eye corrosion	-	0.9761	97.61%
Eye irritation	-	0.8352	83.52%
Skin irritation	-	0.7882	78.82%
Skin corrosion	-	0.9402	94.02%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8053	80.53%
Micronuclear	+	0.9500	95.00%
Hepatotoxicity	+	0.7875	78.75%
skin sensitisation	-	0.8332	83.32%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.8647	86.47%
Acute Oral Toxicity (c)	II	0.5614	56.14%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.8697	86.97%
Thyroid receptor binding	+	0.6880	68.80%
Glucocorticoid receptor binding	+	0.8478	84.78%
Aromatase binding	+	0.8155	81.55%
PPAR gamma	+	0.8916	89.16%
Honey bee toxicity	-	0.6984	69.84%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.7100	71.00%
Fish aquatic toxicity	+	0.9657	96.57%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL284	P27487	Dipeptidyl peptidase IV	94.96%	95.69%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	93.54%	100.00%
CHEMBL1978	P11511	Cytochrome P450 19A1	93.20%	91.76%
CHEMBL1929	P47989	Xanthine dehydrogenase	93.02%	96.12%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.41%	96.09%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	92.07%	93.65%
CHEMBL3401	O75469	Pregnane X receptor	91.45%	94.73%
CHEMBL4015	P41597	C-C chemokine receptor type 2	91.34%	98.57%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.19%	86.33%
CHEMBL2007625	O75874	Isocitrate dehydrogenase [NADP] cytoplasmic	89.92%	99.00%
CHEMBL2047	Q96RI1	Bile acid receptor FXR	89.53%	96.10%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.34%	99.15%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	88.26%	97.23%
CHEMBL4191	Q99685	Monoglyceride lipase	88.01%	97.46%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	87.55%	89.34%
CHEMBL1871	P10275	Androgen Receptor	87.48%	96.43%
CHEMBL2039	P27338	Monoamine oxidase B	87.31%	92.51%
CHEMBL2424504	P29375	Lysine-specific demethylase 5A	86.65%	99.23%
CHEMBL344	Q99705	Melanin-concentrating hormone receptor 1	84.83%	92.50%
CHEMBL249	P25103	Neurokinin 1 receptor	83.98%	99.17%
CHEMBL6007	O75762	Transient receptor potential cation channel subfamily A member 1	83.67%	92.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.51%	96.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.46%	96.90%
CHEMBL5905	Q04828	Aldo-keto reductase family 1 member C1	83.36%	91.79%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	83.24%	86.00%
CHEMBL2535	P11166	Glucose transporter	83.16%	98.75%
CHEMBL4235	P28845	11-beta-hydroxysteroid dehydrogenase 1	83.04%	97.98%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.97%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.34%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.24%	94.45%
CHEMBL2346486	P40261	Nicotinamide N-methyltransferase	81.19%	83.04%
CHEMBL1900	P15121	Aldose reductase	80.88%	92.38%
CHEMBL221	P23219	Cyclooxygenase-1	80.56%	90.17%
CHEMBL230	P35354	Cyclooxygenase-2	80.56%	89.63%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.14%	89.62%

Plants that contains it

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Cross-Links

• PubChem: 3352
• LOTUS: LTS0247186
• wikiData: Q415933