FIPRONIL

Possibly Marketed Outside US

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

HIDE SMILES / InChI

Molecular Formula	C12H4Cl2F6N4OS
Molecular Weight	437.148
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Insect GABAA-gated chloride channels 1	Blocker 537		4.0 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Flea infestations 12	Curative	Approved 8,429	Frontline
Tick infestations 4	Curative	Approved 8,429	Frontline
Chewing lice infestation 1	Curative	Approved 8,429	Frontline

PubMed

Show entries

Title	Date	PubMed
Cabbage root fly control using non-organophosphorus insecticides.	2001	12425060
Preference of food particle size among several urban ant species.	2002 Dec	12539835
Simple method for the determination of trace levels of pesticides in honeybees using matrix solid-phase dispersion and gas chromatography.	2002 Dec 27	12489883
Efficacy of Fipronil and Propoxur in the control of German cockroaches (Dictyoptera: Blatellidae).	2002 Mar	12718344
[An experimental tool essential for the evaluation of insecticides: the testing huts].	2002 Nov	12596384

Showing 1 to 5 of 50 entries

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Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

14C-fipronil absorption through human, rabbit, and rat epidermal membranes, researchers recorded penetration rates after eight hours of 0.08% (rat), 0.07% (rabbit), and 0.01% (human) of the applied dose of 200 g/L fipronil solution.