FLUAZURON

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H10Cl2F5N3O3
Molecular Weight	506.21
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

FC1=CC=CC(F)=C1C(=O)NC(=O)NC2=CC=C(Cl)C(OC3=NC=C(C=C3Cl)C(F)(F)F)=C2

InChI

InChIKey=YOWNVPAUWYHLQX-UHFFFAOYSA-N

InChI=1S/C20H10Cl2F5N3O3/c21-11-5-4-10(29-19(32)30-17(31)16-13(23)2-1-3-14(16)24)7-15(11)33-18-12(22)6-9(8-28-18)20(25,26)27/h1-8H,(H2,29,30,31,32)

HIDE SMILES / InChI

Description
Sources: https://goo.gl/5MUFWD
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27664399 | https://www.ncbi.nlm.nih.gov/pubmed/28527785 | https://www.ncbi.nlm.nih.gov/pubmed/28131090 | https://goo.gl/12Gx4v

Fluazuron (N-[[4-chloro-3-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxyphenyl]carbamoyl]-2,6-difluorobenzamide, trade name Acatak) is an insect growth regulator belonging to the class of benzoyl phenyl urea derivatives, a class of chitin synthesis inhibitors. Fluazuron specifically interferes with chitin formation in ticks during engorgement, molt, and hatching. The substance is intended for tick control in beef cattle applied topically as a pour-on for use at single dose levels of 1.5 and 2.5 mg/kg BW with a possible additional treatment after 3 to 6 months.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Fibroblast growth factor receptor 3 32 Target ID: CHEMBL2742 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27664399	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bladder cancer 16 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27664399	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Factors that influence the prevalence of acaricide resistance and tick-borne diseases.	2004 Oct 28	15476966
Chemical contaminants in feedlot wastes: concentrations, effects and attenuation.	2008 Aug	18055014
Use of a chitin synthesis inhibitor to control fleas on wild rodents important in the maintenance of plague, Yersinia pestis, in California.	2008 Dec	19263847
Allopatric speciation in ticks: genetic and reproductive divergence between geographic strains of Rhipicephalus (Boophilus) microplus.	2009 Feb 25	19243585

Patents

Sample Use Guides

In Vivo Use Guide

For tick control in beef cattle applied topically as a pour-on for use at single dose levels of 1.5 and 2.5 mg/kg bw with a possible additional treatment after 3 to 6 months.

Route of Administration: Topical

In Vitro Use Guide

Human Bladder carcinoma cell lines RT112 and RT4 were used for activity evaluation. 7 x 10^3 cells per well were plated in 96-well plates and allowed to attach for 24 hr before adding testing chemicals. Cells were treated with testing chemicals for 24, 48, and 72 hr. After treatment, 10 μl 5 mg/ml 3-(4,5-methylthiazol-2-yl)-2,5-diphenyl-tetrazolium bromide (MTT) was added and further incubated for 4 hr. The medium was then discarded and the precipitate dissolved in DMSO. The absorbance was measured at 570 nm with a Synergy 2 microplate reader (Bio-Tek Instruments, Inc., Winooski, VT, USA) according to the standard protocol.

Name

Type

Language

FLUAZURON

Official Name

English

FLUAZURON [MART.]

Common Name

English

ACATAK POUR-ON

Brand Name

English

1-(4-CHLORO-3-(3-CHLORO-5-TRIFLUOROMETHYL-2-PYRIDYLOXY)PHENYL)-3-(2,6-DIFLUOROBENZOYL)UREA

Systematic Name

English

1-(4-CHLORO-3-((3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDYL)OXY)PHENYL)-3-(2,6-DIFLUOROBENZOYL)UREA

Systematic Name

English

N-(((4-CHLORO-3-((3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL)OXY)PHENYL)AMINO)CARBONYL)-2,6-DIFLUOROBENZAMIDE

Systematic Name

English

fluazuron [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C737