Lufenuron

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

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Name
Lufenuron
Accession Number
DB11424
Type
Small Molecule
Groups
Experimental, Vet approved
Description

Lufenuron is used in veterinary for the control of flea.

Structure
Thumb
Synonyms
  • 1-(2,5-dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl)-3-(2,6-difluorobenzoyl)urea
  • Fluphenacur
  • Lufenuron
  • Lufenurone
  • Lufenuronum
  • N-({[2,5-dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]amino}carbonyl)-2,6-difluorobenzamide
Categories
UNII
1R754M4918
CAS number
103055-07-8
Weight
Average: 511.15
Monoisotopic: 509.9784228
Chemical Formula
C17H8Cl2F8N2O3
InChI Key
PWPJGUXAGUPAHP-UHFFFAOYSA-N
InChI
InChI=1S/C17H8Cl2F8N2O3/c18-6-5-11(32-17(26,27)14(22)16(23,24)25)7(19)4-10(6)28-15(31)29-13(30)12-8(20)2-1-3-9(12)21/h1-5,14H,(H2,28,29,30,31)
IUPAC Name
1-[2,5-dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-3-(2,6-difluorobenzoyl)urea
SMILES
FC(C(F)(F)F)C(F)(F)OC1=C(Cl)C=C(NC(=O)NC(=O)C2=C(F)C=CC=C2F)C(Cl)=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Ben Ziony Y, Arzi B: Comments on dosing lufenuron. J Am Vet Med Assoc. 2002 Oct 1;221(7):932. [PubMed:12369690]
  2. Strakosch MR: Lufenuron and tick paralysis. Aust Vet J. 2000 Feb;78(2):98. [PubMed:10736668]
  3. Hotz RP, Hassler S, Maurer MP: Determination of Lufenuron in canine skin layers by radioluminography. Schweiz Arch Tierheilkd. 2000 Apr;142(4):173-6. [PubMed:10804842]
  4. Wilson TG, Cryan JR: Lufenuron, a chitin-synthesis inhibitor, interrupts development of Drosophila melanogaster. J Exp Zool. 1997 May 1;278(1):37-44. [PubMed:9136145]
  5. Fisher MA, Jacobs DE, Hutchinson MJ, Dick IG: Evaluation of flea control programmes for cats using fenthion and lufenuron. Vet Rec. 1996 Jan 27;138(4):79-81. [PubMed:8650891]
  6. Hink WF, Zakson M, Barnett S: Evaluation of a single oral dose of lufenuron to control flea infestations in dogs. Am J Vet Res. 1994 Jun;55(6):822-4. [PubMed:7944022]
  7. Dean SR, Meola RW, Meola SM, Sittertz-Bhatkar H, Schenker R: Mode of action of lufenuron on larval cat fleas (Siphonaptera: Pulicidae). J Med Entomol. 1998 Sep;35(5):720-4. [PubMed:9775600]
  8. Bar-Oz B, Ito S, Parks V, Maurer MP, Koren G: Estimation of neonatal exposure after accidental ingestion of lufenuron in a breastfeeding mother. J Hum Lact. 2000 Aug;16(3):229-30. [PubMed:11153158]
  9. Moya P, Flores S, Ayala I, Sanchis J, Montoya P, Primo J: Evaluation of lufenuron as a chemosterilant against fruit flies of the genus Anastrepha (Diptera: Tephritidae). Pest Manag Sci. 2010 Jun;66(6):657-63. doi: 10.1002/ps.1925. [PubMed:20157929]
  10. Miller PF, Peters BA, Hort CA: Comparison of lufenuron and nitenpyram versus imidacloprid for integrated flea control. Vet Ther. 2001 Fall;2(4):285-92. [PubMed:19746650]
External Links
KEGG Drug
D08150
KEGG Compound
C18434
ChemSpider
64813
ChEBI
39384
ChEMBL
CHEMBL1364906
Wikipedia
Lufenuron

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00139 mg/mLALOGPS
logP6.04ALOGPS
logP6.12ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)9.02ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area67.43 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity96.63 m3·mol-1ChemAxon
Polarizability37.68 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0001190000-6338ee07ca91a33540e9

Taxonomy

Description
This compound belongs to the class of organic compounds known as n-phenylureas. These are compounds containing a N-phenylurea moiety, which is structurally characterized by a phenyl group linked to one nitrogen atom of a urea group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
N-phenylureas
Direct Parent
N-phenylureas
Alternative Parents
Phenoxy compounds / Phenol ethers / Dichlorobenzenes / Fluorobenzenes / Aryl chlorides / Aryl fluorides / Organic carbonic acids and derivatives / Propargyl-type 1,3-dipolar organic compounds / Organic oxides / Hydrocarbon derivatives
show 6 more
Substituents
N-phenylurea / Phenoxy compound / 1,4-dichlorobenzene / Phenol ether / Chlorobenzene / Fluorobenzene / Halobenzene / Aryl chloride / Aryl fluoride / Aryl halide
show 17 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
organofluorine compound, aromatic ether, dichlorobenzene, N-acylurea, benzoylurea insecticide (CHEBI:39384) / Pesticides (C18434)

Drug created on February 25, 2016 11:40 / Updated on June 04, 2019 07:21