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Lufenuron

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Identification

Generic Name
Lufenuron
DrugBank Accession Number
DB11424
Background

Lufenuron is used in veterinary for the control of flea.

Type
Small Molecule
Groups
Experimental, Vet approved
Structure
3D
Similar Structures
Weight
Average: 511.15
Monoisotopic: 509.9784228
Chemical Formula
C17H8Cl2F8N2O3
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
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1,4-dichlorobenzene / Alkyl fluoride / Alkyl halide / Aromatic homomonocyclic compound / Aryl chloride / Aryl fluoride / Aryl halide / Carbonic acid derivative / Carbonyl group / Chlorobenzene
show 17 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
organofluorine compound, aromatic ether, dichlorobenzene, N-acylurea, benzoylurea insecticide (CHEBI:39384) / Pesticides (C18434)
Affected organisms
Not Available

Chemical Identifiers

UNII
1R754M4918
CAS number
103055-07-8
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

References

General References
  1. Ben Ziony Y, Arzi B: Comments on dosing lufenuron. J Am Vet Med Assoc. 2002 Oct 1;221(7):932. [Article]
  2. Strakosch MR: Lufenuron and tick paralysis. Aust Vet J. 2000 Feb;78(2):98. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
KEGG Drug
D08150
KEGG Compound
C18434
ChemSpider
64813
RxNav
83586
ChEBI
39384
ChEMBL
CHEMBL1364906
Wikipedia
Lufenuron

Clinical Trials

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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
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0001190000-6338ee07ca91a33540e9
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0200090000-8c2a0e26213cfd3dd9ed
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9326000000-d370f361faacd1bfffb7
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0900010000-f87a5aa578b9df2810bd
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-4409010000-7600bf8b846f6f000df9
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kf-1912100000-6b5a5111d1a5df93b234
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9021000000-b57c7eb813a73a5beb8c
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-195.71022
predicted
DeepCCS 1.0 (2019)
[M+H]+198.10579
predicted
DeepCCS 1.0 (2019)
[M+Na]+204.2122
predicted
DeepCCS 1.0 (2019)

Drug created at February 25, 2016 18:40 / Updated at February 21, 2021 18:53