Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C17H8Cl2F8N2O3 |
| Molecular Weight | 511.15 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
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
InChI
InChIKey=PWPJGUXAGUPAHP-UHFFFAOYSA-N
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)
| Molecular Formula | C17H8Cl2F8N2O3 |
| Molecular Weight | 511.15 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
DescriptionCurator's Comment: description was created based on several sources, including
http://www.peteducation.com/article.cfm?c=26+1303&aid=1471
Curator's Comment: description was created based on several sources, including
http://www.peteducation.com/article.cfm?c=26+1303&aid=1471
Lufenuron is used to fight fungal infections, since fungus cell walls are about one third chitin. Lufenuron is the active ingredient in the veterinary flea control medication Program. FDA approved this drug for use in dogs and cats. Available by prescription. Once the female flea ingests blood from a pet treated with lufenuron, 96% of egg development from fleas on cats and 99% of egg development from fleas on dogs is stopped. This helps prevent a continual flea problem. Lufenuron does not kill the adult flea and does not stop the flea from biting and causing flea allergy dermatitis. The drug is stored in the body fat and released into the bloodstream over the course of a month. Flea eggs laid prior to treating the pet may take several months to hatch; Program will not be effective until these fleas start to lay eggs. Therefore it may take several months to see the product's effectiveness. If quicker results are needed, use a product which will kill adult fleas; these will provide quicker relief for the pet. Cats require a higher dose per pound than dogs. After the cat injectable form is administered, 2-3 weeks are needed to reach therapeutic levels in the blood. The injectable form for cats is effective for 6 months.
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
0.008 μg/g |
0.1 mg/kg single, oral dose: 0.1 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
LUFENURON blood | Rattus norvegicus population: HEALTHY age: UNKNOWN sex: MALE food status: UNKNOWN |
|
0.097 μg/g |
1 mg/kg single, oral dose: 1 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
LUFENURON blood | Rattus norvegicus population: HEALTHY age: UNKNOWN sex: MALE food status: UNKNOWN |
|
0.89 μg/g |
10 mg/kg single, oral dose: 10 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
LUFENURON blood | Rattus norvegicus population: HEALTHY age: UNKNOWN sex: MALE food status: UNKNOWN |
|
1.341 μg/g |
100 mg/kg single, oral dose: 100 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
LUFENURON blood | Rattus norvegicus population: HEALTHY age: UNKNOWN sex: MALE food status: UNKNOWN |
|
0.017 μg/g |
0.1 mg/kg single, intravenous dose: 0.1 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
LUFENURON blood | Rattus norvegicus population: HEALTHY age: UNKNOWN sex: MALE food status: UNKNOWN |
|
1.907 μg/g |
10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
LUFENURON blood | Rattus norvegicus population: HEALTHY age: UNKNOWN sex: MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
0.49 μg × h/g |
0.1 mg/kg single, oral dose: 0.1 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
LUFENURON blood | Rattus norvegicus population: HEALTHY age: UNKNOWN sex: MALE food status: UNKNOWN |
|
10.73 μg × h/g |
1 mg/kg single, oral dose: 1 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
LUFENURON blood | Rattus norvegicus population: HEALTHY age: UNKNOWN sex: MALE food status: UNKNOWN |
|
90.44 μg × h/g |
10 mg/kg single, oral dose: 10 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
LUFENURON blood | Rattus norvegicus population: HEALTHY age: UNKNOWN sex: MALE food status: UNKNOWN |
|
216.36 μg × h/g |
100 mg/kg single, oral dose: 100 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
LUFENURON blood | Rattus norvegicus population: HEALTHY age: UNKNOWN sex: MALE food status: UNKNOWN |
|
0.94 μg × h/g |
0.1 mg/kg single, intravenous dose: 0.1 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
LUFENURON blood | Rattus norvegicus population: HEALTHY age: UNKNOWN sex: MALE food status: UNKNOWN |
|
153.76 μg × h/g |
10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
LUFENURON blood | Rattus norvegicus population: HEALTHY age: UNKNOWN sex: MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
256 h |
0.1 mg/kg single, oral dose: 0.1 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
LUFENURON blood | Rattus norvegicus population: HEALTHY age: UNKNOWN sex: MALE food status: UNKNOWN |
|
256 h |
1 mg/kg single, oral dose: 1 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
LUFENURON blood | Rattus norvegicus population: HEALTHY age: UNKNOWN sex: MALE food status: UNKNOWN |
|
256 h |
10 mg/kg single, oral dose: 10 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
LUFENURON blood | Rattus norvegicus population: HEALTHY age: UNKNOWN sex: MALE food status: UNKNOWN |
|
256 h |
100 mg/kg single, oral dose: 100 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
LUFENURON blood | Rattus norvegicus population: HEALTHY age: UNKNOWN sex: MALE food status: UNKNOWN |
|
232 h |
0.1 mg/kg single, intravenous dose: 0.1 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
LUFENURON blood | Rattus norvegicus population: HEALTHY age: UNKNOWN sex: MALE food status: UNKNOWN |
|
232 h |
10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
LUFENURON blood | Rattus norvegicus population: HEALTHY age: UNKNOWN sex: MALE food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Tissue-specific transcriptomics of the exotic invasive insect pest emerald ash borer (Agrilus planipennis). | 2010-10-28 |
|
| Effects of small Hsp genes on developmental stability and microenvironmental canalization. | 2010-09-16 |
|
| Macroinvertebrate responses to insecticide application between sprayed and adjacent nonsprayed ditch sections of different sizes. | 2010-09 |
|
| Selective effects of natural and synthetic insecticides on mortality of Spodoptera frugiperda (Lepidoptera: Noctuidae) and its predator Eriopis connexa (Coleoptera: Coccinellidae). | 2010-08 |
|
| Minor crops for export: a case study of boscalid, pyraclostrobin, lufenuron and lambda-cyhalothrin residue levels on green beans and spring onions in Egypt. | 2010-08 |
|
| Response of Reticulitermes hesperus (Isoptera: Rhinotermitidae) colonies to baiting with lufenuron in northern California. | 2010-06 |
|
| Evaluation of lufenuron as a chemosterilant against fruit flies of the genus Anastrepha (Diptera: Tephritidae). | 2010-06 |
|
| Mediterranean fruit fly suppression using chemosterilants for area-wide integrated pest management. | 2010-05 |
|
| Impact of five commercial baits containing chitin synthesis inhibitors on the protist community in Reticulitermes flavipes (Isoptera: Rhinotermitidae). | 2010-02 |
|
| Efficacy of some oils and chemical compounds on Insignorthezia insignis (Browne) (Hemiptera: Ortheziidae) infesting Lantana camara in Alexandria, Egypt. | 2010 |
|
| Selectivity of pesticides used in integrated apple production to the lacewing, Chrysoperla externa. | 2010 |
|
| Physiological and histopathological investigations on the effects of alpha-lipoic acid in rats exposed to malathion. | 2010 |
|
| Radiation biology of mosquitoes. | 2009-11-16 |
|
| Bioavailability of insect growth regulator residues in citrus. | 2009-11 |
|
| Impact of a benzoyl urea insecticide on aquatic macroinvertebrates in ditch mesocosms with and without non-sprayed sections. | 2009-10 |
|
| Effects of benzoylphenylurea on chitin synthesis and orientation in the cuticle of the Drosophila larva. | 2009-03 |
|
| Insecticide toxicity to Trichogramma pretiosum (Hymenoptera: Trichogrammatidae) females and effect on descendant generation. | 2009-02 |
|
| A lufenuron pre-treatment may enhance the effects of enilconazole or griseofulvin in feline dermatophytosis? | 2009-02 |
|
| Use of a chitin synthesis inhibitor to control fleas on wild rodents important in the maintenance of plague, Yersinia pestis, in California. | 2008-12 |
|
| Dissipation behavior of lufenuron, benzoylphenylurea insecticide, in/on Chinese cabbage applied by foliar spraying under greenhouse conditions. | 2008-10 |
|
| Simultaneous determination of eight pesticide residues in coconut using MSPD and GC/MS. | 2008-07-30 |
|
| Responses of zooplankton in lufenuron-stressed experimental ditches in the presence or absence of uncontaminated refuges. | 2008-06 |
|
| Use of a sustained release preparation of clotrimazole to treat dermatophytosis in a siamang (Hylobates syndactylus). | 2008-03 |
|
| Development and application of a method for analysis of lufenuron in wheat flour by gas chromatography-mass spectrometry and confirmation of bio-efficacy against Tribolium castaneum (Herbst) (Coleoptera: Tenebrionidae). | 2008-01-01 |
|
| Solid-phase microextraction for the determination of benzoylureas in orange juice using liquid chromatography combined with post-column photochemically induced fluorimetry derivatization and fluorescence detection. | 2008-01 |
|
| A chitin-like component in Aedes aegypti eggshells, eggs and ovaries. | 2007-12 |
|
| Complex regulation of cyp26a1 creates a robust retinoic acid gradient in the zebrafish embryo. | 2007-11 |
|
| Determination of benzoylurea insecticide residues in tomatoes by high-performance liquid chromatography with ultraviolet-diode array and atmospheric pressure chemical ionization-mass spectrometry detection. | 2007-10-25 |
|
| Chemosterilants as control agents of Ceratitis capitata (Diptera: Tephritidae) in field trials. | 2007-08 |
|
| Transposable elements are enriched within or in close proximity to xenobiotic-metabolizing cytochrome P450 genes. | 2007-03-23 |
|
| New method for the photo-chemiluminometric determination of benzoylurea insecticides based on acetonitrile chemiluminescence. | 2007-03 |
|
| Agrichemical impact on growth and survival of non-target apple phyllosphere microorganisms. | 2007-01 |
|
| Laboratory evaluation of five chitin synthesis inhibitors against the colorado potato beetle, Leptinotarsa decemlineata. | 2007 |
|
| Dissipation of insect growth regulators in fresh orange and orange juice. | 2007 |
|
| Bioavailability of insect growth regulators in citrus and stone fruits. | 2007 |
|
| A comparison of Drosophila melanogaster detoxification gene induction responses for six insecticides, caffeine and phenobarbital. | 2006-12 |
|
| Heat-shock promoters: targets for evolution by P transposable elements in Drosophila. | 2006-10-06 |
|
| Effectiveness of two insect growth regulators against Bemisia tabaci (Gennadius) (Homoptera: Aleyrodidae) and Helicoverpa armigera (Hübner) (Lepidoptera: Noctuidae) and their impact on population densities of arthropod predators in cotton in Pakistan. | 2006-10 |
|
| Hazards and uptake of chitin synthesis inhibitors in bumblebees Bombus terrestris. | 2006-08 |
|
| Effects of lufenuron on Lobesia botrana (Lepidoptera: Tortricidae) egg, larval, and adult stages. | 2006-04 |
|
| In vitro and in vivo effects of lufenuron on dermatophytes isolated from cases of canine and feline dermatophytoses. | 2006-04 |
|
| Determination of benzoylureas in ground water samples by fully automated on-line pre-concentration and liquid chromatography-fluorescence detection. | 2006-01-27 |
|
| Selectivity of pesticides used on cotton (Gossypium hirsutum) to Trichogramma pretiosum reared on two laboratory-reared hosts. | 2006-01 |
|
| In vitro availability of insect growth regulators from vegetables. | 2006 |
|
| Synergistic effect of entomogenous fungi on some insecticides against Bihar hairy caterpillar Spilarctia obliqua (Lepidoptera: Arctiidae). | 2006 |
|
| In vitro efficacy of lufenuron against filamentous fungi and blood concentrations after PO administration in horses. | 2005-12-17 |
|
| Photochemical-spectrofluorimetric method for the determination of benzoylurea insecticides: applications in river water samples and in technical formulations. | 2001-01-26 |
|
| Control of fleas on dogs and cats and in homes with the combination of oral lufenuron and nitenpyram. | 2001 |
|
| Comparison of lufenuron and nitenpyram versus imidacloprid for integrated flea control. | 2001 |
|
| Screening of compounds for antimicrosporidial activity in vitro. | 1998 |
Patents
Sample Use Guides
for animals:
Dogs were treated once by oral administration of lufenuron tablets at doses ranging from 54.2 to 68.3 mg/kg (24.6 to 31.0 mg/lb) of body weight.
Cats were treated once by oral administration of lufenuron suspension in doses ranging from 51.2 to 266 mg/kg (23.3 to 120.9 mg/lb)
Route of Administration:
Oral
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:55:31 GMT 2025
by
admin
on
Mon Mar 31 18:55:31 GMT 2025
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| Record UNII |
1R754M4918
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C737
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EPA PESTICIDE CODE |
118205
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CFR |
21 CFR 520.1288
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CFR |
21 CFR 520.1447
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WHO-VATC |
QP53BC51
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CFR |
21 CFR 520.1443
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CFR |
21 CFR 522.1289
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CFR |
21 CFR 520.1289
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admin on Mon Mar 31 18:55:31 GMT 2025 , Edited by admin on Mon Mar 31 18:55:31 GMT 2025
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WHO-VATC |
QP53BC01
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admin on Mon Mar 31 18:55:31 GMT 2025 , Edited by admin on Mon Mar 31 18:55:31 GMT 2025
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1370779
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1R754M4918
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759097
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m6924
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C76874
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DB11424
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103055-07-8
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C070364
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100000082270
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71777
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1R754M4918
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CHEMBL1364906
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lufenuron
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39384
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DTXSID5034357
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6804
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SUB08615MIG
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LUFENURON
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83586
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PRIMARY | RxNorm |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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ENANTIOMER -> RACEMATE |
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TARGET -> INHIBITOR |
inhibits chitin biosynthesis
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ENANTIOMER -> RACEMATE |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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IMPURITY -> PARENT |
for veterinary use
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
for veterinary use
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
for veterinary use
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
for veterinary use
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
for veterinary use
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
for veterinary use
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
for veterinary use
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
for veterinary use
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |
