Details
| Stereochemistry | MIXED |
| Molecular Formula | C25H22ClNO3 |
| Molecular Weight | 419.9 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 0 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)C(C(=O)OC(C#N)C1=CC=CC(OC2=CC=CC=C2)=C1)C3=CC=C(Cl)C=C3
InChI
InChIKey=NYPJDWWKZLNGGM-UHFFFAOYSA-N
InChI=1S/C25H22ClNO3/c1-17(2)24(18-11-13-20(26)14-12-18)25(28)30-23(16-27)19-7-6-10-22(15-19)29-21-8-4-3-5-9-21/h3-15,17,23-24H,1-2H3
| Molecular Formula | C25H22ClNO3 |
| Molecular Weight | 419.9 |
| Charge | 0 |
| Count |
|
| Stereochemistry | MIXED |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Fenvalerate is type II pyrethroid and widely used pesticide. Fenvalerate is listed under Class IV of the U.S. Food and Drug Administration (USFDA) Surveillance Index Classification, indicating a low hazard potential to humans from both exposure and toxicological standpoints. Fenvalerate irreversibly prolongs the sodium current during depolarization. The sensitization of sodium channels, probably tetrodotoxin-resistant (TTX-R) sodium channels, by the long-term activation of protein kinase C may play an important role in the enhancement of the duration of fenvalerate-induced nociceptive behavior in diabetic mice. Fenvalerate inhibits testosterone synthesis via pathways involving intracellular Ca(2+) and circadian clock genes (Bmal1, Rev-Erb alpha, Ror alpha) as well as StAR mRNA expression in TM3 cells. It potently inhibits human CYP2D6 and moderately CYP3A4. Fenvalerate has an anxiolytic effect on rats.
CNS Activity
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P48452 Gene ID: 286852.0 Gene Symbol: PPP3CA Target Organism: Bos taurus (Bovine) |
3.0 nM [IC50] | ||
Target ID: CHEMBL289 |
|||
Target ID: CHEMBL340 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Sublethal toxicity of orchard stormwater runoff in Sacramento splittail (Pogonichthys macrolepidotus) larvae. | 2005-04 |
|
| Haemato-biochemical and immuno-pathophysiological effects of chronic toxicity with synthetic pyrethroid, organophosphate and chlorinated pesticides in broiler chicks. | 2004-12-15 |
|
| Alterations of FSH-stimulated progesterone production and calcium homeostasis in primarily cultured human luteinizing-granulosa cells induced by fenvalerate. | 2004-10-15 |
|
| Genotoxic effects on human spermatozoa among pesticide factory workers exposed to fenvalerate. | 2004-10-15 |
|
| The involvement of microsomal oxidases in pyrethroid resistance in Helicoverpa armigera from Asia. | 2004-08 |
|
| Evaluating toxicity of Asana XL (esfenvalerate) amendments in agricultural ditch mesocosms. | 2004-08 |
|
| Identification, expression, and purification of a pyrethroid-hydrolyzing carboxylesterase from mouse liver microsomes. | 2004-07-09 |
|
| Pathophysiological effects of chronic toxicity with synthetic pyrethroid, organophosphate and chlorinated pesticides on bone health of broiler chicks. | 2004-06-19 |
|
| Molecular and cellular biomarker responses to pesticide exposure in juvenile chinook salmon (Oncorhynchus tshawytscha). | 2004-06-05 |
|
| Neurodevelopment and endocrine disruption. | 2004-06 |
|
| Soil photolysis in a moisture- and temperature-controlled environment. 2. Insecticides. | 2004-05-05 |
|
| Fenvalerate-induced changes in a catfish, Clarias batrachus: metabolic enzymes, RNA and protein. | 2004-05 |
|
| Role of alpha-tocopherol and beta-carotene in ameliorating the fenvalerate-induced changes in oxidative stress, hemato-biochemical parameters, and semen quality of male rats. | 2004-05 |
|
| Capacitive chemical sensor for fenvalerate assay based on electropolymerized molecularly imprinted polymer as the sensitive layer. | 2004-05 |
|
| Direct high-performance liquid chromatographic method for enantioselective and diastereoselective determination of selected pyrethroic acids. | 2004-04-30 |
|
| Consequences of a short pulse of pesticide exposure for survival and reproduction of Gammarus pulex. | 2004-04-28 |
|
| Electron ionization gas chromatography-mass spectrometric determination of residues of thirteen pyrethroid insecticides in whole blood. | 2004-04-05 |
|
| [Investigation of pesticide residues in foods distributed in Kitakyushu City]. | 2004-04 |
|
| Assessing estrogenic activity of pyrethroid insecticides using in vitro combination assays. | 2004-04 |
|
| Screening for estrogen and androgen receptor activities in 200 pesticides by in vitro reporter gene assays using Chinese hamster ovary cells. | 2004-04 |
|
| Identification of factors responsible for insecticide resistance in Helicoverpa armigera. | 2004-03 |
|
| Effects of pesticides and their hydrolysates on catalase activity in soil. | 2004-03 |
|
| Determination of pyrethrin and pyrethroid pesticides in urine and water matrixes by liquid chromatography with diode array detection. | 2004-02-26 |
|
| Efficacy of fenvalerate as contact poison against the larval development and viability of mutant form (Sepia) of Drosophila melanogaster (Meigen). | 2004-01 |
|
| [Effect of fenvalerate on the ovarian calcium homeostasis and the serum steroid hormone]. | 2004-01 |
|
| Innovative uses of vegetated drainage ditches for reducing agricultural runoff. | 2004 |
|
| Comparison of the pharmacological properties of rat Na(V)1.8 with rat Na(V)1.2a and human Na(V)1.5 voltage-gated sodium channel subtypes using a membrane potential sensitive dye and FLIPR. | 2004 |
|
| Toxicity and residue studies of fenvalerate to the freshwater fish Channa punctatus (Bloch). | 2003-12 |
|
| Hematological responses in a freshwater fish Channa punctatus due to fenvalerate. | 2003-12 |
|
| Genetic basis of resistance and studies on cross-resistance in a population of diamondback moth, Plutella xylostella (Lepidoptera: Plutellidae). | 2003-11 |
|
| Effect of fenvalerate technical grade on acetyl cholinesterase activity in Indian bullfrog Haplobatrachus tigerinus (Daudin). | 2003-10 |
|
| Insecticide-resistant pollen beetles (Meligethes aeneus F) found in Danish oilseed rape (Brassica napus L) fields. | 2003-09 |
|
| Relationship between lice infestation and leather damage in cattle. | 2003-08-30 |
|
| A longitudinal study of a natural lice infestation in growing cattle over two winter periods. | 2003-08-29 |
|
| Fluorescence quenching competitive immunoassay in micro droplets. | 2003-08-01 |
|
| [Sublethal effects of insecticides on fecundity of multicolored Asian ladybird Harmonia axyridis]. | 2003-08 |
|
| Recycling and utilization of metabolic wastes for energy production is an index of biochemical adaptation of fish under environmental pollution stress. | 2003-08 |
|
| Bioaccumulation of fenvalerate technical grade in different organs of the frog Haplobatrachus tigerinus (Daudin). | 2003-07 |
|
| Application of solid-phase microextraction for the determination of pyrethroid residues in vegetable samples by GC-MS. | 2003-06 |
|
| Effect of HCH and fenvalerate on growth and distribution of microorganisms in relation to persistence of the insecticides in the rhizosphere soils of wetland rice. | 2003-05 |
|
| Pyrethroid insecticides influence the signal transduction in T helper lymphocytes from atopic and nonatopic subjects. | 2003-04 |
|
| Assessment of comparative hemotoxicity of cybil and fenvalerate in Rattus norvegicus. | 2003-04 |
|
| Mechanisms of resistance to DDT and pyrethroids in Patagonian populations of Simulium blackflies. | 2003-03 |
|
| Determination of pyrethroid pesticide residues in processed fruits and vegetables by gas chromatography with electron capture and mass spectrometric detection. | 2003-02-28 |
|
| Joint acute toxicity of esfenvalerate and diazinon to larval fathead minnows (Pimephales promelas). | 2003-02 |
|
| Product studies and laser flash photolysis of direct and 2,4,6-triphenylpyrylium-zeolite Y photocatalyzed degradation of fenvalerate. | 2002-12 |
|
| Steroidogenic alterations in testes and sera of rats exposed to formulated Fenvalerate by inhalation. | 2002-11 |
|
| Effect of fenvalerate-20EC on sericigenous insects. II. Digestive enzymes in the nutritive physiology of silkworm, Bombyx mori L. | 2002-10 |
|
| Effect of fenvalerate-20EC on sericigenous insects. I. Food utilization in the late-age larva of the silkworm, Bombyx mori L. | 2002-10 |
|
| Fenvalerate-induced macromolecular changes in the catfish, Clarias batrachus. | 2002-04 |
Sample Use Guides
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:28:57 GMT 2025
by
admin
on
Mon Mar 31 18:28:57 GMT 2025
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| Record UNII |
Z6MXZ39302
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| Record Status |
Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
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EPA PESTICIDE CODE |
109301
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WHO-VATC |
QP53AC14
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NCI_THESAURUS |
C737
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FDA ORPHAN DRUG |
872122
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WHO-VATC |
QP53AX02
Created by
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| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
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6640
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PRIMARY | |||
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C017690
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PRIMARY | |||
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m5307
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PRIMARY | Merck Index | ||
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5014
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FENVALERATE
Created by
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257-326-3
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DTXSID101017940
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3347
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PRIMARY | |||
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CHEMBL492491
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PRIMARY | |||
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300000029136
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Z6MXZ39302
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fenvalerate
Created by
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C65672
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51630-58-1
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