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 |
|---|---|---|
| Fenvalerate-induced macromolecular changes in the catfish, Clarias batrachus. | 2002 Apr |
|
| Product studies and laser flash photolysis of direct and 2,4,6-triphenylpyrylium-zeolite Y photocatalyzed degradation of fenvalerate. | 2002 Dec |
|
| Steroidogenic alterations in testes and sera of rats exposed to formulated Fenvalerate by inhalation. | 2002 Nov |
|
| Effect of fenvalerate-20EC on sericigenous insects. II. Digestive enzymes in the nutritive physiology of silkworm, Bombyx mori L. | 2002 Oct |
|
| Effect of fenvalerate-20EC on sericigenous insects. I. Food utilization in the late-age larva of the silkworm, Bombyx mori L. | 2002 Oct |
|
| Pyrethroid insecticides influence the signal transduction in T helper lymphocytes from atopic and nonatopic subjects. | 2003 Apr |
|
| Assessment of comparative hemotoxicity of cybil and fenvalerate in Rattus norvegicus. | 2003 Apr |
|
| [Sublethal effects of insecticides on fecundity of multicolored Asian ladybird Harmonia axyridis]. | 2003 Aug |
|
| Recycling and utilization of metabolic wastes for energy production is an index of biochemical adaptation of fish under environmental pollution stress. | 2003 Aug |
|
| Fluorescence quenching competitive immunoassay in micro droplets. | 2003 Aug 1 |
|
| A longitudinal study of a natural lice infestation in growing cattle over two winter periods. | 2003 Aug 29 |
|
| Relationship between lice infestation and leather damage in cattle. | 2003 Aug 30 |
|
| Toxicity and residue studies of fenvalerate to the freshwater fish Channa punctatus (Bloch). | 2003 Dec |
|
| Hematological responses in a freshwater fish Channa punctatus due to fenvalerate. | 2003 Dec |
|
| Joint acute toxicity of esfenvalerate and diazinon to larval fathead minnows (Pimephales promelas). | 2003 Feb |
|
| Determination of pyrethroid pesticide residues in processed fruits and vegetables by gas chromatography with electron capture and mass spectrometric detection. | 2003 Jan-Feb |
|
| Bioaccumulation of fenvalerate technical grade in different organs of the frog Haplobatrachus tigerinus (Daudin). | 2003 Jul |
|
| Application of solid-phase microextraction for the determination of pyrethroid residues in vegetable samples by GC-MS. | 2003 Jun |
|
| Mechanisms of resistance to DDT and pyrethroids in Patagonian populations of Simulium blackflies. | 2003 Mar |
|
| 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 May |
|
| Genetic basis of resistance and studies on cross-resistance in a population of diamondback moth, Plutella xylostella (Lepidoptera: Plutellidae). | 2003 Nov |
|
| Determination of pyrethrin and pyrethroid pesticides in urine and water matrixes by liquid chromatography with diode array detection. | 2003 Nov-Dec |
|
| Effect of fenvalerate technical grade on acetyl cholinesterase activity in Indian bullfrog Haplobatrachus tigerinus (Daudin). | 2003 Oct |
|
| Insecticide-resistant pollen beetles (Meligethes aeneus F) found in Danish oilseed rape (Brassica napus L) fields. | 2003 Sep |
|
| 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 |
|
| [Investigation of pesticide residues in foods distributed in Kitakyushu City]. | 2004 Apr |
|
| Assessing estrogenic activity of pyrethroid insecticides using in vitro combination assays. | 2004 Apr |
|
| Screening for estrogen and androgen receptor activities in 200 pesticides by in vitro reporter gene assays using Chinese hamster ovary cells. | 2004 Apr |
|
| Consequences of a short pulse of pesticide exposure for survival and reproduction of Gammarus pulex. | 2004 Apr 28 |
|
| Direct high-performance liquid chromatographic method for enantioselective and diastereoselective determination of selected pyrethroic acids. | 2004 Apr 30 |
|
| Electron ionization gas chromatography-mass spectrometric determination of residues of thirteen pyrethroid insecticides in whole blood. | 2004 Apr 5 |
|
| The involvement of microsomal oxidases in pyrethroid resistance in Helicoverpa armigera from Asia. | 2004 Aug |
|
| Evaluating toxicity of Asana XL (esfenvalerate) amendments in agricultural ditch mesocosms. | 2004 Aug |
|
| Molecular and cellular biomarker responses to pesticide exposure in juvenile chinook salmon (Oncorhynchus tshawytscha). | 2004 Aug-Dec |
|
| Haemato-biochemical and immuno-pathophysiological effects of chronic toxicity with synthetic pyrethroid, organophosphate and chlorinated pesticides in broiler chicks. | 2004 Dec 15 |
|
| Efficacy of fenvalerate as contact poison against the larval development and viability of mutant form (Sepia) of Drosophila melanogaster (Meigen). | 2004 Jan |
|
| [Effect of fenvalerate on the ovarian calcium homeostasis and the serum steroid hormone]. | 2004 Jan |
|
| Identification, expression, and purification of a pyrethroid-hydrolyzing carboxylesterase from mouse liver microsomes. | 2004 Jul 9 |
|
| Neurodevelopment and endocrine disruption. | 2004 Jun |
|
| Identification of factors responsible for insecticide resistance in Helicoverpa armigera. | 2004 Mar |
|
| Effects of pesticides and their hydrolysates on catalase activity in soil. | 2004 Mar |
|
| Fenvalerate-induced changes in a catfish, Clarias batrachus: metabolic enzymes, RNA and protein. | 2004 May |
|
| 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 May |
|
| Capacitive chemical sensor for fenvalerate assay based on electropolymerized molecularly imprinted polymer as the sensitive layer. | 2004 May |
|
| Soil photolysis in a moisture- and temperature-controlled environment. 2. Insecticides. | 2004 May 5 |
|
| Pathophysiological effects of chronic toxicity with synthetic pyrethroid, organophosphate and chlorinated pesticides on bone health of broiler chicks. | 2004 May-Jun |
|
| Alterations of FSH-stimulated progesterone production and calcium homeostasis in primarily cultured human luteinizing-granulosa cells induced by fenvalerate. | 2004 Oct 15 |
|
| Genotoxic effects on human spermatozoa among pesticide factory workers exposed to fenvalerate. | 2004 Oct 15 |
|
| Sublethal toxicity of orchard stormwater runoff in Sacramento splittail (Pogonichthys macrolepidotus) larvae. | 2005 Apr |
Sample Use Guides
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:28:31 UTC 2023
by
admin
on
Fri Dec 15 16:28:31 UTC 2023
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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
Created by
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WHO-VATC |
QP53AC14
Created by
admin on Fri Dec 15 16:28:31 UTC 2023 , Edited by admin on Fri Dec 15 16:28:31 UTC 2023
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NCI_THESAURUS |
C737
Created by
admin on Fri Dec 15 16:28:31 UTC 2023 , Edited by admin on Fri Dec 15 16:28:31 UTC 2023
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FDA ORPHAN DRUG |
872122
Created by
admin on Fri Dec 15 16:28:31 UTC 2023 , Edited by admin on Fri Dec 15 16:28:31 UTC 2023
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WHO-VATC |
QP53AX02
Created by
admin on Fri Dec 15 16:28:31 UTC 2023 , Edited by admin on Fri Dec 15 16:28:31 UTC 2023
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| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
6640
Created by
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PRIMARY | |||
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C017690
Created by
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PRIMARY | |||
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m5307
Created by
admin on Fri Dec 15 16:28:31 UTC 2023 , Edited by admin on Fri Dec 15 16:28:31 UTC 2023
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PRIMARY | Merck Index | ||
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5014
Created by
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PRIMARY | |||
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FENVALERATE
Created by
admin on Fri Dec 15 16:28:31 UTC 2023 , Edited by admin on Fri Dec 15 16:28:31 UTC 2023
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PRIMARY | |||
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257-326-3
Created by
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PRIMARY | |||
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DTXSID101017940
Created by
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PRIMARY | |||
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3347
Created by
admin on Fri Dec 15 16:28:31 UTC 2023 , Edited by admin on Fri Dec 15 16:28:31 UTC 2023
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PRIMARY | |||
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CHEMBL492491
Created by
admin on Fri Dec 15 16:28:31 UTC 2023 , Edited by admin on Fri Dec 15 16:28:31 UTC 2023
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PRIMARY | |||
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300000029136
Created by
admin on Fri Dec 15 16:28:31 UTC 2023 , Edited by admin on Fri Dec 15 16:28:31 UTC 2023
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Z6MXZ39302
Created by
admin on Fri Dec 15 16:28:31 UTC 2023 , Edited by admin on Fri Dec 15 16:28:31 UTC 2023
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PRIMARY | |||
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fenvalerate
Created by
admin on Fri Dec 15 16:28:31 UTC 2023 , Edited by admin on Fri Dec 15 16:28:31 UTC 2023
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PRIMARY | |||
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C65672
Created by
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51630-58-1
Created by
admin on Fri Dec 15 16:28:31 UTC 2023 , Edited by admin on Fri Dec 15 16:28:31 UTC 2023
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| Related Record | Type | Details | ||
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