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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
Structure of FENVALERATE

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

HIDE SMILES / InChI

Molecular Formula C25H22ClNO3
Molecular Weight 419.9
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 0 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency
3.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Rat: 1, 10, or 30 mg/kg
Route of Administration: Oral
In Vitro Use Guide
p27 mRNA was significantly downregulated and protein levels were decreased in human uterine leiomyoma (UtLM) cells and uterine smooth muscle cells treated with 10 uM fenvalerate for 24 h compared with respective controls.
Substance Class Chemical
Record UNII
Z6MXZ39302
Record Status Validated (UNII)
Record Version