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Details

Stereochemistry MIXED
Molecular Formula C24H25NO3
Molecular Weight 375.4602
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYPHENOTHRIN

SMILES

CC(C)=CC1C(C(=O)OC(C#N)C2=CC=CC(OC3=CC=CC=C3)=C2)C1(C)C

InChI

InChIKey=FJDPATXIBIBRIM-UHFFFAOYSA-N
InChI=1S/C24H25NO3/c1-16(2)13-20-22(24(20,3)4)23(26)28-21(15-25)17-9-8-12-19(14-17)27-18-10-6-5-7-11-18/h5-14,20-22H,1-4H3

HIDE SMILES / InChI

Molecular Formula C24H25NO3
Molecular Weight 375.4602
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 0 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Cyphenothrin is one of the type II pyrethroid insecticide, in combination with fipronil it used to provide dogs with protection to common topical parasites in dogs. Cyphenothrin primarily affects sodium channels in excitable membranes causing a prolongation of the sodium current during excitation. The prolonged sodium current results in the development of a depolarizing after potential following the action and is responsible for the induction of repetitive activity, which is the most characteristic effect of pyrethroid poisoning in the nervous system. At low concentrations, insects and other arthropods suffer from hyperactivity. At high concentrations, they are paralyzed and die.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Parastar® Plus

PubMed

Sample Use Guides

In Vivo Use Guide
for dogs: The dose of Parastar Plus® (Fipronil mixed with a second ingredient cyphenothrin) and Fiproguard Max® (is the same product as Parastar Plus but by a different manufacturer) is based on the weight of the dog and pipettes are available in 0.67 mL (for dogs from 4 to 22 pounds), 1.34 mL (for dogs 23 to 44 pounds), 2.68 mL (for dogs 45 to 88 pounds) and 4.02 mL (for dogs 89 to 132 pounds). One pipette is applied topically every 30 days. The duration of administration depends on the condition being treated, response to the medication and the development of any adverse effects.
Route of Administration: Oral
In Vitro Use Guide
Experiments were performed using the mouse neuroblastoma cell line NIE-115. Three main effects of the cyphenothrin (25 uM) was found: (1) the peak amplitude of the sodium current increased; (2) the declining phase of the sodium current during depolarization was greatly slowed down resuilting in a marked residual current towards the end of tlhe 15 ms pulse; and (3) after repolarization of the membrane to the holding potential a large, slowly decaying sodium tail current remained.
Substance Class Chemical
Record UNII
S0IU5Y1R32
Record Status Validated (UNII)
Record Version