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Details

Stereochemistry MIXED
Molecular Formula C23H26O3
Molecular Weight 350.4507
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENOTHRIN

SMILES

CC(C)=CC1C(C(=O)OCC2=CC=CC(OC3=CC=CC=C3)=C2)C1(C)C

InChI

InChIKey=SBNFWQZLDJGRLK-UHFFFAOYSA-N
InChI=1S/C23H26O3/c1-16(2)13-20-21(23(20,3)4)22(24)25-15-17-9-8-12-19(14-17)26-18-10-6-5-7-11-18/h5-14,20-21H,15H2,1-4H3

HIDE SMILES / InChI

Molecular Formula C23H26O3
Molecular Weight 350.4507
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

Phenothrin, also called sumithrin and d-phenothrin, a synthetic pyrethroid compound, is widely used to control agricultural and household insects, as well as to eliminate human louse infestation, but studies conducted in Paris, France and the United Kingdom have shown widespread resistance to phenothrin. Synthetic pyrethroids, including phenothrin, have a similar mode of action as organochlorines. They act on the membrane of nerve cells of insects blocking the closure of the ion gates of the sodium channel during re-polarization. This strongly disrupts the transmission of nervous impulses. At low concentrations insects suffer from hyperactivity. At high concentrations they are paralyzed and die. The EPA has not assessed its effect on cancer in humans. However, one study performed by the Mt. Sinai School of Medicine links sumithrin with breast cancer; the link made by sumithrin's effect on increasing the expression of a gene responsible for mammary tissue proliferation.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
losion. mousse
Route of Administration: Topical
In Vitro Use Guide
phenothrin induces statistically significant, dose-dependent DNA damage in the absence of marked cytotoxicity at concentrations higher than 20 μM and 50 μM in human blood peripheral lymphocytes and hepatocytes, respectively
Substance Class Chemical
Record UNII
707484X33X
Record Status Validated (UNII)
Record Version