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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

Description
Curator's Comment: description was created based on several sources, including http://parasitipedia.net/index.php?option=com_content&view=article&id=2463&Itemid=2731

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Assessing estrogenic activity of pyrethroid insecticides using in vitro combination assays.
2004 Apr
Residual efficacy of field-applied permethrin, d-phenothrin, and resmethrin on plant foliage against adult mosquitoes.
2008 Dec
Evaluation of a new formulation of adulticide, DUET, against West Nile virus vector mosquitoes.
2010 Jun
Efficacy of spray formulations containing binary mixtures of clove and eucalyptus oils against susceptible and pyrethroid/ malathion-resistant head lice (Anoplura: Pediculidae).
2010 May
Prallethrin-induced excitation increases contact between sprayed ultralow volume droplets and flying mosquitoes (Diptera: Culicidae) in a wind tunnel.
2010 Nov
Antiplasmodial and antitrypanosomal activity of pyrethrins and pyrethroids.
2011 Sep 14
Patents

Sample Use Guides

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
Name Type Language
HEGOR ANTIPOUX
Preferred Name English
PHENOTHRIN
HSDB   INN   ISO   MART.   MI   WHO-DD  
INN  
Official Name English
phenothrin [INN]
Common Name English
SUMITHRIN
Common Name English
PHENOTHRIN [HSDB]
Common Name English
PHENOTHRIN [JAN]
Common Name English
NSC-758668
Code English
PHENOTHRIN [ISO]
Common Name English
PHENOTHRIN [MART.]
Common Name English
D-PHENOTRHIN
Common Name English
S-2539F
Code English
PHENOTHRIN [MI]
Common Name English
Phenothrin [WHO-DD]
Common Name English
M-PHENOXYBENZYL (±)-CIS,TRANS-2,2-DIMETHYL-3-(2-METHYLPROPENYL)CYCLOPROPANECARBOXYLATE
Common Name English
3-PHENOXYBENZYL 2,2-DIMETHYL-3-(2-METHYLPROPENYL)CYCLOPROPANECARBOXYLATE
Systematic Name English
Classification Tree Code System Code
WHO-ATC P03AC53
Created by admin on Mon Mar 31 18:21:20 GMT 2025 , Edited by admin on Mon Mar 31 18:21:20 GMT 2025
EPA PESTICIDE CODE 69005
Created by admin on Mon Mar 31 18:21:20 GMT 2025 , Edited by admin on Mon Mar 31 18:21:20 GMT 2025
WHO-ATC P03AC03
Created by admin on Mon Mar 31 18:21:20 GMT 2025 , Edited by admin on Mon Mar 31 18:21:20 GMT 2025
WHO-VATC QP53AC03
Created by admin on Mon Mar 31 18:21:20 GMT 2025 , Edited by admin on Mon Mar 31 18:21:20 GMT 2025
Code System Code Type Description
CHEBI
34916
Created by admin on Mon Mar 31 18:21:20 GMT 2025 , Edited by admin on Mon Mar 31 18:21:20 GMT 2025
PRIMARY
CAS
26002-80-2
Created by admin on Mon Mar 31 18:21:20 GMT 2025 , Edited by admin on Mon Mar 31 18:21:20 GMT 2025
PRIMARY
PUBCHEM
4767
Created by admin on Mon Mar 31 18:21:20 GMT 2025 , Edited by admin on Mon Mar 31 18:21:20 GMT 2025
PRIMARY
EPA CompTox
DTXSID7032688
Created by admin on Mon Mar 31 18:21:20 GMT 2025 , Edited by admin on Mon Mar 31 18:21:20 GMT 2025
PRIMARY
NCI_THESAURUS
C166974
Created by admin on Mon Mar 31 18:21:20 GMT 2025 , Edited by admin on Mon Mar 31 18:21:20 GMT 2025
PRIMARY
RXCUI
33303
Created by admin on Mon Mar 31 18:21:20 GMT 2025 , Edited by admin on Mon Mar 31 18:21:20 GMT 2025
PRIMARY RxNorm
EVMPD
SUB09777MIG
Created by admin on Mon Mar 31 18:21:20 GMT 2025 , Edited by admin on Mon Mar 31 18:21:20 GMT 2025
PRIMARY
INN
5705
Created by admin on Mon Mar 31 18:21:20 GMT 2025 , Edited by admin on Mon Mar 31 18:21:20 GMT 2025
PRIMARY
ChEMBL
CHEMBL1322884
Created by admin on Mon Mar 31 18:21:20 GMT 2025 , Edited by admin on Mon Mar 31 18:21:20 GMT 2025
PRIMARY
DRUG CENTRAL
4686
Created by admin on Mon Mar 31 18:21:20 GMT 2025 , Edited by admin on Mon Mar 31 18:21:20 GMT 2025
PRIMARY
FDA UNII
707484X33X
Created by admin on Mon Mar 31 18:21:20 GMT 2025 , Edited by admin on Mon Mar 31 18:21:20 GMT 2025
PRIMARY
SMS_ID
100000091961
Created by admin on Mon Mar 31 18:21:20 GMT 2025 , Edited by admin on Mon Mar 31 18:21:20 GMT 2025
PRIMARY
ECHA (EC/EINECS)
247-404-5
Created by admin on Mon Mar 31 18:21:20 GMT 2025 , Edited by admin on Mon Mar 31 18:21:20 GMT 2025
PRIMARY
NSC
758668
Created by admin on Mon Mar 31 18:21:20 GMT 2025 , Edited by admin on Mon Mar 31 18:21:20 GMT 2025
PRIMARY
HSDB
3922
Created by admin on Mon Mar 31 18:21:20 GMT 2025 , Edited by admin on Mon Mar 31 18:21:20 GMT 2025
PRIMARY
ALANWOOD
phenothrin
Created by admin on Mon Mar 31 18:21:20 GMT 2025 , Edited by admin on Mon Mar 31 18:21:20 GMT 2025
PRIMARY
WIKIPEDIA
PHENOTHRIN
Created by admin on Mon Mar 31 18:21:20 GMT 2025 , Edited by admin on Mon Mar 31 18:21:20 GMT 2025
PRIMARY
DRUG BANK
DB13717
Created by admin on Mon Mar 31 18:21:20 GMT 2025 , Edited by admin on Mon Mar 31 18:21:20 GMT 2025
PRIMARY
MERCK INDEX
m8595
Created by admin on Mon Mar 31 18:21:20 GMT 2025 , Edited by admin on Mon Mar 31 18:21:20 GMT 2025
PRIMARY Merck Index