U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Estrogenic potential of certain pyrethroid compounds in the MCF-7 human breast carcinoma cell line.
1999 Mar
Sumithrin: from inception to integration within West Nile virus programs.
2001 Dec
[Synthesis of hapten 3-phenoxybenzyl-2,2-dimetheyl-cyclopropane-1,3-dicarboxylate].
2001 Nov
Head lice infestation: bug busting vs. traditional treatment.
2001 Nov
Evaluation of safety and efficacy of acaricides for control of the African tortoise tick (Amblyomma marmoreum) on leopard tortoises (Geochelone pardalis).
2002 Mar
Effects of pyrethroid insecticides and estrogen on WNT10B proto-oncogene expression.
2002 Nov
Enzyme-linked immunosorbent assay for the pyrethroid deltamethrin.
2002 Sep 25
Prevalence and treatment of Pediculus humanus capitis with 1% permethrin and 0.4% d-phenothrin in Turkey.
2003
Lack of estrogenic or (anti-)androgenic effects of d-phenothrin in the uterotrophic and Hershberger assays.
2003 Apr 22
Isocratic reversed-phase liquid chromatographic method for the simultaneous determination of (S)-methoprene, MGK264, piperonyl butoxide, sumithrin and permethrin in pesticide formulation.
2003 Jan 3
Pyrethroid stimulation of ion transport across frog skin.
2003 Jun
Epidemic of gynecomastia among haitian refugees: exposure to an environmental antiandrogen.
2003 Sep-Oct
Assessing estrogenic activity of pyrethroid insecticides using in vitro combination assays.
2004 Apr
Toxicity of a synergized formulation of sumithrin to Daphnia magna.
2004 Jun
Diagnostic dose of synergized d-phenothrin for insecticide susceptibility testing by bottle bioassay.
2004 Jun
Burns and Phenothrin anti-lice lotion.
2004 Sep
A comparison of the toxicity of synergized and technical formulations of permethrin, sumithrin, and resmethrin to trout.
2005 Feb
Simultaneous determination of pyrethroid and pyrethrin metabolites in human urine by gas chromatography-high resolution mass spectrometry.
2005 Jan 25
Treatment of head louse infestation with 4% dimeticone lotion: randomised controlled equivalence trial.
2005 Jun 18
Human exposure to mosquito-control pesticides--Mississippi, North Carolina, and Virginia, 2002 and 2003.
2005 Jun 3
Toxicity of three mosquito insecticides to crayfish.
2006 Apr
Comparison of different mass spectrometric detection techniques in the gas chromatographic analysis of pyrethroid insecticide residues in soil after microwave-assisted extraction.
2006 Feb
Space treatments of insecticide for control of dengue virus vector Aedes aegypti in southern Mexico. I. Baseline penetration trials in open field and houses.
2006 Jun
A human-health risk assessment for West Nile virus and insecticides used in mosquito management.
2006 Mar
The photochemical behaviour of five household pyrethroid insecticides and a synergist as studied by photo-solid-phase microextraction.
2007 Jul
Randomised, controlled, assessor blind trial comparing 4% dimeticone lotion with 0.5% malathion liquid for head louse infestation.
2007 Nov 7
Comparison of dilute and neat formulations of Anvil by ultra-low volume ground application against Anopheles quadrimaculatus in Arkansas.
2007 Sep
Insecticide resistance in potential vector mosquitoes for West Nile virus in Japan.
2007 Sep
Behavioral-based educational intervention directed toward Egyptian agricultural families to protect children from pesticide exposure.
2007-2008
Residual efficacy of field-applied permethrin, d-phenothrin, and resmethrin on plant foliage against adult mosquitoes.
2008 Dec
Pyrethroid pesticides and their metabolites in vacuum cleaner dust collected from homes and day-care centers.
2008 Nov
Head lice.
2009 Jan 14
Simultaneous determination of 18 pyrethroids in indoor air by gas chromatography/mass spectrometry.
2009 Jun 26
Toxicity of delta-phenothrin and resmethrin to non-target insects.
2009 Mar
Pyrethroids as promising marine antifoulants: laboratory and field studies.
2009 Mar-Apr
Recent rapid rise of a permethrin knock down resistance allele in Aedes aegypti in México.
2009 Oct 13
Use of biocidal products (insect sprays and electro-vaporizer) in indoor areas--exposure scenarios and exposure modeling.
2009 Sep
Use of semipermeable membrane devices for monitoring pesticides in indoor air.
2009 Sep-Oct
A rapid and sensitive analytical method for the determination of 14 pyrethroids in water samples.
2010 Apr 9
Simultaneous determination of nine pyrethroids in indoor insecticide products by capillary gas chromatography.
2010 Feb 5
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
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
HEGOR ANTIPOUX
Brand 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 Fri Dec 15 16:11:30 GMT 2023 , Edited by admin on Fri Dec 15 16:11:30 GMT 2023
EPA PESTICIDE CODE 69005
Created by admin on Fri Dec 15 16:11:30 GMT 2023 , Edited by admin on Fri Dec 15 16:11:30 GMT 2023
WHO-ATC P03AC03
Created by admin on Fri Dec 15 16:11:30 GMT 2023 , Edited by admin on Fri Dec 15 16:11:30 GMT 2023
WHO-VATC QP53AC03
Created by admin on Fri Dec 15 16:11:30 GMT 2023 , Edited by admin on Fri Dec 15 16:11:30 GMT 2023
Code System Code Type Description
CHEBI
34916
Created by admin on Fri Dec 15 16:11:30 GMT 2023 , Edited by admin on Fri Dec 15 16:11:30 GMT 2023
PRIMARY
CAS
26002-80-2
Created by admin on Fri Dec 15 16:11:30 GMT 2023 , Edited by admin on Fri Dec 15 16:11:30 GMT 2023
PRIMARY
PUBCHEM
4767
Created by admin on Fri Dec 15 16:11:30 GMT 2023 , Edited by admin on Fri Dec 15 16:11:30 GMT 2023
PRIMARY
EPA CompTox
DTXSID7032688
Created by admin on Fri Dec 15 16:11:30 GMT 2023 , Edited by admin on Fri Dec 15 16:11:30 GMT 2023
PRIMARY
NCI_THESAURUS
C166974
Created by admin on Fri Dec 15 16:11:30 GMT 2023 , Edited by admin on Fri Dec 15 16:11:30 GMT 2023
PRIMARY
RXCUI
33303
Created by admin on Fri Dec 15 16:11:30 GMT 2023 , Edited by admin on Fri Dec 15 16:11:30 GMT 2023
PRIMARY RxNorm
EVMPD
SUB09777MIG
Created by admin on Fri Dec 15 16:11:30 GMT 2023 , Edited by admin on Fri Dec 15 16:11:30 GMT 2023
PRIMARY
INN
5705
Created by admin on Fri Dec 15 16:11:30 GMT 2023 , Edited by admin on Fri Dec 15 16:11:30 GMT 2023
PRIMARY
ChEMBL
CHEMBL1322884
Created by admin on Fri Dec 15 16:11:30 GMT 2023 , Edited by admin on Fri Dec 15 16:11:30 GMT 2023
PRIMARY
DRUG CENTRAL
4686
Created by admin on Fri Dec 15 16:11:30 GMT 2023 , Edited by admin on Fri Dec 15 16:11:30 GMT 2023
PRIMARY
FDA UNII
707484X33X
Created by admin on Fri Dec 15 16:11:30 GMT 2023 , Edited by admin on Fri Dec 15 16:11:30 GMT 2023
PRIMARY
SMS_ID
100000091961
Created by admin on Fri Dec 15 16:11:30 GMT 2023 , Edited by admin on Fri Dec 15 16:11:30 GMT 2023
PRIMARY
ECHA (EC/EINECS)
247-404-5
Created by admin on Fri Dec 15 16:11:30 GMT 2023 , Edited by admin on Fri Dec 15 16:11:30 GMT 2023
PRIMARY
NSC
758668
Created by admin on Fri Dec 15 16:11:30 GMT 2023 , Edited by admin on Fri Dec 15 16:11:30 GMT 2023
PRIMARY
HSDB
3922
Created by admin on Fri Dec 15 16:11:30 GMT 2023 , Edited by admin on Fri Dec 15 16:11:30 GMT 2023
PRIMARY
ALANWOOD
phenothrin
Created by admin on Fri Dec 15 16:11:30 GMT 2023 , Edited by admin on Fri Dec 15 16:11:30 GMT 2023
PRIMARY
WIKIPEDIA
PHENOTHRIN
Created by admin on Fri Dec 15 16:11:30 GMT 2023 , Edited by admin on Fri Dec 15 16:11:30 GMT 2023
PRIMARY
DRUG BANK
DB13717
Created by admin on Fri Dec 15 16:11:30 GMT 2023 , Edited by admin on Fri Dec 15 16:11:30 GMT 2023
PRIMARY
MERCK INDEX
m8595
Created by admin on Fri Dec 15 16:11:30 GMT 2023 , Edited by admin on Fri Dec 15 16:11:30 GMT 2023
PRIMARY Merck Index