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

Molecular Formula C23H26O3
Molecular Weight 350.4507
Charge 0
Count
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 0 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Antiplasmodial and antitrypanosomal activity of pyrethrins and pyrethroids.
2011-09-14
Prallethrin-induced excitation increases contact between sprayed ultralow volume droplets and flying mosquitoes (Diptera: Culicidae) in a wind tunnel.
2010-11
Evaluation of a new formulation of adulticide, DUET, against West Nile virus vector mosquitoes.
2010-06
Efficacy of spray formulations containing binary mixtures of clove and eucalyptus oils against susceptible and pyrethroid/ malathion-resistant head lice (Anoplura: Pediculidae).
2010-05
A rapid and sensitive analytical method for the determination of 14 pyrethroids in water samples.
2010-04-09
Simultaneous determination of nine pyrethroids in indoor insecticide products by capillary gas chromatography.
2010-02-05
Use of semipermeable membrane devices for monitoring pesticides in indoor air.
2009-11-18
Recent rapid rise of a permethrin knock down resistance allele in Aedes aegypti in México.
2009-10-13
Use of biocidal products (insect sprays and electro-vaporizer) in indoor areas--exposure scenarios and exposure modeling.
2009-09
Simultaneous determination of 18 pyrethroids in indoor air by gas chromatography/mass spectrometry.
2009-06-26
Toxicity of delta-phenothrin and resmethrin to non-target insects.
2009-03
Head lice.
2009-01-14
Behavioral-based educational intervention directed toward Egyptian agricultural families to protect children from pesticide exposure.
2009-01-10
Residual efficacy of field-applied permethrin, d-phenothrin, and resmethrin on plant foliage against adult mosquitoes.
2008-12
Pyrethroid pesticides and their metabolites in vacuum cleaner dust collected from homes and day-care centers.
2008-11
Pyrethroids as promising marine antifoulants: laboratory and field studies.
2008-01-05
Randomised, controlled, assessor blind trial comparing 4% dimeticone lotion with 0.5% malathion liquid for head louse infestation.
2007-11-07
Comparison of dilute and neat formulations of Anvil by ultra-low volume ground application against Anopheles quadrimaculatus in Arkansas.
2007-09
Insecticide resistance in potential vector mosquitoes for West Nile virus in Japan.
2007-09
The photochemical behaviour of five household pyrethroid insecticides and a synergist as studied by photo-solid-phase microextraction.
2007-07
Space treatments of insecticide for control of dengue virus vector Aedes aegypti in southern Mexico. I. Baseline penetration trials in open field and houses.
2006-06
Pesticide exposure: the hormonal function of the female reproductive system disrupted?
2006-05-31
Biomarker of pyrethrum exposure.
2006-04-10
Toxicity of three mosquito insecticides to crayfish.
2006-04
A human-health risk assessment for West Nile virus and insecticides used in mosquito management.
2006-03
Comparison of different mass spectrometric detection techniques in the gas chromatographic analysis of pyrethroid insecticide residues in soil after microwave-assisted extraction.
2006-02
Aircraft disinsection: exposure assessment and evaluation of a new pre-embarkation method.
2006-01
Insecticide resistance in Culex pipiens from New York.
2005-09
Aerial ultra-low-volume assessment of ANVIL 10+10 against Anopheles quadrimaculatus.
2005-09
Treatment of head louse infestation with 4% dimeticone lotion: randomised controlled equivalence trial.
2005-06-18
Human exposure to mosquito-control pesticides--Mississippi, North Carolina, and Virginia, 2002 and 2003.
2005-06-03
A comparison of the toxicity of synergized and technical formulations of permethrin, sumithrin, and resmethrin to trout.
2005-02
Simultaneous determination of pyrethroid and pyrethrin metabolites in human urine by gas chromatography-high resolution mass spectrometry.
2005-01-25
Burns and Phenothrin anti-lice lotion.
2004-09
Pesticide spraying for West Nile virus control and emergency department asthma visits in New York City, 2000.
2004-08
Toxicity of a synergized formulation of sumithrin to Daphnia magna.
2004-06
Diagnostic dose of synergized d-phenothrin for insecticide susceptibility testing by bottle bioassay.
2004-06
Assessing estrogenic activity of pyrethroid insecticides using in vitro combination assays.
2004-04
Development of an enzyme-linked immunosorbent assay for the pyrethroid cypermethrin.
2004-03-10
Determination of pyrethrin and pyrethroid pesticides in urine and water matrixes by liquid chromatography with diode array detection.
2004-02-26
Epidemic of gynecomastia among haitian refugees: exposure to an environmental antiandrogen.
2003-10-30
Phthirus pubis infestation of the eyelashes and scalp hairs in a girl.
2003-07-19
Pyrethroid stimulation of ion transport across frog skin.
2003-06
Lack of estrogenic or (anti-)androgenic effects of d-phenothrin in the uterotrophic and Hershberger assays.
2003-04-22
Isocratic reversed-phase liquid chromatographic method for the simultaneous determination of (S)-methoprene, MGK264, piperonyl butoxide, sumithrin and permethrin in pesticide formulation.
2003-01-03
Prevalence and treatment of Pediculus humanus capitis with 1% permethrin and 0.4% d-phenothrin in Turkey.
2003
Effects of pyrethroid insecticides and estrogen on WNT10B proto-oncogene expression.
2002-11
Enzyme-linked immunosorbent assay for the pyrethroid deltamethrin.
2002-09-25
Evaluation of safety and efficacy of acaricides for control of the African tortoise tick (Amblyomma marmoreum) on leopard tortoises (Geochelone pardalis).
2002-03
[Synthesis of hapten 3-phenoxybenzyl-2,2-dimetheyl-cyclopropane-1,3-dicarboxylate].
2001-11
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
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:21:20 GMT 2025
Edited
by admin
on Mon Mar 31 18:21:20 GMT 2025
Record UNII
707484X33X
Record Status Validated (UNII)
Record Version
  • Download
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
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