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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
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
Estrogenic potential of certain pyrethroid compounds in the MCF-7 human breast carcinoma cell line.
1999 Mar
Enzyme-linked immunosorbent assay for the pyrethroid deltamethrin.
2002 Sep 25
Pyrethroid stimulation of ion transport across frog skin.
2003 Jun
Epidemic of gynecomastia among haitian refugees: exposure to an environmental antiandrogen.
2003 Sep-Oct
A comparison of the toxicity of synergized and technical formulations of permethrin, sumithrin, and resmethrin to trout.
2005 Feb
Pyrethroid pesticides and their metabolites in vacuum cleaner dust collected from homes and day-care centers.
2008 Nov
Recent rapid rise of a permethrin knock down resistance allele in Aedes aegypti in México.
2009 Oct 13
Simultaneous determination of nine pyrethroids in indoor insecticide products by capillary gas chromatography.
2010 Feb 5
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 Fri Dec 15 16:11:30 GMT 2023
Edited
by admin
on Fri Dec 15 16:11:30 GMT 2023
Record UNII
707484X33X
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
ACTIVE MOIETY