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Details

Stereochemistry ACHIRAL
Molecular Formula C12H15N2O3PS
Molecular Weight 298.298
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of PHOXIM

SMILES

CCOP(=S)(OCC)ON=C(C#N)C1=CC=CC=C1

InChI

InChIKey=ATROHALUCMTWTB-UHFFFAOYSA-N
InChI=1S/C12H15N2O3PS/c1-3-15-18(19,16-4-2)17-14-12(10-13)11-8-6-5-7-9-11/h5-9H,3-4H2,1-2H3

HIDE SMILES / InChI

Molecular Formula C12H15N2O3PS
Molecular Weight 298.298
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
Curator's Comment: The description was created based on several sources, including https://goo.gl/7nWvuq | https://www.drugs.com/international/phoxim.html | https://www.ncbi.nlm.nih.gov/pubmed/21858910

Phoxim (Diethyl-O-(alpha-cyanobenzylideneamino)-thiophosphate) is an organophosphorus insecticide used in veterinary medicine for the control of mites, lice and other ectoparasites in cattle, pigs, sheep, and goats. Phoxim is also used for plant protection, in tea production. The insecticidal activity of phoxim is mediated through inhibition of cholinesterase. Phoxim is an insecticide with selective properties: it is toxic to insects but virtually non-toxic to mammals. Although differences in sensitivity to cholinesterase inhibition contribute to this selectivity, metabolism plays a more important role. In both insects and mammals, phoxim is oxidatively desulfurated to the oxo-analog, PO-phoxim, which is a more potent inhibitor of cholinesterases than phoxim itself. In mammals, however, PO-phoxim is an extremely short-lived intermediate and, together with phoxim, is rapidly hydrolyzed to non-toxic products.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Baymite

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Effects of organophosphorous pesticides used in china on various mammalian cells.
2005
JWA--a novel environmental-responsive gene, involved in estrogen receptor-associated signal pathway in MCF-7 and MDA-MB-231 breast carcinoma cells.
2005 Mar 26
Company amplification of estalpha2/estbeta2 and correlation between esterase gene copy number and resistance to insecticides in the field Culex pipiens pallens strains collected from Beijing, China.
2009 May
Acetylcholinesterase biosensor based on Prussian blue-modified electrode for detecting organophosphorous pesticides.
2010 Aug 15
Molecular cloning, expression and antioxidant characterisation of a typical thioredoxin gene (AccTrx2) in Apis cerana cerana.
2013 Sep 15
Patents

Patents

Sample Use Guides

In Vivo Use Guide
As a veterinary drug, phoxim is administered topically either as a wash, spray, pour-on or dip. For wash and spray treatment, a 500 to 1000 mg phoxim/1 solution should be applied at approximate volumes of 3 to 4 litres for cattle, 0.5 to 1 litre for pigs and 2 to 3 litres for sheep, to be repeated after 14 days. For dip treatment of sheep, animals are dipped for at least 30 seconds in a solution containing 500 mg phoxim/l. For pour-on treatment of pigs, a solution of 75 mg phoxim/ml is applied topically at a dose of 30 mg phoxim/kg bw, to be repeated after 14 days.
Route of Administration: Topical
Toxicity of Phoxim was measured using a leaf-dip bioassay method. Cabbage leaves were soaked in a cleanser for at least 2 h, and the cutin was brushed away. Then the leaves were washed using distilled water containing 1 g/L TritonX-100 and dried naturally. Leaf discs (6 cm in diameter) were cut and dipped into the different concentrations of insecticides for 10 s and allowed to air dry for a period of 1.5 h. The discs were then placed individually into petri dishes. A total of 10ā€“15 third-instar larvae were placed in each dish, and three replications were done for each concentration (treatment), resulting in at least 30 larvae per treatment. In each bioassay, 5ā€“7 treatments and one control of distilled water containing 1 g Lāˆ’1 of Triton X-100 were tested in each bioassay. The mortality was assessed at 24 h after treatment for phoxim.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:18:24 GMT 2023
Edited
by admin
on Fri Dec 15 16:18:24 GMT 2023
Record UNII
6F5V775VPO
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHOXIM
INN   ISO   MART.   MI  
INN  
Official Name English
BAYER-9053
Code English
VALEXON
Brand Name English
PHOXIM [MI]
Common Name English
PHOXIM [ISO]
Common Name English
PHENYLGLYOXYLNITRILE OXIME O,O-DIETHYL PHOSPHOROTHIOATE
Systematic Name English
PHOXIM [MART.]
Common Name English
BAYTHION
Brand Name English
phoxim [INN]
Common Name English
VOLATON
Brand Name English
BAY 77488
Code English
PHOXIME
Common Name English
BAYER 9053
Code English
BAY-77488
Common Name English
SEBACIL (INSECTICIDE)
Brand Name English
(E,Z)-N-((DIETHOXYPHOSPHOROTHIOYL)OXY)BENZENECARBOXIMIDOYL CYANIDE
Systematic Name English
Classification Tree Code System Code
WHO-VATC QP53AF01
Created by admin on Fri Dec 15 16:18:24 GMT 2023 , Edited by admin on Fri Dec 15 16:18:24 GMT 2023
NCI_THESAURUS C737
Created by admin on Fri Dec 15 16:18:24 GMT 2023 , Edited by admin on Fri Dec 15 16:18:24 GMT 2023
EPA PESTICIDE CODE 598800
Created by admin on Fri Dec 15 16:18:24 GMT 2023 , Edited by admin on Fri Dec 15 16:18:24 GMT 2023
Code System Code Type Description
CHEBI
38812
Created by admin on Fri Dec 15 16:18:24 GMT 2023 , Edited by admin on Fri Dec 15 16:18:24 GMT 2023
PRIMARY
PUBCHEM
26927
Created by admin on Fri Dec 15 16:18:24 GMT 2023 , Edited by admin on Fri Dec 15 16:18:24 GMT 2023
PRIMARY
EVMPD
SUB09797MIG
Created by admin on Fri Dec 15 16:18:24 GMT 2023 , Edited by admin on Fri Dec 15 16:18:24 GMT 2023
PRIMARY
FDA UNII
6F5V775VPO
Created by admin on Fri Dec 15 16:18:24 GMT 2023 , Edited by admin on Fri Dec 15 16:18:24 GMT 2023
PRIMARY
ECHA (EC/EINECS)
238-887-3
Created by admin on Fri Dec 15 16:18:24 GMT 2023 , Edited by admin on Fri Dec 15 16:18:24 GMT 2023
PRIMARY
EPA CompTox
DTXSID8034324
Created by admin on Fri Dec 15 16:18:24 GMT 2023 , Edited by admin on Fri Dec 15 16:18:24 GMT 2023
PRIMARY
NCI_THESAURUS
C80605
Created by admin on Fri Dec 15 16:18:24 GMT 2023 , Edited by admin on Fri Dec 15 16:18:24 GMT 2023
PRIMARY
CAS
14816-18-3
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PRIMARY
MERCK INDEX
m8748
Created by admin on Fri Dec 15 16:18:24 GMT 2023 , Edited by admin on Fri Dec 15 16:18:24 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
PHOXIM
Created by admin on Fri Dec 15 16:18:24 GMT 2023 , Edited by admin on Fri Dec 15 16:18:24 GMT 2023
PRIMARY
ALANWOOD
phoxim
Created by admin on Fri Dec 15 16:18:24 GMT 2023 , Edited by admin on Fri Dec 15 16:18:24 GMT 2023
PRIMARY
ChEMBL
CHEMBL1906626
Created by admin on Fri Dec 15 16:18:24 GMT 2023 , Edited by admin on Fri Dec 15 16:18:24 GMT 2023
PRIMARY
MESH
C003135
Created by admin on Fri Dec 15 16:18:24 GMT 2023 , Edited by admin on Fri Dec 15 16:18:24 GMT 2023
PRIMARY
SMS_ID
100000082468
Created by admin on Fri Dec 15 16:18:24 GMT 2023 , Edited by admin on Fri Dec 15 16:18:24 GMT 2023
PRIMARY
INN
2565
Created by admin on Fri Dec 15 16:18:24 GMT 2023 , Edited by admin on Fri Dec 15 16:18:24 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY