PHOXIM

Possibly Marketed Outside US

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7624853
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Plutella xylostella 1 Target ID: CHEMBL614677 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21858910	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Ectoparasitic disease 2 Sources: https://goo.gl/7nWvuq	Primary		Approved 8583	Baymite Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
294 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8345567/	50 mg/kg single, topical dose: 50 mg/kg route of administration: Topical experiment type: SINGLE co-administered:		PHOXIM plasma	Sus scrofa population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
5848 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8345567/	10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		PHOXIM plasma	Sus scrofa population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
2789.5 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8345567/	50 mg/kg single, topical dose: 50 mg/kg route of administration: Topical experiment type: SINGLE co-administered:		PHOXIM plasma	Sus scrofa population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
9.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8345567/	10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		PHOXIM plasma	Sus scrofa population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP19A1 429 CYP1A2 2153 CYP2C19 2057	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/9570290#section=BioAssay-Results Page: 8.0	inconclusive [IC50 9.4392 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/9570290#section=BioAssay-Results Page: 2.0	yes [IC50 0.2245 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/9570290#section=BioAssay-Results Page: 3.0	yes [IC50 1.2302 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/9570290#section=BioAssay-Results Page: 4.0	yes [IC50 1.5487 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/9570290#section=BioAssay-Results Page: 10.0	yes [IC50 13.8029 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/9570290#section=BioAssay-Results Page: 5.0	yes [IC50 2.0005 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/9570290#section=BioAssay-Results Page: 120 \| 124	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/9570290#section=BioAssay-Results Page: 11.0

PubMed

Title	Date	PubMed
Molecular cloning, expression and antioxidant characterisation of a typical thioredoxin gene (AccTrx2) in Apis cerana cerana.	2013-09-15	23747404
Acetylcholinesterase biosensor based on Prussian blue-modified electrode for detecting organophosphorous pesticides.	2010-08-15	20466535
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.	2009-05	19496425
JWA--a novel environmental-responsive gene, involved in estrogen receptor-associated signal pathway in MCF-7 and MDA-MB-231 breast carcinoma cells.	2005-03-26	15799245
Effects of organophosphorous pesticides used in china on various mammalian cells.	2005	15793557

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

In Vitro Use Guide

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 10–15 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, 5–7 treatments and one control of distilled water containing 1 g L−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 `Mon Mar 31 18:24:36 GMT 2025` Edited by `admin` on `Mon Mar 31 18:24:36 GMT 2025`
Record UNII	6F5V775VPO
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

BAYTHION

Preferred Name

English

PHOXIM

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

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