PHOSMET

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H12NO4PS2
Molecular Weight	317.321
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COP(=S)(OC)SCN1C(=O)C2=CC=CC=C2C1=O

InChI

InChIKey=LMNZTLDVJIUSHT-UHFFFAOYSA-N

InChI=1S/C11H12NO4PS2/c1-15-17(18,16-2)19-7-12-10(13)8-5-3-4-6-9(8)11(12)14/h3-6H,7H2,1-2H3

HIDE SMILES / InChI

Molecular Formula	C11H12NO4PS2
Molecular Weight	317.321
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://pmep.cce.cornell.edu/profiles/extoxnet/metiram-propoxur/phosmet-ext.html | https://www3.epa.gov/pesticides/chem_search/ppls/000059-00235-19910813.pdf

Phosmet is a non-systemic, organophosphate insecticide used on both plants and animals. Phosmet is mainly used on apple trees for control of coddling moth, though it is used on a wide range of fruit crops, ornamentals and vines for the control of aphids, suckers, mites and fruit flies. Phosmet is a moderately potent cholinesterase inhibitor.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sarcoptes scabiei 1 Target ID: Sarcoptes scabiei Sources: https://www.ncbi.nlm.nih.gov/pubmed/8128575	Inhibitor 8504
Acetylcholinesterase 209 Target ID: CHEMBL3199 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26948591 \| http://pmep.cce.cornell.edu/profiles/extoxnet/metiram-propoxur/phosmet-ext.html \| https://ec.europa.eu/food/sites/food/files/safety/docs/sci-com_ssc_out18_en.pdf	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Scabies 9 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8128575	Preventing		Approved 8583	Prolate I-E Approved Use A beef and non-lactating dairy cattle insecticide for the control of lice, cattle ticks, southern cattle ticks, winter ticks, lone star ticks, gulf coast ear ticks, hornflies, sarcoptic mange and scabies mites and a swine insecticide for control of lice and sarcoptic mange. Launch Date 1991

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252 inducer 1087	inhibitor 2438 substrate 1193	inhibitor 2507 substrate 1388	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 2057 MATE2-K 77 OATP1B1 1079 OCT1 620 MATE1 415 BCRP 910 OCT2 779 OAT3 747 CYP1A2 2153 OAT1 725 P-gp 1741 CYP19A1 429	CYP2A6 626 P-gp 2052 CYP2C18 149 CYP2C19 1119 CYP2B6 776 CYP1A1 389 CYP1A2 1197

Drug as perpetrator

Target	Modality	Activity
OATP1B1 1095	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/29448871/	no [IC50 >100 uM]
CYP3A4 2633	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/12901#section=Biological-Test-Results Page: 353.0	no
MATE2-K 77	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/29448871/	no
MRP1 232	activator 342 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/12901#section=Biological-Test-Results Page: 59.0	no
OAT1 730	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/29448871/	no
OAT3 749	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/29448871/	no
P-gp 1932	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/12901#section=Biological-Test-Results Page: 81.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/12901#section=Biological-Test-Results	yes [IC50 0.4365 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/12901#section=Biological-Test-Results	yes [IC50 0.7762 uM]
OCT1 656	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/29448871/	yes [IC50 10.4 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/12901#section=Biological-Test-Results Page: 12.0	yes [IC50 15.4871 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/12901#section=Biological-Test-Results Page: 4.0	yes [IC50 2.4545 uM]
BCRP 985	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/36149323/	yes [IC50 42 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/12901#section=Biological-Test-Results Page: 8.0	yes [IC50 6.9178 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/12901#section=Biological-Test-Results Page: 9.0	yes [IC50 7.7507 uM]
OCT2 782	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/29448871/	yes [IC50 7.9 uM]
MATE1 416	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/29448871/	yes
OATP2B1 162	activator 342 Sources: https://pubmed.ncbi.nlm.nih.gov/29448871/	yes

Drug as victim

Target	Modality	Activity
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/32590074/	major [Km 1.496 uM]
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/32590074/	minor [Km 16.01 uM]
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/32590074/	minor [Km 340.7 uM]
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/12901#section=Biological-Test-Results Page: 346 \| 354	no
CYP2C18 149	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/32590074/	yes [Km 1.288 uM]
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/32590074/	yes [Km 16.44 uM]
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/32590074/	yes [Km 2.195 uM]
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/32590074/	yes [Km 229.7 uM]
CYP1A1 389	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/32590074/	yes [Km 4.01 uM]
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/32590074/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/12901#section=Biological-Test-Results Page: 206.0

PubMed

Title	Date	PubMed
Spectroscopic characterization and structural modeling of prolamin from maize and pearl millet.	2004-07	14508615
Polyhydroxyalkanoate (PHA) granule formation in Ralstonia eutropha cells: a computer simulation.	2004-06	14758517
Wavefront technology in cataract surgery.	2004-02	14743021
A finite B-spline basis set for accurate diatomic molecule calculations.	2004-02	14696071
Predicted electric field near small superconducting ellipsoids.	2004-01-09	14754006
Correlation of tumor volume and surface area with lymph node status in patients with multifocal/multicentric breast carcinoma.	2004-01-01	14692020
Interactions of the neurotoxin vipoxin in solution studied by dynamic light scattering.	2004-01	14695289
Organophosphorous and organochlorine pesticides affect human placental phosphoinositides metabolism and PI-4 kinase activity.	2004	14994277
Solution conformation of a nitrobenzoxadiazole derivative of the polyene antibiotic nystatin: a FRET study.	2003-12-05	14644562
Clinical significance of 3D reconstruction of arteriovenous malformation using digital subtraction angiography and its modification with CT information in stereotactic radiosurgery.	2003-12-01	14630278
The interobserver reliability of ovarian volume measurement is improved with three-dimensional ultrasound, but dependent upon technique.	2003-12	14698335
Microsomal transformation of organophosphorus pesticides by white rot fungi.	2003-12	14669870
The magnetic lead field theorem in the quasi-static approximation and its use for magnetoencephalography forward calculation in realistic volume conductors.	2003-11-21	14680264
Spherical aberration after laser in situ keratomileusis and photorefractive keratectomy. Clinical results and theoretical models of etiology.	2003-11	14670417
Vibration of prolate spheroidal shells with shear deformation and rotatory inertia: axisymmetric case.	2003-11	14650015
Acoustic backscattering by Hawaiian lutjanid snappers. 1. Target strength and swimbladder characteristics.	2003-11	14650010
The ontogenetic scaling of hydrodynamics and swimming performance in jellyfish (Aurelia aurita).	2003-11	14555752
Structural and functional characterization of the human NBC3 sodium/bicarbonate co-transporter carboxyl-terminal cytoplasmic domain.	2003-10-28	14578046
Biomolecular stress-sensitive gauges: surface-mediated immobilization of mechanosensitive membrane protein.	2003-10-22	14558816
Photolysis experiments on phosmet, an organophosphorus insecticide.	2003-09-24	13129307
Morphology-dependent resonances of nearly spherical particles in random orientation.	2003-09-20	14526845
A comparison of CT scan to transrectal ultrasound-measured prostate volume in untreated prostate cancer.	2003-09-01	12909212
Effect of electric field induced transmembrane potential on spheroidal cells: theory and experiment.	2003-09	12712266
Management of insecticide resistance in Oriental fruit moth (Grapholita molesta; Lepidoptera: Tortricidae) populations from Ontario.	2003-08	12916773
The shape parameter of liposomes and DNA-lipid complexes determined by viscometry utilizing small sample volumes.	2003-08	12885666
A new radionuclide approach for the quantification of left ventricular volumes: the 'geometric count based' method.	2003-08	12869825
A general gel layer model for the transport of colloids and macroions in dilute solution.	2003-07-01	12804889
Bacteriophage phi29 scaffolding protein gp7 before and after prohead assembly.	2003-07	12778115
Two-dimensional packing in prolate granular materials.	2003-05	12786141
Effect of pesticide use in fruit production orchards on shallow ground water.	2003-05	12716049
The use of a new miniature cryoprobe for ablation of bone tissue: in vivo assessment of the probe and application of the method to bone in a sheep model.	2003-04-22	12709264
The primary electroviscous effect of prolate silica sols.	2003-04-15	12686195
Trifluoperazine effects on anionic and zwitterionic micelles: a study by small angle X-ray scattering.	2003-04-15	12686194
The effects of acute pesticide exposure on neuroblastoma cells chronically exposed to diazinon.	2003-03-14	12505446
Near-field calculations for a rigid spheroid with an arbitrary incident acoustic field.	2003-03	12656356
Mathematical model of corneal surface smoothing after laser refractive surgery.	2003-03	12614741
New shape isomer in the self-conjugate nucleus 72Kr.	2003-02-28	12633421
The primary electroviscous effect, free solution electrophoretic mobility, and diffusion of dilute prolate ellipsoid particles (minor axis = 3 nm) in monovalent salt solution.	2003-02-15	12618099
Cataract surgery in patients with prior refractive surgery.	2003-02	12544810
Study of corneal topographic patterns with single continuous suturing techniques in penetrating keratoplasty.	2003-01	12502939
The importance of prostatic measuring by transrectal ultrasound in surgical management of patients with clinically benign prostatic hyperplasia.	2003	14515048
A characterization of the lumenal region of human tapasin reveals the presence of two structural domains.	2002-12-10	12463753
Prospective randomized trial of an anterior surface modified prolate intraocular lens.	2002-12-03	12458862
A new intraocular lens design to reduce spherical aberration of pseudophakic eyes.	2002-12-03	12458861
Contrast-assisted destruction-replenishment ultrasound for the assessment of tumor microvasculature in a rat model.	2002-12	12625773
Backbone dynamics of the cytotoxic ribonuclease alpha-sarcin by 15N NMR relaxation methods.	2002-12	12522295
Shapes of phospholipid [correction of phosholipid] vesicles with beadlike protrusions.	2002-12	12451418
Geodesic chaos around quadrupolar deformed centers of attraction.	2002-10	12443353
Three-axis ellipsoidal fitting of videokeratoscopic height data after penetrating keratoplasty.	2002-06	12525969
[Pollen morphology of bee plants in Changbai Mountain area].	2001-04	12525044

Patents

Sample Use Guides

In Vivo Use Guide

Cattle and swine: Dip Spray Use at the following dilutions of drug: water - Use for the control of grubs; apply dips at 1:60, pour-ons at 1:2, and sprays at 1:49. - Use for the control of lice; apply dips at 1:60, pour-ons at 1:2 or 1:5, and sprays at 1:49 or 1:100. - Use for the control of horn flies; apply dips at 1:60 and sprays at 1:49 or 1:100. - Use for the control of cattle ticks; apply dips at 1:60 or 1:240 and sprays at 1:49. - Use for the control of Southern cattle ticks; apply dips at 1:60 or 1:240 and sprays at 1:49. - Use for the control of scabies mites; apply dips at 1:60. - Use for the control of Lone Star ticks; apply dips at 1:60 and sprays at 1:49 or 1:100.

Route of Administration: Topical

In Vitro Use Guide

Phosmet (1-1000 uM) reduced cell viability and induced cellular injury in JEG-3 cells. After 24 h of incubation with Phosmet at 10 or 100 uM, 25.4% and 29.6% of annexin-V positive JEG-3 cells could be detected, respectively.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:11:25 GMT 2025` Edited by `admin` on `Mon Mar 31 18:11:25 GMT 2025`
Record UNII	VN04LI540Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

O,O-DIMETHYL S-PHTHALIMIDOMETHYL PHOSPHORODITHIOATE

Preferred Name

English

PHOSMET

Common Name

English

PHOSMET [MART.]

Common Name

English

PHOSMET [ISO]

Common Name

English

O,O-DIMETHYL PHTHALIMIDOMETHYL PHOSPHORODITHIOATE

Systematic Name

English

PHOSMET [GREEN BOOK]

Common Name

English

N-(MERCAPTOMETHYL) PHTHALIMIDE S-(O,O-DIMETHYL PHOSPHORODITHIOATE)

Systematic Name

English

PHOSMET [HSDB]

Common Name

English

PHOSMET [MI]

Common Name

English

S-((1,3-DIHYDRO-1,3-DIOXO-2H-ISOINDOL-2-YL)METHYL) O,O-DIMETHYL PHOSPHORODITHIOATE

Systematic Name

English

Classification Tree Code System Code

WHO-VATC

QP53BB03