This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Phosmet
DrugBank Accession Number
DB11448
Background

Phosmet is a phthalimide-derived organophosphate. It is a non-specific insecticide. It is mainly used on apple trees to control codling moths. It is also used on other fruit crops, ornamentals, and vines to control aphids, suckers, mites, and fruit flies.

Type
Small Molecule
Groups
Vet approved
Structure
Thumb
Weight
Average: 317.31
Monoisotopic: 316.994537216
Chemical Formula
C11H12NO4PS2
Synonyms
  • Decemthion
  • Fosmet
  • O,O-Dimethyl phthalimidomethyl phosphorodithioate
  • O,O-Dimethyl S-(phthalimidomethyl) dithiophosphate
  • O,O-Dimethyl S-phthalimidomethyl phosphorodithioate
  • PMP
  • S-((1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl)phosphorodithioic acid O,O-dimethyl ester
  • S-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl] O,O-dimethyl dithiophosphate

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcrivastineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Phosmet.
AdenosineThe risk or severity of QTc prolongation can be increased when Phosmet is combined with Adenosine.
AjmalineThe risk or severity of QTc prolongation can be increased when Ajmaline is combined with Phosmet.
AlfuzosinThe risk or severity of QTc prolongation can be increased when Alfuzosin is combined with Phosmet.
AlimemazineThe risk or severity of QTc prolongation can be increased when Alimemazine is combined with Phosmet.
AmantadineThe risk or severity of QTc prolongation can be increased when Amantadine is combined with Phosmet.
AmifampridineThe risk or severity of QTc prolongation can be increased when Phosmet is combined with Amifampridine.
AmiodaroneThe risk or severity of QTc prolongation can be increased when Phosmet is combined with Amiodarone.
AmisulprideThe risk or severity of QTc prolongation can be increased when Amisulpride is combined with Phosmet.
AmitriptylineThe risk or severity of QTc prolongation can be increased when Phosmet is combined with Amitriptyline.
Interactions
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Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phthalimides. These are aromatic heterocyclic compounds containing a 1,3-dioxoisoindoline moiety. They are imide derivatives of phthalic anhydrides.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Isoindoles and derivatives
Sub Class
Isoindolines
Direct Parent
Phthalimides
Alternative Parents
Isoindoles / N-substituted carboxylic acid imides / Dithiophosphate S-esters / Dithiophosphate O-esters / Benzenoids / Sulfenyl compounds / Organothiophosphorus compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds
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Substituents
Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carboxylic acid derivative / Carboxylic acid imide / Carboxylic acid imide, n-substituted / Dithiophosphate o-ester / Dithiophosphate s-ester / Hydrocarbon derivative / Isoindole
show 11 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organic thiophosphate, organothiophosphate insecticide, phthalimides (CHEBI:38786) / Organophosphorus insecticides (C18756)
Affected organisms
Not Available

Chemical Identifiers

UNII
VN04LI540Y
CAS number
732-11-6
InChI Key
LMNZTLDVJIUSHT-UHFFFAOYSA-N
InChI
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
IUPAC Name
O,O-dimethyl {[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]sulfanyl}phosphonothioate
SMILES
COP(=S)(OC)SCN1C(=O)C2=CC=CC=C2C1=O

References

General References
  1. Cheon S, Yang H, Park KM, Kim TH, Kim J: Phosmet: O,O-dimethyl S-phthalimidomethyl phospho-rodithio-ate. Acta Crystallogr Sect E Struct Rep Online. 2010 Jul 31;66(Pt 8):o2137. doi: 10.1107/S1600536810029338. [Article]
  2. Sinderhauf K, Schwack W: Photolysis experiments on phosmet, an organophosphorus insecticide. J Agric Food Chem. 2003 Sep 24;51(20):5990-5. [Article]
  3. Bleyl DW: [Embryotoxicity and teratogenicity of phosmet in mice]. Arch Exp Veterinarmed. 1980;34(5):791-5. [Article]
  4. Warren BC, Yeoman GH: Phosmet as a warble control agent. Vet Rec. 1977 Dec 17;101(25):504-5. [Article]
  5. Liu C, Gan J, Zhang Y, Liang M, Shu X, Shu J, Yang B: Heterogeneous reaction of suspended phosmet particles with NO3 radicals. J Phys Chem A. 2011 Oct 6;115(39):10744-8. doi: 10.1021/jp205175p. Epub 2011 Sep 14. [Article]
  6. Vargova M, Batora I, Jakubovsky J, Kobzova D, Gajdova M, Batorova A, Lipkova V: On the mechanism of acute toxicity of phosmet. Czech Med. 1986;9(3):130-42. [Article]
  7. Gajdova M, Vargova M, Jakubovsky J, Grunt J, Valky J, Galbavy S: [Estrogenic effect of phosmet on the uterus of neonatal rats]. Bratisl Lek Listy. 1988 Nov;89(11):843-7. [Article]
  8. Hewett GR, Heard TW: Phosmet for the systemic control of pig mange. Vet Rec. 1982 Dec 11;111(24):558. [Article]
  9. Dulak K, Jonas F: Determination of phosmet by high-performance liquid chromatography. J Chromatogr. 1987 Jun 19;396:433-6. [Article]
KEGG Drug
D08372
KEGG Compound
C18756
ChemSpider
12367
BindingDB
79427
ChEBI
38786
ChEMBL
CHEMBL1481873
ZINC
ZINC000000001934
Wikipedia
Phosmet

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0443 mg/mLALOGPS
logP2.7ALOGPS
logP2.15ChemAxon
logS-3.8ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area55.84 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity79.77 m3·mol-1ChemAxon
Polarizability30.05 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0900000000-b19820d3eaa3e9d1dc43
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0900000000-66479cf96aa22f5da506
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0900000000-1a70229d4ed126c9b2d8
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0900000000-3a5634a2d3df7c5b6729
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03e9-1900000000-c59e05b23007bdd07bd7
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-06sj-3900000000-b97e04c432c88f5fa05e
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-2900000000-5416ea123f416f399b05

Drug created at February 25, 2016 18:51 / Updated at June 12, 2020 16:53