NAV

Fenthion

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

Identification

Generic Name
Fenthion
DrugBank Accession Number
DB11412
Background

Fenthion is an organothiophosphate drug used as an insecticide, avicide, and acaricide. Its mode of action is explained by cholinesterase enzyme inhibition, which is similar to other organophosphates. Fenthion is listed as a restricted use compound by the United States Environmental Protection Agency due to its potential to cause cholinesterase inhibition in humans and animals.

Type
Small Molecule
Groups
Vet approved
Structure
3D
Similar Structures
Weight
Average: 278.328
Monoisotopic: 278.020022238
Chemical Formula
C10H15O3PS2
Synonyms
  • 4-methylmercapto-3-Methylphenyl dimethyl thiophosphate
  • Mercaptophos
  • MPP
  • O,O-Dimethyl O-[3-methyl-4-(methylsulfanyl)phenyl] thiophosphate
  • O,O-Dimethyl O-4-(methylmercapto)-3-methylphenyl phosphorothioate
  • O,O-Dimethyl O-4-methylthio-m-tolyl phosphorothioate
  • O,O-Dimethyl-O-4-(methylmercapto)-3-methylphenyl thiophosphate
  • Phosphorothioic acid, O,O-dimethyl O-(3-methyl-4-(methylthio)phenyl) ester
External IDs
  • LSM-25615
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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

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Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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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
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AcebutololFenthion may increase the bradycardic activities of Acebutolol.
AcetylcholineThe risk or severity of adverse effects can be increased when Fenthion is combined with Acetylcholine.
AclidiniumFenthion may increase the neuromuscular blocking activities of Aclidinium.
AcrivastineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Fenthion.
AdenosineThe risk or severity of QTc prolongation can be increased when Fenthion is combined with Adenosine.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenyl thiophosphates. These are organothiophosphorus compounds that contain a thiophosphoric acid O-esterified with a phenyl group.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Organic thiophosphoric acids and derivatives
Sub Class
Thiophosphoric acid esters
Direct Parent
Phenyl thiophosphates
Alternative Parents
Thiophosphate triesters / Thiophenol ethers / Phenoxy compounds / Toluenes / Alkylarylthioethers / Sulfenyl compounds / Organooxygen compounds / Hydrocarbon derivatives
Substituents
Alkylarylthioether / Aromatic homomonocyclic compound / Aryl thioether / Benzenoid / Hydrocarbon derivative / Monocyclic benzene moiety / Organic oxygen compound / Organooxygen compound / Organosulfur compound / Phenoxy compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
organic thiophosphate (CHEBI:34761) / Organophosphorus insecticides (C14420)
Affected organisms
Not Available

Chemical Identifiers

UNII
BL0L45OVKT
CAS number
55-38-9
InChI Key
PNVJTZOFSHSLTO-UHFFFAOYSA-N
InChI
InChI=1S/C10H15O3PS2/c1-8-7-9(5-6-10(8)16-4)13-14(15,11-2)12-3/h5-7H,1-4H3
IUPAC Name
O,O-dimethyl O-3-methyl-4-(methylsulfanyl)phenyl phosphorothioate
SMILES
COP(=S)(OC)OC1=CC=C(SC)C(C)=C1

References

General References
  1. Wang T, Kadlac T, Lenahan R: Persistence of fenthion in the aquatic environment. Bull Environ Contam Toxicol. 1989 Mar;42(3):389-94. [Article]
  2. Tuler SM, Bowen JM: Chronic fenthion toxicity in laying hens. Vet Hum Toxicol. 1999 Oct;41(5):302-7. [Article]
  3. Kitamura S, Kadota T, Yoshida M, Jinno N, Ohta S: Whole-body metabolism of the organophosphorus pesticide, fenthion, in goldfish, Carassius auratus. Comp Biochem Physiol C Toxicol Pharmacol. 2000 Jul;126(3):259-66. [Article]
  4. Amvrazi EG, Albanis TA: Multiclass pesticide determination in olives and their processing factors in olive oil: comparison of different olive oil extraction systems. J Agric Food Chem. 2008 Jul 23;56(14):5700-9. doi: 10.1021/jf703783u. Epub 2008 Jun 18. [Article]
  5. Wadia RS, Amin RB: Fenthion poisoning. J Pediatr. 1988 Nov;113(5):950. [Article]
  6. Mortensen ME: Therapy for fenthion poisoning. J Pediatr. 1988 Sep;113(3):616-7. [Article]
  7. Authors unspecified: Fenthion--and heartworm disease. J Am Vet Med Assoc. 1972 Oct 15;161(8):870. [Article]
  8. Zinkl JG, Jessup DA, Bischoff AI, Lew TE, Wheeldon EB: Fenthion poisoning of wading birds. J Wildl Dis. 1981 Jan;17(1):117-9. [Article]
  9. Zadrozinska J: [Fenthion breakdown in selected plants]. Rocz Panstw Zakl Hig. 1972;23(4):409-16. [Article]
  10. FRANCIS JI, BARNES JM: STUDIES ON THE MAMMALIAN TOXICITY OF FENTHION. Bull World Health Organ. 1963;29:205-12. [Article]
  11. Serrano N, Fedriani J: Fenthion suicide poisoning by subcutaneous injection. Intensive Care Med. 1997 Jan;23(1):129. [Article]
  12. METCALF RL, FUKUTO TR, WINTON MY: CHEMICAL AND BIOLOGICAL BEHAVIOUR OF FENTHION RESIDUES. Bull World Health Organ. 1963;29:219-26. [Article]
  13. Yannai, Shmuel (2003). Dictionary of Food Compounds with : Additives, Flavors, and Ingredients. CRC Press LLC. [ISBN:1584884169]
Human Metabolome Database
HMDB0033209
KEGG Drug
D07950
KEGG Compound
C14420
ChemSpider
3229
ChEBI
34761
ChEMBL
CHEMBL1604375
ZINC
ZINC000000001443
Wikipedia
Fenthion

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 Solubility0.0042 mg/mLALOGPS
logP3.93ALOGPS
logP3.8Chemaxon
logS-4.8ALOGPS
Physiological Charge0Chemaxon
Hydrogen Acceptor Count0Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area27.69 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity73.67 m3·mol-1Chemaxon
Polarizability27.22 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0ik9-1970000000-38f4eb65b0f142b27c42
GC-MS Spectrum - EI-BGC-MSsplash10-00os-4930000000-d917f6fe7c279d0326ef
Mass Spectrum (Electron Ionization)MSsplash10-004i-7970000000-bc43a51c3e0e0f2a8537
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0090000000-cfc6cc7271f15039d91e
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014j-0940000000-4c4cfaec8b9d90f02220
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0gb9-0910000000-30762456be8c99676446
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0gi0-0900000000-fc2e0d1f56a644607b35
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0g4i-0900000000-89a0ce8c9a4d4a49d57c
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-0290000000-9da11dc2725fc111b8c4
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0290000000-310114d394f902981a1f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0090000000-78d1f5ceeb8e6cc68ac9
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-1910000000-96bd776e096dc5f88d2e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004l-0890000000-ea9d4f4f6493f0992270
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-4900000000-dd039cd6346f5d7b74f6
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-2900000000-1db97b31b09bed12e3f4
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-171.4453902
predicted
DarkChem Lite v0.1.0
[M-H]-170.4533902
predicted
DarkChem Lite v0.1.0
[M-H]-171.3561902
predicted
DarkChem Lite v0.1.0
[M-H]-153.9611
predicted
DeepCCS 1.0 (2019)
[M+H]+156.31912
predicted
DeepCCS 1.0 (2019)
[M+Na]+162.4124
predicted
DeepCCS 1.0 (2019)

Drug created at February 25, 2016 18:30 / Updated at June 12, 2020 16:53