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Permethrin

July 24, 2017
Common Name

Permethrin Description

Permethrin is only found in individuals that have used or taken this drug. It is a pyrethroid insecticide commonly used in the treatment of lice infestations and scabies. It is a yellow to light orange-brown, low melt-ing solid or viscous liquid.Permethrin acts on the nerve cell membrane to disrupt the sodium channel current by which the polarization of the membrane is regliated. Delayed repolarization and paralysis of the pests are the consequences of this disturbance. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (3-Phenoxyphenyl)methyl (+-)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylateChEBI 3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid, (3-phenoxyphenyl) methyl esterChEBI (3-Phenoxyphenyl)methyl (+-)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acidGenerator 3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropane carboxylate, (3-phenoxyphenyl) methyl esterGenerator 3-Phenoxybenzyl-(+-)-cis,trans-2,2-dichlorovinyl-2,2-dimethyl-cyclopropylcarboxylic acid, esterMeSH NRDC 143MeSH Permethrin, (1R-cis)-isomerMeSH Permethrin, (1S-cis)-isomerMeSH Permethrin, (cis)-isomerMeSH Permethrin, (cis-(+-))-isomerMeSH Permethrin, (trans)-isomerMeSH trans-(1Rs)-PermethrinMeSH NRDC 147MeSH NRDC143MeSH Permethrin, (1R-trans)-isomerMeSH Permethrin, (1S-trans)-isomerMeSH Permethrin, trans-(1Rs)-isomerMeSH cis-(1Rs)-PermethrinMeSH trans PermethrinMeSH (m-Phenoxybenzyl)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylateMeSH 3-Phenoxybenzyl-cis,trans-(1Rs)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylateMeSH AmbushMeSH ElimiteMeSH NRDC-143MeSH cis-PermethrinMeSH Permethrin, cis-(1Rs)-isomerMeSH NRDC-147MeSH NRDC147MeSH NittiforMeSH Permethrin, (trans-(+-))-isomerMeSH cis PermethrinMeSH trans-PermethrinMeSH

Chemical Formlia

C21H20Cl2O3 Average Molecliar Weight

391.288 Monoisotopic Molecliar Weight

390.07894992 IUPAC Name

(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Traditional Name

permethrin CAS Registry Number

52645-53-1 SMILES

CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC(OC2=CC=CC=C2)=CC=C1

InChI Identifier

InChI=1S/C21H20Cl2O3/c1-21(2)17(12-18(22)23)19(21)20(24)25-13-14-7-6-10-16(11-14)26-15-8-4-3-5-9-15/h3-12,17,19H,13H2,1-2H3

InChI Key

RLLPVAHGXHCWKJ-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as pyrethroids. These are organic compounds similar to the pyrethrins. Some pyrethroids containing a chrysanthemic acid esterified with a cyclopentenone (pyrethrins), or with a phenoxybenzyl group. Kingdom

Chemical entities Super Class

Organic compounds Class

Lipids and lipid-like moleclies Sub Class

Fatty Acyls Direct Parent

Pyrethroids Alternative Parents

  • Diphenylethers
  • Diarylethers
  • Benzyloxycarbonyls
  • Phenoxy compounds
  • Phenol ethers
  • Cyclopropanecarboxylic acids and derivatives
  • Ketene acetals
  • Carboxylic acid esters
  • Vinyl chlorides
  • Monocarboxylic acids and derivatives
  • Chloroalkenes
  • Organochlorides
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • Substituents

  • Pyrethroid skeleton
  • Diphenylether
  • Diaryl ether
  • Benzyloxycarbonyl
  • Phenoxy compound
  • Phenol ether
  • Monocyclic benzene moiety
  • Cyclopropanecarboxylic acid or derivatives
  • Benzenoid
  • Carboxylic acid ester
  • Ketene acetal or derivatives
  • Carboxylic acid derivative
  • Chloroalkene
  • Haloalkene
  • Ether
  • Vinyl halide
  • Monocarboxylic acid or derivatives
  • Vinyl chloride
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organohalogen compound
  • Organochloride
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound

    • Molecliar Framework

    Aromatic homomonocyclic compounds External Descriptors

  • cyclopropanes (CHEBI:34911 )
  • cyclopropanecarboxylate ester (CHEBI:34911 )
  • a monoterpenoid (CPD-13115 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Cell signaling
  • Enzyme Inhibitors
  • Fuel and energy storage
  • Fuel or energy source
  • Insecticides
  • Membrane integrity/stability

    • Application

  • Nutrients
  • Pharmaceutical
  • Stabilizers
  • Surfactants and Emlisifiers

    • Cellliar locations

  • Extracellliar
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point34 °CNot Available Boiling PointNot AvailableNot Available Water Solubility6.91e-05 g/LNot Available LogP6.50HANSCH,C ET AL. (1995)

    Predicted Properties

    Property Value Source Water Solubility6.91e-05 mg/mLALOGPS logP6.24ALOGPS logP5.7ChemAxon logS-6.8ALOGPS pKa (Strongest Basic)-7.1ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count1ChemAxon Hydrogen Donor Count0ChemAxon Polar Surface Area35.53 Å2ChemAxon Rotatable Bond Count7ChemAxon Refractivity114.28 m3·mol-1ChemAxon Polarizability39.43 Å3ChemAxon Number of Rings3ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-0002-1900000000-956860faa94e3dea2ee2View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-0002-1900000000-ce2901f0a3049806d95fView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-0002-1900000000-b5846ca870454df7f44fView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-0002-0900000000-474995c2ccb155f0975cView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-0002-1900000000-261c3708f1e50c4a8418View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-006t-2900000000-4915b2e2cee108c117a2View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Extracellliar
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04930

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04930

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Predicted Concentrations

    Biofluid Value Original age Original sex Original condition Comments Blood0-3 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities Blood0-1 umol/mmol creatinineAdlit (>18 years old)BothNormalPredicted based on drug qualities

    Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB04930 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    36845 KEGG Compound ID

    C14388 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Permethrin NuGOwiki Link

    HMDB15604 Metagene Link

    HMDB15604 METLIN ID

    Not Available PubChem Compound

    40326 PDB ID

    Not Available ChEBI ID

    34911

    Product: Y-321

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Abedin S, Narang M, Gandhi V, Narang S: Efficacy of permethrin cream and oral ivermectin in treatment of scabies. Indian J Pediatr. 2007 Oct;74(10):915-6. [PubMed:17978449 ]

    Enzymes

    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
    Gene Name:
    CYP3A4
    Uniprot ID:
    P08684
    Molecular weight:
    57255.585
    References
    1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
    Gene Name:
    CYP2B6
    Uniprot ID:
    P20813
    Molecular weight:
    56277.81
    References
    1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
    General function:
    Involved in ion channel activity
    Specific function:
    Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient
    Gene Name:
    SCN1A
    Uniprot ID:
    P35498
    Molecular weight:
    228969.5
    References
    1. Cao Z, Shafer TJ, Murray TF: Mechanisms of pyrethroid insecticide-induced stimulation of calcium influx in neocortical neurons. J Pharmacol Exp Ther. 2011 Jan;336(1):197-205. doi: 10.1124/jpet.110.171850. Epub 2010 Sep 29. [PubMed:20881019 ]
    2. Liu N, Xu Q, Li T, He L, Zhang L: Permethrin resistance and target site insensitivity in the mosquito Culex quinquefasciatus in Alabama. J Med Entomol. 2009 Nov;46(6):1424-9. [PubMed:19960691 ]
    3. Breckenridge CB, Holden L, Sturgess N, Weiner M, Sheets L, Sargent D, Soderlund DM, Choi JS, Symington S, Clark JM, Burr S, Ray D: Evidence for a separate mechanism of toxicity for the Type I and the Type II pyrethroid insecticides. Neurotoxicology. 2009 Nov;30 Suppl 1:S17-31. doi: 10.1016/j.neuro.2009.09.002. Epub 2009 Sep 18. [PubMed:19766671 ]
    4. Chang C, Shen WK, Wang TT, Lin YH, Hsu EL, Dai SM: A novel amino acid substitution in a voltage-gated sodium channel is associated with knockdown resistance to permethrin in Aedes aegypti. Insect Biochem Mol Biol. 2009 Apr;39(4):272-8. doi: 10.1016/j.ibmb.2009.01.001. Epub 2009 Jan 10. [PubMed:19171193 ]
    5. McMahon C, Krober T, Guerin PM: In vitro assays for repellents and deterrents for ticks: differing effects of products when tested with attractant or arrestment stimuli. Med Vet Entomol. 2003 Dec;17(4):370-8. [PubMed:14651650 ]

    PMID: 15152028

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