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Record Information
Version3.6
Creation Date2012-09-06 15:16:52 UTC
Update Date2014-09-23 05:25:40 UTC
HMDB IDHMDB15604
Secondary Accession NumbersNone
Metabolite Identification
Common NamePermethrin
DescriptionPermethrin 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 regulated. Delayed repolarization and paralysis of the pests are the consequences of this disturbance.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC21H20Cl2O3
Average Molecular Weight391.288
Monoisotopic Molecular Weight390.07894992
IUPAC Name(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
Traditional IUPAC Namepermethrin
CAS Registry Number52645-53-1
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 KeyRLLPVAHGXHCWKJ-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassFatty Acid Esters
Sub ClassPyrethroids
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • Aromatic Homopolycyclic Compounds
  • a monoterpenoid(Cyc)
  • cyclopropanecarboxylate ester(ChEBI)
  • cyclopropanes(ChEBI)
Substituents
  • Benzyloxycarbonyl
  • Carboxylic Acid Ester
  • Cyclopropane
  • Ketene Acetal Or Derivative
  • Organic Halide
  • Organochloride
Direct ParentPyrethroids
Ontology
StatusExpected and 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 Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point34 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility6.91e-05 g/LNot Available
LogP6.50HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility6.910E-05 g/LALOGPS
logP6.24ALOGPS
logP5.7ChemAxon
logS-6.8ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity114.28ChemAxon
Polarizability39.43ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04930
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04930
  • Not Applicable
details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-3 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-1 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04930
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID36845
KEGG Compound IDC14388
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPermethrin
NuGOwiki LinkHMDB15604
Metagene LinkHMDB15604
METLIN IDNot Available
PubChem Compound40326
PDB IDNot Available
ChEBI ID34911
References
Synthesis ReferenceNot 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. 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. 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. 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. 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. 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