Human Metabolome Database Version 3.5

Showing metabocard for Permethrin (HMDB15604)

Record Information
Version 3.5
Creation Date 2012-09-06 09:16:52 -0600
Update Date 2013-02-08 17:34:05 -0700
Secondary Accession Numbers None
Metabolite Identification
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 regulated. Delayed repolarization and paralysis of the pests are the consequences of this disturbance.
Structure Thumb
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Display: 2D Structure | 3D Structure
Synonyms Not Available
Chemical Formula C21H20Cl2O3
Average Molecular Weight 391.288
Monoisotopic Molecular Weight 390.07894992
IUPAC Name (3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
Traditional IUPAC Name permethrin
CAS Registry Number 52645-53-1
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
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acid Esters
Sub Class Pyrethroids
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • Aromatic Homopolycyclic Compounds
  • a monoterpenoid(Cyc)
  • cyclopropanecarboxylate ester(ChEBI)
  • cyclopropanes(ChEBI)
  • Benzyloxycarbonyl
  • Carboxylic Acid Ester
  • Cyclopropane
  • Ketene Acetal Or Derivative
  • Organic Halide
  • Organochloride
Direct Parent Pyrethroids
Status Expected and Not Quantified
  • Drug
  • Cell signaling
  • Enzyme Inhibitors
  • Fuel and energy storage
  • Fuel or energy source
  • Insecticides
  • Membrane integrity/stability
  • Nutrients
  • Pharmaceutical
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 34 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 6.91e-05 g/L Not Available
LogP 6.50 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
LogP 6.24 ALOGPS
LogP 5.7 ChemAxon
LogS -6.75 ALOGPS
pKa (strongest basic) -7.1 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 35.53 A2 ChemAxon
Rotatable Bond Count 7 ChemAxon
Refractivity 114.28 ChemAxon
Polarizability 39.43 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB04930
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB04930
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB04930 Link_out
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 Link_out
KEGG Compound ID C14388 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Permethrin Link_out
NuGOwiki Link HMDB15604 Link_out
Metagene Link HMDB15604 Link_out
METLIN ID Not Available
PubChem Compound 40326 Link_out
PDB ID Not Available
ChEBI ID 34911 Link_out
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 Link_out

Name: Cytochrome P450 3A4
Reactions: Not Available
Gene Name: CYP3A4
Uniprot ID: P08684 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2B6
Reactions: Not Available
Gene Name: CYP2B6
Uniprot ID: P20813 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sodium channel protein type 1 subunit alpha
Reactions: Not Available
Gene Name: SCN1A
Uniprot ID: P35498 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA