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Identification
NamePermethrin
Accession NumberDB04930
Typesmall molecule
Groupsapproved, investigational
Description

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.

Structure
Thumb
Synonyms
SynonymLanguageCode
3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid, (3-phenoxyphenyl) methyl esterNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
ActicinNot Available
ElimiteNot Available
LyclearJohnson & Johnson
NixNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number52645-53-1
WeightAverage: 391.288
Monoisotopic: 390.07894992
Chemical FormulaC21H20Cl2O3
InChI KeyRLLPVAHGXHCWKJ-UHFFFAOYSA-N
InChI
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
IUPAC Name
(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
SMILES
CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC(OC2=CC=CC=C2)=CC=C1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassFatty Acid Esters
SubclassPyrethroids
Direct parentPyrethroids
Alternative parentsDiarylethers; Benzyloxycarbonyls; Benzylethers; Phenol Ethers; Cyclopropanecarboxylic Acids and Derivatives; Carboxylic Acid Esters; Dialkyl Ethers; Enolates; Polyamines; Acetals; Organochlorides
Substituentsdiaryl ether; benzyloxycarbonyl; benzylether; phenol ether; benzene; cyclopropanecarboxylic acid or derivative; carboxylic acid ester; carboxylic acid derivative; polyamine; ether; dialkyl ether; enolate; acetal; organohalogen; organochloride
Classification descriptionThis compound belongs to the pyrethroids. These are organic compounds similar to the pyrethrins. Some pyrethroids containing a chrysanthemic acid esterified with a cyclopentenone (pyrethrins), or with a phenoxybenzyl.
Pharmacology
IndicationFor the treatment of infestation with Sarcoptes scabiei (scabies).
PharmacodynamicsPermethrin, a pyrethroid, is active against a broad range of pests including lice, ticks, fleas, mites, and other arthropods.
Mechanism of actionPermethrin 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.
AbsorptionPoorly absorbed through the skin.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Rapidly metabolized by ester hydrolysis to inactive metabolites which are excreted primarily in the urine.

Route of eliminationPermethrin is rapidly metabolized by ester hydrolysis to inactive metabolites which are excreted primarily in the urine.
Half lifeNot Available
ClearanceNot Available
ToxicityOral, rat LD50: 430 - 4000 mg/kg; skin, rabbit LD50: 2000 mg/kg.
Affected organisms
  • Scabies (Sarcoptes scabei) and other insects
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 1.0
Blood Brain Barrier + 0.8736
Caco-2 permeable + 0.7366
P-glycoprotein substrate Non-substrate 0.5532
P-glycoprotein inhibitor I Inhibitor 0.5224
P-glycoprotein inhibitor II Non-inhibitor 0.8671
Renal organic cation transporter Non-inhibitor 0.8116
CYP450 2C9 substrate Non-substrate 0.7366
CYP450 2D6 substrate Non-substrate 0.9023
CYP450 3A4 substrate Substrate 0.672
CYP450 1A2 substrate Inhibitor 0.7309
CYP450 2C9 substrate Non-inhibitor 0.5985
CYP450 2D6 substrate Non-inhibitor 0.8796
CYP450 2C19 substrate Inhibitor 0.7386
CYP450 3A4 substrate Non-inhibitor 0.8296
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8687
Ames test AMES toxic 0.9107
Carcinogenicity Non-carcinogens 0.6594
Biodegradation Not ready biodegradable 0.9918
Rat acute toxicity 2.9777 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9758
hERG inhibition (predictor II) Non-inhibitor 0.9091
Pharmacoeconomics
Manufacturers
  • Allergan inc
  • Actavis mid atlantic llc
  • Perrigo new york inc
  • Glaxosmithkline
  • Insight pharmaceuticals corp
Packagers
Dosage forms
FormRouteStrength
CreamTopical
LiquidTopical
LotionTopical
Prices
Unit descriptionCostUnit
Elimite 5% Cream 60 gm Tube83.61USDtube
Permethrin 5% Cream 60 gm Tube30.42USDtube
Acticin 5% Cream 60 gm Tube30.31USDtube
Permethrin 1% Lotion 59ml Bottle16.99USDbottle
Elimite 5% cream1.33USDg
Permethrin technical liquid1.32USDg
Acticin 5% cream0.49USDg
Permethrin 5% cream0.49USDg
Sm lice treatment permethrin0.18USDml
Nix 1% creme rinse liquid0.15USDml
Sm lice bedding spray0.04USDg
CVS Pharmacy lice bedding spray0.03USDg
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point34 °CPhysProp
boiling point220 °C at 5.00E-02 mm HgPhysProp
water solubility0.006 mg/L (at 20 °C)USDA PESTICIDE PROP DATABASE
logP6.50HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility6.91e-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
number of rings3ChemAxon
bioavailability1ChemAxon
rule of fiveNoChemAxon
Ghose filterNoChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleYesChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General Reference
  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
External Links
ResourceLink
KEGG DrugD05443
KEGG CompoundC14388
PubChem Compound40326
PubChem Substance46505374
ChemSpider36845
ChEBI34911
ChEMBLCHEMBL1525
Therapeutic Targets DatabaseDAP001235
PharmGKBPA164743137
Drug Product Database771368
RxListhttp://www.rxlist.com/cgi/generic/elimite.htm
Drugs.comhttp://www.drugs.com/cdi/permethrin-cream.html
WikipediaPermethrin
ATC CodesP03AC04
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelshow(171 KB)
MSDSshow(60.4 KB)
Interactions
Drug InteractionsSearched, but no interactions found.
Food InteractionsNot Available

Targets

1. Sodium channel protein type 1 subunit alpha

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Sodium channel protein type 1 subunit alpha P35498 Details

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
  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
  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
  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
  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

Enzymes

1. Cytochrome P450 2B6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inducer

Components

Name UniProt ID Details
Cytochrome P450 2B6 P20813 Details

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

2. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

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

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Drug created on October 21, 2007 16:23 / Updated on September 16, 2013 17:26